DIMETHYLFORMAMIDE (DMETLFORMAMD)

CAS No.: 68-12-2

EC No.: 200-679-5

Synonyms:

DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; N,N-DIMETHYLFORMAMIDE; Dimethylformamide; 68-12-2; N,N-Dimethylmethanamide; Dimethyl formamide; N-Formyldimethylamine; Formamide, N,N-dimethyl-; Dimethylformamid; Dimethylformamide; DimethylformamideA; Dimetilformamide; Dwumetyloformamid; Formyldimethylamine; N,N-Dimethyl formamide; Dimethylforamide; Dimetylformamidu; Dimethylformamide (amide); NCI-C60913; dimethyl-Formamide; n,n,dimethylformamide; N,N-Dimethylformamid; Dimethylamid kyseliny mravenci; Caswell No. 366A; Dimetylformamidu [Czech]; Dimethylformamid [German]; Dimetilformamide [Italian]; Dwumetyloformamid [Polish]; MFCD00003284; HSDB 78; U-4224; UNII-8696NH0Y2X; CCRIS 1638; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; N,N-Dimetilformamida [Spanish]; n,n-dimethyl-Formamide; N, N-dimethylformamide; N,N’-Dimethylformamide; N,N- Dimethylformamide; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; N,N-Dimethylformaldehyde; NSC 5356; Formic acid, amide, N,N-dimethyl-; EINECS 200-679-5; UN2265; Dimethylamid kyseliny mravenci [Czech]; EPA Pesticide Chemical Code 366200; AI3-03311; DTXSID6020515; CHEBI:17741; NSC5356; 8696NH0Y2X; NSC-5356; DSSTox_CID_515; DSSTox_RID_75636; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DSSTox_GSID_20515; N,N Dimethylformamide; CAS-68-12-2; N,N-Dimethylformamide, 99+%, extra pure; N,N-Dimetilformamida; N,N-Dimethylformamide, 99.5%, for analysis; N,N-Dimethylformamide, for HPLC, >=99.9%; N,N-Dimethylformamide, 99.8+%, ACS reagent; N,N-Dimethylformamide, 99.8%, for spectroscopy; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; N,N-Dimethylformamide, ACS reagent, >=99.8%; N, N-dimethyl formamide; Dimethylformamide, N,N-; N,N-Dimethylformamide, 99.8%, for peptide synthesis; 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DMETLFORMAMD; N,N dimethyl formamide; N,N’ dimethylformamide; N,N-di methylformamide; N,N-di-methylformamide; N,N-dime-thylformamide; N,N-dimehtyl formamide; N,N-dimethylfor mamide; N,N-dimethylfor-mamide; N,N-dimethylform-amide; N,N-dimethylformamide-; PubChem23341; N,N-di-methylforrnamide; Dimethyl Fornamide,(S); Dimethylformamide (dimethylformamide); n,n,-dimethyl formamide; N, N’-dimethylformamide; N, N- dimethylformamide; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; N, N-di-methylformamide; N, N-dimethyl-formamide; N,N- dimethyl formamide; N,N-di-methyl formamide; N,N-di-methyl-formamide; N,N-dimethyl -formamide; N,N-dimethyl- formamide; N, N-dimethylformaldehyde; bmse000709; EC 200-679-5; D.M.F; HCON(CH3)2; Dynasolve 100 (Salt/Mix); KSC352S1B; BIDD:ER0600; WLN: VHN1&1; ACMC-20976q; CHEMBL268291; D.M.F.; CTK2F2910; KS-00000UCQ; N,N-Dimethylformamide, 99.8%; N,N-Dimethylformamide HPLC grade; N,N-Dimethylformamide, ACS grade; ZINC901648; Dimethylformamide Reagent Grade ACS; N,N-Dimethylformamide, HPLC Grade; Tox21_201259; Tox21_300039; ANW-13584; s6192; STL264197; N,N-Dimethylformamide, LR, >=99%; AKOS000121096; FORMIN ACID,AMIDE,N,N-DIMETHYL; DB01844; EBD2222506; LS-1577; MCULE-6290117712; UN 2265; N,N-Dimethylformamide, p.a., 99.8%; N,N-Dimethylformamide, AR, >=99.5%; NCGC00090785-01; NCGC00090785-02; NCGC00090785-03; NCGC00090785-04; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; NCGC00090785-05; NCGC00254093-01; NCGC00258811-01; K124; SC-18318; Dimethylformamide, n,n- Reagent Grade ACS; N,N-Dimethylformamide, analytical standard; N,N-Dimethylformamide, anhydrous, 99.8%; N,N-Dimethylformamide, 99.5%, for HPLC; 191-EP1441224A2; 191-EP2269610A2; 191-EP2269975A2; 191-EP2269977A2; 191-EP2269978A2; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; 191-EP2269979A1; 191-EP2269985A2; 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70936-EP2308833A2; 70936-EP2374788A1; N,N-Dimethylformamide, AldraSORB(TM), 99.8%; N,N-Dimethylformamide, ReagentPlus(R), >=99%; A836012; N,N-Dimethylformamide, biotech. grade, >=99.9%; Q409298; N,N-Dimethylformamide [UN2265] [Flammable liquid]; N,N-Dimethylformamide, p.a., ACS reagent, 99.8%; N,N-Dimethylformamide, SAJ first grade, >=99.0%; N,N-Dimethylformamide [UN2265] [Flammable liquid]; N,N-Dimethylformamide, anhydrous, ZerO2(TM), 99.8%; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; DIMETHYLFORMAMIDE; Dimetilformamid; DMETLFORMAMD; N,N-Dimethylformamide, for molecular biology, >=99%; N,N-Dimethylformamide, JIS special grade, >=99.5%; N,N-Dimethylformamide, UV HPLC spectroscopic, 99.7%; N,N-Dimethylformamide, ACS spectrophotometric grade, >=99.8%; N,N-Dimethylformamide, B&J Brand (product of Burdick & Jackson); N,N-Dimethylformamide, Vetec(TM) reagent grade, anhydrous, >=99.8%; Dimethylformamide, Pharmaceutical Secondary Standard; Certified Reference Material; N,N-Dimethylformamide, 99.8%, Extra Dry, AcroSeal(R), package of 4x25ML bottles; 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DIMETHYLFORMAMIDE

