Cyanamide

Title: Cyanamide
CAS Registry Number: 420-04-2
Additional Names: Carbodiimide; hydrogen cyanamide; carbimide; cyanogenamide; amidocyanogen
Molecular Formula: CH2N2
Molecular Weight: 42.04
Percent Composition: C 28.57%, H 4.80%, N 66.64%
Line Formula: H2NCºN
Literature References: Prepd commercially by continuous carbonation of calcium cyanamide in water. Ref. "Cyanamide," Process Chemicals Dept., Am. Cyanamid (New York, 1959) p 19. Acute toxicity data: J. Doull et al., Survey of Compounds for Radiation Protection (AD277689, USAF Radiation Lab., 1962) 124 p.
Properties: Deliquescent, orthorhombic, elongated, six-sided tablets from dimethyl phthalate. d420 1.282. mp 45-46°. bp0.5 83°. Formn of dicyandiamide begins at 122°. Dipole moment in benzene at 20°: 3.8. Cryoscopic constant (water) 26.8-28.4. Sp ht 0.547 cal/g/°C between 0° and 39°. Heat of formation 14.05 kcal/mole (25°); heat of combustion -176.4 kcal/mole (25°); heat of fusion 2.1 kcal/mole. Heat of vaporization 16.4 kcal/mole. Soly (g/100 g soln) in water at 15°: 77.5, at 43°: 100; in butanol at 20°: 28.8, in methyl ethyl ketone: 50.5, in ethyl acetate: 42.4. Sol in alcohols, phenols, amines, ethers, ketones. Very sparingly sol in benzene, halogenated hydrocarbons. Practically insol in cyclohexane. Solid cyanamide should be stored in a cool, dry place. Polymerizes at 122°. Optimum pH for storage of solns is ~4. Attacks various metals. Solns can be stored in glass provided they are stabilized with phosphoric, acetic, sulfuric, or boric acid. LD50 i.p. in male mice: 200-300 mg/kg (Doull).
Melting point: mp 45-46°
Boiling point: bp0.5 83°
Density: d420 1.282
Toxicity data: LD50 i.p. in male mice: 200-300 mg/kg (Doull)
NOTE: Term "cyanamide" is also used to designate calcium cyanamide.
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; eye, skin burns; miosis, salivation, lacrimation, twitching; Antabuse-like effects. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 80.
Cyanazine Cyanic Acid Cyanidin Chloride Cyanoacetamide Cyanoacetic Acid

Cyanamide
Cyanamide.svg
Cyanamide-3D-balls.png
Identifiers
CAS number 420-04-2 YesY
PubChem 9864
ChemSpider 9480 YesY
UNII 21CP7826LC YesY
EC number 206-992-3
UN number 2811
DrugBank DB02679
KEGG D00123 YesY
ChEBI CHEBI:16698 YesY
ChEMBL CHEMBL56279 YesY
RTECS number GS5950000
Jmol-3D images Image 1
Properties
Molecular formula CH2N2
Molar mass 42.040 g/mol
Appearance Crystalline solid
Density 1.28 g/cm3
Melting point 44 °C
Boiling point 260 °C (decomposes)
83 °C at 6.7 Pa
140 °C at 2.5 kPa
Solubility in water 85 g/100 ml (25 °C)
Solubility in organic solvents soluble
Hazards
MSDS ICSC 0424
EU Index 615-013-00-2
EU classification Toxic (T)
R-phrases R20, R25, R27, R36/38, R43
S-phrases (S1/2), S3, S22, S36/37, S45
NFPA 704
NFPA 704.svg
1
4
3
Flash point 141 °C; 286 °F; 414 K
Related compounds
Related compounds Calcium cyanamide
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol deterrent drug in Canada, Europe and Japan. The molecule features a nitrile group attached to an amino group. Although it is similar in structure to hydrogen cyanide, it is not as toxic. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).