Oxamide Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

162.99°C (rough estimate)

Density 

1,667 g/cm³

refractive index 

1.4264 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

0.37g/l

form 

Fine Crystalline Powder

pka

13.28±0.50(Predicted)

color 

White

Water Solubility 

insoluble

Merck 

14,6918

BRN 

1743262

InChI

1S/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6)

InChIKey

YIKSCQDJHCMVMK-UHFFFAOYSA-N

SMILES

NC(=O)C(N)=O

CAS DataBase Reference

471-46-5(CAS DataBase Reference)

NIST Chemistry Reference

Oxalamide(471-46-5)

EPA Substance Registry System

Ethanediamide (471-46-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

2811

WGK Germany 

3

RTECS 

RO4900000

TSCA 

TSCA listed

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29241900

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2

Toxicity

LD50 orl-rat: 447 mg/kg GISAAA 47(7),78,82

MSDS

• Language:English Provider:Oxamide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Oxamide Usage And Synthesis

Chemical Properties

white fine crystalline powder

Chemical Properties

Oxamide, H2NCOCONH2, mol wt 80.07, is sparingly soluble in water and insoluble in various organic solvents. It melts at about 350 °C, with accompanying decomposition. Because of the low solubility in water, the compound is granulated and used as a slow-release nitrogen fertilizer.

Uses

Oxamide is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP rocket motors as a high performance burn rate suppressant.

Preparation

Oxamide can be prepared, for example, by pyrolyzing ammonium oxalate or by allowing hydrogen cyanide to react with hydrogen peroxide. It is also known to prepare oxamide by a reaction between dimethyl oxalate and ammonia, wherein methanol is produced in addition to oxamide. The preparation was carried out as a batch process in a liquid phase, with methanol acting as a solvent into which the dimethyl oxalate and ammonia are fed. The oxamide was separated from the solution by crystallization, and the remaining mother liquor was distilled to recover methanol and ammonia, which had been left over from the reaction.

Definition

ChEBI: A dicarboxylic acid diamide of oxalic acid.

Agricultural Uses

Oxamide (H₂ NCOCONH₂ ), a diamide of oxalic acid, is a white crystalline and non-hygroscopic fertilizer containing about 32% nitrogen, most of which is waterinsoluble at 25°C. Oxamide is made from cyanogen hydrolysis in an acid medium. It releases nitrogen slowly and hence is used as a slow-release fertilizer. It is decomposed by soil micro-organisms in the soil.

Safety Profile

Poison by ingestion and intraperitoneal routes. An eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also AMIDES.

Synthesis

Oxalide is a simple dicarboxylic acid diamide, primarily synthesized from the corresponding acid or ester precursor. The most common industrial synthesis method is the ammonolysis of dimethyl oxalate . This process typically involves reacting dimethyl oxalate with ammonia in a solvent (usually methanol) under controlled temperature and pressure. This reaction is a simple nucleophilic acyl substitution reaction, where ammonia replaces the methoxy group, producing oxalamide and methanol as byproducts. Another important industrial synthesis method is the hydrolysis of dicyandiamide or the ammonolysis of oxalic acid ($HOOCCOOH) or its salts, but the dimethyl oxalate method is generally preferred due to its high yield and purity. In the laboratory, oxalamide can also be prepared by reacting oxalyl chloride (ClCOCOCl) with ammonia; this method is faster but more expensive. Due to its low solubility, oxalamide is widely used as a slow-release nitrogen fertilizer.

Purification Methods

Crystallise oxamide from water, grind it and dry it in an oven at 150o. [Beilstein 2 IV 1860.]

Oxamide(471-46-5)Related Product Information

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• Folic acid
• Formamide
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• Acetamide
• Ethyl 2-(Chlorosulfonyl)acetate
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• Oxalic acid
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• N,N'-BIS(2-HYDROXYETHYL)OXAMIDE
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