bromotrimethylsilane

• ChemBase ID: 78793
• Molecular Formular: C3H9BrSi
• Molecular Mass: 153.09306
• Monoisotopic Mass: 151.96568882
• SMILES: [Si](C)(C)(C)Br
• Canonical SMILES: C[Si](Br)(C)C
• InChI: InChI=1S/C3H9BrSi/c1-5(2,3)4/h1-3H3
• InChIKey: IYYIVELXUANFED-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bromotrimethylsilane
• IUPAC Traditional name: bromotrimethylsilane
• Synonyms: Trimethylsilyl bromide; TMBS; Bromotrimethylsilane; Trimethylbromosilane; Bromotrimethylsilane; TMS bromide; 三甲基溴化硅; 三甲基溴硅烷; 溴三甲基硅烷; 三甲基溴硅烷

Database IDs

• CAS Number: 2857-97-8
• EC Number: 220-672-0
• MDL Number: MFCD00000048
• Beilstein Number: 1731135
• PubChem SID: 24851651; 162043556
• PubChem CID: 76113

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3134
• LogD (pH = 7.4): 2.3134
• Log P: 2.3134
• Molar Refractivity: 26.0755 cm^3
• Polarizability: 11.969929 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -44°C; -44°C
• Boiling Point: 78-80°C; 78-80°C; 79 °C(lit.)
• Flash Point: 25 °C; 25°C; -3°C(26°F); 77 °F
• Density: 1.16; 1.16 g/mL at 25 °C(lit.); 1.183
• Refractive Index: 1.424; 1.4250; n20/D 1.424; n20/D 1.424(lit.)

Safety Information

• Storage Warning: Corrosive/Flammable/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2920; UN2924
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 2; II
• Risk Statements: 10-14-34; 11-14-34
• Safety Statements: 16-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314-H318; H226-H314
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (AT); 97%; 97%, stab. with copper powder or silver wire
• Grade: purum
• Contains: copper as stabilizer; silver wool as stabilizer
• Linear Formula: (CH3)3SiBr

DETAILS

Sigma Aldrich - 194409

Application
Used with InCl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.1
Packaging
25, 100 g in Sure/Seal™
5 g in glass bottle

Sigma Aldrich - 92337

Other Notes
Powerful silylating agent 1,2; Cleavage of ethers 3; Smooth cleavage of phosphonic and phosphoric alkyl esters 4

REFERENCES

• Epoxides, oxetanes and THF are cleaved by the reagent: Synthesis, 383 (1981), as are small ring lactones: Angew. Chem. Int. Ed., 18, 689 (1979). The cleavage of acyclic ethers and esters is markedly catalyzed by IBr: J. Org. Chem., 48, 1678 (1983).
• In combination with DMSO and Et₃N, effects the bromolactonization of unsaturated acids: J. Chem. Soc., Perkin 1, 847 (1994).
• Effective catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives: Org. Lett., 5, 1661 (2003).
• Compare also Iodotrimethylsilane, A12902.
• Converts alcohols to alkyl bromides: Tetrahedron Lett., 4483 (1978), and acyl chlorides to acyl bromides: Synthesis, 216 (1981).
• Silylating agent; see Appendix 4. About 10⁴x more reactive than TMSCl in the conversion of ketones to their silyl enol ethers in the presence of Et₃N: Liebigs Ann. Chem., 1718 (1980).
• Acetals, including MOM and THP ethers are readily cleaved, as are trityl and TBDMS ethers: Tetrahedron Lett., 25, 2515 (1984). Methyl glycosides are converted to the glycosyl bromides: Tetrahedron Lett., 22, 513 (1981).