Formamide

Title: Formamide
CAS Registry Number: 75-12-7
Additional Names: Methanamide; carbamaldehyde
Molecular Formula: CH3NO
Molecular Weight: 45.04
Percent Composition: C 26.67%, H 6.71%, N 31.10%, O 35.52%
Line Formula: HCONH2
Literature References: Prepd on a large scale from carbon monoxide and ammonia at high press. and temp: Meyer, Orthner, Ber. 54, 1705 (1921); 55, 857 (1922); Meyer, DE 390798 (1924); DE 392409 (1924); DE 414257 (1925 to BASF); Wietzel, Herbst, US 1843434 (1932 to I. G. Farben). Toxicity study: Pham-Huu-Chank et al., Toxicol. Appl. Pharmacol. 26, 596 (1973). Review: C. L. Eberling in Kirk-Othmer Encyclopedia of Chemical Technology vol. 11 (Wiley-Interscience, New York, 3rd ed., 1980) pp 258-263.
Properties: Slightly viscous, odorless, colorless liq. Industrial grades may have faint odor of ammonia. mp 2.55°. bp760 210.5° (partial decomp into CO and NH3 at atm pressure beginning at 180°); bp400 193.5°; bp200 175.5°; bp60 147.0°; bp20 122.5°; bp10 109.5°; bp1.0 70.5°. d415 1.13756; d420 1.13340; d430 1.12483. Dielectric constant e = 84. Viscosity h ´ 105 at 15° = 4320, at 30° = 2926. Surface tension g at 20° = 58.35. nD15 1.44911; nD20 1.44754; nD110 1.4170; nD130 1.4095. Flash pt, open cup: 310°F (154°C). pH of 0.5 molar aq soln 7.1. Misc with water, methanol, ethanol, acetone, acetic acid, dioxane, ethylene glycol, U.S.P. glycerol, phenol. Very slightly sol in ether, benzene. Dissolves casein, glucose, zein, tannins, starch, lignin, polyvinyl alcohol, cellulose acetate, nylon, the chlorides of copper, lead, zinc, tin, cobalt, iron, aluminum, nickel, the acetates of the alkali metals, some inorganic sulfates and nitrates. LD50 in mice, rats (g/kg): 4.6, 5.7 i.p. (Pham-Huu-Chanh).
Melting point: mp 2.55°
Boiling point: bp760 210.5° (partial decomp into CO and NH3 at atm pressure beginning at 180°); bp400 193.5°; bp200 175.5°; bp60 147.0°; bp20 122.5°; bp10 109.5°; bp1.0 70.5°
Flash point: Flash pt, open cup: 310°F (154°C)
Index of refraction: nD15 1.44911; nD20 1.44754; nD110 1.4170; nD130 1.4095
Density: d415 1.13756; d420 1.13340; d430 1.12483
Toxicity data: LD50 in mice, rats (g/kg): 4.6, 5.7 i.p. (Pham-Huu-Chanh)
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin, mucous membranes; drowsiness, fatigue; nausea, acidosis; skin eruptions. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 148.
Use: As ionizing solvent, manuf formic esters, hydrocyanic acid by catalytic dehydration, as softener for paper, animal glues, water-sol gums.
Formanilide Formestane Formic Acid Formicin Formocortal

Formamide
Structural formula of the formamide molecule Space-filling model of the formamide molecule
Identifiers
CAS number 75-12-7 YesY
PubChem 713
ChemSpider 693 YesY
KEGG C00488 YesY
ChEBI CHEBI:48431 YesY
ChEMBL CHEMBL266160 YesY
Jmol-3D images Image 1
Properties
Molecular formula CH3NO
Molar mass 45.04 g/mol
Appearance Colorless, oily liquid[1]
Density 1.133 g/cm3
Melting point 2 to 3 °C; 36 to 37 °F; 275 to 276 K
Boiling point 210 °C; 410 °F; 483 K
Solubility in water Miscible
Vapor pressure 0.08 mmHg at 20 °C
Acidity (pKa) 23.5 (in DMSO)[2]
Hazards
NFPA 704
NFPA 704.svg
1
2
0
Flash point 154 °C (closed cup)
Related compounds
Related compounds Carbamic acid
Dimethylformamide
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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

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.[3]

Formamide will begin to partially decompose into carbon monoxide and ammonia at 180 °C. When heated strongly, formamide decomposes to hydrogen cyanide (HCN) and water vapor.