Benzyltrimethylammonium bromide 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

Toxicity

LD50 subcutaneous in mouse: 45mg/kg

MSDS

• Language:English Provider:Benzyltrimethylammonium bromide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Benzyltrimethylammonium bromide 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

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(5350-41-4)Related Product Information

• Allyl bromide
• Tetrapropylammonium bromide
• Ethidium bromide
• Ammonium bromide
• Rocuronium bromide
• Sodium bromate
• Benzyltributylammonium bromide
• Tetraethylammonium bromide
• TRIMETHYLSULFOXONIUM BROMIDE
• Benzyltrimethylammonium chloride
• Trimethylsulfonium bromide
• Tetrabutylammonium bromide
• Benzyl chloromethyl ether
• Benzyltriethylammonium bromide
• BENZYLTRIMETHYLAMMONIUM BROMIDE DIBROMIDE,Benzyltrimethylammonium bromide dibromide, BTMABr3
• BENZYLTRIMETHYLAMMONIUM TETRACHLOROIODATE
• BENZYLTRIETHYLAMMONIUM IODIDE
• N-Phenyl-N,N,N-trimethylammonium bromide