Dimethylformamide

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Dimethylformamide

Skeletal formula of dimethylformamide with one explicit hydrogen added

Ball and stick model of dimethylformamide

Spacefill model of dimethylformamide

Names

Preferred IUPAC name

N,N-Dimethylformamide[2]

Other names

Dimethylformamide

N,N-Dimethylmethanamide[1]

MeSH Dimethylformamide

Infobox references

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as Dimethylformamide (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. Dimethylformamide is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging degraded samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is a derivative of formamide, the amide of formic acid. Dimethylformamide is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

Contents

1 Structure and properties

2 Reactions

3 Production

4 Applications

4.1 Proper uses

5 Safety

6 Toxicity

7 References

8 External links

Structure and properties

As for most amides, the spectroscopic evidence indicates partial double bond character for the C-N and C-O bonds. Thus, the infrared spectrum shows a C=O stretching frequency at only 1675 cm−1, whereas a ketone would absorb near 1700 cm−1.[6]

Dimethylformamide is a classic example of a fluxional molecule.[7]

DimethylformamideDNMR.png

The ambient temperature 1H NMR spectrum shows two methyl signals, indicative of hindered rotation about the (O)C-N bond.[6] At temperatures near 100 °C, the 500 MHz NMR spectrum of this compound shows only one signal for the methyl groups.

