Bromotrimethylsilane
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Basic information
- CAS
2857-97-8- Standard SMILES
C[Si](C)(C)Br- InChIKey
IYYIVELXUANFED-UHFFFAOYSA-N- Molecular formula
- C3H9BrSi
- Average molar mass
- 153.09 g/mol
- Monoisotopic mass
- 151.96568892
Names & identifiers
- Preferred name
- Bromotrimethylsilane
- IUPAC
- bromo(trimethyl)silane
- English name
- Bromotrimethylsilane
- Molecular formula
- C3H9BrSi
- Molecular weight
- 153.09
Names & synonyms
Bromotrimethylsilane2857-97-8TrimethylbromosilaneTrimethylsilyl bromideSilane, bromotrimethyl-tmsbrJHH5G299BXNSC-139857DTXSID1062671RefChem:121650DTXCID3037838220-672-0
Show more names
(CH3)3SiBrCT2928BromotrimethyL
bromo(trimethyl)silaneTrimethylsilicon bromideTMS bromidetrimethylsilylbromideMFCD00000048bromotrimethyl silaneTMBSC3H9BrSi
Database identifiers
- CAS
2857-97-8- PubChem CID
- 76113
- DTXSID
DTXSID1062671- UNII
- JHH5G299BX
- EC Number
- 220-672-0
- Nikkaji
- J150.732J
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 28.4
Experimental & physicochemical properties
SpringerMaterials Properties29Si nuclear magnetic resonance spectrum
Density1.16 @25 °C
Boiling Point79 °C @760 [mm Hg]
Physicochemical properties
- Melting point
- -43 °C · -43 °C
- Boiling point
- 79 °C · 79 °C(lit.)
- Density
- 1.16 g/mL · 1.16 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.424(lit.)
- Flash point
- 90 °F · 90 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- DECOMPOSES
- form
- Liquid
- Specific Gravity
- 1.1725 · 1.1725
- color
- Clear colorless to yellow
- Water Solubility
- DECOMPOSES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H225 (15.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24353
Bromotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Liq. 2 (15.1%)
Safety & protection
Protective Action Criteria (PAC)
1.2 [mg/m3]
13 [mg/m3]
79 [mg/m3]
Safety data
- F
- 10-21
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 2920 8/PG 2
- hs_code
- 29310095
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationSilane, bromotrimethyl-: ACTIVE
Applications
UsesBromotrimethylsilane can protect or deprotect functional groups selectively, act as silane blocking agent, which is widely used in the syntheses of drugs.
UsesAdefovir intermediate
UsesPowerful silylating agent
UsesBromotrimethylsilane 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).
General DescriptionBromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.
Preparation methods
Preparationalthough 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.
Upstream & downstream products
Upstream raw materials
Related reactions
912 records
Compound notes
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