O-PHTHALALDEHYDE
o-Phthalaldehyde is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
o-Phthalaldehyde is commonly used as a high-level disinfectant for medical instruments and in certain methods of winemaking.
o-Phthalaldehyde is a chemical reagent that forms fluorescent conjugation products with primary amines and is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
CAS Number: 643-79-8
EC Number: 211-402-2
Chemical Formula: C8H6O2
Molar Mass: 134.134 g·mol−1
Synonyms: o-Phthalaldehyde, 643-79-8, PHTHALALDEHYDE, o-Phthaldialdehyde, 1,2-Benzenedicarboxaldehyde, Benzene-1,2-dicarboxaldehyde, Phthaldialdehyde, Phthalic aldehyde, Phthalic dialdehyde, Phthalyldicarboxaldehyde, ortho-Phthalaldehyde, Phthalic dicarboxaldehyde, o-Phthaldehyde, benzene-1,2-dicarbaldehyde, Phthalaldialdehyde, o-Phthalicdicarboxaldehyde, 1,2-Diformylbenzene, 2-PHTHALALDEHYDE, 1,2-Phthalic dicarboxaldehyde, ortho Phthalaldehyde, o-Phthalic dicarboxaldehyde, OPA, 1,2-BENZENEDICARBALDEHYDE, OPTA, NSC 13394, UNII-4P8QP9768A, CHEBI:70851, 2-PHTHALDIALDEHYDE, MFCD00003335, 4P8QP9768A, 1,2-Benzenedicarboxaldehyde, homopolymer, NCGC00166206-01, DSSTox_CID_12514, DSSTox_RID_78962, DSSTox_GSID_32514, 25750-62-3, Phtalaldehydes, Phtalaldehydes [French], CAS-643-79-8, EINECS 211-402-2, BRN 0878317, phthalaldehyd, o-Phthalaldehyd, o-phthal aldehyde, orthophthalaldehyde, Phtharal (JAN), Disopa (TN), 2-PHTHALDEHYDE, Phthaldialdehyde Reagent, o-Phthalaldehyde-[d6], ORTHO-PHTHALADEHYDE, Epitope ID:176774, O-PHTHALIC DIALDEHYDE, 2-Phthaldehyde, High purity, SCHEMBL33393, Benzene-1,2-dicarboxakdehyde, 4-07-00-02138, 1,2-Phthalic dicarboxyaldehyde, CHEMBL160145, Ortho-Phthalic Aldehyde (OPA), BENZENE-1,2-DIALDEHYDE, DTXSID6032514, HSDB 8456, TIMTEC-BB SBB008450, BCP29465, NSC13394, STR01056, ZINC1729594, Tox21_112347, Tox21_300404, 1,2-Benzenedialdehyde;Phthalaldehyde, BBL027435, NSC-13394, STK802214, AKOS000119186, Tox21_112347_1, AS03002, CS-W013385, LS11855, MCULE-5731001647, NCGC00166206-02, NCGC00166206-04, NCGC00254339-01, AC-10388, FLUORALDEHYDE(TM) O-PHTHALALDEHYDE, Phthaldialdehyde Reagent, Solution Complete, AM20050101, FT-0632732, P0280, Phthaldialdehyde Reagent, Solution Incomplete, 43P798, D03470, P-6600, SR-01000944839, Q5933776, SR-01000944839-, Phthaldialdehyde, for fluorescence, >=99.0% (HPLC), 6-Oxomethylene-5-[(E)-hydroxymethylene]cyclohexa-1,3-diene, 6-Oxomethylene-5-[(Z)-hydroxymethylene]cyclohexa-1,3-diene, Phthaldialdehyde, >=97% (HPLC), powder (may contain lumps), Phthaldialdehyde, suitable for HPLC fluorimetric detection of amino acids, >=99% (HPLC), powder, qw23r54
o-Phthalaldehyde is the chemical compound with the formula C6H4(CHO)2.
o-Phthalaldehyde is one of three isomers of benzene dicarbaldehyde, related to phthalic acid.
o-Phthalaldehyde is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
o-Phthalaldehyde dissolves in water solution at pH < 11.5.
o-Phthalaldehydes solutions degrade upon UV illumination and exposure to air.
o-Phthalaldehyde, Reagent is a reagent in the analysis of amino acids and involved in the synthesis of heterocyclic compounds.
