tert- Butylamine is an organic substance of composition C 4 H 11 N, belonging to the class of amines . Can be considered an ammonia derivative containing a tert- butyl substituent. It is a colorless liquid with a "fish" smell, characteristic of other amines.
Tert-butylamine | |
|---|---|
 | |
 | |
Are common | |
| Systematic name | tert-butylamine |
| Chem. formula | C₄H₁₁N |
Physical properties | |
| condition | colorless liquid with a characteristic odor |
| Molar mass | 73.14 g / mol |
| Density | 0.6958 g / cm³ (25 ° C) |
Thermal properties | |
| T. melt. | −67.5 ° C |
| T. Kip. | 44.4 ° C |
| T. v. | –9 ° C |
Chemical properties | |
| pK a | +10.45 |
Optical properties | |
| Refractive index | 1.384 |
Classification | |
| CAS number | |
| Pubchem | |
| Chemspider | |
| EINECS number | 200-888-1 |
| RTECS | EO3330000 |
| CHEBI | 44639 |
| UN number | 3286 |
SMILES | |
CC (C) (C) N | |
Inchi | |
1S / C4H11N / c1-4 (2,3) 5 / h5H2.1-3H3 | |
Security | |
| LD 50 | 464 mg / kg, rat, orally |
| R-phrases | R11 , R20 / 22 , R35 |
| S-phrases | S16 , S26 , S36 / 37/39 , S45 |
| H-phrases | H225 , H302 , H314 , H331 |
| P-phrases | P210 , P261 , P280 , P305 + P351 + P338 , P310 |
| Signal word | Dangerously |
| GHS pictograms |    |
| NFPA 704 |  four 3 0 |
| Data are given for standard conditions (25 ℃, 100 kPa) , unless otherwise specified. | |
Content
Getting
Tert- Butylamine is very difficult or impossible to obtain by methods common in industry (from alcohols, carbonyl compounds, nitriles, etc.), therefore it is synthesized by the Ritter reaction, adding hydrogen cyanide to isobutylene in an acidic medium. The process is carried out at 30-60 ° C, and the resulting intermediate is hydrolyzed at 100 ° C. The use of the Ritter reaction is very limited, since it involves the use of toxic hydrogen cyanide that causes corrosion, as well as the formation of a significant amount of side salts (3.3 kg per 1 kg of tert-butylamine ) and the need for their utilization [1] .
Under laboratory conditions, tert-butylamine can be obtained by hydrogenolysis of 2,2-dimethylaziridine on Raney nickel [2] .
Chemical Properties
The chemical properties of tert - butylamine are determined by the presence of a lone electron pair on the nitrogen atom, as well as by the mobility of the hydrogen atoms of the amino group . In this regard, it exhibits chemical properties typical of aliphatic amines , forming salts with acids, giving amides of carboxylic acids and sulfonic acids, reacting with carbonyl compounds , alkylation reactions , oxidation , etc. [1]
Application
Tert- Butylamine is primarily used to synthesize vulcanization accelerators, for example, TBBS ( N - tert -butyl-2-benzothiazolylsulfenamide) and TBSI ( N - tert -butyl-2-benzothiazolylsulfenimide). It also finds application in the synthesis of herbicides ( terbacil , terbutilazin , terbumeton , terbutrin ) and the insecticide diafentiuron [1] .
Notes
- ↑ 1 2 3 Eller K., Henkes E., Rossbacher R., Höke H. Amines, Aliphatic (Eng.) // Ullmann's Encyclopedia of Industrial Chemistry. - 2000. - DOI : 10.1002 / 14356007.a02_001 .
- ↑ Campbell KN, Sommers AH, Campbell BK tert -Butylamine (Eng.) // Org. Synth .. - 1947. - Vol. 27 . - P. 12 . - DOI : 10.15227 / orgsyn.027.0012 .
Links
- Sigma-Aldrich. IR spectrum of tert - butylamine in a condensed state . The appeal date is January 2, 2015.
- Sigma-Aldrich. CR spectrum of tert - butylamine . The appeal date is January 2, 2015.
- Sigma-Aldrich. NMR spectrum of tert - butylamine . The appeal date is January 2, 2015.