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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:
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

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW4843
MKCR4106
MKCP5395
MKCM9199
MKCG6906

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Some physical properties of aqueous solutions of tetramethylammonium bromide and tetramethylammonium iodide
Levien BJ.
Australian Journal of Chemistry, 18(8), 1161-1170 (1965)
Viscosity of aqueous solutions. III. Tetramethylammonium bromide and the role of the tetraalkylammonium ions.
Nightingale Jr ER.
The Journal of Physical Chemistry, 66(5), 894-897 (1962)
Heat capacities and thermodynamic properties of two tetramethylammonium halides.
Chang SS and Westrum Jr EF.
J. Chem. Phys. , 36(9), 2420-2423 (1962)
An efficient synthesis of pyrroles by a one-pot, three-component condensation of a carbonyl compound, an amine and a nitroalkene in a molten ammonium salt.
Ranu BC and Dey SS.
Tetrahedron Letters, 44(14), 2865-2868 (2003)
Polycondensation of new optically active diacid with diisocyanates in the presence of tetrabutylammonium bromide as a green media under microwave heating.
Mallakpour S and Sepehri S.
Reactive functional Polymers, 68(10), 1459-1466 (2008)
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