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
• General Description: **Null** (The provided abstracts do not contain relevant information about the properties, applications, or specific characteristics of *tert*-Butylchlorodiphenylsilane beyond its use as a protecting group reagent in syntheses.)

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:

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

propene

tert-butyl(pent-4-en-1-yloxy)diphenylsilane

tert-Butyl-diphenyl-vinyloxy-silane

Refernces

Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis

10.1021/ol802426v

The research details the first total synthesis of brevisamide (1), a marine cyclic ether alkaloid derived from the dinoflagellate Karenia brevis. The synthesis was achieved in 21 linear steps starting from cis-but-2-ene-1,4-diol, with a key highlight being the Suzuki-Miyaura coupling between an ether ring fragment and a dienol side chain. The synthetic strategy involved constructing an amino cyclic ether fragment 2 and an iododienol unit 3 from a common starting material, and then coupling these fragments. Reactants used in the synthesis included cis-but-2-ene-1,4-diol, TBDPSCl, O3, (+)-(Z)-crotyldiisopinocampheylborane, and various other reagents for oxidation, Wittig reaction, hydrogenation, transesterification, and coupling reactions. The structure and stereochemistry were confirmed through 1H and 13C NMR spectroscopy, optical rotation, and other analytical techniques, with the final synthetic product matching the natural brevisamide's NMR spectra.

SYNTHESIS AND REACTIONS OF tert-BUTYLDIPHENYLSILYL ETHERS OF SUCROSE

10.1016/S0008-6215(00)80792-2

The research aimed to investigate the selective protection of hydroxyl groups in sucrose using tert-butyldiphenylsilyl chloride (t-BDPS) as a reagent. The purpose was to explore the preferential blocking of primary hydroxyl groups in sugar derivatives, recognizing the value of t-BDPS for this purpose due to its stability towards acid and hydrogenolysis compared to related silyl and trityl ethers. The study focused on the synthesis and reactions of 6’-mono-, 6,6’-di-, and 6,1’,6’-tri-t-BDPS ethers of sucrose. The researchers found that the reaction of sucrose with t-BDPS chloride in pyridine, in the presence of 4-dimethylaminopyridine, yielded the crystalline 6’-t-BDPS ether without the need for column chromatography. Further reactions led to the formation of 4,6,1’-trichloride and other derivatives, with the 6,1’,6’-tri-t-BDPS ether being the major product when using 4.6 mol. equiv. of the silylating reagent. The study concluded that the t-BDPS group is an important synthetic intermediate in carbohydrate chemistry due to its stability and the preferential removal of other protecting groups in its presence. Key chemicals used in the process included t-BDPS chloride, pyridine, 4-dimethylaminopyridine, sulphuryl chloride, tetrabutylammonium fluoride, acetic anhydride, and benzoyl chloride.

Synthesis and biophysical evaluation of 2′,4′-Constrained 2′O-Methoxyethyl and 2′,4′-Constrained 2′O-Ethyl nucleic acid analogues

10.1021/jo902560f

The research focuses on the synthesis and biophysical evaluation of 20,40-constrained 20O-methoxyethyl (cMOE) and 20,40-constrained 20O-ethyl (cEt) nucleic acid analogues. The purpose of this study was to develop nucleoside modifications that combine the structural elements of 2O-methoxyethyl (MOE) and locked nucleic acid (LNA) to improve the potency and therapeutic index of antisense oligonucleotides while mitigating the hepatotoxicity associated with LNA. The key chemicals used in the synthesis include diacetone allofuranose, 2-bromomethyl naphthalene, tert-butyldiphenylsilyl chloride, and various nucleobases such as uracil, adenine, and guanine. The researchers employed a cycloetherification strategy to synthesize the cMOE and cEt nucleoside phosphoramidites, utilizing a 2-naphthylmethyl protecting group that provided crystalline intermediates and enabled clean deprotection under mild conditions. The biophysical evaluation revealed that cMOE- and cEt-containing oligonucleotides exhibited hybridization and mismatch discrimination attributes similar to LNA but with significantly improved resistance to exonuclease digestion. The study concludes that these modifications offer a promising approach for enhancing the stability and efficacy of antisense oligonucleotides, potentially leading to more effective and safer therapeutic applications.

Enantioselective synthesis of (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol: a Colorado potato beetle pheromone

10.1016/j.tetlet.2008.10.092

The research focuses on the enantioselective synthesis of (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol, a pheromone of the Colorado potato beetle, which is a significant pest causing substantial agricultural damage. The study presents a novel synthetic approach that yields the pheromone in seven steps with an overall yield of 46.54% and 98.6% enantiomeric purity. Key reactants include mannitol as the starting material, aldehyde 1, (4-methylpent-3-enyl)-magnesium bromide for the Grignard reaction, PCC for oxidation to ketone 3, and a combination of MeLi and SnCl4 for stereoselective methylation to produce the key intermediate tertiary alcohol 4. The synthesis also involves PPTS in methanol for acetonide protection cleavage, TBDPSCl for selective protection of the primary hydroxyl group, and Swern oxidation for the oxidation step. Analyses used to determine the isomeric and enantiomeric purity include chiral GC analysis. The research also explores the production of analogues to study structure–activity relationships, aiming to optimize the efficacy of semiochemicals in integrated pest management.

A new synthetic route towards the mono-O-protected anti-conformationally constrained pyrimidine acyclic nucleoside.

10.1248/cpb.50.1028

The study focuses on the development of a new synthetic route for the production of mono-O-protected anti-conformationally constrained pyrimidine acyclic nucleosides, which are potentially useful as antiviral and antitumoral agents, as well as tools in molecular biology. The researchers replaced 1,3-dibenzyloxypropan-2-ol with 1-benzyloxy-3(tert-butyldiphenylsilyloxy)propan-2-one (compound 4) as a key building block in the synthesis process. Various chemicals were utilized in this study, including epichlorohydrin, benzyl glycidyl ether, iodine, acetonitrile, water, tert-butylchlorodiphenylsilane, 4-N,N-dimethylaminopyridine (DMAP), pyridinium chlorochromate (PCC), n-butyllithium, tetrahydrofuran, and 2,4-dimethoxy-6-methylpyrimidine, among others. These chemicals served specific purposes in the synthesis process, such as acting as reagents, solvents, catalysts, or protecting groups, and were used in a series of reactions including ring-opening, silylation, oxidation, and dealkylation to achieve the desired nucleoside compounds with improved properties for applications in automated oligonucleotide synthesizers.