Dimethylformamide is miscible with water.[8] The vapour pressure at 20 °C is 3.5 hPa.[9] A Henry’s law constant of 7.47 × 10−5 hPa m3 mol−1 can be deduced from an experimentally determined equilibrium constant at 25 °C.[10] The partition coefficient log POW is measured to −0.85.[11] Since the density of Dimethylformamide (0.95 g cm−3 at 20 °C[8]) is similar to that of water, significant flotation or stratification in surface waters in case of accidental losses is not expected.

right: two resonance structures of Dimethylformamide. Right: illustration highlighting delocalization.

Reactions

Dimethylformamide is hydrolyzed by strong acids and bases, especially at elevated temperatures. With sodium hydroxide, Dimethylformamide converts to formate and dimethylamine. Dimethylformamide undergoes decarbonylation near its boiling point to give dimethylamine. Distillation is therefore conducted under reduced pressure at lower temperatures.[12]

In one of its main uses in organic synthesis, Dimethylformamide was a reagent in the Vilsmeier–Haack reaction, which is used to formylate aromatic compounds.[13][14] The process involves initial conversion of Dimethylformamide to a chloroiminium ion, [(CH3)2N=CH(Cl)]+, known as a Vilsmeier reagent,[15] which attacks arenes.

Organolithium compounds and Grignard reagents react with Dimethylformamide to give aldehydes after hydrolysis in a reaction named after Bouveault.[16]

Dimethylformamide forms 1:1 adducts with a variety of Lewis acids such as the soft acid I2, and the hard acid phenol. It is classified as a hard Lewis base and its ECW model base parameters are EB= 2.19 and CB= 1.31.[17] Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.[18][19]

Production

Dimethylformamide was first prepared in 1893 by the French chemist Albert Verley (8 January 1867 – 27 November 1959), by distilling a mixture of dimethylamine hydrochloride and potassium formate.[20]

Dimethylformamide is prepared by combining methyl formate and dimethylamine or by reaction of dimethylamine with carbon monoxide.[21]

Although currently impractical, Dimethylformamide can be prepared from supercritical carbon dioxide using ruthenium-based catalysts.[22]

Applications

The primary use of Dimethylformamide is as a solvent with low evaporation rate. Dimethylformamide is used in the production of acrylic fibers and plastics. It is also used as a solvent in peptide coupling for pharmaceuticals, in the development and production of pesticides, and in the manufacture of adhesives, synthetic leathers, fibers, films, and surface coatings.[8]

It is used as a reagent in the Bouveault aldehyde synthesis[23][24][25] and in the Vilsmeier-Haack reaction,[13][14] another useful method of forming aldehydes.

It is a common solvent in the Heck reaction.[26]

It is also a common catalyst used in the synthesis of acyl halides, in particular the synthesis of acyl chlorides from carboxylic acids using oxalyl or thionyl chloride. The catalytic mechanism entails reversible formation of an imidoyl chloride:[27][28]

Me2NC(O)H + (COCl)2 → CO + CO2 + [Me2N=CHCl]Cl

The iminium intermediate reacts with the carboxylic acid, abstracting an oxide, and regenerating the Dimethylformamide catalyst.[27]

Reaction to give acyl chloride and Dimethylformamide.png

Dimethylformamide penetrates most plastics and makes them swell. Because of this property Dimethylformamide is suitable for solid phase peptide synthesis and as a component of paint strippers.

Dimethylformamide is used as a solvent to recover olefins such as 1,3-butadiene via extractive distillation.

It is also used in the manufacturing of solvent dyes as an important raw material. It is consumed during reaction.

Pure acetylene gas cannot be compressed and stored without the danger of explosion. Industrial acetylene is safely compressed in the presence of dimethylformamide, which forms a safe, concentrated solution. The casing is also filled with agamassan, which renders it safe to transport and use.

Proper uses

As a cheap and common reagent, Dimethylformamide has many uses in a research laboratory.

Dimethylformamide is effective at separating and suspending carbon nanotubes, and is recommended by the NIST for use in near infrared spectroscopy of such.[29]

Dimethylformamide can be utilized as a standard in proton NMR spectroscopy allowing for a quantitative determination of an unknown compound.

