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A16058 Glyoxylic acid monohydrate, 97%

CAS Number
563-96-2
Synonyms
Oxoacetic acid monohydrate

Stock No. Size Price ($) Quantity Availability
A16058-14 25g 35.70
A16058-22 100g 92.30
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Glyoxylic acid monohydrate, 97%

MDL
MFCD00149497
EINECS
206-058-5

Chemical Properties

Formula
OHCCO2H•H2O
Formula Weight
92.06 (74.04anhy)
Melting point
48-52°
Boiling Point
100°
Flash Point
>110°(230°F)
Storage & Sensitivity
Keep Cold. Hygroscopic. Store under Nitrogen.
Solubility
Soluble in water, dimethyl sulfoxide and alcohol. Insoluble in diethyl ether and hydrocarbons.

Applications

Glyoxylic acid is a reagent for sulfinylmaleate synthesis. It is one of the chemicals used in the Hopkins Cole reaction. It is involved to check the presence of tryptophan in proteins. It is condensed with urea and 1,2-diaminobenzene to form heterocycles. It also undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl) acetic acid and a beta-carboline respectively. It is employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions.

Notes

Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible withbases, oxidizing agents and reducing agents.

Literature References

For reaction with tryptamine hydrochloride, followed by cyclization to give 1,2,3,4-tetrahydro-ß-carboline, see: Org. Synth. Coll., 6, 965 (1988).

Reagent for transthioacetalization of dithioacetal groups from protected aldehydes and ketones in acetic acid catalyzed by mineral acid: Synthesis, 694 (1976); for alternative methods of dithioacetal cleavage, see 1,3-Dithiane, A10505.

Lundell, J.;  Olbert-Majkut, A. Isolated glyoxylic acid-water 1: 1 complexes in low temperature argon matrices. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2015, 136, 113-121.

Ghimbeu, C. M.; Vidal, L.; Delmotte, L.; Le Meins, J. M.; Vix-Guterl, C. Catalyst-free soft-template synthesis of ordered mesoporous carbon tailored using phloroglucinol/glyoxylic acid environmentally friendly precursors. Green Chem. 2014, 16 (6), 3079-3088.

Lundell, J.;  Olbert-Majkut, A. Isolated glyoxylic acid-water 1: 1 complexes in low temperature argon matrices. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2015, 136, 113-121.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H317-H500

Causes severe skin burns and eye damage. May cause an allergic skin reaction. May form combustible dust concentrations in air

Precautionary Statements: P260-P264b-P272-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P333+P313-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,4511
Beilstein
969535
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2918.30
TSCA
Yes
RTECS
MD4550000

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