Isobutylamine

Isobutylamine

Skeletal formula of isobutylamine
Names
Preferred IUPAC name 2-Methylpropan-1-amine
Other names (2-Methylpropyl)amine
Identifiers
CAS Number	78-81-9  Y
3D model (JSmol)	Interactive image
Beilstein Reference	385626
ChEBI	CHEBI:15997  Y
ChemSpider	6310  Y
ECHA InfoCard	100.001.042
EC Number	201-145-4
Gmelin Reference	81862
KEGG	C02787  Y
MeSH	isobutylamine
PubChem CID	6558
RTECS number	NP9900000
UNII	1H60H4LOHZ  Y
UN number	1214
CompTox Dashboard (EPA)	DTXSID9025459
InChI InChI=1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3 Y Key: KDSNLYIMUZNERS-UHFFFAOYSA-N Y
SMILES CC(C)CN
Properties
Chemical formula	C4H11N
Molar mass	73.139 g·mol−1
Appearance	Colorless liquid
Odor	Fishy, ammoniacal
Density	736 mg mL−1
Melting point	−86.6 °C; −124.0 °F; 186.5 K
Boiling point	67 to 69 °C; 152 to 156 °F; 340 to 342 K
Solubility in water	Miscible
Magnetic susceptibility (χ)	−59.8·10−6 cm3/mol
Refractive index (nD)	1.397
Viscosity	500 μPa s (at 20 °C)
Thermochemistry
Heat capacity (C)	194 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−133.0 – −132.0 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−3.0139 – −3.0131 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H314
Precautionary statements	P210, P280, P301+P310, P305+P351+P338, P310
Flash point	−9 °C (16 °F; 264 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	224 mg kg−1(oral, rat)
Related compounds
Related alkanamines	Ethylamine Ethylenediamine Propylamine Isopropylamine 1,2-Diaminopropane 1,3-Diaminopropane tert-Butylamine n-Butylamine sec-Butylamine Putrescine
Related compounds	2-Methyl-2-nitrosopropane N-Methylisobutylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Isobutylamine is an organic chemical compound (specifically, an amine) with the formula (CH₃)₂CHCH₂NH₂, and occurs as a colorless liquid. ^{[1] [2]} Isobutylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and tert-butylamine. It is the decarboxylated form of the amino acid valine, and the product of the metabolism thereof by the enzyme valine decarboxylase.

Production

Isobutylamine can be obtained by reaction of isobutanol with ammonia in presence of a catalyst ^[3] :

• (CH₃)₂CHCH₂OH + NH₃ → (CH₃)₂CHCH₂NH₂ + H₂O

Isobutylamine can also be produced from the reaction of Isobutyl chloride with ammonia ^[4] :

• (CH₃)₂CHCH₂Cl + NH₃ → (CH₃)₂CHCH₂NH₂ + HCl

A alternative method of producing Isobutylamine is the decarboxylation of Valine with the enzyme Valine decarboxylase ^[5] or the thermal decarboxylation:

• H₂NCH(CH(CH₃)₂)COOH → (CH₃)₂CHCH₂NH₂ + CO₂

Uses

Isobutylamine is an odorant binding to TAAR3 in mice and can trigger sexual behaviour in male mice dependent on the cluster of TAAR2 through TAAR9. ^[6]

References

1. Isobutylamine chemicalbook.com
2. Isobutylamine Chemblink.com
3. US3347926A,Zech, John D.,"Ammonolysis process for producing aliphatic amines",issued 1967-10-17 
4. US8349977B2,Koenig, Hannah Maria; Muelbach, Klaus& Kiefer, Matthiaset al.,"Process for preparing high-reactivity isobutene homo- or copolymers",issued 2013-01-08 
5. US7851188B2,Donaldson, Gail K.; Eliot, Andrew C.& Flint, Denniset al.,"Fermentive production of four carbon alcohols",issued 2010-12-14 
6. Harmeier A, Meyer CA, Staempfli A, Casagrande F, Petrinovic MM, Zhang YP, Künnecke B, Iglesias A, Höner OP, Hoener MC (2018). "How Female Mice Attract Males: A Urinary Volatile Amine Activates a Trace Amine-Associated Receptor That Induces Male Sexual Interest". Frontiers in Pharmacology. 9: 924. doi: 10.3389/fphar.2018.00924 . PMC   6104183 . PMID   30158871.