In the synthesis of organometallic compounds, it is used as a source of carbon monoxide ligands.

Dimethylformamide is a common solvent used in electrospinning.

Dimethylformamide is commonly used in the solvothermal synthesis of Metal–Organic Frameworks.

Dimethylformamide-d7 in the presence of a catalytic amount of KOt-Bu under microwave heating is a reagent for deuteration of polyaromatic hydrocarbons.

Safety

Reactions including the use of sodium hydride in Dimethylformamide as a solvent are somewhat hazardous; exothermic decompositions have been reported at temperatures as low as 26 °C. On a laboratory scale any thermal runaway is (usually) quickly noticed and brought under control with an ice bath and this remains a popular combination of reagents. On a pilot plant scale, on the other hand, several accidents have been reported.[30]

On the 20 of June 2018, the Danish Environmental Protective Agency published an article about the Dimethylformamide’s use in squishies. The density of the compound in the toy resulted in all squishes being removed from the Danish market. All squishies were recommended to be thrown out as household waste. [31]

DMETLFORMAMD

Dimetilformamid

Gezintiye atlaArama yapmak için atla

Dimetilformamid

Dimetilformamidin iskelet formülü, açk bir hidrojen eklenmi

Dimetilformamidin bilye ve çubuk modeli

Dimetilformamidin boluk doldurma modeli

simler

Tercih edilen IUPAC ad

N, N-Dimetilformamid [2]

Dier isimler

Dimetilformamid

N, N-Dimetilmetanamid [1]

MeSH Dimetilformamid

Bilgi kutusu referanslar

Dimetilformamid, (CH3) 2NC (O) H formülüne sahip organik bir bileiktir. Genellikle Dimetilformamid olarak ksaltlr (bu balangç bazen dimetilfuran veya dimetil fumarat için kullanlsa da), bu renksiz sv su Dimetilformamid ve organik svlarn çou ile karabilir. Dimetilformamid, kimyasal reaksiyonlar için yaygn bir çözücüdür. Dimetilformamid kokusuzdur, ancak teknik snfta veya bozulmu örneklerde genellikle dimetilaminin safszlndan dolay balk kokusu vardr. Dimetilamin bozunmas katklar, bozulmu numunelerin argon gibi bir inert gazla serpilmesi veya numunelerin düük basnç altnda sonike edilmesiyle giderilebilir. Adndan da anlalaca gibi, Dimetilformamid formik asitin amidi olan formamidin bir türevidir. Dimetilformamid, yüksek kaynama noktasna sahip polar (hidrofilik) bir aprotik çözücüdür. SN2 reaksiyonlar gibi polar mekanizmalar takip eden reaksiyonlar kolaylatrr.

çindekiler

1 Dimetilformamid Yaps ve özellikleri

2 Dimetilformamid Reaksiyonlar

3 Dimetilformamid Üretim

4 Dimetilformamid Uygulamalar

4.1 Dimetilformamid Uygun kullanmlar

5 Dimetilformamid Güvenlik

6 Dimetilformamid Toksisite

7 Dimetilformamid Referanslar

8 Dimetilformamid D balantlar

Dimetilformamid Yaps ve özellikleri

Dimetilformamid Çou amide gelince, spektroskopik kantlar C-N ve C-O balar için ksmi çift ba karakterini gösterir. Bu nedenle, kzlötesi spektrum sadece 1675 cm-1’de C = O uzama frekans gösterirken, bir keton 1700 cm-1 civarnda sourabilir. [6]

Dimetilformamid, akkan bir molekülün klasik bir örneidir. [7]

DimetilformamidDNMR.png

Ortam scakl 1H NMR spektrumu, (O) C-N ba etrafnda engellenmi dönüü gösteren iki metil sinyali gösterir. [6] 100 ° C’ye yakn scaklklarda, bu bileiin 500 MHz NMR spektrumu, metil gruplar için yalnzca bir sinyal gösterir.

