TRIMETHYLBROMOSILANE

Product Code: SIT8430.0
CAS No: 2857-97-8
SDS Sheets: EU | US
COMMERCIAL
2857-97-8
Pack Size
Quantity
Price
 
25 g
$86.00
2.5 kg
$1,395.00
20 kg
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200 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    220-672-0
  • Synonyms

    BROMOTRIMETHYLSILANE
  • HMIS

    3-4-2-X
  • Molecular Formula

    C3H9BrSi
  • Molecular Weight (g/mol)

    153.09
  • TSCA

    Yes
  • Delta H Vaporization (kJ/mol)

    30.8 kj/mole
  • Boiling Point (˚C/mmHg)

    80°
  • Density (g/mL)

    1.1725
  • Flash Point (˚C)

    -3°C (27°F)
  • Melting Point (˚C)

    -44°
  • Refractive Index @ 20˚C

    1.422

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents
  • Application

    Review of synthetic utility.1
    Converts acid chlorides to acid bromides.2
    Deesterifies phosphorus esters.3
    Converts nitroalkanes to nitroalkenes.4
    Catalyzes the cross-coupling of heteroaromatics.5
    Used in the synthesis of unsymmetrical phosphine oxides.6

    Fieser

    F&F: Vol. 9, p 73; Vol. 10, p 59; Vol. 11, p 59; Vol. 12, p 799; Vol. 15, p 51; Vol. 16, p 50; Vol. 18, p 380; Vol. 19, p 373; Vol. 20, p 404.

    Reference

    1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 92-100.
    2. Schmidt, A. H. et al. Synthesis 1981, 216.
    3. Chovinard, P. M.; Bartlett, P. A. J. Org. Chem. 1986, 51, 75.
    4. Kunetsky, R. A. et al. Tetrahedron Lett. 2005, 46, 5203.
    5. Kita, Y. et al. J. Am. Chem. Soc. 2009, 131, 1668.
    6. Fougére, C. et al. Eur. J. Org. Chem. 2009, 6048.

    Safety

  • Packaging Under

    Nitrogen
  • Trimethylsilyl Blocking Agent

    Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.

    Trimethylbromosilane; Bromotrimethylsilane; Trimethylsilyl bromide; TMBS

  • More reactive than SIT8510.0 Less reactive, but more Less reactive, photolytically stable than SIT8564.0
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure