17082-61-0

Basic information

• Product Name: 1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE
• Synonyms: BIS(TRIMETHYLSILOXY)CYCLOBUTENE;1,2-BIS(TRIMETHYLSILOXY)CYCLOBUTENE;1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE;1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE, 9 5+%;1,2-Bis(trimethylsiloxy)cyclobutenepurum;95+%(gc);1,2-BIS(TRIMETHYLSILOXY)CYCLOBUTENE PURUM 95+ % (GC);BIS(TRIMETHYLSILOXY)CYCLOBUTENE ,95%
• CAS NO: 17082-61-0
• Molecular Formula: C₁₀H₂₂O₂Si₂
• Molecular Weight: 230.45
• Product Categories: Cyclobutanes & Cyclobutenes;Monoalkoxysilanes;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Simple 4-Membered Ring Compounds;Si-O Compounds;Synthetic Organic Chemistry;Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 17082-61-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 58-59 °C2 mm Hg(lit.)
• Flash Point: 142 °F
• Appearance: clear colorless liquid
• Density: 0.897 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.22mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Storage Temp.: 2-8°C
• BRN: 1367530
• CAS DataBase Reference: 1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE(17082-61-0)
• EPA Substance Registry System: 1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE(17082-61-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 1993
• WGK Germany: 3
• F: 10-21
• TSCA: No
• Hazardous Substances Data: 17082-61-0(Hazardous Substances Data)

Usage

Description

1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE is a clear colorless liquid that is a useful chemical reactant in various chemical reactions and has significant biological activity. It is known for its ability to undergo photocycloaddition with 2-cyclohexenones and participate in Aldol condensation reactions with carbonyl compounds. Additionally, it reacts with Br2 to produce cyclobutanedione.

Uses

Used in Pharmaceutical Industry:
1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE is used as a chemical reactant for the preparation of serine and threonine β-lactones, which are inhibitors of the hepatitis A virus 3C cysteine proteinase. This application is significant in the development of antiviral drugs and treatments for hepatitis A.
Used in Chemical Synthesis:
1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE is used as a reactant in photocycloaddition reactions with 2-cyclohexenones, contributing to the synthesis of various chemical compounds. Its ability to undergo Aldol condensation with carbonyl compounds also makes it a valuable reactant in the creation of new molecules and compounds.
Used in Organic Chemistry Research:
As a clear colorless liquid with unique reactivity, 1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE is used in organic chemistry research to study and understand the mechanisms of various chemical reactions, such as photocycloaddition and Aldol condensation. This knowledge can be applied to develop new synthetic methods and improve existing ones.

InChI:InChI=1/C10H22O2Si2/c1-13(2,3)11-9-7-8-10(9)12-14(4,5)6/h7-8H2,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 123-25-1 succinic acid diethyl ester 
• 141-28-6 diethyl adipate 
• 106-65-0 Dimethyl succinate 

Downstream Products

• 65213-35-6 4-Cyclohexylidene-4-trimethylsilanyloxy-butyric acid ethyl ester 
• 65268-62-4 methyl-4-(4-tert-butylcyclohexylidene)-4-(trimethylsiloxy)butanoate 
• 31411-71-9 2,3-bis(trimethylsilyloxy)-1,3-butadiene 
• 74962-05-3 C₃₃H₃₄O₉Si 
• 6853-01-6 2-phenylcyclopentane-1,3-dione 
• 125536-69-8 2-methyl-2-phenyl-1,3-cyclopentanedione 
• 3883-58-7 2,2-dimethylcyclopentane-1,3-dione 
• 19576-08-0 (+/-)-7a-methyl-2,3,7,7a,tetrahydro-1H-indene-1,5(6H)-dione 
• 118458-36-9 N-benzyl-4,5-bis(trimethylsilyloxy)-cis-Δ⁴-tetrahydrophthalimide 
• 84629-36-7 2--2-(trimethylsilyloxy)cyclobutanon 
• 69152-08-5 2-(1-methoxycyclohexyl)-2-(trimethylsiloxy)cyclobutanone 
• 69152-09-6 2-(1-ethoxycyclohexyl)-2-(trimethylsiloxy)cyclobutanone 
• 88441-80-9 2-(c-3-methyl-r-1-methoxycyclohexyl)-2-(trimethylsiloxy)cyclobutanone 
• 69152-10-9 2-(Ethoxy-phenyl-methyl)-2-trimethylsilanyloxy-cyclobutanone 

Related news

Regioselective synthesis of spiro-cyclopropanated 1-aminopyrrol-2-ones by Bi(OTf)3-catalyzed one-pot ‘Mukaiyama–Michael addition/cyclization/ring-contraction’ reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes08/11/2019

Unknown spiro-cyclopropanated 1-aminopyrrol-2-ones are regioselectively prepared in high yields by Bi(OTf)3-catalyzed one-pot ‘Mukaiyama–Michael addition/cyclization/ring-contraction’ reactions of 1,2-bis(trimethylsilyloxy)cyclobutene with 1,2-diaza-1,3-butadienes at room temperature.detailed

Relevant articles and documents

Diastereo- and Enantioselective Synthesis of (+)- and (-)-cis-2-Aminocyclobutanols

The hitherto unknown (+)- and (-)-cis-2-aminocyclobutanols 6a,b and 7a,b, as well as the corresponding benzyloxycyclobutanamines 8a,b, have been synthesized by means of asymmetric reductive amination, with de values of 100percent and ee values ranging from 96.9 to 99.8percent. The relative cis configuration has been established by NO experiments, whereas the absolute stereochemistry has been deduced from the CD spectra of the corresponding salicylidene derivatives and confirms the like induction at C-1.

Convenient Preparation of 'High-Surface Sodium' in Liquid Ammonia: Use in the Acyloin Reaction

'Sodium on solid support' (5-20 wt.% of Na on NaCl, glass powder, poly(ethylene) and poly(propylene)) can be conveniently prepared via low-temperature (-33°C) deposition of sodium from its solution in liquid ammonia. Use of this reagent in the acyloin reaction of carboxylic esters gave the corresponding products in good yields.

A convenient one-pot preparation of stable equivalents of cyclobutane-1,2-dione and cyclobutanetrione

A very short, high-yielding, one-pot procedure has been developed for the preparation of half-protected cyclobutane-1,2-dione. This compound is much more stable than cyclobutane-1,2-dione itself and allowed further transformation to give diprotected cyclobutanetrione equivalents. Copyright Taylor & Francis Group, LLC.

1. 2 - double-trimethyl siloxy cyclobutene and its preparation process

The invention belongs to the field of chemical material production, and especially relates to 1,2-bis(trimethylsilyloxy)cyclobutene, and a preparation method thereof. Preparation chemical equation of 1,2-bis(trimethylsilyloxy)cyclobutene is represented by a formula in the invention. According to the preparation method, existing of unreacted metallic sodium residue in a reaction mixture is indicated based on a phenomenon that a blue compound is obtained via reaction of benzophenone with metallic sodium in an anhydrous solution; and a convenient and feasible method used for determining metallic sodium residual after reaction is provided, and potential safety hazards in post treatment processes are avoided completely.