6142-73-0

Basic information

• Product Name: METHYLENECYCLOPROPANE; >98%DISCONTINUED
• Synonyms: METHYLENECYCLOPROPANE; >98%DISCONTINUED;Cyclopropane, methylene-;cyclopropane,methylene;1-Methylenecyclopropane;2-Methylenecyclopropane;3-Methylenecyclopropane;Einecs 228-142-0;XSGHLZBESSREDT-UHFFFAOYSA-N
• CAS NO: 6142-73-0
• Molecular Formula: C₄H₆
• Molecular Weight: 54.09044
• EINECS: 228-142-0
• Product Categories: Acyclic;Alkenes;Organic Building Blocks
• Mol File: 6142-73-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: -138.7 °C
• Boiling Point: 9-12 °C
• Appearance: /
• Density: 0.80 g/mL at 20 °C(lit.)
• Vapor Pressure: 1380mmHg at 25°C
• Refractive Index: 1.431
• Storage Temp.: −20°C
• CAS DataBase Reference: METHYLENECYCLOPROPANE; >98%DISCONTINUED(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLENECYCLOPROPANE; >98%DISCONTINUED(6142-73-0)
• EPA Substance Registry System: METHYLENECYCLOPROPANE; >98%DISCONTINUED(6142-73-0)

Safety Data

• Hazard Codes: F+,Xn
• Statements: 12-22
• RIDADR: UN 2037 2.1
• WGK Germany: 3
• HazardClass: 2.1
• Hazardous Substances Data: 6142-73-0(Hazardous Substances Data)

Usage

General Description

METHYLENECYCLOPROPANE is a chemical compound that has been discontinued and is no longer widely available. It is composed of carbon and hydrogen atoms and is typically used as a reagent or building block in organic synthesis. Methylene cyclopropane is highly reactive due to the strain in its three-membered ring, and it is not commonly found in nature. Due to its discontinued status, it is important to note that limited information may be available regarding its properties, hazards, and potential uses.

InChI:InChI=1/C4H6/c1-4-2-3-4/h1-3H2

Upstream product

• 109-99-9 tetrahydrofuran 
• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 503-17-3 dimethylacetylene 
• 33742-81-3 1,1-dibromocyclobutane 
• 15456-25-4 3-methylenecyclobutanone 
• 3100-04-7 Methylcyclopropen 
• 74-88-4 methyl iodide 
• 822-35-5 cyclobutene 
• 563-47-3 3-Chloro-2-methylpropene 
• 1186-52-3 tetradeuterioacetic acid 
• 1130147-98-6 1-(trimethylsilylmethyl)cyclopropyl mesylate 
• 10496-76-1 4-Methylene-1,2-diazacyclopentene 
• 693-25-4 n-pentylmagnesium bromide 
• 563-79-1 2,3-Dimethyl-2-butene 

Downstream Products

• 101349-91-1 1,2,2,4-tetrabromo-butane 
• 68423-23-4 1-Brom-1-phenylspiropentan 
• 33742-80-2 1-bromo-1-(bromomethyl)cyclopropane 
• 21426-37-9 Dispiro <2.0.2.2.>octan 
• 52086-82-5 1,3-dimethylelecylohexane 
• 51567-07-8 cyclopropane, 1-(2-methylene-3-butenyl)?1-(1-methylenepropyl)- 
• 51567-08-9 8-methylenedispiro[2.1.2.4]undecane 
• 50915-29-2 (1-bromocyclopropyl)methanol 
• 167300-50-7 benzylmethylenecyclopropane 
• 97778-19-3 [2-(2-Trimethylsilanyl-cycloprop-1-enyl)-1-trimethylsilanyloxy-ethyl]-benzene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 97778-18-2 (1-Benzyl-2-methylene-cyclopropyl)-trimethyl-silane 
• 97778-15-9 Trimethyl-(2-methylene-1-pent-4-enyl-cyclopropyl)-silane 
• 126812-39-3 1-(phenylamino)-1-phenylpent-1-en-3-one 

Relevant articles and documents

Studies of Inactivation of General Acyl-CoA Dehydrogenase by Racemic (Methylenecyclopropyl)acetyl-CoA: New Evidence Suggesting a Radical Mechanism of This Enzyme-Catalyzed Reaction

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Activation and Functionalization of C-C σ Bonds of Alkylidene Cyclopropanes at Main Group Centers

Aluminum(I) and magnesium(I) compounds are reported for the C-C σ-bond activation of strained alkylidene cyclopropanes. These reactions result in the formal addition of the C-C σ bond to the main group center either at a single site (Al) or across a metal-metal bond (Mg-Mg). Mechanistic studies suggest that rather than occurring by a concerted oxidative addition, these reactions involve stepwise processes in which substrate binding to the main group metal acts as a precursor to α- or β-alkyl migration steps that break the C-C σ bond. This mechanistic understanding is used to develop the magnesium-catalyzed hydrosilylation of the C-C σ bonds of alkylidene cyclopropanes.

Systematic repression of β-silyl carboeation stabilization

Solvolysis of 1-(trimethylsilylmethyl)cyclopropyl mesylate in CD 3CO2D gives ring-opened products as well as methylenecyclopropane. The rate enhancement due to the β-trimethylsilyl group is a factor of about 106. The large