2857-97-8

Basic information

• Product Name: Bromotrimethylsilane
• Synonyms: Bromotrimethylsilane Trimethylsilylbromide;TMBS, Trimethylbromosilane, Trimethylsilyl bromide;Bromotrimethylsilane,98%;Bromotrimethylsilane,TMBS, Trimethylbromosilane, Trimethylsilyl bromide;Bromotrimethylsilane, AcroSeal, 98%;BroMotriMethylsilane, Stab. With Copper Powder or Silver Wire;Trimethylsilyl bromide, TMBS;BroMotriMethylsilane, 98% 100GR
• CAS NO: 2857-97-8
• Molecular Formula: C₃H₉BrSi
• Molecular Weight: 153.09
• EINECS: 220-672-0
• Product Categories: Synthetic Organic Chemistry;Alkyl Silanes;Blocking Agents;Protective Agents;Silylating Agents;Pharmaceutical Intermediates;Si-X (F, Br, I) Compounds;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis)
• Mol File: 2857-97-8.mol
• Article Data: 75

Chemical Properties

• Melting Point: -43 °C
• Boiling Point: 79 °C(lit.)
• Flash Point: 90 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.16 g/mL at 25 °C(lit.)
• Vapor Pressure: 100mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 2-8°C
• Solubility: DECOMPOSES
• Water Solubility: DECOMPOSES
• Sensitive: Moisture Sensitive
• Stability: Stable. Flammable. Incompatible with strong acids, strong oxidizing agents. May decompose on exposure to water or moist air.
• BRN: 1731135
• CAS DataBase Reference: Bromotrimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Bromotrimethylsilane(2857-97-8)
• EPA Substance Registry System: Bromotrimethylsilane(2857-97-8)

Safety Data

• Hazard Codes: C
• Statements: 10-34-29-14
• Safety Statements: 16-26-36/37/39-45-8
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 2857-97-8(Hazardous Substances Data)

Usage

Chemical Description

Bromotrimethylsilane is a reagent used for the protection of hydroxyl groups in organic synthesis.

Uses

Different sources of media describe the Uses of 2857-97-8 differently. You can refer to the following data:
1. Bromotrimethylsilane can protect or deprotect functional groups selectively, act as silane blocking agent, which is widely used in the syntheses of drugs.
2. Bromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15).
3. Adefovir intermediate
4. Powerful silylating agent

Chemical Properties

Clear yellow liquid

Physical properties

bp 79°C; d 1.188 g cm?3; n20 D 1.4240; fp 32°C.

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 (eq 1); alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts (eq 2).4 TMS-Br may also be generated by reaction of hexamethyldisiloxane and aluminum bromide (eq 3).However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.

General Description

Bromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.

Purification Methods

Purify it by repeated fractional distillation and store it in sealed ampoules in the dark. [McCusker & Reilly J Am Chem Soc 75 1583 1953.] Also fractionate it through a 15-plate column (0.8 x 32cm packed with 1/16in single turn helices of Pt-Ir wire). [Gilliam et al. J Am Chem Soc 68 1161 1946, Pray et al. J Am Chem Soc 70 433 1948, Beilstein 4 IV 4008.]

InChI:InChI=1/C3H9BrSi/c1-5(2,3)4/h1-3H3

Upstream product

• 74-83-9 methyl bromide 
• 4095-10-7 dimethyldibromosilane 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 1825-62-3 ethyl trimethylsilyl ether 
• 18171-06-7 me3Si(pr-2-Br) 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 2295-12-7 1,1-dimethylsilacyclobutane 
• 109-04-6 2-bromo-pyridine 
• 754-05-2 ethenyltrimethylsilane 
• 115-17-3 bromal 
• 1795-31-9 tris(trimethylsilyl) phosphite 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 535-11-5 Ethyl 2-bromopropionate 
• 533-68-6 2-bromobutyric acid ethyl ester 

Downstream Products

• 3555-47-3 1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 2754-27-0 trimethylsilyl acetate 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 1118-02-1 trimethylsilyl isocyanate 
• 7677-24-9 trimethylsilyl cyanide 
• 75-77-4 chloro-trimethyl-silane 
• 107-46-0 Hexamethyldisiloxane 
• 34714-03-9 1-bromo-2-[(trimethylsilyl)oxy]ethane 
• 34176-76-6 6-Bromhexansaeure-trimethylsilylester 
• 18187-28-5 3-Brompropionsaeure-O-trimethylsilylester 
• 21001-84-3 (2-bromocyclohexyloxy)trimethylsilane 
• 1000-62-0 trimethylsilylethoxyacetylene 
• 18291-41-3 vinylphosphonic acid bis(trimethylsilyl) ester 

Relevant articles and documents

Redistribution equilibria of substituents between the methyl- and trimethylsilicon moieties

Scrambling equilibria resulting from the exchange of pairs of monofunctional substituents (halogen, methoxyl, methylthio, and dimethylamino) between the methyl- and trimethylsilicon moieties have been studied by proton nuclear magnetic resonance. Unexpect

The First Gallium-Arsenic Compound containing a Single Ga3As Unit: Isolation and Crystal Structure of 3As (thf=tetrahydrofuran)

3As (thf=tetrahydrofuran), isolated from the products of the reaction of (Me3Si)3As with GaBr3, has been shown by X-ray crystallographic analysis to be the first example of a compound containing a single Ga3As unit.

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C3-Heteroaroyl cannabinoids as photolabeling ligands for the CB2 cannabinoid receptor

A series of tricyclic cannabinoids incorporating a heteroaroyl group at C3 were prepared as probes to explore the binding site(s) of the CB1 and CB2 receptors. This relatively unexplored structural motif is shown to be CB2 selective with Ki values at low nanomolar concentrations when the heteroaromatic group is 3-benzothiophenyl (41) or 3-indolyl (50). When photoactivated, the lead compound 41 was shown to successfully label the CB2 receptor through covalent attachment at the active site while 50 failed to label. The benzothiophenone moiety may be a photoactivatable moiety suitable for selective labeling.

Homolytic reactions of N-bromohexamethyldisilazane with trialkyl(phenylalkoxy) derivatives of silicon and tin

The main product of the photoinduced reaction of N- bromohexamethyldisilazane with trialkyl-(benzyloxy)derivatives of silicon and tin R3MO(CH2)nPh (R = Me, Et; M = Si, Sn; n = 1) is N,N-dibenzylidene-C-phenylmethanediamine (hydrobenzamide). For M = Si, with increase of the length of the methylene chain between the oxygen atom and the phenyl group (n = 2, 3), the similar reaction affords the product of bromination of the benzylic carbon atom R3MO(CH2) n-1CHBrPh. For M = Sn, the reaction results in the formation of 2-phenyloxacycloalkanes PhCHO(CH2)n-1. Pleiades Publishing, Ltd., 2010.