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194409

Sigma-Aldrich

Bromotrimethylsilane

97%

Synonym(s):

TMBS, Trimethylbromosilane, Trimethylsilyl bromide

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About This Item

Linear Formula:
(CH3)3SiBr
CAS Number:
2857-97-8
Molecular Weight:
153.09
Beilstein:
1731135
EC Number:
220-672-0
MDL number:
MFCD00000048
UNSPSC Code:
12352103
PubChem Substance ID:
24851651
NACRES:
NA.22

Quality Level

200

Assay

97%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.424 (lit.)

bp

79 °C (lit.)

density

1.16 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)Br

InChI

1S/C3H9BrSi/c1-5(2,3)4/h1-3H3

InChI key

IYYIVELXUANFED-UHFFFAOYSA-N

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Application

Used with InCl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.

Signal Word

Danger

Hazard Statements

H226,H314,H335,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F

Flash Point(C)

32 °C

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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Takahiro Saito et al.
The Journal of organic chemistry, 71(22), 8516-8522 (2006-10-27)
The combination of InCl3 and Me3SiBr provided an enhanced Lewis acid system that can be used to promote a wide range of direct coupling reactions between alcohols and silyl nucleophiles in non-halogenated solvents, such as hexane or MeCN. The enhanced
Aldrichimica Acta, 14, 31-31 (1981)
Tetrahedron Letters, 34, 7713-7713 (1993)
M Nomizu et al.
International journal of peptide and protein research, 37(2), 145-152 (1991-02-01)
A new two-step deprotection/cleavage procedure for t-butoxycarbonyl (Boc) based solid phase peptide synthesis is reported. First the protective groups are removed from 4-(oxymethyl)-phenylacetamidomethyl (PAM) resin attached peptide with the weak hard acid, trimethylsilyl bromide-thioanisole/trifluoroacetic acid (TFA). In the second step
J T Sparrow et al.
Peptide research, 9(5), 218-222 (1996-09-01)
The original trimethylsilyl bromide (TMSBr) method of peptide resin deprotection and cleavage has been modified for convenience and applicability to larger peptides. Equal amounts of a 66-residue test peptide resin were cleaved by the standard hydrogen fluoride (HF) procedure, the
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