2-oxoacetic acid hydrate

• ChemBase ID: 102881
• Molecular Formular: C2H4O4
• Molecular Mass: 92.05076
• Monoisotopic Mass: 92.01095861
• SMILES: O.OC(=O)C=O
• Canonical SMILES: O=CC(=O)O.O
• InChI: InChI=1S/C2H2O3.H2O/c3-1-2(4)5;/h1H,(H,4,5);1H2
• InChIKey: MOOYVEVEDVVKGD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-oxoacetic acid hydrate
• IUPAC Traditional name: glyoxalate, glyoxylate hydrate; glyoxylic acid hydrate
• Synonyms: Oxoacetic Acid; Formylformic Acid; Glyoxalic Acid; GLYOXYLIC ACID MONOHYDRATE FREE ACID; GLYOXYLIC ACID, 97%; Oxoethanoic acid; Glyoxylic acid monohydrate; 2-Oxoacetic Acid Monohydrate; Glyoxalic Acid Monohydrate; Formylformic Acid Monohydrate; NSC 27785 Monohydrate; Oxalaldehydic Acid Monohydrate; Oxoacetic Acid Monohydrate; Oxoethanoic Acid Monohydrate; α-Ketoacetic Acid Monohydrate; Glyoxylic Acid Monohydrate; 单水合乙醛酸; 氧代乙酸; 甲酰甲酸; 乙醛酸 一水合物

Database IDs

• CAS Number: 563-96-2
• EC Number: 206-058-5
• MDL Number: MFCD00149497
• Beilstein Number: 969535
• Merck Index: 144511
• PubChem SID: 24895036; 24873398; 162088776
• PubChem CID: 15620607

CALCULATED PROPERTIES

• Acid pKa: 2.6053126
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.9385595
• LogD (pH = 7.4): -3.6401994
• Log P: -0.13367504
• Molar Refractivity: 13.5 cm^3
• Polarizability: 5.255616 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble0.1 g/mL, clear
• Apperance: Off-White Solid
• Melting Point: ~57 °C; 48-52°C; 49-51°C; 49-52 °C(lit.); 50-52°C
• Boiling Point: 100 °C(lit.); 100°C; 100°C
• Flash Point: > 110°C; >110°C(230°F); 110 °C; 230 °F
• Density: 1.4 g/ml

Safety Information

• Storage Condition: 0°C, Desiccate; Refrigerator, Under Inert Atmosphere
• Storage Warning: Hygroscopic
• RTECS: MD4550000
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3261; UN3261
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 2; III
• Australian Hazchem: 2X
• Risk Statements: 34; 34-43; 41-43; R:34
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39; 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C4
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H317-H303; H317-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ~98%; ≥97.0% (T); 97%; 98%
• Grade: purum
• Linear Formula: HCOCO2H · H2O

DETAILS

MP Biomedicals - 02104891

Monohydrate
Free Acid
Crystalline
Purity: ~98%

MP Biomedicals - 05208201

MP Biomedicals Rare Chemical collection

Sigma Aldrich - G10601

Packaging
10, 25, 100 g in poly bottle
Application
Employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions.1 Undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl)acetic acid2 and a β-carboline,3 respectively.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G10601.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - G755000

Occurs in unripe fruit and in young green leaves; has also been found in very young sugar beets.

REFERENCES

• Lelieveld, J., et al.: Nature, 452, 737 (2008)
• da Silva, G., et al.: Environ. Sci. Technol., 44, 250 (2008)
• For reaction with tryptamine hydrochloride, followed by cyclization to give 1,2,3,4-tetrahydro-?-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.