(2-BROMOALLYL)TRIMETHYLSILANE

Base Information

• Chemical Name: (2-BROMOALLYL)TRIMETHYLSILANE
• CAS No.: 81790-10-5
• Molecular Formula: C6H13 Br Si
• Molecular Weight: 193.159
• European Community (EC) Number: 620-917-5
• DSSTox Substance ID: DTXSID80400261
• Nikkaji Number: J534.044F
• Wikidata: Q82203143
• Mol file: 81790-10-5.mol

Synonyms:Silane,(2-bromo-2-propenyl)trimethyl- (9CI); 2-Bromo-3-(trimethylsilyl)propene;2-Bromoallyltrimethylsilane

Chemical Property of (2-BROMOALLYL)TRIMETHYLSILANE

Chemical Property:

• Vapor Pressure: 6.14mmHg at 25°C
• Refractive Index: n20/D 1.462(lit.)
• Boiling Point: 82-85 °C60 mm Hg(lit.)
• Flash Point: 87 °F
• PSA: 0.00000
• Density: 1.121 g/mL at 25 °C(lit.)
• LogP: 3.23320
• Storage Temp.: 2-8°C
• Solubility.: sol alcohol, acetone, ether, THF, pentane; insol water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 191.99699
• Heavy Atom Count: 8
• Complexity: 91.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2-Bromoallyl)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CC(=C)Br
• Physical properties: bp 46–50°C/20 mmHg,64–65°C/38– 39 mmHg.
• Uses: 2-Bromo-3-trimethylsilyl-1-propene can be used as synthon for CH2=C?CH2TMS1–3 and CH2=CBrC?H2;2 for synthesis of 1-trimethylsilylmethyl-substituted 1,3-butadienes.The 1-trimethylsilylmethylvinyl anion CH2=C(M)CH2TMS (2) (M = Li, Mg, Cu, etc.), readily prepared from 2-bromo-3-trimethylsilyl-1-propene (1) under typical conditions, allows the introduction of the synthetically useful 1-trimethylsilylmethylvinyl group to a wide variety of substrates. Ring opening of 1-butene oxide with the Grignard reagent (2) (M = MgBr) in the presence of copper(I) iodide gives only one regioisomer. Subsequent desilylative oxidation of this allyl alcohol to α-methylene-γ-lactones provides further utility of (1) as a 1-hydroxymethylvinyl anion equivalent, i.e. CH2=?C?CH2OH (eq 1).Alternatively, the alcohol from trans-2,3-epoxybutane provides a route to the unstable sixmembered β,γ-unsaturated lactone (eq 2).The copper-catalyzed 1,4-addition to the typically unreactive mesityl oxide proceeds smoothly. The versatility of the allylsilane moiety is again illustrated in the ethylaluminum dichloride-induced cyclization of the adduct to a tertiary cyclopentanol in high yield (eq 3).

Technology Process of (2-BROMOALLYL)TRIMETHYLSILANE

There total 8 articles about (2-BROMOALLYL)TRIMETHYLSILANE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(Trimethylsilyl)copper (91899-54-6) + 2-bromoallyl bromide (513-31-5) → (2-bromoallyl)trimethylsilane (81790-10-5)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; for 1.5h; Ambient temperature;

DOI:10.1021/jo00196a002

Reference yield: 70.0%

methylmagnesium bromide (75-16-1) + 2-bromoallyl bromide (513-31-5) → (2-bromoallyl)trimethylsilane (81790-10-5)

Guidance literature:

2-bromoallyl bromide; With trichlorosilane; triethylamine; copper(l) chloride; In diethyl ether; at 0 - 20 ℃; for 15h;

methylmagnesium bromide; In diethyl ether; at 0 ℃; for 15h;

DOI:10.1016/S0040-4039(02)01054-7

Reference yield: 68.0%

trimethylsilyllithium (18000-27-6) + 2-bromoallyl bromide (513-31-5) → (2-bromoallyl)trimethylsilane (81790-10-5)

Guidance literature:

With copper(l) iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; for 1.5h; Ambient temperature;

upstream raw materials:

1-acetoxy-2-bromo-2-propene

Tris(trimethylsilyl)aluminium

methylmagnesium bromide

2-bromo-3-trichlorosilylprop-1-ene

Downstream raw materials:

2,3-bis(trimethylsilyl)prop-1-ene

1,1-diphenyl-2-(trimethylsilyl)methyl-2-propen-1-ol

2-bromo-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propene

1-(2-Bromo-allyl)-cyclohexanol