Dimetilformamid su ile karabilir. [8] 20 ° C’de buhar basnc 3,5 hPa’dr. [9] 7,47 × 10−5 hPa m3 mol − 1 olan Henry yasas sabiti, 25 ° C’de deneysel olarak belirlenen bir denge sabitinden çkarlabilir. [10] Bölme katsays log POW, -0,85 olarak ölçülür. [11] Dimetilformamidin younluu (20 ° C’de 0,95 g cm-3 [8]) suya benzer olduundan, kazara kayplar durumunda yüzey sularnda önemli yüzdürme veya tabakalama beklenmemektedir.

sada: Dimetilformamidin iki rezonans yaps. Sada: yerelletirmeyi vurgulayan resim.

Tepkiler

Dimetilformamid, özellikle yüksek scaklklarda güçlü asitler ve bazlar tarafndan hidrolize edilir. Sodyum hidroksit ile Dimetilformamid, format ve dimetilamine dönüür. Dimetilformamid, dimetilamin vermek için kaynama noktasna yakn dekarbonilasyona urar. Bu nedenle damtma, daha düük scaklklarda düük basnç altnda gerçekletirilir. [12]

Organik sentezdeki ana kullanmlarndan birinde Dimetilformamid, aromatik bileikleri formüle etmek için kullanlan Vilsmeier-Haack reaksiyonunda bir reaktifti. [13] [14] Proses, Dimetilformamidin, arenlere saldran bir kloroiminyum iyonuna [(CH3) 2N = CH (Cl)] +, Vilsmeier reaktifi olarak [15] dönütürülmesini içerir.

Organolithium bileikleri ve Grignard reaktifleri, Bouveault adn tayan bir reaksiyonda hidrolizden sonra aldehitler vermek için Dimetilformamid ile reaksiyona girer. [16]

Dimetilformamid, yumuak asit I2 ve sert asit fenol gibi çeitli Lewis asitleri ile 1: 1 eklentiler oluturur. Sert Lewis baz olarak snflandrlr ve ECW modeli temel parametreleri EB = 2.19 ve CB = 1.31’dir. [17] Dier Lewis bazlarna kar bir dizi aside kar bal donör gücü C-B grafikleri ile gösterilebilir. [18] [19]

Üretim

Dimetilformamid ilk olarak 1893 ylnda Fransz kimyager Albert Verley (8 Ocak 1867 – 27 Kasm 1959) tarafndan, bir dimetilamin hidroklorür ve potasyum format karm damtlarak hazrland. [20]

Dimetilformamid, metil format ve dimetilaminin birletirilmesi veya dimetilaminin karbon monoksit ile reaksiyona sokulmasyla hazrlanr. [21]

u anda pratik olmamasna ramen, Dimetilformamid süper kritik karbondioksitten rutenyum bazl katalizörler kullanlarak hazrlanabilir. [22]

Uygulamalar

Dimetilformamidin birincil kullanm, düük buharlama oranna sahip bir çözücüdür. Dimetilformamid akrilik elyaf ve plastik üretiminde kullanlmaktadr. Ayn zamanda farmasötikler için peptid birletirmesinde, pestisitlerin gelitirilmesinde ve üretiminde ve yaptrclarn, sentetik derilerin, liflerin, filmlerin ve yüzey kaplamalarnn üretiminde bir çözücü olarak kullanlmaktadr. [8]

Dimetilformamid Bouveault aldehit sentezinde [23] [24] [25] ve Vilsmeier-Haack reaksiyonunda [13] [14] reaktif olarak kullanlr, Dimetilformamid [13] [14] aldehit oluturmann baka bir yararl yöntemi.

Heck reaksiyonunda yaygn bir Dimetilformamid çözücüdür. [26]

Ayn zamanda, asil halojenürlerin sentezinde, özellikle de asil klorürlerin oksalil veya tiyonil klorür kullanlarak karboksilik asitlerden sentezinde kullanlan yaygn bir katalizördür. Katalitik mekanizma, geri dönüümlü bir imidoil klorür oluumunu gerektirir: [27] [28]

Me2NC (O) H + (COCl) 2 → CO + CO2 + [Me2N = CHCl] Cl

minyum ara maddesi karboksilik asit ile reaksiyona girerek bir oksit çkarr ve Dimetilformamid katalizörünü yeniden oluturur. [27]

Asil klorür ve Dimethylformamide.png vermek için reaksiyon

Dimetilformamid çou plastie nüfuz eder ve onlar iirir. Bu özelliinden dolay Dimetilformamid, kat faz peptit sentezi için ve boya syrclarn bir bileeni olarak uygundur.

Dimetilformamid, özütleyici damtma yoluyla 1,3-bütadien gibi olefinlerin geri kazanlmas için bir çözücü olarak kullanlr.

Dimetilformamid boyalarn üretiminde de önemli bir hammadde olarak kullanlmaktadr. Reaksiyon srasnda tüketilir.

Saf asetilen gaz, patlama tehlikesi olmadan sktrlp depolanamaz. Endüstriyel asetilen, güvenli, konsantre bir çözelti oluturan dimetilformamid varlnda güvenli bir ekilde sktrlr. Muhafaza ayrca, tanmasn ve kullanlmasn güvenli klan agamassan ile doldurulmutur.

Uygun kullanmlar

Ucuz ve yaygn bir reaktif olarak Dimetilformamidin bir aratrma laboratuvarnda birçok kullanm vardr.

Dimetilformamid, karbon nanotüplerin ayrlmas ve askya alnmasnda etkilidir ve bu türlerin yakn kzlötesi spektroskopisinde kullanlmas NIST tarafndan önerilmektedir. [29]

Dimetilformamid, bilinmeyen bir bileiin kantitatif tespitine izin veren proton NMR spektroskopisinde bir standart olarak kullanlabilir.

Organometalik bileiklerin sentezinde bir karbon monoksit ligand kayna olarak kullanlr.

Dimetilformamid, elektrospinning’de kullanlan yaygn bir çözücüdür.

Dimetilformamid, Metal-Organik Çerçevelerin solvotermal sentezinde yaygn olarak kullanlmaktadr.

Mikrodalga stma altnda katalitik miktarda KOt-Bu varlnda dimetilformamid-d7, poliaromatik hidrokarbonlarn döterasyonu için bir reaktiftir.

Emniyet

Dimetilformamid içinde bir çözücü olarak sodyum hidrür kullanmn içeren reaksiyonlar bir ekilde tehlikelidir; 26 ° C’ye kadar düük scaklklarda ekzotermik ayrmalar bildirilmitir. Laboratuvar ölçeinde herhangi bir termal kaçak (genellikle) hzl bir ekilde fark edilir ve bir buz banyosu ile kontrol altna alnr ve bu, reaktiflerin popüler bir kombinasyonu olarak kalr. Pilot tesis ölçeinde ise birkaç kaza rapor edilmitir. [30]

20 Haziran 2018’de, Danimarka Çevre Koruma Ajans Dimetilformamidin squishies’te kullanm hakknda bir makale yaynlad. Oyuncaktaki bileiin younluu, tüm ezmelerin Danimarka pazarndan çkarlmasna neden oldu. Tüm ezmelerin evsel atk olarak atlmas önerildi. [31]

Dimetilformamid

Gezintiye atlaArama yapmak için atla

Dimetilformamid

Dimetilformamidin iskelet formülü, açk bir hidrojen eklenmi

Dimetilformamidin bilye ve çubuk modeli

Dimetilformamidin boluk doldurma modeli

simler

Tercih edilen IUPAC ad

N, N-Dimetilformamid [2]

Dier isimler

Dimetilformamid

N, N-Dimetilmetanamid [1]

