17985-72-7

Basic information

• Product Name: 1,2-Bis(dimethylsilyl)benzene
• Synonyms: 1,2-Bis(dimethylsilyl)benzene,98%;1,2-Bis(dimethylsily)benzene;O-PHENYLEN-BIS-(DIMETHYLSILAN);1,2-BIS(DIMETHYLSILYL)BENZENE;1,2-PHENYLENEBIS(DIMETHYLSILANE);Silane, 1,2-phenylenebisdimethyl-;o-phenylenebis(dimethylsilane);1,2-BIS(DIMETHYLSILYL)BENZENE 98%
• CAS NO: 17985-72-7
• Molecular Formula: C₁₀H₁₈Si₂
• Molecular Weight: 194.42
• Product Categories: Synthetic Organic Chemistry;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Si-H Compounds;Silicon Compounds (for Synthesis)
• Mol File: 17985-72-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: <25°C
• Boiling Point: 101 °C13 mm Hg(lit.)
• Flash Point: 158 °F
• Appearance: /Liquid
• Density: 0.898 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.171mmHg at 25°C
• Refractive Index: n20/D 1.51(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: insoluble
• BRN: 2937027
• CAS DataBase Reference: 1,2-Bis(dimethylsilyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(dimethylsilyl)benzene(17985-72-7)
• EPA Substance Registry System: 1,2-Bis(dimethylsilyl)benzene(17985-72-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10
• TSCA: No
• Hazardous Substances Data: 17985-72-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

1,2-Bis(dimethylsilyl)benzene is a protecting group-reagent for amines and amino acids forming "benzostabase" derivatives. It is an important raw material and in organic synthesis.

InChI:InChI=1/C10H18Si2/c1-11(2)9-7-5-6-8-10(9)12(3)4/h5-8,11-12H,1-4H3

Upstream product

• 1066-35-9 dimethylmonochlorosilane 
• 583-53-9 2,3-dibromobenzene 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 142208-04-6 1-Dimethylsilanyl-2-(ethyl-dimethyl-silanyl)-benzene 
• 142208-05-7 1-(Ethyl-methyl-silanyl)-2-trimethylsilanyl-benzene 
• 140675-98-5 1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-benzo[1,4]disiline 
• 140675-89-4 1,1,2,3,3-Pentamethyl-2,3-dihydro-1H-benzo[1,3]disilole 
• 142208-06-8 1-(Dimethyl-octyl-silanyl)-2-dimethylsilanyl-benzene 
• 131081-00-0 2-Heptyl-1,1,3,3-tetramethyl-2,3-dihydro-1H-benzo[1,3]disilole 
• 78108-69-7 2-(2,2-Diphenyl-vinyl)-1,1,3,3-tetramethyl-2,3-dihydro-1H-benzo[1,2,5]azadisilole 
• 139605-10-0 1,1,4,4-Tetramethyl-3-[1-phenyl-meth-(E)-ylidene]-1,2,3,4-tetrahydro-benzo[1,2,5]azadisiline 
• 82475-35-2 benzyla amine N,N-disiliciee 
• 132273-07-5 2-(p-bromobenzyl)-1,1,3,3-tetramethyl-1,3-disilaisoindoline 
• 132273-14-4 2-(3-Bromo-phenyl)-1,1,3,3-tetramethyl-2,3-dihydro-1H-benzo[1,2,5]azadisilole 
• 139605-15-5 1,1,3,3-Tetramethyl-2-(1-phenyl-vinyl)-2,3-dihydro-1H-benzo[1,2,5]azadisilole 
• 156578-45-9 o-bis(allyldimethylsilyl)benzene 
• 882159-05-9 2-methyl-6-(1,1,3,3-tetramethyl-1,3-dihydro-benzo[1,2,5]azadisilol-2-yl)-quinoline 

Relevant articles and documents

Zinc/Indium Bimetallic Lewis Acid Relay Catalysis for Dehydrogenative Silylation/Hydrosilylation Reaction of Terminal Alkynes with Bis(hydrosilane)s

When mixed with two different Lewis acid catalysts of zinc and indium, terminal alkynes were found to react with bis(hydrosilane)s to selectively provide 1,1-disilylalkenes from among several possible products, by way of a sequential dehydrogenative silylation/intramolecular hydrosilylation reaction. Adding a pyridine base is crucial in this reaction; a switch as a catalyst of the zinc Lewis acid is turned on by forming a zinc?pyridine-base complex. A range of the 1,1-disilylalkenes can be obtained by a combination of aryl and aliphatic terminal alkynes plus aryl-, heteroaryl-, and naphthyl-tethered bis(hydrosilane)s. The 1,1-disilylalkene prepared here is available as a reagent for further transformations by utilizing its C?Si or C=C bond. The former includes Hiyama cross-coupling, bismuth-catalyzed ether formation, and iododesilylation; the latter includes double alkylation and epoxidation. Mechanistic studies clarified the role of the two Lewis acids: the zinc–pyridine-base complex catalyzes the dehydrogenative silylation as a first stage, and, following on this, the indium Lewis acid catalyzes the ring-closing hydrosilylation as a second stage, thus leading to the 1,1-disilylalkene. (Figure presented.).

Copper-Free Double Silylation of 1,2-Dibromobenzenes Using a Mg/LiCl/DMI System

The reaction of 1,2-dibromobenzenes with chlorotrimethylsilane efficiently proceeded in the presence of Mg and LiCl in DMI under mild conditions, giving 1,2-bis(trimethylsilyl)benzenes in good to high yields. The reaction of 1,2-dibromobenzenes with chlorodimethylsilane under the same conditions afforded the corresponding 1,2-bis(dimethylsilyl)benzenes in high yields. Functional group transformations of 1,2-bis(trimethylsilyl)benzene were conducted to demonstrate the synthetic utility.

Cholic Acid as an Architectural Component in Biomimetic/Molecular Recogition Chemistry; Synthesis of "Cholaphanes" With Facial Differentiation of Functionality

Facially-differentiated cholaphanes (2) were synthesized in good yields from cholic acid (1).Key steps were the selective 3,7-bis-O-acetylation of methyl cholate (3), the 12-O-benzylation of diacetate 4, and the introduction of a 3β-(p-aminomethyl)phenyl substituent using an arylmanganese reagent and employing the novel ''benzostabase'' N-protection methodology.