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
Show more names
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
- Formal charge
- 0
- Complexity
- 86.8
Experimental & physicochemical properties
Pesticides
Pesticides -> Insect Repellents
Environmental transformation -> Pesticide transformation products (metabolite, successor)
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)
- form
- Crystalline Powder
- pka
- 1.6 · 1.60±0.20(Predicted)
- color
- White
- Water Solubility
- 108 mg/mL · Soluble in water 108 mg/mL.
- Merck
- 14 · 14,6917
- BRN
- 1743294 · 1743294
- InChI
- InChI=1S/C2H3NO3/c3-1(4)2(5)6/h(H2,3,4)(H,5,6)
- InChIKey
- SOWBFZRMHSNYGE-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C(N)=O
- CAS DataBase Reference
- 471 · 471-47-6(CAS DataBase Reference)
- FDA UNII
- 60 N5OPLG · QU60N5OPLG
- EPA Substance Registry System
- Oxamic acid (471-47-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 29241990 · 29241990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
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
Hazards Summary
See Oxamic acid.
A skin and strong eye irritant; [Alfa Aesar MSDS] See Oxamide. See Acetic acid.
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
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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