Oxamic Acid

HCID 974CAS 471-47-6

Basic information

Standard SMILES
NC(=O)C(=O)O
InChIKey
SOWBFZRMHSNYGE-UHFFFAOYSA-N
Molecular formula
C2H3NO3
Average molar mass
89.05 g/mol
Monoisotopic mass
89.01129296

Overview

Oxamic acid is a dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia. It has a role as an Escherichia coli metabolite. It is a conjugate acid of an oxamate.

Names & identifiers

Preferred name
Oxamic Acid
IUPAC
oxamic acid
English name
Oxamic acid
Molecular formula
C2H3NO3
Molecular weight
89.05

Names & synonyms

OXAMIC ACID471-47-6oxamateAcetic acid, aminooxo-Oxalic acid monoamideAminooxoacetic acidOxalamic acidcarbamoylformic acidOxamidic acidGlycine, 2-oxo-Formic acid, (aminocarbonyl)-QU60N5OPLG
Show more names
2-aMino-2-oxoacetic acidOxamic acid Oxalic acid monoamideOxamicAcid>Oxamicacid,98%Oxamic acid 98%
Oxalic monoamideDTXSID6060052CHEBI:18058NSC-47001NSC-49416NSC-53102Acid, OxalamicAcid, Oxamidic

Database identifiers

CAS
471-47-6、66257-53-2
PubChem CID
974
DTXSID
DTXSID6060052
ChEMBL
CHEMBL15976
ChEBI
CHEBI:18058
UNII
QU60N5OPLG
EC Number
207-443-0
Nikkaji
J5.942K

Properties

Computed structural properties

XLogP
-0.9
Topological polar surface area
80.4 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amino Carboxylic Acids
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesBoiling point
Pesticides · 2 items

Pesticides -> Insect Repellents

Environmental transformation -> Pesticide transformation products (metabolite, successor)

Vapor Pressure0.00000046 [mmHg]
Physical DescriptionSolid; [Merck Index] White powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
207 · 207-210 °C (dec.) (lit.)
Boiling point
165.08 °C · 165.08°C (rough estimate)
Density
1.6193 · 1.6193 (rough estimate)
refractive index
1.4264 · 1.4264 (estimate)
storage temp.
2 · 2-8°C(protect from light)
solubility
DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationAcetic acid, aminooxo-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary · 2 items

See Oxamic acid.

A skin and strong eye irritant; [Alfa Aesar MSDS] See Oxamide. See Acetic acid.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29241990
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Uses & manufacturing

UsesInsect attractant, repellent and chemosterilant; [ChemIDplus]
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing InformationAcetic acid, 2-amino-2-oxo-: ACTIVE
Applications · 2 items

DescriptionOxamic acids also known to as oxalic acid monoamides have emerged as potent precursors for the generation of the carbamoyl radical. Oxamic acids can easily undergo decarboxylation through a single electron oxidation resulting in the generation of the reactive carbamoyl radical, which can then engage in diverse radical reactions or undergo a second single electron oxidation as originally unveiled by Minisci. Oxamic acids are thus versatile intermediates for the synthesis of nitrogen-containing organic molecules[1]. The oxidative decarboxylation of oxamic acids can be mediated through thermal, photochemical, electrochemical or photoelectrochemical means, generating carbamoyl radicals, which may further add to unsaturated systems to provide a broad range of important amides. Oxidative decarboxylation of oxamic acids also offers a straightforward entry for the preparation of urethanes, ureas, and thioureas.

UsesOxamic acid is an ozone oxidation product and is used in the synthesis of hydroxybenzimidazoles preparation as potential anti tumor agents targeting human lactate dehydrogenase A.This compound is suitable for lactate dehydrogenase (LDH) related research.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]

Additional notes

DefinitionChEBI: Oxamic acid is a dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia. It has a role as an Escherichia coli metabolite. It is a conjugate acid of an oxamate.

Related reactions

24 records

Linked notes

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