88180-40-9

Basic information

• Product Name: Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 8-methylene-
• CAS NO: 88180-40-9
• Molecular Formula: C9H6O
• Molecular Weight: 130.146
• Mol File: 88180-40-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 8-methylene-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 8-methylene-(88180-40-9)
• EPA Substance Registry System: Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 8-methylene-(88180-40-9)

Safety Data

• Hazardous Substances Data: 88180-40-9(Hazardous Substances Data)

Upstream product

• 1020701-98-7 benzofuran-2-ylmethyl benzoate 
• 1020701-94-3 benzoic 3-methyl-2-benzofurancarboxylic anhydride 
• 1020701-95-4 benzoic 2-methyl-3-benzofurancarboxylic anhydride 
• 200957-26-2 (7-oxa-1-benzonorbornenyl)methyl benzoate 

Downstream Products

• 480-90-0 1H-inden-1-one 
• 38846-64-9 2-ethynylbenzaldehyde 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Syntheses and pyrolyses of benzofuran analogues of α-oxo-o- quinodimethane. A study on vinylcarbene-cyclopropene rearrangement

(Chemical Equation Presented) Flash vacuum pyrolyses (FVP) of benzoic 3-methyl-2-benzofurancarboxylic anhydride (12) and benzoic 2-methyl-3- benzofurancarboxylic anhydride (13) at 550°C and ca. 10-2 torr both give methylenebenzocyclobutenone (21) as the major product and indenone (22) as the minor one. A mechanism involving generation of α-oxo-o- quinodimethane 11 as the primary pyrolysis product from FVP of 13, followed by elimination of a CO molecule to give carbene 24, which undergoes a vinylcarbene-cyclopropene rearrangement and a ring contraction of the resulting carbene 23, is proposed to account for the observed results. The proposed mechanism is further supported by a deuterium-labeling study on FVP of (2-benzofuryl)methyl-α,α-d2 benzoate (28-d2).