MeSH Dimetilformamid

Bilgi kutusu referanslar

çindekiler

1 Dimetilformamid Yaps ve özellikleri

2 Dimetilformamid Reaksiyonlar

3 Dimetilformamid Üretim

4 Dimetilformamid Uygulamalar

4.1 Dimetilformamid Uygun kullanmlar

5 Dimetilformamid Güvenlik

6 Dimetilformamid Toksisite

7 Dimetilformamid Referanslar

8 Dimetilformamid D balantlar

Dimetilformamid Yaps ve özellikleri

Dimetilformamid, akkan bir molekülün klasik bir örneidir. [7]

DimetilformamidDNMR.png

sada: Dimetilformamidin iki rezonans yaps. Sada: yerelletirmeyi vurgulayan resim.

Tepkiler

Organolithium bileikleri ve Grignard reaktifleri, Bouveault adn tayan bir reaksiyonda hidrolizden sonra aldehitler vermek için Dimetilformamid ile reaksiyona girer. [16]

Üretim

Dimetilformamid ilk olarak 1893 ylnda Fransz kimyager Albert Verley (8 Ocak 1867 – 27 Kasm 1959) tarafndan, bir dimetilamin hidroklorür ve potasyum format karm damtlarak hazrland. [20]

Dimetilformamid, metil format ve dimetilaminin birletirilmesi veya dimetilaminin karbon monoksit ile reaksiyona sokulmasyla hazrlanr. [21]

u anda pratik olmamasna ramen, Dimetilformamid süper kritik karbondioksitten rutenyum bazl katalizörler kullanlarak hazrlanabilir. [22]

Uygulamalar

Dimetilformamid Bouveault aldehit sentezinde [23] [24] [25] ve Vilsmeier-Haack reaksiyonunda [13] [14] reaktif olarak kullanlr, Dimetilformamid [13] [14] aldehit oluturmann baka bir yararl yöntemi.

Heck reaksiyonunda yaygn bir Dimetilformamid çözücüdür. [26]

Me2NC (O) H + (COCl) 2 → CO + CO2 + [Me2N = CHCl] Cl

minyum ara maddesi karboksilik asit ile reaksiyona girerek bir oksit çkarr ve Dimetilformamid katalizörünü yeniden oluturur. [27]

Asil klorür ve Dimethylformamide.png vermek için reaksiyon

Dimetilformamid çou plastie nüfuz eder ve onlar iirir. Bu özelliinden dolay Dimetilformamid, kat faz peptit sentezi için ve boya syrclarn bir bileeni olarak uygundur.

Dimetilformamid, özütleyici damtma yoluyla 1,3-bütadien gibi olefinlerin geri kazanlmas için bir çözücü olarak kullanlr.

Dimetilformamid boyalarn üretiminde de önemli bir hammadde olarak kullanlmaktadr. Reaksiyon srasnda tüketilir.

Uygun kullanmlar

Ucuz ve yaygn bir reaktif olarak Dimetilformamidin bir aratrma laboratuvarnda birçok kullanm vardr.

Dimetilformamid, karbon nanotüplerin ayrlmas ve askya alnmasnda etkilidir ve bu türlerin yakn kzlötesi spektroskopisinde kullanlmas NIST tarafndan önerilmektedir. [29]

Dimetilformamid, bilinmeyen bir bileiin kantitatif tespitine izin veren proton NMR spektroskopisinde bir standart olarak kullanlabilir.

Organometalik bileiklerin sentezinde bir karbon monoksit ligand kayna olarak kullanlr.

Dimetilformamid, elektrospinning’de kullanlan yaygn bir çözücüdür.

Dimetilformamid, Metal-Organik Çerçevelerin solvotermal sentezinde yaygn olarak kullanlmaktadr.

Mikrodalga stma altnda katalitik miktarda KOt-Bu varlnda dimetilformamid-d7, poliaromatik hidrokarbonlarn döterasyonu için bir reaktiftir.

Emniyet

DIMETHYLFORMAMIDE (DMETLFORMAMD)

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