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426296

Sigma-Aldrich

Tetramethylammonium bromide

ACS reagent, ≥98.0%

Synonym(s):

N,N,N-trimethyl-methanaminium bromide, TMAB

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About This Item

Linear Formula:
(CH3)4N(Br)
CAS Number:
64-20-0
Molecular Weight:
154.05
Beilstein/REAXYS Number:
3620955
EC Number:
200-581-2
MDL number:
MFCD00011626
UNSPSC Code:
12352100
PubChem Substance ID:
24866694
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

assay

≥98.0%

form

powder

impurities

≤0.5% trimethylamine hydrobromide
≤0.5% trimethylamine

mp

>300 °C (lit.)

SMILES string

[Br-].C[N+](C)(C)C

InChI

1S/C4H12N.BrH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1

InChI key

DDFYFBUWEBINLX-UHFFFAOYSA-M

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General description

Tetrabutylammonium bromide is a quaternary ammonium compound that is widely used as a phase transfer catalyst. Absolute viscosities of its aqueous solutions have been measured at various temperatures (20,25 and 30°C). Various physical properties (activity coefficient up to saturation, conductance, density and solubility in water) of TMABr have been evaluated.

Application

Tetrabutylammonium bromide (TBAB) may be used in the molten state in the following processes:
  • Synthesis of (2S)-5-(3-phenyl-2-phthalimidylpropanoylamino)isophthalic acid.
  • Synthesis of alkyl-substituted pyrroles in the absence of catalyst and organic solvent.
  • Synthesis of dithioacetals from acetals by transthioacetalisation in a solvent free environment.
  • Synthesis of polyamides (PAs) by the polymerization of terephthalic acid and diisocyanates.
  • Catalyze the addition of thiols to conjugated alkenes.
  • Dehydrochlorination of poly(vinyl chloride).

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Dehydrochlorination of poly (vinyl chloride) by aqueous sodium hydroxide solution under two-phase conditions.
Kise H.
Journal of Polymer Science Part A: Polymer Chemistry, 20(11), 3189-3197 (1982)
Heat capacities and thermodynamic properties of two tetramethylammonium halides.
Chang SS and Westrum Jr EF.
J. Chem. Phys. , 36(9), 2420-2423 (1962)
Catalysis by ionic liquids: solvent-free efficient transthioacetalisation of acetals by molten tetrabutylammonium bromide.
Ranu BC, et al.
Journal of the Chemical Society. Perkin Transactions 1, 13, 1520-1522 (2002)
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