A reagent that forms fluorescent conjugation products with primary amines.
o-Phthalaldehyde is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
Phthalaldehyde is the chemical compound with the formula C6H4(CHO)2.
o-Phthalaldehyde is one of three isomers of benzene dicarbaldehyde.
o-Phthalaldehyde is commonly used as a high-level disinfectant for medical instruments, as a polymerizer as well as in certain methods of wine making.
o-Phthalaldehyde is the chemical compound with the formula C6H4(CHO)2.
Often abbreviated o-Phthalaldehyde, the molecule is a dialdehyde, consisting of two formyl (CHO) groups attached to adjacent carbon centres on a benzene ring.
This pale yellow solid is a building block in the synthesis of heterocyclic compounds and a reagent in the analysis of amino acids.
o-Phthalaldehyde is a chemical reagent that forms fluorescent conjugation products with primary amines.
o-Phthalaldehyde is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
o-Phthalaldehyde is approved by FDA for use in test systems to detect blood urea nitrogen (BUN) for the diagnosis and treatment of certain renal and metabolic diseases.
o-Phthalaldehyde is also a known desinfectant and has been approved for high-level sterilization of heat-sensitive medical instruments and is increasingly being used as a replacement in the healthcare industry for glutaraldehyde.
o-Phthalaldehyde has also been approved for use as an indoor antimicrobial pesticide; an intermediate for the synthesis of pharmaceuticals, medicines, and other organic compounds.
o-Phthalaldehyde is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
o-Phthalaldehyde is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
o-Phthalaldehyde is a dialdehyde in which two formyl groups are attached to adjacent carbon centres on a benzene ring.
o-Phthalaldehyde has a role as an epitope.
o-Phthalaldehyde is a dialdehyde and a member of benzaldehydes.
Fluoraldehyde Reagent Solution contains o-Phthalaldehyde, which reacts with primary amines of amino acids, peptide and proteins to enable fluorescent detection and quantitation.
The reagent is that can be used as a protein or peptide assay reagent or as a pre- or post-column detection reagent for amino acid analysis (HPLC).
Reaction of o-Phthalaldehyde with proteins and peptides yields linear results over a wide range of concentrations.
The Fluoraldehyde Reagent Solution is supplied ready to use and enables fast quantitation of proteins or peptides in solution.
Fast and catalyst-free cross-linking strategy is of great significance for construction of covalently cross-linked hydrogels.
Here, we report the condensation reaction between o-phthalaldehyde and N-nucleophiles (primary amine, hydrazide and aminooxy) for hydrogel formation for the first time.
When four-arm poly(ethylene glycol) (4aPEG) capped with o-Phthalaldehyde was mixed with various N-nucleophile-terminated 4aPEG as building blocks, hydrogels were formed with superfast gelation rate, higher mechanical strength and markedly lower critical gelation concentrations, compared to benzaldehyde-based counterparts.
Small molecule model reactions indicate the key to these cross-links is the fast formation of heterocycle phthalimidine product or isoindole (bis)hemiaminal intermediates, depending on the N-nucleophiles.
The second-order rate constant for the formation of phthalimidine linkage (4.3 M−1 s−1) is over 3000 times and 200 times higher than those for acylhydrazone and oxime formation from benzaldehyde, respectively, and comparable to many cycloaddition click reactions.
Based on the versatile o-Phthalaldehyde chemistry, various hydrogels can be readily prepared from naturally derived polysaccharides, proteins or synthetic polymers without complicated chemical modification.
Moreover, biofunctionalit is facilely imparted to the hydrogels by introducing amine-bearing peptides via the reaction between o-Phthalaldehyde and amino group.
o-Phthalaldehyde is used in precolumn derivatization of amino acids for HPLC separation.
o-Phthalaldehyde is also used for flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde is reagent that forms fluorescent conjugation products with primary amines.
o-Phthalaldehyde is used for the detection of many biogenic amines, peptides, and proteins in nanogram quantities in body fluids.
o-Phthalaldehyde can be polymerized.
In the polymer, one of the oxygen atoms forms a bridge to the other non-ring carbon of the same o-Phthalaldehyde unit, while the other bridges to a non-ring carbon of another phthalaldehyde unit.
o-Phthalaldehyde is used in making a photoresist.
