116377-23-2

Basic information

• Product Name: 2-cyano-3-(3',4',5'-trimethoxybenzyl)-4-methylanisole
• CAS NO: 116377-23-2
• Molecular Weight: 327.38
• Mol File: 116377-23-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-cyano-3-(3',4',5'-trimethoxybenzyl)-4-methylanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-3-(3',4',5'-trimethoxybenzyl)-4-methylanisole(116377-23-2)
• EPA Substance Registry System: 2-cyano-3-(3',4',5'-trimethoxybenzyl)-4-methylanisole(116377-23-2)

Safety Data

• Hazardous Substances Data: 116377-23-2(Hazardous Substances Data)

Upstream product

• 22002-45-5 2-bromo-4-methylanisole 
• 13338-63-1 2-(3,4,5-trimethoxyphenyl)acetonitrile 

Relevant articles and documents

Synthesis of Polysubstituted Benzenes via the Tandem Addition-Rearrangement Aryne Reaction of Substituted 2-Bromoanisoles

Lithioarenenitriles add regiospecifically to substituted 3-methoxybenzynes generated in situ from the corresponding haloarenes by using lithium diisopropylamide as a base.The addition to methoxybenzynes substituted with an electron-releasing group is followed by rearrangement to substituted 2-cyano-3-(arylmethyl)anisoles.The rearrangement pathway involves cyclization of the initially formed nitrile-aryne adducts to benzocyclobutanone imines which are converted to rearranged products after ring opening and neutralization.In contrast, 3-methoxybenzynes substituted withan electron-attracting group proceed via the usual aryne pathway, yielding products of simple anion addition.Disubstituted 3-methoxybenzynes possessing an electron-releasing group and an electron-attracting substituent yield mixtures of rearranget and typical nitrile products.An explanation in terms of the ability of the substituents to influence the nucleophilicity of the 2-lithio cyclization site of the initially formed nitrile-aryne adducts is presented.