Allyltrichlorosilane

Base Information

• Chemical Name: Allyltrichlorosilane
• CAS No.: 107-37-9
• Molecular Formula: C3H5 Cl3 Si
• Molecular Weight: 175.517
• Hs Code.: 29319090
• European Community (EC) Number: 203-485-9
• NSC Number: 20940
• UN Number: 1724
• UNII: UB3N98803N
• DSSTox Substance ID: DTXSID3059347
• Nikkaji Number: J54.318G
• Wikipedia: Allyltrichlorosilane
• Wikidata: Q27290990
• Mol file: 107-37-9.mol

Synonyms:allyltrichlorosilane

Chemical Property of Allyltrichlorosilane

Chemical Property:

• Appearance/Colour: Clear colorless to slightly yellow liquid
• Vapor Pressure: 10 mm Hg ( 16.1 °C)
• Melting Point: 35℃
• Refractive Index: n20/D 1.443(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 1.625g/cm³
• LogP: 2.82770
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in MeCN, THF, CH2Cl2, toluene, benzene, etc.; not compatible with protic solvents, acetone, and other ketones. Dipolar aprotic solvents (DMF, DMSO, HMPA, etc.) coordinate Si, thereby increasing the reactivity of C3H5SiCl3 with electrophiles.
• Water Solubility.: Soluble in THF, toluene, benzene. Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 173.922610
• Heavy Atom Count: 7
• Complexity: 65.1
• Transport DOT Label: Corrosive Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Allyltrichlorosilane 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-33-36/37/39-43-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chlorosilanes
• Canonical SMILES: C=CC[Si](Cl)(Cl)Cl
• General Description: Allyltrichlorosilane is a versatile allylating agent used in organic synthesis, particularly for the efficient allylation of N-Boc and N-Cbz imines to produce homoallylic amines, which are valuable intermediates in the preparation of biologically active nitrogen-containing compounds. Its reactivity is enhanced by activators such as DMF, enabling high-yielding transformations under mild conditions. ALLYLTRICHLOROSILANE's ability to participate in such reactions highlights its utility in synthetic chemistry for constructing complex molecular frameworks.

Technology Process of Allyltrichlorosilane

There total 31 articles about Allyltrichlorosilane 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: 81.0%

3-chloroprop-1-ene (107-05-1) → allyltrichlorosilane (107-37-9) + 1,1,1,3,3,3-hexachloro-1,3-disilapropane (4142-85-2) + Phenyltrichlorosilane (98-13-5) + 3-(Dichloro-trichlorosilanylmethyl-silanyl)-propene + 1,1,3,3-tetrachloro-1,3-disilacyclohex-4-ene (59361-35-2)

Guidance literature:

With hexachlorodisilane; at 500 ℃; for 0.00833333h; Product distribution; Mechanism;

Reference yield: 73.0%

3-chloroprop-1-ene (107-05-1) → allyltrichlorosilane (107-37-9)

Guidance literature:

With tetrachlorosilane; triethylamine; copper(l) chloride;

DOI:10.1021/ja00013a035

Reference yield: 72.0%

3-chloroprop-1-ene (107-05-1) → allyltrichlorosilane (107-37-9) + 1,3-bis(trichlorosilyl)propane (18171-50-1)

Guidance literature:

With trichlorosilane; tetra-n-butylphosphonium chloride; at 130 ℃; for 2h;

DOI:10.1021/ja005814u

upstream raw materials:

isoquinoline

3-chloropropyltrichlorosilane

E/Z-1,3-Dichloropropene

(n-pr-1-Cl)SiCl₃

Downstream raw materials:

Allylchlorodimethylsilane

allyldichloromethylsilane

allyltriethoxysilane

allyl-trimethyl-silane

Refernces

Facile allylation of N-Boc and N-Cbz imines with allyltrichlorosilane promoted by DMF

10.1080/00397910701860422

The research focuses on the facile allylation of N-Boc and N-Cbz imines using allyltrichlorosilane, promoted by N,N-dimethylformamide (DMF) as the activator. The study aimed to develop an efficient method for the synthesis of homoallylic amines, which are important precursors to nitrogen-containing compounds of biological significance. The experiments involved the allylation of various N-Boc and N-Cbz imines under mild conditions, using a mixed solvent system of DMF and CH3CN or CH2Cl2. The reaction yields were optimized by adjusting the solvent ratios and the reaction conditions. The reactants included N-Boc and N-Cbz imines derived from amines and aldehydes, and allyltrichlorosilane as the allylating agent. The analyses used to determine the success of the reactions and the yields of the products included isolation of the products, purification by flash-column chromatography on silica, and characterization by 1H NMR to determine the syn/anti ratios of the products. The study successfully obtained N-Boc and N-Cbz homoallylic amines in good to high yields, demonstrating the effectiveness of DMF as an activator for this class of imines.

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