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Sigma-Aldrich

Benzyltrimethylammonium bromide

97%

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About This Item

Linear Formula:
C6H5CH2N(Br)(CH3)3
CAS Number:
5350-41-4
Molecular Weight:
230.14
Beilstein:
3917251
EC Number:
226-320-2
MDL number:
MFCD00011780
UNSPSC Code:
12352116
PubChem Substance ID:
24848805
NACRES:
NA.22

Assay

97%

form

solid

mp

230-232 °C (lit.)

SMILES string

[Br-].C[N+](C)(C)Cc1ccccc1

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

InChI key

UUZYBYIOAZTMGC-UHFFFAOYSA-M

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Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Benzyltrimethylammonium fluorochromate (VI): a novel, efficient and selective oxidant
Rekha S and Seema K
Indian Journal of Chemistry, 41A, 541-546 (2002)
Nickel-Catalyzed Benzylation of C- H Bonds in Aromatic Amides with Benzyltrimethylammonium Halides
Sasagawa A, et al.
Israel Journal of Chemistry, 57(10-11), 964-967 (2017)
Benzyltrimethylammonium fluorochromate (VI): a novel, efficient and selective oxidant
Kassaee MZ, et al.
Acta Chimica Slovenica, 51, 743-750 (2004)
J M Sanders et al.
Xenobiotica; the fate of foreign compounds in biological systems, 25(3), 303-313 (1995-03-01)
1. Benzyltrimethylammonium chloride (BTMAC)-derived radioactivity was rapidly eliminated from the F344 rat and the B6C3F1 mouse following p.o. administration of 0.63-63 mg/kg of [ring-U-14C] BTMAC. Greater than 90% of the radioactivity was excreted in urine and faeces within 24-h post-dosing.
Purushothaman Gopinath et al.
The Journal of organic chemistry, 74(16), 6291-6294 (2009-07-22)
An efficient protocol is reported for the synthesis of thioesters from carboxylic acids with use of acyloxy phosphonium salts as intermediates and benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent.
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