1251715-87-3

Basic information

• Product Name: (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate
• Synonyms: (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate
• CAS NO: 1251715-87-3
• Molecular Weight: 510.595
• Mol File: 1251715-87-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate(CAS DataBase Reference)
• NIST Chemistry Reference: (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate(1251715-87-3)
• EPA Substance Registry System: (1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium-2-yl)(phenylthio)dihydroborate(1251715-87-3)

Safety Data

• Hazardous Substances Data: 1251715-87-3(Hazardous Substances Data)

Upstream product

• 2973-86-6 lithium thiophenoxide 
• 108-98-5 thiophenol 
• 956972-12-6 1,3-bis(2,6-diiopropylphenyl)imidazol-2-ylidene borane 
• 882-33-7 diphenyldisulfane 

Relevant articles and documents

Mechanistic and preparative studies of radical chain homolytic substitution reactions of n-heterocyclic carbene boranes and disulfides

Reactions of 1,3-dimethylimidazol-2-ylidene-borane (diMe-Imd-BH 3) and related NHC-boranes with diaryl and diheteroaryl disulfides provide diverse NHC-boryl monosulfides (diMe-Imd-BH2SAr) and NHC-boryl disulfides (diMe-Imd-BH(SAr)2). Heating in the dark with 1 equiv of disulfide favors monosulfide formation, while irradiation with 2 equiv disulfide favors disulfide formation. With heteroaryl disulfides, the NHC-borane in the primary NHC-boryl sulfide product migrates from sulfur to nitrogen to give new products with a thioamide substructure. Most substitution reactions are thought to proceed through radical chains in which homolytic substitution of a disulfide by an NHC-boryl radical is a key step. However, with electrophilic disulfides under dark conditions, a competing ionic path may also be possible.