157142-25-1

Basic information

• Product Name: 6,7-Bis(methylene)-4,8-dodecadiyne
• CAS NO: 157142-25-1
• Molecular Weight: 186.297
• Mol File: 157142-25-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 6,7-Bis(methylene)-4,8-dodecadiyne(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-Bis(methylene)-4,8-dodecadiyne(157142-25-1)
• EPA Substance Registry System: 6,7-Bis(methylene)-4,8-dodecadiyne(157142-25-1)

Safety Data

• Hazardous Substances Data: 157142-25-1(Hazardous Substances Data)

Upstream product

• 1653-19-6 2,3-dichlorobuta-1,3-diene 
• 41246-05-3 pent-1-ynyl-magnesium bromide 
• 627-19-0 1-Pentyne 

Relevant articles and documents

Novel dienes and dienophiles, VII: Preparation and chemical behavior of 2,3-diethynyl-1,3-butadiene

The two 2,3-diethynyl-1,3-butadiene derivatives 1b and 1c were prepared from 2,3-dichloro-1,3-butadiene (26) and the Grignard reagents 19b and 19c by Kumada coupling. Desilylation of 1b provided the parent molecule 1a. The title compounds were used for the preparation of numerous new enediyne systems by [2 + 4] cycloaddition. The dienophiles employed include maleic anhydride (27a), diethyl fumarate (29), tetracyanoethylene (31), diethyl azodicarboxylate (33), and dimethyl acetylenedicarboxylate (35). With p-quinones such as p-benzoquinone (44) as dienophiles the expected mono-and bisadducts are formed which were dehydrogenated to the bis- and tetrakis(trimethylsilylethynyl)naphtho- and -anthraquinones 47 and 48, respectively, by treatment with DDQ. Heating of 1b in THF at 65°C caused dimerization to the 1,5-cyclooctadiene derivative 56, which was desilylated to 1,2,5,6-tetraethynyl-1,5-cyclooctadiene (59) by treatment with potassium fluoride in DMF. 1b is approximately 15 times less reactive than 2,3-dimethyl-1,3-butadiene (54) towards maleic anhydride (27a). VCH Verlagsgesellschaft mbH, 1996.