Common NameFormamide
DescriptionFormamide, also known as methanamide or ameisensaeureamid, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms. Formamide exists in all living organisms, ranging from bacteria to humans. Formamide has been detected, but not quantified in several different foods, such as hyssops, rose hips, asian pears, brassicas, and green bell peppers. It has been used as a softener for paper and fiber. Inhalation of large amounts of formamide vapor may require medical attention. In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating:HCOOH + NH3 → HCOO−NH+4HCOO−NH+4 → HCONH2 + H2O. Formamide is also generated by aminolysis of ethyl formate: HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH. The current industrial process for the manufacture of formamide involves either the carbonylation of ammonia: CO + NH3 → HCONH2. An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol: CO + CH3OH → HCOOCH3HCO2CH3 + NH3 → HCONH2 + CH3OH. Formamide is used in the industrial production of hydrogen cyanide. Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption.
Structure
Molecular FormulaCH3NO
Average Mass45.04060
Monoisotopic Mass45.02146
IUPAC Nameformamide
Traditional NameFormamide
CAS Registry Number1975-12-07
SMILESNC=O
InChI IdentifierInChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)
InChI KeyZHNUHDYFZUAESO-UHFFFAOYSA-N
CHEBI IDCHEBI:16397
HMDB IDHMDB0001536
StateNot Available
Water Solubility5.03e+02 g/l
logP-1.53
logS1.05
pKa (Strongest Acidic)16.67
pKa (Strongest Basic)-1.03
Hydrogen Acceptor Count1
Hydrogen Donor Count1
Polar Surface Area43.09 Ų
Rotatable Bond Count0
Physiological Charge0
Formal Charge0
Refractivity9.98 m³·mol⁻¹
Polarizability3.83

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