139100-52-0

Basic information

• Product Name: 1,3-Benzenedicarbonitrile, 4,6-bis(1,1-dimethylethyl)-
• CAS NO: 139100-52-0
• Molecular Formula: C16H20N2
• Molecular Weight: 240.348
• Mol File: 139100-52-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3-Benzenedicarbonitrile, 4,6-bis(1,1-dimethylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenedicarbonitrile, 4,6-bis(1,1-dimethylethyl)-(139100-52-0)
• EPA Substance Registry System: 1,3-Benzenedicarbonitrile, 4,6-bis(1,1-dimethylethyl)-(139100-52-0)

Safety Data

• Hazardous Substances Data: 139100-52-0(Hazardous Substances Data)

Upstream product

• 626-17-5 benzene-1,3-dicarbonitrile 
• 558-17-8 tert-Butyl iodide 
• 6135-54-2 2-tert-Butyl-2-methyl-1,3-dioxolane 
• 132381-82-9 5-tert-Butyl-1,2,4-Benzenetricarbonitrile 
• 712-74-3 1,2,4,5-tetracyanobenzene 
• 507-19-7 t-butyl bromide 
• 89379-02-2 tert-butylmercury iodide 
• 38442-51-2 tert-butylmercury chloride 

Relevant articles and documents

Homolytic base-promoted aromatic alkylations by alkyl halides

Electron-transfer chain reactions leading to regioselective alkylations of benzenes bearing electron-withdrawing substituents can be observed with alkyl halides in the presence of the radical initiator (Bu3Sn)2 and the proton acceptor 1,4-diazabicyclo[2.2.2]octane (DABCO). Yields vary from low to high depending on the benzene derivatives. The role of DABCO is to abstract a proton from the substituted cyclohexadienyl adduct radical to form a radical anion which then transfers an electron to RX and is converted to the alkylated product itself. The rate of this electron-transfer step is probably not fast enough to sustain a good radical chain reaction so that further generation of R· from excess (Bu3Sn)2 and RX is necessary.

Electron Transfer Photoinduced Cleavage of Acetals. A Mild Preparation of Alkyl Radicals

Electron transfer from 2-alkyl- and 2,2-dialkyldioxolanes as well as from open-chain ketals to singlet excited benzene-1,2,4,5-tetracarbonitrile (TCNB) is followed by fragmentation of the donors radical cation to yield alkyl radicals and dialkoxy carbocations.The first species are trapped by TCNB to yield alkylbenzenetricarbonitriles (substitution of a second cyano group can be obtained sequentially) and in a minor path are reduced to alkanes, while the latter ones react with nucleophiles to give ortho acid derivatives.In view of the results of radical clock experiments, it is assumed that part of the process is a concerted (radical cation cleavage-addition to the aromatic) reaction, while another part involves the free-radical cation.On the other hand, intersystem crossing from the singlet radical ion pair to the triplet manifold causes cleavage of the acetal to the corresponding carbonyl derivative.This reaction offers a mild method for the preparation of alkyl radicals via C-C bonds cleavage.