58469-00-4

Basic information

• Product Name: Benzene, [(2-methyl-2-butenyl)thio]-, (Z)-
• CAS NO: 58469-00-4
• Molecular Formula: C11H14S
• Molecular Weight: 178.298
• Mol File: 58469-00-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzene, [(2-methyl-2-butenyl)thio]-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(2-methyl-2-butenyl)thio]-, (Z)-(58469-00-4)
• EPA Substance Registry System: Benzene, [(2-methyl-2-butenyl)thio]-, (Z)-(58469-00-4)

Safety Data

• Hazardous Substances Data: 58469-00-4(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 78-79-5 isoprene 
• 497-02-9 (E)-2-methyl-2-buten-1-ol 
• 28127-58-4 sec-butyl tiglate 

Relevant articles and documents

Boron Lewis Acid-Catalyzed Regioselective Hydrothiolation of Conjugated Dienes with Thiols

A transition-metal-free hydrothiolation of 1,3-dienes for the synthesis of secondary and tertiary allylic sulfides is reported. The boron Lewis acids tris(pentafluorophenyl)borane, B(C6F5)3, and BF3·Et2O are shown to catalyze the regioselective hydrothiolation of a wide range of terminal 1-aryl-1,3-dienes. In the case of internal 1,3-dienes, B(C6F5)3 is by far the better catalyst than BF3·Et2O. The process features mild reaction conditions, broad scope, and low catalyst loading, and it can be scaled up quickly over a short reaction time. The reactions are rate-limited by the 1-aryl-directed protonation of 1,3-dienes with thiol-boron Lewis acid complexes, followed by sulfide anion transfer to the resultant allyl cations, as revealed by high-level DFT calculations.