Tert-Butylamine

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tert-Butylamine
Skeletal formula of tert-butylamine Tert-Butylamin Strukturformel.svg
Skeletal formula of tert-butylamine
Tert-Butylamine molecule ball.png
Names
Preferred IUPAC name
2-Methylpropan-2-amine
Other names
  • 2-Aminoisobutane
  • 2-Amino-2-methylpropane
  • Dimethylethylamine
  • 2-Methyl-2-aminopropane
  • 2-Methyl-2-propylamine
  • Trimethylaminomethane
  • Erbumine (INN)
Identifiers
3D model (JSmol)
605267
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.808 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-888-1
1867
MeSH tert-butylamine
PubChem CID
RTECS number
  • EO3330000
UNII
UN number 3286
  • InChI=1S/C4H11N/c1-4(2,3)5/h5H2,1-3H3 Yes check.svgY
    Key: YBRBMKDOPFTVDT-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)N
Properties
C4H11N
Molar mass 73.139 g·mol−1
AppearanceColorless liquid
Odor fishy, ammoniacal
Density 0.696 g/mL
Melting point −67.50 °C; −89.50 °F; 205.65 K
Boiling point 43 to 47 °C; 109 to 116 °F; 316 to 320 K
Miscible
log P 0.802
Vapor pressure 39.29 kPa (at 20 °C)
1.377
Thermochemistry
191.71 J K−1 mol−1
233.63 J K−1 mol−1
−151.1–−150.1 kJ mol−1
−2.9959–−2.9951 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg
Danger
H225, H302, H314, H331
P210, P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
3
4
0
Flash point −38 °C (−36 °F; 235 K)
380 °C (716 °F; 653 K)
Explosive limits 1.7–9.8%
Lethal dose or concentration (LD, LC):
464 mg kg−1(oral, rat)
Safety data sheet (SDS) rose-hulman.edu
Related compounds
Related alkanamines
Related compounds
2-Methyl-2-nitrosopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

tert-Butylamine is an organic chemical compound with the formula (CH3)3CNH2. It is a colorless liquid with a typical amine-like odor. tert-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine.

Contents

Preparation

tert-Butylamine is produced commercially by direct amination of isobutylene using zeolite catalysts:

NH3 + CH2=C(CH3)2 → H2NC(CH3)3

The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste. [1]

(CH3)2C=CH2 + HCN + H2O → (CH3)3CNHCHO
(CH3)3CNHCHO + H2O → (CH3)3CNH2 + HCO2H

In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide. [2]

Uses

tert-Butylamine is used as an intermediate in the preparation of the sulfenamides such as N-tert-butyl-2-benzothiazylsulfenamide and N-tert-butyl-2-benzothiazylsulfenimide. As rubber accelerators, these compounds modify the rate of vulcanization of rubber. A variety of pesticides are derived from this amine, including terbacil, terbutryn, and terbumeton.

In pharmacology under the name erbumine, tert-butylamine has been used as a counterion in drug substances such as perindopril erbumine.

See also

Related Research Articles

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an acid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

Amination is the process by which an amine group is introduced into an organic molecule. This type of reaction is important because organonitrogen compounds are pervasive.

Isobutylene Chemical compound

Isobutylene (or 2-methylpropene) is a hydrocarbon with the formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.

An isocyanide is an organic compound with the functional group -N≡C. It is the isomer of the related nitrile (-C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.

Sodium bis(trimethylsilyl)amide Chemical compound

Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula ( 3Si)2NNa. This species, usually called NaHMDS, is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether, but also in aromatic solvents, like benzene and toluene by virtue of the lipophilic TMS groups.

Di-<i>tert</i>-butyl dicarbonate Chemical compound

Di-tert-butyl dicarbonate is a reagent widely used in organic synthesis. Since this compound can be regarded formally as the acid anhydride derived from a tert-butoxycarbonyl (Boc) group, it is commonly referred to as Boc anhydride. This pyrocarbonate reacts with amines to give N-tert-butoxycarbonyl or so-called Boc derivatives. These carbamate derivatives do not behave as amines, which allows certain subsequent transformations to occur that would be incompatible with the amine functional group. The Boc group can later be removed from the amine using moderately strong acids. Thus, Boc serves as a protective group, for instance in solid phase peptide synthesis. Boc-protected amines are unreactive to most bases and nucleophiles, allowing for the use of the fluorenylmethyloxycarbonyl group (Fmoc) as an orthogonal protecting group.

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

<i>tert</i>-Butyloxycarbonyl protecting group

The tert-butyloxycarbonyl protecting group or tert-butoxycarbonyl protecting group is a protecting group used in organic synthesis.

Chloramines refer to derivatives of ammonia and organic amines wherein one or more N-H bonds have been replaced by N-Cl bonds. Two classes of compounds are considered: inorganic chloramines and organic chloramines.

The carbylamine reaction is the synthesis of an isocyanide by the reaction of a primary amine, chloroform, and base. The conversion involves the intermediacy of dichlorocarbene.

<i>n</i>-Butylamine Chemical compound

n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Vapors heavier than air and it produces toxic oxides of nitrogen during combustion.

<i>sec</i>-Butylamine Chemical compound

sec-Butylamine is an organic chemical compound (specifically, an amine) with the formula CH3CH2CH(NH2)CH3. It is a colorless liquid. sec-Butylamine is one of the four isomeric amines of butane, the others being n-butylamine, tert-butylamine, and isobutylamine. sec-Butylamine is chiral and therefore can exist in either of two enantiomeric forms.

tert-Butyl isocyanide is an organic compound with the formula Me3CNC (Me = methyl, CH3). It is an isocyanide, commonly called isonitrile or carbylamine, as defined by the functional group C≡N-R. tert-Butyl isocyanide, like most alkyl isocyanides, is a reactive colorless liquid with an extremely unpleasant odor. It forms stable complexes with transition metals and can insert into metal-carbon bonds.

Triisopropylamine is an organic chemical compound consisting of three isopropyl groups bound to a central nitrogen atom. As a hindered tertiary amine, it can be used as a non-nucleophilic base and as a stabilizer for polymers; however, its applications are limited by its relatively high cost and difficult synthesis.

2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol or tri-tert-butylcarbinol is an organic compound with formula C13H28O, ((H3C)3C)3COH, or tBu3COH. It is an alcohol that can be viewed as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH.

The Ritter reaction is a chemical reaction that transforms a nitrile into an N-alkyl amide using various electrophilic alkylating reagents. The original reaction formed the alkylating agent using an alkene in the presence of a strong acid.

Aminomethyl propanol Chemical compound

Aminomethyl propanol is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds.

<i>tert</i>-Butyl hypochlorite Chemical compound

tert-Butyl hypochlorite is the organic compound with the formula (CH3)3COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It is produced by chlorination of tert-butyl alcohol in the presence of base:

<i>tert</i>-Butoxybis(dimethylamino)methane Chemical compound

tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2. The compound is classified as an aminal ester, i.e. the tert-butyl alcohol derivative of the aminal bis(dimethylamino)methane. It is a colorless liquid with a amine odor.

<i>tert</i>-Butyl nitrite Chemical compound

tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.

References

  1. Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
  2. Kenneth N. Campbell, Armiger H. Sommers, Barbara K. Campbell (1947). "tert'-Butylamine". Organic Syntheses. 47: 12. doi:10.15227/orgsyn.027.0012.{{cite journal}}: CS1 maint: multiple names: authors list (link)