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BROMOTRIMETHYLSILANE
Bromotrimethylsilane is used as a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers.
Further, Bromotrimethylsilane is used as a brominating agent and an effective reagent for the formation of silyl enol ethers.
Bromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.
CAS: 2857-97-8
European Community (EC) Number: 220-672-0
IUPAC Name: bromo(trimethyl)silane
Molecular Formula: C3H9BrSi
Molecular Weight: 153.09 g/mol
Solubility: Miscible with carbon tetrachloride, chloroform, dichloroethane, acetonitrile, toluene, dichloromethane and hexane.
Preparation
Although many methods are reported, only a few are provided here: chlorotrimethylsilane undergoes halogen exchange with either magnesium bromide in Et2O or sodium bromide in MeCN, which allows in situ reagent formation; alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts.
Bromotrimethylsilane may also be generated by reaction of hexamethyldisiloxane and aluminum bromide.
However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.
Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals.
Bromotrimethylsilane can protect or deprotect functional groups selectively, act as silane blocking agent, which is widely used in the syntheses of drugs.
Bromotrimethylsilane is used as a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers.
Further, Bromotrimethylsilane is used as a brominating agent and an effective reagent for the formation of silyl enol ethers.
Bromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.
Specifications
Melting Point: -43.0°C
Color: Colorless to Yellow
Density: 1.1600g/mL
Boiling Point: 79.0°C
Flash Point: 32°C
Infrared Spectrum: Authentic
Purification Methods
Purify it by repeated fractional distillation and store it in sealed ampoules in the dark.
Also fractionate it through a 15-plate column (0.8 x 32cm packed with 1/16in single turn helices of Pt-Ir wire).
SYNONYMS:
Bromotrimethylsilane
2857-97-8
Trimethylbromosilane
Trimethylsilyl bromide
Silane, bromotrimethyl-
bromo(trimethyl)silane
Trimethylsilicon bromide
bromotrimethyl silane
TMBS
trimethylsilylbromide
JHH5G299BX
MFCD00000048
NSC-139857
tmsbr
TMS bromide
bromotrimethylsilan
Bromotrimethysilane
trimethysilylbromide
Me3SiBr
bromo trimethylsilane
EINECS 220-672-0
trimethyl bromosilane
trimethysilyl bromide
bromo trimethyl silan
bromo-trimethyl-silane
NSC 139857
TMS-Br
trimethyl silyl bromide
(CH3)3SiBr
Bromotrimethylsilane, 97%
UNII-JHH5G299BX
EC 220-672-0
SCHEMBL37498
DTXSID1062671
AMY39323
STR08345
CT2928
NSC139857
AKOS000121902
Trimethylbromosilane Bromotrimethylsilane
BP-10636
B1087
FT-0623269
NS00050020
Bromotrimethylsilane, purum, >=97.0% (AT)
EN300-29777
D88750
S03130
J-519952
Q62455523
F0001-0898
