tert-Butylchlorodiphenylsilane

Base Information

• Chemical Name: tert-Butylchlorodiphenylsilane
• CAS No.: 58479-61-1
• Deprecated CAS: 1401972-84-6,1629388-51-7
• Molecular Formula: C16H19ClSi
• Molecular Weight: 274.865
• Hs Code.: 29310095
• European Community (EC) Number: 261-282-0
• NSC Number: 617386
• UNII: 3BEU48UI4E
• DSSTox Substance ID: DTXSID5069259
• Nikkaji Number: J149.823A
• Wikidata: Q27257003
• Mol file: 58479-61-1.mol

Synonyms:tert-Butylchlorodiphenylsilane;58479-61-1;tert-Butyldiphenylchlorosilane;TBDPSCl;tert-Butyl(chloro)diphenylsilane;Silane, chloro(1,1-dimethylethyl)diphenyl-;t-Butyldiphenylchlorosilane;tert-butyl-chloro-diphenylsilane;t-butylchlorodiphenylsilane;tert-butyldiphenyl chlorosilane;TERT-BUTYLDIPHENYLSILYL CHLORIDE;C16H19ClSi;t-butyldiphenylsilyl chloride;TBDPS-Cl;MFCD00000497;132183-16-5;UNII-3BEU48UI4E;3BEU48UI4E;tert-butylchloro-diphenylsilane;(tert-Butyl)(chloro)diphenylsilane;EINECS 261-282-0;NSC-617386;Benzene, 1,1'-(chloro(1,1-dimethylethyl)silylene)bis-;diphenyl-tert-butylchlorosilane;tert-butylchlorodiphenyl silane;TBDPS chloride;TBDPS-chloride;tert-butyl-chloro-diphenyl-silane;NSC617386;TBDPSCI;T-BUPH2SICL;terbutyldiphenylchlorosilane;t-butyldiphenylsilylchloride;chloro t-butyldiphenylsilane;t-butyl chlorodiphenylsilane;t-butyl diphenylchlorosilane;t-butyl-chlorodiphenylsilane;t-butylchlorodiphenyl silane;t-butyldiphenyl chlorosilane;t-butyldiphenylchloro silane;SCHEMBL4241;tert-butylchorodiphenylsilane;t-butyldiphenyl-silylchloride;tert-Butydiphenylchlorosilane;tertbutyldiphenylsilylchloride;chloro t-butyl diphenylsilane;chloro(t-butyl)diphenylsilane;t-butyl -chlorodiphenylsilane;t-butyl chlorodiphenyl silane;t-butyl-diphenyl-chlorosilane;tert-butyidiphenylchlorosilane;C16-H19-Cl-Si;t-butyl diphenylsilyl chloride;t-butyl-diphenylsilyl chloride;tert-butyldiphenylsilylchloride;tertbutyldiphenylsilyl chloride;tert- butyldiphenylchlorosilane;tert-butydiphenylsilyl chloride;tert-butyl diphenylchlorosilane;tert-butyl-chlorodiphenylsilane;tert-butyl-diphenylchlorosilane;tert-butylchlorodiphenyl-silane;tert-butyldiphenyl-chlorosilane;tert-butyldiphenysilyl chloride;tert.-butylchlorodiphenylsilane;diphenyl tert-butylsilylchloride;tert-butyl diphenylsilylchloride;tert-butyl-diphenylsilylchloride;tert-butyldiphenyl-silylchloride;chloro(tert-butyl)diphenylsilane;tert-Butyidiphenylsilyl chloride;tert-butyl diphenyl-chlorosilane;tert-butyl-diphenyl-chlorosilane;DTXSID5069259;tert-butyl diphenylsilyl chloride;tert-butyl(diphenyl)silylchloride;tert-butyl-diphenylsilyl chloride;tert-butyldiphenyl-silyl chloride;chloro-tert-butyl(diphenyl)silane;MHYGQXWCZAYSLJ-UHFFFAOYSA-;tert-butyl (chloro)diphenylsilane;tert-butyldiphenylsilanyl chloride;Chloro-tert-butyl-diphenyl-silane;Tert-Butyl Diphenyl Chloro Silane;tert-butyl diphenyl silyl chloride;tert-butyl(diphenyl)silyl chloride;tert.butyl diphenyl silyl chloride;t-BUTYLCHLORODIPHENYL-SILANE;tert-butyl-chloro-di(phenyl)silane;AMY39325;tert-butyl (diphenyl)silyl chloride;CB2805;AKOS008901066;1,1-dimethylethyldiphenylsilyl chloride;tert-Butyl(chloro)diphenylsilane, 98%;1,1-dimethyl-ethyl-diphenylchlorosilane;1,1-dimethyl-ethyldiphenyl-chlorosilane;chloro(1,1-dimethylethyl)diphenylsilane;1,1-dimethyl-ethyl-diphenyl-chlorosilane;AS-11826;BP-21169;TERT-BUTYLDIPHENYLCHLOROSILANE [MI];diphenyl-(2-methylprop-2-yl)silyl chloride;B1223;CS-0017207;FT-0640528;EN300-39946;D72524;A934169;J-524842;Q27257003;1,1'-(CHLORO(1,1-DIMETHYLETHYL)SILYLENE)BISBENZENE;tert-Butyl(chloro)diphenylsilane, for GC derivatization, >=98.0% (GC);1H-1,4-DIAZEPINE-5-CARBOXYLICACID,HEXAHYDRO-1,4-BIS(PHENYLMETHYL)-,METHYLESTER

