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

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

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 
• 100-42-5 styrene 
• 93685-07-5 diazocyclobutane 
• 503-17-3 dimethylacetylene 
• 33742-81-3 1,1-dibromocyclobutane 
• 31038-07-0 1-Bromo-1-chlorocyclobutane 
• 822-35-5 cyclobutene 
• 693-25-4 n-pentylmagnesium bromide 
• 1186-52-3 tetradeuterioacetic acid 
• 1130147-98-6 1-(trimethylsilylmethyl)cyclopropyl mesylate 
• 563-79-1 2,3-Dimethyl-2-butene 
• 563-47-3 3-Chloro-2-methylpropene 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 219618-21-0 1-bromo-1-(phenylsulfonylmethyl)cyclopropane 
• 17903-30-9 1-phenylsilacyclopentane 
• 157-41-5 1-Oxaspiro<2,2>pentan 
• 78656-80-1 [(2-methylidenecyclopropyl)sulfanyl]benzene 
• 1391608-81-3 2-(2,4-difluorophenyl)spiro(cyclopropane-1,4'-1',2',3',4'-tetrahydroquinoline)-6-carboxylic acid methyl ester 
• 1353970-91-8 2-(5-fluoro-2-methyl-phenyl)-spiro(cyclopropane-l,4'-l',2',3',4'-tetrahydroquinoline)-6-carboxylic acid methyl ester 
• 1335000-11-7 [Pt(η2-methylenecyclopropane)(η2-C2H4)(PPh3)] 
• 1335000-13-9 [Pt(η2-methylenecyclopropane)2(PPh3)] 
• 1335000-14-0 [Pt(η2-methylenecyclopropane)2(PCy3)] 
• 1335000-12-8 [Pt(η2-methylenecyclopropane)(η2-C2H4)(PCy3)] 
• 1335000-00-4 [Pt(η2-methylenecyclopropane)(1,3-bis(diphenylphosphino)propane)] 
• 37668-25-0 bis(dimethylphenylphosphine)(1-3-η-1-methylallyl)platinum(II) hexafluorophosphate 
• 478833-13-5 bis(η5-indenyl)-5,6-diphenyl-4-zirconaspiro[2.4]hept-5-ene 
• 478833-10-2 bis(η5-cyclopentadienyl)-5,6-diphenyl-4-zirconaspiro[2.4]hept-5-ene 

Relevant articles and documents

Directed Regioselective Carbometallation of 1,2-Dialkyl-Substituted Cyclopropenes

A regio- and diastereoselective copper-catalyzed carbomagnesiation of 1,2-dialkylated cyclopropenes is reported. The regioselectivity is controlled by a subtle tethered Lewis basic moiety. The chelating moieties allow the differentiation between two electronically tantamount organometallic intermediates. Further functionalization grants access to polysubstituted stereodefined cyclopropanes bearing up to five alkyl groups.

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.

Boron Complexes With Gradual 1- Methylcyclopropene Releasing Capability

Compounds having one of the following formulae: wherein R1 and R2 are alkyl or aryl and R1 and R2 may be the same or different, wherein R1 is alkyl o aryl, or wherein alkyl is a liner or branched, saturated or unsaturated alkyl having C1-20 and wherein aryl is an aromatic ring having C1-15. Also methods of using the compounds, including method of inhibiting and ethylene response in a plant.

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

Highly efficient synthesis of methylenecyclopropane

An efficient procedure for the preparation of methylenecyclopropane (3), a valuable starting material in organic synthesis, has been developed from methallyl chloride (1) and alkali metal [bis(trimethylsilyl)]amide [M(BTMSA) (M = Na, K), 2b,c]. The advantages of this new method are the higher yield of methylenecyclopropane up to 79% and a homogenous reaction mixture, i.e. both substrates are soluble in organic solvents such as toluene and dibutyl ether.

Products from photochemical reactions and electrochemical oxidation of methylenecyclopropane

The reactivity of methylenecyclopropane (MCP, 1) and its radical cation (1+.) have been studied in the presence and absence of a nucleophile (methanol). Photochemical reactions of 1 in the presence of an electron-acceptor (1,4-dicyanobenzene, 6) and a codonor (biphenyl, 7) in acetonitrile (with and without methanol present) or chloroform lead to cycloadditions (ortho, meta, and para; products 12-17) rather than products from photoinduced electron transfer (PET). Based on the measured (cyclic voltammetry, CV) oxidation potential, using the Weller equation, electron transfer (ET) was predicted to occur. It was shown that the measured oxidation potential of 1 represents the adiabatic ionization potential. For PET processes the value for the vertical ionization potential must be used. Electrochemical (EC) generation of 1+. without a nucleophile present results in the formation of one major product: tert-butyl acetamide (25). A series of rearrangements leading to the tert-butyl cation is proposed. Addition of a nucleophile (methanol) to the mixture leads to the formation of 3-methoxy-2-(methoxymethyl)-1-propene (26). This product may arise from trapping of the initially formed ring-opened (trimethylenemethane) radical cation (1a+.), which undergoes a second oxidation and nucleophilic addition (ECE).

Laser-Powered Decomposition of Spiroalkanes (n = 2-5)

The laser heating of spiroalkanes (n=2-5) and of their 1,1,2,2-tetradeuterated isotopomers reveals dissimilar modes of their thermal decomposition.Spiropentane decomposes into ethene and propadiene via two competing routes: the direct cleavage and the more important cleavage via intermediary methylenecyclobutane.Spirohexane decomposes through two important concurrent pathways which are the expulsions of ethene from the three-membered ring and a more feasible expulsion of ethene from the four-membered ring.Spiroheptane and spirooctane decompose by a radical-chain mechanism and afford complex mixtures of products; upon addition of propene both compounds rearrange into two cycloalkanes wherein the larger ring of the spiroalkane is preserved and substituted with ethylidene and a vinyl group.