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Benzyltrimethylammonium bromide

Product NameBenzyltrimethylammonium bromide
CAS5350-41-4
MFC10H16BrN
MW230.14
EINECS226-320-2
MOL File5350-41-4.mol

Chemical Properties

Melting point	230-232 °C (lit.)
storage temp.	Inert atmosphere,Room Temperature
Water Solubility	Soluble in water
form	Crystalline Powder
color	White to off-white
Sensitive	Hygroscopic
BRN	3917251
InChI	InChI=1S/C10H16N.BrH/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H/q+1;/p-1
InChIKey	UUZYBYIOAZTMGC-UHFFFAOYSA-M
SMILES	C1(=CC=CC=C1)C[N+](C)(C)C.[Br-]
CAS DataBase Reference	5350-41-4(CAS DataBase Reference)
NIST Chemistry Reference	Benzyltrimethylammonium bromide(5350-41-4)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-37/39
RIDADR	UN 2811
WGK Germany	3
RTECS	BO8392000
F	3
Hazard Note	Irritant
HS Code	29239000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxicity	LD50 subcutaneous in mouse: 45mg/kg

MSDS

Provider	Language
Benzyltrimethylammonium bromide	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Benzyltrimethylammonium bromide (BTMAB) can be used as a starting material for the synthesis of benzyltrimethylammonium fluorochromate (BTMAFC) by treating with an aqueous solution of CrO₃ and HF. BTMAFC can be utilized as an efficient oxidizing reagent for the selective oxidation of oximes into ketones or aldehydes, and primary, secondary, allylic as well as benzylic alcohols to their corresponding carbonyl compounds.

BTMAB can be also used as:

An oxidizing reagent for the conversion of monosubstituted benzylamines into corresponding aldimines in the presence of DMSO.
A benzylating reagent for the benzylation of aryl amide C-H bond using Ni catalyst.

Synthesis

100-39-0

75-50-3

5350-41-4

GENERAL METHOD: Benzyl halide 9 (1 eq.) was dissolved in THF (50 ml/g benzyl halide) with reference to the method described in the literature 4, followed by the addition of 1.5 eq. of trimethylamine 10 (33 wt% ethanol solution). The reaction mixture was stirred at room temperature for 24 h. The product precipitated as a white solid during the reaction. The suspension was cooled to 0 °C, filtered, washed with pre-cooled ether and finally dried under vacuum to afford the target product benzyltrimethylammonium bromide 6 in a yield consistent with literature reports.

References

[1] Synlett, 2016, vol. 27, # 13, p. 1963 - 1968
[2] Journal of the American Chemical Society, 2015, vol. 137, # 27, p. 8730 - 8737
[3] Patent: KR2018/8481, 2018, A. Location in patent: Paragraph 0290-0292
[4] B.Ph.P., 1907, vol. 9, p. 477

Benzyltrimethylammonium bromide

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