138777-66-9

Basic information

• Product Name: Benzene, [(1-chloro-2,2-dimethylcyclopropyl)ethynyl]-
• CAS NO: 138777-66-9
• Molecular Formula: C13H13Cl
• Molecular Weight: 204.699
• Mol File: 138777-66-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, [(1-chloro-2,2-dimethylcyclopropyl)ethynyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(1-chloro-2,2-dimethylcyclopropyl)ethynyl]-(138777-66-9)
• EPA Substance Registry System: Benzene, [(1-chloro-2,2-dimethylcyclopropyl)ethynyl]-(138777-66-9)

Safety Data

• Hazardous Substances Data: 138777-66-9(Hazardous Substances Data)

Upstream product

• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 2579-22-8 Phenylpropargyl aldehyde 
• 100-42-5 styrene 
• 34372-27-5 (1-bromo-3,3,3-trichloropropyl)benzene 
• 115-11-7 isobutene 
• 23691-27-2 1,1,1,3-tetrachloro-3-phenylpropane 
• 13524-09-9 (3,3-dichloroprop-1-yn-1-yl)benzene 

Downstream Products

• 1173191-63-3 (5E)-5-benzylidene-7,7-dimethylhexahydro-1H-pyrrolo[1,2-a]imidazole 
• 1173191-64-4 (5Z)-5-benzylidene-7,7-dimethylhexahydro-1H-pyrrolo[1,2-a]imidazole 
• 1173191-66-6 (E)-8,8-dimethyl-6-phenylmethyleneoctahydropyrrolo[1,2-a]pyrimidine 
• 1173191-67-7 (E)-1,8,8-trimethyl-6-phenylmethyleneoctahydropyrrolo[1,2-a]pyrimidine 

Relevant articles and documents

Alkynylhalocarbenes 4. Generation of (alk-1-ynyl)halocarbenes from 3-substituted 1,1,1,3-tetrahalopropanes under the action of bases

When treated with KOH under phase-transfer catalysis or with Bu tOK, 3-substituted (alkyl or phenyl) 1,1,3-tribromo-1-fluoropropanes 1a-c exclusively generate previously unknown (alk-1-ynyl)fluorocarbenes 5a-c, which react with olefins to give 1-(alk-1-ynyl)-1-fluorocyclopropanes 6a-h in 12-69% yields. Under analogous conditions, 3-alkyl- and 3-aryl-3-bromo-1,1,1-trichloropropanes 2a-c selectively afford (alk-1-ynyl)chlorocarbenes 7a-c, which are trapped by olefins to form the corresponding 1-(alk-1-ynyl)-1-chlorocyclopropanes 8a-k in 35-70% yields. (Phenylethynyl)chlorocarbene 7a is also selectively generated from 1,1,1,3-tetrachloro-3-phenylpropane (3a) upon its treatment with Bu tOK. With an excess of 2,3-dimethylbut-2-ene or 2-methylpropene, carbene 7a yields 1-chloro-1-(phenylethynyl)cyclopropanes 8a or 8c, respectively. In contrast, 1,1,1,3-tetrachloroheptane 3b and 3-alkyl- and 3-phenyl-1,1,1,3-tetrabromopropanes 4a,c,f react with bases in the presence of olefins to give, along with the corresponding 1-(alk-1-ynyl) -1-halocyclopropanes 8a,c,d and 11a-f, vinylidenecyclopropanes 12a,c-g, which suggests the generation, under these conditions, both (alk-1-ynyl)halocarbenes 7b and 9a-c and vinylidenecarbenes 10 and 11a-c. The composition and structures of intermediate products in the reactions of tetrahalides 1b, 2a, 2b, 3a, and 3b with ButOK were determined and the mechanisms for carbene generation in these reactions were proposed.

Alkynylhalocarbenes: Generation from 1,1-Dihaloalk-2-ynes by Base Solvolysis and Reaction with Alkenes

A series of 1,1-dihaloalk-2-ynes 1-3 has been prepared by halogenation of the formylacetylenes 8 with PCl5 or an equimolar mixture of PCl5 and Br2.A simple, general means of access to the alkynylhalocarbenes 5 has been developed via base-initiated α-elimination of 1,1-dihalo-2-ynes (1-3).The carbenes 5a-i have been trapped by alkenes, to form 1-alkynyl-1-halocyclopropanes (11) in up to 90percent yield.Under the same conditions compound 1g was converted into the butadiene 12.Experimental evidence for the electrophilicity and the singlet nature of carbenes 5 has been obtained.