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4-methylidenecyclobut-2-en-1-one is a chemical compound with the molecular formula C6H8O. It is a cyclic ketone with a double bond and a methyl group attached to the carbon backbone. 4-methylidenecyclobut-2-en-1-one is characterized by its unique structure, which features a four-membered ring with a carbonyl group at position 1 and a methylidene group (a carbon-carbon double bond with a hydrogen atom attached) at position 4. Due to its reactive nature, 4-methylidenecyclobut-2-en-1-one can participate in various chemical reactions, such as cycloadditions and rearrangements, making it a potentially useful intermediate in organic synthesis. Its properties and reactivity are influenced by the strained ring system and the presence of the electron-withdrawing carbonyl group, which can affect its stability and behavior in different chemical environments.

42827-31-6

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42827-31-6 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 42827-31-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,8,2 and 7 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 42827-31:
(7*4)+(6*2)+(5*8)+(4*2)+(3*7)+(2*3)+(1*1)=116
116 % 10 = 6
So 42827-31-6 is a valid CAS Registry Number.

42827-31-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-methylidenecyclobut-2-en-1-one

1.2 Other means of identification

Product number -
Other names Methylenecyclobutanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:42827-31-6 SDS

42827-31-6Relevant academic research and scientific papers

Syntheses and pyrolyses of furan analogues of α-Oxo- o -quinodimethanes. Formation of methylenecyclobutenone and 1-buten-3-yne via a vinylcarbene-cyclopropene rearrangement

Tseng, Pen-Wen,Kung, Chen-Yu,Chen, Hsing-Yin,Chou, Chin-Hsing

experimental part, p. 8440 - 8446 (2011/12/04)

Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3-methyl-2-furoic anhydride (13) at 550 °C and ca. 10 -2 Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of α-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective carbenes 34 and 36 is proposed. Carbenes 34 and 36 are interconvertible via a cyclopropene intermediate 35. A ring contraction from 36 will give 16, whereas a ring-opening of 34 followed by elimination of a CO molecule then leads to 17. The proposed mechanism is supported by substituent- and deuterium-labeling study on FVP of the derivatives of 12.

Butatrien durch Thermolyse von Propiolsaeure-(2-propinyl)ester

Bilinski, Vanda,Dreiding, Andre S.,Hollenstein, Hans

, p. 2322 - 2329 (2007/10/02)

Flow thermolysis of 2-propynyl propiolate (5) at 580 deg C afforded butatriene (6) (ca. 50percent) and as by-products, 4-methylene-2-cyclobuten-1-one (7), 2-ethynylpropenal (8), 1-penten-4-yn-3-one (9), 4-penten-2-ynal (10) (tottal ca. 10percent), along with some propynal, acetylene, CO2 and CO.In the same way, propiolic acid (1,1-D2)-2-propynyl propiolate (11) led to (1,1-D2)-butatriene (12) and a litle 4-((D2)methylene)-2-cyclobuten-1-one (13).A mechanism is proposed for the transformation of 5 into 6 and of 11 into 12, which also accounts for the formation of 7, 8, 9 and 10, as well as 13.The position of one of the published 13C-NMR signal of butatriene (6) must be revised.Thermolysis of methyl-(1) and ethyl propiolate (2) resulted in small yields of 2-buten-4-olide (3) and 2-penten-4-olide (4).

CYCLOBUTENDION UND METHYLENCYCLOBUTENON. SYNTHESE, DIENOPHILE REAKTIVITAET UND EXO, ENDO-SELECTIVITAET

Martin, Hans-Dieter,Oftring, Alfred,Iden, Ruediger,Schwichtenberg, Evelyn,Schiwek, Hans-Joachim

, p. 841 - 844 (2007/10/02)

A new synthesis of cyclobutenedione and methylenecyclobutenone and their reactions with 1,3-dienes are described.

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