// Workers AI · dad joke modeIs isobutylamine a good party guest? No, it's a-mine to stay home.
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| Names | |
|---|---|
| Preferred IUPAC name
2-Methylpropan-1-amine | |
| Other names
(2-Methylpropyl)amine | |
| Identifiers | |
3D model (JSmol) |
|
| Abbreviations | i-BuNH2 iBuNH2 iBuNH2 |
| 385626 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.042 |
| EC Number |
|
| 81862 | |
| KEGG | |
| MeSH | isobutylamine |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1214 |
CompTox Dashboard (EPA) |
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| Properties | |
| 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 |
| Miscible | |
| −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: | |
   | |
| Danger | |
| H225, H301, H314 | |
| 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 |
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Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]Isobutylamine can be obtained by reaction of isobutanol with ammonia in presence of a catalyst[3]:
![{\displaystyle {(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CHCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {OH} {}+{}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{3}}{}\mathrel {\longrightarrow } {}(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CHCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {H} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {O} }}](https://wikimedia.org/api/rest_v1/media/math/render/svg/daa488ad99fe335249ebef3004008624f385ceb5)
Isobutylamine can also be produced from the reaction of Isobutyl chloride with ammonia[4]:
![{\displaystyle {(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CHCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {Cl} {}+{}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{3}}{}\mathrel {\longrightarrow } {}(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CHCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {HCl} }}](https://wikimedia.org/api/rest_v1/media/math/render/svg/001edf72712f54838b3e5626848d35bf16809074)
A alternative method of producing Isobutylamine is the decarboxylation of Valine with the enzyme Valine decarboxylase[5] or the thermal decarboxylation:
![{\displaystyle {\mathrm {H} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {NCH} (\mathrm {CH} (\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{2}})\mathrm {COOH} {}\mathrel {\longrightarrow } {}(\mathrm {CH} {\vphantom {A}}_{\smash[{t}]{3}}){\vphantom {A}}_{\smash[{t}]{2}}\mathrm {CHCH} {\vphantom {A}}_{\smash[{t}]{2}}\mathrm {NH} {\vphantom {A}}_{\smash[{t}]{2}}{}+{}\mathrm {CO} {\vphantom {A}}_{\smash[{t}]{2}}}}](https://wikimedia.org/api/rest_v1/media/math/render/svg/867210aa90fe3ccaa8d1d87cd84d87a063aaf4d7)
Uses
[edit]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
[edit]- ↑ Isobutylamine chemicalbook.com
- ↑ Isobutylamine Chemblink.com
- ↑ US3347926A, Zech, John D., "Ammonolysis process for producing aliphatic amines", issued 1967-10-17
- ↑ US8349977B2, Koenig, Hannah Maria; Muelbach, Klaus & Kiefer, Matthias et al., "Process for preparing high-reactivity isobutene homo- or copolymers", issued 2013-01-08
- ↑ US7851188B2, Donaldson, Gail K.; Eliot, Andrew C. & Flint, Dennis et al., "Fermentive production of four carbon alcohols", issued 2010-12-14
- ↑ 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.