Chemical Property of tert-Butylchlorodiphenylsilane

Chemical Property:

• Appearance/Colour: Colorless-light yellow to brown liquid
• Vapor Pressure: 0.000249mmHg at 25°C
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 334.4 °C at 760 mmHg
• Flash Point: 143.3 °C
• PSA: 0.00000
• Density: 1.04 g/cm³
• LogP: 3.78520
• Storage Temp.: Store at 5°C
• Sensitive.: Moisture Sensitive
• Solubility.: miscible in most organic solvents.
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 274.0944548
• Heavy Atom Count: 18
• Complexity: 239

Purity/Quality:

98.0% ^*data from raw suppliers

tert-Butyl diphenylchlorosilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, C
• Hazard Codes: C,Xi
• Statements: 14-34-37-29-20/21/22-40
• Safety Statements: 26-36/37/39-45-8

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)Cl
• Physical properties: colorless liquid, bp 93–95°C/0.015 mmHg; n20 D 1.5680; d 1.057 g cm?3.
• Uses: Several newmethods have been developed for using the reagent to protect primary and secondary alcohols as their TBDPS ethers. In the presence of ammonium nitrate or ammonium perchlorate, reaction between TBDPS-Cl and a primary alcohol, such as benzyl alcohol, in DMF provided excellent yields of the corresponding silyl ethers in just 15 min (eq 1).19 When silver nitrate was used as promoter, the reactions gave inferior yields under otherwise identical conditions.When TBDPS-Cl is used to react with hemiacetals, it converts hemiacetals into ring-opened silyl ether carbonyl compounds, instead of mixed acetals.Presumably, the sizable TBDPS group presents too much steric hindrance for the formation of the corresponding mixed silyl acetals. tert-Butyldiphenylchlorosilane acts as a silylating reagent used to protect alcohols and in the preparation of silyl ethers. It plays a major role as a raw material and a precursor in organic synthesis and pharmaceuticals. It is also used for the synthesis of interphenylene phenyloxazoles which can be used for the treatment of circulatory disorders, angina and stroke. tert-Butylchlorodiphenylsilane can be used to prepare 1-benzyloxy-3-(tert-butyldiphenylsilyloxy)propan-2-ol, a key intermediate for the synthesis of mono-O-protected pyrimidine acyclic nucleosides.

Technology Process of tert-Butylchlorodiphenylsilane

There total 13 articles about tert-Butylchlorodiphenylsilane 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: 92.0%

tert.-butyl lithium (594-19-4) + diphenylsilyl dichloride (80-10-4) → tert-butylchlorodiphenylsilane (58479-61-1)

Guidance literature:

In hexane; for 4h; Reflux;

DOI:10.1002/ejic.202100342

Reference yield: 87.0%

tertiary butyl chloride (507-20-0) + diphenylsilyl dichloride (80-10-4) → tert-butylchlorodiphenylsilane (58479-61-1)

Guidance literature:

tertiary butyl chloride; With magnesium; In tetrahydrofuran; at 60 ℃; for 2h;

With lithium chloride; copper(I) bromide; In tetrahydrofuran; at 20 ℃; for 1h;

diphenylsilyl dichloride; In tetrahydrofuran; at 50 ℃; for 6h; Reagent/catalyst; Temperature;

Reference yield: 86.0%

tert-butyl(methoxy)diphenylsilane (76358-47-9) → tert-butylchlorodiphenylsilane (58479-61-1)

Guidance literature:

With iron(III) chloride; acetyl chloride; In 1,2-dichloro-ethane; for 72h;

DOI:10.1021/om300066v

upstream raw materials:

t-butyl diphenylsilanol

p-toluenesulfonyl chloride

(1S,3S,5R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexan-3-ol

tertiary butyl chloride

Downstream raw materials:

6-hydroxybenzofuran t-butyldiphenylsilyl ether

5-<<(tert-Butyldiphenylsilyl)oxy>methyl>-2,2-dimethyl-5-nitro-1,3-dioxane

Propionic acid (1R,2R,4R)-5-(tert-butyl-diphenyl-silanyloxy)-2,4-dimethyl-1-vinyl-pentyl ester

(tert-Butyl-diphenyl-silanyl)-cyclohexyl-amine

Refernces

• 1、 Bauer, Jonathan O.,Espinosa-Jalapa, Noel Angel,Fontana, Nicolò,G?tz, Tobias,Falk, Alexander. "Functional Group Variation in tert-Butyldiphenylsilanes (TBDPS): Syntheses, Reactivities, and Effects on the Intermolecular Interaction Pattern in the Molecular Crystalline State". . p. 2636 - 2642. Retrieved 2021/06/17.
• 2、 Fan, Xuanzi,Xiao, Pin,Jiao, Zeqing,Yang, Tingting,Dai, Xiaojuan,Xu, Wengang,Tan, Jin Da,Cui, Ganglong,Su, Hongmei,Fang, Weihai,Wu, Jie. "Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane". supporting information. p. 12580 - 12584. Retrieved 2019/08/16.