Uses of o-Phthalaldehyde:
o-Phthalaldehyde can be widely used for precolumn derivatization of amino acids in HPLC separation or Capillary electrophoresis.
o-Phthalaldehyde used for flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde can be used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde is precolumn derivatization reagent for primary amines and amino acids.
The fluorescent derivative can be detected by reverse-phase HPLC.
The reaction requires o-Phthalaldehyde, primary amine and a sulfhydryl.
In the presence of excess sulfhydryl, amines can be quantitated.
o-Phthalaldehyde can be used as disinfectant.
o-Phthalaldehyde is reagent in fluorometric determination of primary amines and thiols.
o-Phthalaldehyde is used as a disinfectant and in the fluorometric determination of primary amines and thiols;Used to sterilize medical and dental equipment, as an enzyme inhibitor, indicator, chemical intermediate, diagnostic agent, tanning agent for leather, in water treatment, pulp and paper manufacturing, oil field water flooding, hair colorings, wood treatment, and antifouling paints
o-Phthalaldehyde used in winemaking.
The Nitrogen by O-Phthaldialdehyde Assay (NOPA) is one of the methods used in winemaking to measure yeast assimilable nitrogen (or YAN) needed by wine yeast in order to successfully complete fermentation.
o-Phthalaldehyde is used in the following products: biocides (e.g. disinfectants, pest control products).
o-Phthalaldehyde is used in the following areas: health services.
Other release to the environment of o-Phthalaldehyde is likely to occur from: indoor use as processing aid and indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters).
Applications of o-Phthalaldehyde:
o-Phthalaldehyde is a compound used in precolumn derivatization of amino acids for HPLC separation.
Analytical reagents in the chemical field: As an amine alkaloid reagent, o-Phthalaldehyde is used for the determination of primary amines and peptide bond decomposition products by fluorescence method.
Organic synthesis: also a pharmaceutical intermediate.
o-Phthalaldehyde is fluorescent reagent for separating amino acid derivatives by HPLC before column chromatography, and measuring thiol groups of proteins by flow cytometry.
o-Phthalaldehyde is used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups.
o-Phthalaldehyde is used for fluorometric determination of histamine, histidine and other amino acids.
o-Phthalaldehyde is also used for cholesterol assay in the picomole range.
o-Phthalaldehyde is a compound that reacts with primary amines to produce a product that emits a highly fluorescent blue colour.
o-Phthalaldehyde is used for the quick visualization of histamine, characterized by the appearance of a yellow stain.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
Typical Procedure:
5-10 µL aliquots of amino acid standards or unknown samples are mixed with 5 µL of a solution prepared by dissolving of o-phthalaldehyde (50 mg) in absolute MeOH (1.25 mL) followed by the addition of 2-mercaptoethanol (50 µL) and 0.4 M sodium borate (pH 9.5) (11.2 mL).
After 1 min, 0.1 M sodium acetate (pH 7.0) (20-100 µL) are added, the solution mixed and a 20-µL sample is subjected to analysis.
O-Phthalaldehyde, in the presence of 2-mercaptoethanol, reacts with primary amines to form highly fluorescent products.
Picomole quantities of amino acids, peptides, and proteins can be detected easily.
o-Phthalaldehyde is five to ten times more sensitive than fluorescamine and is soluble and stable in aqueous buffers.
o-Phthalaldehyde has been used:
in the preparation of reagent for determining the degree of hydrolysis of milk proteins
in the measurement of free amino acids of milk samples by O-phthaldialdehyde/N-acetyl-L-cysteine (OPA/NAC) assay
in the derivatization of putrescine samples
For precolumn derivatization of amino acids for HPLC separation.
For flow cytometric measurements of protein thiol groups.
Biochemistry of o-Phthalaldehyde:
o-Phthalaldehyde is used in a very sensitive fluorescent reagent for assaying amines or sulfhydryls in solution, notably contained in proteins, peptides, and amino acids, by capillary electrophoresis and chromatography.
o-Phthalaldehyde reacts specifically with primary amines above their isoelectric point Pi in presence of thiols.
o-Phthalaldehyde reacts also with thiols in presence of an amine such as n-propylamine or 2-aminoethanol.
The method is spectrometric (fluorescent emission at 436-475 nm (max 455 nm) with excitation at 330-390 nm (max. 340 nm)).
