Carbamoyl

Carbamic acid

Names

IUPAC name

Carbamic acid

Other names

Aminomethanoic Acid

Identifiers

CAS Number

463-77-4^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:28616^Y

ChemSpider

271^Y

DrugBank

DB04261^Y

KEGG

C01563^Y

MeSH

Carbamic+acid

PubChem CID

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

Related compounds

Formamide
Dithiocarbamate
Carbonic acid
Urea
Ethyl carbamate
Glycine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Carbamic acid is the compound with the formula NH₂COOH. 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.

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

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

carbamic acid group

carbamate group

carbamoyl (Cbm) 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.

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