TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE

Base Information

• Chemical Name: TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE
• CAS No.: 76782-82-6
• Molecular Formula: C9H18 O Si
• Molecular Weight: 170.327
• Hs Code.: 2931900090
• European Community (EC) Number: 833-860-8
• DSSTox Substance ID: DTXSID20392530
• Nikkaji Number: J1.052.550K
• Mol file: 76782-82-6.mol

Synonyms:TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE;TERT-BUTYLDIMETHYL(PROP-2-YNYLOXY)SILANE

Chemical Property of TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE

Chemical Property:

• Vapor Pressure: 3.51mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 157.8 °C at 760 mmHg
• Flash Point: 38.8 °C
• PSA: 9.23000
• Density: 0.838 g/cm³
• LogP: 2.64140
• Solubility.: Diethyl Ether, Ethyl Acetate, Hexane
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 170.112691728
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

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

3-(tert-Butyldimethylsilyloxy)-1-propyne ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OCC#C
• Uses: tert-Butyldimethyl(2-propynyloxy)silane is an alkyne used in organinc synthesis. tert-Butyldimethyl(2-propynyloxy)silane may be used in the synthesis of (R)-2,3-pentadecadien-1-ol and (S)-ethyl 5-(tert-butyldimethylsilyloxy)-2-hydroxy-2-phenylpent-3-ynoate.

Technology Process of TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE

There total 6 articles about TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + propargyl alcohol (107-19-7) → tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1002/anie.200700321

Reference yield: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + allyl alcohol (107-18-6) → tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 22h;

DOI:10.1021/ja016585u

Reference yield: 59.0%

propargyl alcohol (107-19-7) → tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tet.2013.02.064

upstream raw materials:

tert-butyldimethylsilyl chloride

propargyl alcohol

ethyl bromide

allyl alcohol

Downstream raw materials:

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose

trans-1-<3-(tert-butyldimethylsiloxy)-1-propynyl>-2-(methylthio)cyclohexane

6-(tert-butyl-dimethyl-silanyloxy)-1,3-diphenyl-hex-4-yn-1-one

(1R-{6S-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-tetrahydro-pyran-2R-yl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Refernces

• 1、 Perreault, Stephane,Spino, Claude. "Meldrum's acid-derived thione dienophile in a convergent and stereoselective synthesis of a tetracyclic quassinoid intermediate". . p. 4385 - 4388. Retrieved 2006.
• 2、 Xu, Caiding,Negishi, Ei-ichi. "A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation, trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing (Z)-γ-alkylidenebu". . p. 431 - 434. Retrieved 1999.
• 3、 Tius, Marcus A.,Hu, Huaping. "Synthesis of α-substituted α,β-unsaturated acylsilanes". . p. 5937 - 5940. Retrieved 1998.
• 4、 Ley, Steven V.,Simpkins, Nigel S.,Whittle, Alan J.. "The Total Synthesis of the Clerodane Diterpene Insect Antifeedant Ajugarin I". . p. 503 - 505. Retrieved 1983.
• 5、 Hamashima, Yoshitaka,Hirokawa, Ryo,Hisanaga, Tatsunari,Ichikawa, Mamoru,Kawato, Yuji,Nagao, Yoshihiro,Takita, Ryo,Watanabe, Kohei,Yamashita, Kenji. "Mechanistic Details of Asymmetric Bromocyclization with BINAP Monoxide: Identification of Chiral Proton-Bridged Bisphosphine Oxide Complex and Its Application to Parallel Kinetic Resolution". supporting information. p. 3913 - 3924. Retrieved 2022/03/15.
• 6、 -. "3,6-DIAMINO-PYRIDAZIN-3-YL DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USES AS PRO-APOPTOTIC AGENTS". Page/Page column 130. . Retrieved 2021/02/05.