3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE

Base Information

• Chemical Name: 3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE
• CAS No.: 38002-45-8
• Molecular Formula: C6H11BrSi
• Molecular Weight: 191.143
• Hs Code.: 29319090
• European Community (EC) Number: 609-506-1
• DSSTox Substance ID: DTXSID80349040
• Nikkaji Number: J534.042J
• Wikidata: Q72514548
• Mol file: 38002-45-8.mol

Synonyms:Silane,(3-bromo-1-propynyl)trimethyl- (9CI);(3-Bromo-1-propyn-1-yl)trimethylsilane;(3-Bromo-1-propynyl)trimethylsilane;(Bromomethyl)(trimethylsilyl)acetylene;(Trimethylsilyl)propargyl bromide;1-Bromo-3-trimethylsilyl-2-propyne;1-Bromo-3-trimethylsilylyprop-2-yne;3-(Trimethylsilyl)propargyl bromide;3-Bromo-1-(trimethylsilyl)-1-propyne;3-Bromo-1-(trimethylsilyl)propyne;3-Trimethylsilyl-2-propynyl bromide;1-(Trimethylsilyl)-3-bromopropyne;

Chemical Property of 3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Vapor Pressure: 0.579mmHg at 25°C
• Melting Point: <0°C
• Refractive Index: n20/D 1.483(lit.)
• Boiling Point: 195.8 °C at 760 mmHg
• Flash Point: 62.8 °C
• PSA: 0.00000
• Density: 1.196 g/cm³
• LogP: 2.26210
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: Immiscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 189.98134
• Heavy Atom Count: 8
• Complexity: 120

Purity/Quality:

99% ^*data from raw suppliers

3-Bromo-1-(trimethylsilyl)-1-propyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-28-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CCBr
• Uses: 3-Bromo-1-(trimethylsilyl)-1-propyne may be used in the preparation of tetrahydroisoquinoline-3-carboxylic acid derivatives. It may be used as reagent for the alkylation of dianion of β-keto esters at γ-carbon. It may be employed in the preparation of terminal conjugated enynes and allenic alcohols.

Technology Process of 3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE

There total 14 articles about 3-BROMO-1-(TRIMETHYLSILYL)-1-PROPYNE 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%

3-trimethylsilyl-2-propyn-1-ol (5272-36-6) → 3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8)

Guidance literature:

With phosphorus tribromide; In diethyl ether; at 25 ℃; for 18.5h;

DOI:10.1002/anie.201403651

Reference yield: 83.0%

3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne (36551-06-1) → 3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8)

Guidance literature:

With bromine; triphenylphosphine; In dichloromethane; at -10 - 20 ℃;

DOI:10.1002/ejoc.200400668

Reference yield: 82.0%

bromine (7726-95-6) + 1-trimethylsilyl-3-trimethylgermyl-1-propyne (129577-85-1) → 3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8) + 1-bromo-1-(trimethylsilyl)propadiene (38002-44-7)

Guidance literature:

In tetrachloromethane; dropwise addn. of a soln. of Br2 to a soln. of Ge-compound cooled to -60°C; distn.;

upstream raw materials:

3-trimethylsilyl-2-propyn-1-ol

(3-methoxy-1-propyn-1-yl)trimethylsilane

trimethylsilyl bromide

3-Bromo-1-triethylstannyl-1-propyne

Downstream raw materials:

2-Methyl-2-(3-trimethylsilanyl-prop-2-ynyl)-cyclohexanone

1-methyl-1-phenyl-4-(trimethylsilyl)-3-butyn-1-ol

(3-trimethylsilyl-2-propynyl)triphenylphosphonium bromide

2-phenyl-5-trimethylsilyl-4-pentynoic acid

Refernces

• 1、 Bodinier, Florent,Sanogo, Youssouf,Ardisson, Janick,Lannou, Marie-Isabelle,Sorin, Geoffroy. "Low-valent dialkoxytitanium(ii): a useful tool for the synthesis of functionalized seven-membered ring compounds". supporting information. p. 3603 - 3606. Retrieved 2021/04/14.
• 2、 Tian, Tian,Wang, Xin,Lv, Leiyang,Li, Zhiping. "Iron-Catalyzed [2+2+2] Annulation of Aliphatic Bridged 1,n-Enynes with Aldehydes for the Synthesis of Fused Pyrans". supporting information. p. 4425 - 4428. Retrieved 2020/06/05.