Preparation of o-Phthalaldehyde:
o-Phthalaldehyde is a high-level chemical disinfectant that is commonly used for disinfection of dental and medical instruments as an alternative to glutaraldehyde, which is a known skin and respiratory sensitizer.
A variety of processes for manufacturing o-phthalaldehyde have been reported in the literature.
o-Phthalaldehyde is produced by heating pure benzaldehyde and chloroform with potassium hydroxide solution.
The resulting solution is further acidified with hydrochloric acid and cooled to yield a colorless powder of o-phthalaldehyde.
o-Phthalaldehyde is also produced by ozonization of naphthalene in alcohol followed by catalytic hydrogenation.
Catalytic oxidation of various chemicals is also used in manufacturing o-phthalaldehyde.
o-Phthalaldehyde can be manufactured by oxidation of phthalan by nitrogen monoxide in acetonitrile with N-hydroxyphthalimide as the catalyst to yield 80% to 90%.
Synthesis and Reactions of o-Phthalaldehyde:
o-Phthalaldehyde was first described in 1887 when it was prepared from α,α,α’,α’-tetrachloro-ortho-xylene.
A more modern synthesis is similar: the hydrolysis of the related tetrabromo-o-xylene using potassium oxalate, followed by purification by steam distillation.
The reactivity of o-Phthalaldehyde is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4(CHO)(CH(OH)2) and C6H4(CH(OH))2O, respectively.
Phthalaldehydes reactions with nucleophiles often involves the reaction of both carbonyl groups.
o-Phthalaldehyde is mainly used as a high-level disinfectant (a low-temperature chemical method) for heat-sensitive medical and dental equipment such as endoscopes and thermometers; in recent years, o-Phthalaldehyde has gained popularity as a safe and better alternative to glutaraldehyde.
There are some researches show, pH7.5 contains the sterilizing agent of o-phthalaldehyde 0.5%, and its sterilizing power, sterilization speed, stability and toxicity all are better than glutaraldehyde, can kill mycobacterium in the 5min, the bacterium number reduces by 5 logarithmic value, and o-phthalaldehyde is very stable, tasteless in pH3～9 scopes, non-stimulated to human nose, eye mucosa, and need not activate before using, various materials are had good consistency, have tangible microbiocidal activity.
The reactivity of o-Phthalaldehyde is complicated by the fact that in water it forms both a mono- and dihydrate, C6H4(CHO)(CH(OH)2) and C6H4(CH(OH))2O, respectively.
o-Phthalaldehyde’s reactions with nucleophiles often involves the reaction of both carbonyl groups.
Disinfection of o-Phthalaldehyde:
o-Phthalaldehyde is commonly used as a high-level disinfectant for medical instruments, commonly sold under the brand names of Cidex o-Phthalaldehyde or TD-8.
Disinfection with o-Phthalaldehyde is indicated for semi-critical instruments that come into contact with mucous membranes or broken skin, such as specula, laryngeal mirrors, and internal ultrasound probes.
Safety of o-Phthalaldehyde:
Flash Point: 132°C
DOT/IATA/IMDG: UN2923 – HC 8(6.1) – PG II
Risk Statements: R25,R34,R41,R43,R50
Safety Statements: S13,S22,S24/25,S26,S27,S36/37/39,S45,S61
Hazard Statements: H301-H314-H317-H400
Personal Protective Equipment: Faceshields, full-face respirator, Gloves, Goggles, respirator filter
Purity: ≥98%
RTECS Number: TH6950000
Safety Symbol: GHS05, GHS06, GHS09
Potential Exposure of o-Phthalaldehyde:
The primary routes of human exposure to o-phthalaldehyde are by inhalation and through the skin, which may occur through accidental or occupational exposures.
Along with o-Phthalaldehydes increasing popularity as a chemical sterilizer, o-phthalaldehyde has many applications in analytical methods and in diagnostic kits.
o-Phthalaldehyde is also used as an intermediate in the synthesis of pharmaceuticals and as a reagent in the tanning industry, hair colorings, wood treatment, and antifouling paints.
o-Phthalaldehyde was approved for use as an indoor antimicrobial pesticide in 1997; however, o-Phthalaldehyde is no longer registered with the United States Environmental Protection Agency (USEPA) for this use.
Identifiers of o-Phthalaldehyde:
CAS Number: 643-79-8
ChEBI: CHEBI:70851 check
ChemSpider: 4642
ECHA InfoCard: 100.010.367
EC Number: 211-402-2
RTECS number: TH6950000
UNII: 4P8QP9768A
UN number 2923
CompTox Dashboard (EPA): DTXSID6032514
InChI: InChI=1S/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H
SMILES: O=Cc1ccccc1C=O
Product Number: P0280
Purity / Analysis Method: >99.0%(GC)
Molecular Formula / Molecular Weight: C8H6O2 = 134.13
Physical State (20 deg.C): Solid
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Air Sensitive
CAS RN: 643-79-8
Reaxys Registry Number: 878317
PubChem Substance ID: 87574516
SDBS (AIST Spectral DB): 1434
Merck Index (14): 7368
MDL Number: MFCD00003335
Article No.: 05270
Grade: AR
CAS No.: 643-79-8
Molecular Formula: C8H6O2
Molecular Weight: 134.14
H.S. Code: 2912.2990
Shelf Life: 24 Months
CAS #: 643-79-8
EC Number: 211-402-2
Format: Crystals
Molecular Formula: C8H6O2
Molecular Weight: 134.134 g/mol
Appearance: Light yellow to Yellow to Green powder to crystal
Purity(GC): min. 99.0 %
Melting point: 55.0 to 58.0 °C
Properties of o-Phthalaldehyde:
Formulation: 0.8 mg/mL o-phthalaldehyde in proprietary buffer, pH 10
Form: Clear, colorless to slightly yellow liquid
Reactive toward: Primary amines (—NH2)
Detection: Fluorescence (excitation/emission = 340 nm/455 nm)
Application: Pre- or post-column derivatization for detection by HPLC
Melting Point: 56 °C
Boiling Point: 84 °C/0.8 mmHg
Solubility (soluble in): Methanol
Chemical formula: C8H6O2
Molar mass: 134.134 g·mol−1
Appearance: Yellow solid
Density: 1.19 g/mL
Melting point: 55.5 to 56 °C (131.9 to 132.8 °F; 328.6 to 329.1 K)
Boiling point: 266.1 °C (511.0 °F; 539.2 K)
Solubility in water: Low
pH: 7
Melting Point: 54°C
Packaging: Glass Jar
Quantity: 5g
SMILES: O=CC1=CC=CC=C1C=O
Molecular Weight (g/mol): 134.13
ChEBI: CHEBI:70851
Physical Form: Solid
Molecular Weight: 134.13
XLogP3: 1.2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 134.036779430
Monoisotopic Mass: 134.036779430
Topological Polar Surface Area: 34.1 Ų
Heavy Atom Count: 10
Complexity: 115
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of o-Phthalaldehyde:
Label or Dye: OPA (o-phthaldialdehyde)
Quantity: 945 mL
Format: Liquid
Product Type: o-Phthaldialdehyde Reagent Solution
Chemical Reactivity: Amine
Product Line: Fluoraldehyde
Alternate Names: 2-Carboxybenzaldehyde; Phthaldialdehyde; o-Phthalic dicarboxaldehyde; Benzene-1,2-dicarboxaldehyde; OPA
Application Notes: o-Phthalaldehyde is used for precolumn derivatization of amino acids for HPLC separation and for flow cytometric measurements of protein thiol groups. Used for fluorometric determination of histamine, histidine and other amino acids. Also used for cholesterol assay in the picomole range.
Base Catalog Number: 102648
Beilstein Registry Number: 878317
Isomeric phthalaldehydes:
isophthalaldehyde (benzene-1,3-dicarbaldehyde)
terephthalaldehyde (benzene-1,4-dicarbaldehyde)
Names of o-Phthalaldehyde:
IUPAC name:
Phthalaldehyde
Preferred IUPAC name:
Benzene-1,2-dicarbaldehyde
Other name:
Benzene-1,2-dicarboxaldehyde
o-Phthalaldehyde
o-Phthalic dicarboxaldehyde
Phthaldialdehyde
MeSH of o-Phthalaldehyde:
Aldehyde, ortho-Phthalic
o Phthalaldehyde
o Phthaldialdehyd
o-Phthalaldehyde
o-Phthaldialdehyde
ortho Phthalaldehyde
ortho Phthalic Aldehyde
ortho-Phthalaldehyde
ortho-Phthalic Aldehyde
Orthophthaldialdehyde