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

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

Uses

Used in Organic Synthesis:
1,2-Bis(dimethylsilyl)benzene is used as a protecting group-reagent for amines and amino acids, facilitating the formation of "benzostabase" derivatives. This application is crucial in organic synthesis, where it plays a significant role in the protection of functional groups during chemical reactions, ensuring the selective modification of target groups without affecting others.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2-Bis(dimethylsilyl)benzene serves as an important raw material for the synthesis of various drugs and drug candidates. Its ability to protect amines and amino acids during chemical reactions is particularly useful in the development of complex molecular structures, which are often required for the creation of effective and targeted therapeutic agents.
Used in Chemical Research:
1,2-Bis(dimethylsilyl)benzene is also utilized in chemical research, where it can be employed to study the reactivity and selectivity of various functional groups. This knowledge is essential for the development of new synthetic methods and the optimization of existing ones, ultimately contributing to the advancement of the field of chemistry.

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

Downstream Products

• 15074-38-1 1,1,3,3-tetramethyl-1,3-dihydrobenzo[c][1,2,5]oxadisilole 
• 131080-99-4 2,3-dihydro-1,1,3,3-tetramethyl-2-(phenylmethyl)-1H-1,3-disilaindene 
• 140675-93-0 2-(4-Methoxy-benzyl)-1,1,3,3-tetramethyl-2,3-dihydro-1H-benzo[1,3]disilole 
• 140675-92-9 1,1,3,3-Tetramethyl-2-(4-methyl-benzyl)-2,3-dihydro-1H-benzo[1,3]disilole 
• 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 
• 133316-59-3 benzostabase of Phe-OMe 
• 139215-45-5 1,2-bis(bromodimethylsilyl)benzene 
• 139605-10-0 1,1,4,4-Tetramethyl-3-[1-phenyl-meth-(E)-ylidene]-1,2,3,4-tetrahydro-benzo[1,2,5]azadisiline 

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.).

1,2-Bis(dimethylsilyl)phenylidene bridged zirconocene and hafnocene dichloride complexes as precatalysts for ethylene polymerization

The synthesis and characterization of a new class of ansa bis(indenyl) complexes of zirconium and hafnium is described. Two indenyl moieties are linked at the 1-,1′-positions via a 1,2-bis(dimethylsilyl)benzene unit. The ligand precursor was prepared via

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.

Synthesis of a new hypervalent iodine compound, [2-(hydroxydimethylsilyl)phenyl](phenyl)iodonium triflate as a convenient approach to benzyne

A new benzyne precursor, [2-(hydroxydimethylsilyl)phenyl](phenyl)iodonium triflate, is prepared from 1,2-dibromobenzene in good yield. This procedure avoids the use of carcinogenic HMPA and the severe reaction conditions. The reaction of the benzyne precursor with Bu4NF in the presence of a trapping agent under very mild conditions efficiently generates benzyne and gives the benzyne adduct in high yield. (C) 2000 Elsevier Science Ltd.

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.

N-bis-silylation of α-amino acids: "benzostabases" as amino protecting group

N-Bis-trimethylsilylation of α-amino acids using the powerful trimethylsilyl triflate reagent is difficult, and is rendered impossible in the case of bulky side-chains (valine). However, favorable entropy changes resulting from a cyclization reaction allow the formation of "benzostabase" N-diprotections regardless of the side-chain bulk.