Carbamic acid

Carbamic acid

Names
IUPAC name Carbamic acid
Other names Aminomethanoic Acid
Identifiers
CAS Number	463-77-4 Y
ChEBI	CHEBI:28616 Y
ChEMBL	ChEMBL125278 Y
ChemSpider	271 Y
DrugBank	DB04261 Y
Jmol 3D model	Interactive image
KEGG	C01563 Y
MeSH	Carbamic+acid
PubChem	277
InChI InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) Y Key: KXDHJXZQYSOELW-UHFFFAOYSA-N Y InChI=1/CH3NO2/c2-1(3)4/h2H2,(H,3,4) Key: KXDHJXZQYSOELW-UHFFFAOYAC
SMILES O=C(O)N
Properties
Chemical formula	CH3NO2
Molar mass	61.040 g/mol
Vapor pressure	{{{value}}}
Related compounds
Related compounds	Formamide Dithiocarbamate Carbonic acid Urea Ethyl carbamate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Carbamic acid is the compound with the formula H₂NCO₂H. The attachment of the acid group to a nitrogen or amine (instead of carbon) distinguishes it from carboxylic acid and an amide. Many derivatives and analogues of carbamic acid are known. They are generally unstable, reverting to the parent amine and carbon dioxide. The deprotonated anion (or conjugate base) of this functional group is a carbamate. Carbamic acid is a planar molecule.

Occurrence

Carbamic acid is an intermediate in the production of urea, which involves the reaction of carbon dioxide and ammonia.

CO₂ + NH₃ → H₂N-CO₂H

H₂N-CO₂H + NH₃ → CO(NH₂)₂ + H₂O

"Carbamoyltransferases" are transferase enzymes classified under EC number 2.1.3.

Derivatives of carbamic acid

• 

  carbamic acid group

• 

  carbamate group

• 

  carbamoyl group

• 

  carbamoyl chloride group

Carbamic acids are intermediates in the decomposition of carbamate protecting groups; the hydrolysis of an ester bond produces carbamic acid the evolution of carbon dioxide drives the deprotection reaction forward, yielding the unprotected amine.

Carbamates usually refer to esters of carbamic acid. Methyl carbamate is the simplest ester of carbamic acid. Unlike carbamic acids, the esters are stable. They are prepared by reaction of carbamoyl chlorides with alcohols, the addition of alcohols to isocyanates, and the reaction of carbonate esters with ammonia.

Some esters have use as muscle relaxants which bind to the barbiturate site of the GABA_A receptor, while others are used as insecticides, for example aldicarb.

See also

• Carbamoyl phosphate
• M03BA Carbamic acid esters