170222-00-1

Basic information

• Product Name: (S)-1-(4-methoxyphenyl)ethyl-1,3,2-benzodioxaborole
• Synonyms: (S)-1-(4-methoxyphenyl)ethyl-1,3,2-benzodioxaborole
• CAS NO: 170222-00-1
• Molecular Weight: 254.093
• Mol File: 170222-00-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-1-(4-methoxyphenyl)ethyl-1,3,2-benzodioxaborole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(4-methoxyphenyl)ethyl-1,3,2-benzodioxaborole(170222-00-1)
• EPA Substance Registry System: (S)-1-(4-methoxyphenyl)ethyl-1,3,2-benzodioxaborole(170222-00-1)

Safety Data

• Hazardous Substances Data: 170222-00-1(Hazardous Substances Data)

Upstream product

• 637-69-4 4-Methoxystyrene 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 

Downstream Products

• 188198-35-8 [(S)-1-(4-Methoxy-phenyl)-ethyl]-dimethyl-borane 
• 285132-40-3 CH₃OC₆H₄CH(CH₃)B(C₂H₅)2 
• 281664-25-3 (R)-(+)-N-4-Methoxybenzyl-1-(4-methoxyphenyl)ethylamine 
• 14429-03-9 (R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine 
• 120343-46-6 (S)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine 
• 1517-70-0 (S)-1-(4-Methoxyphenyl)ethanol 
• 1517-70-0 (R)-1-(4-Methoxyphenyl)ethanol 

Relevant articles and documents

Metal promoted asymmetry in the 1,2-diboroethylarene synthesis: Diboration versus dihydroboration

Metal catalysed addition of diboranes to vinylarenes produces the desired 1,2-bis(boronate)ester and mono(boronate)esters as by-products. Their relative rate is a sensitive function between the nature of the catalytic system and the electronic effects of the substrate, that influences the mechanistic steps of the catalytic cycle. However, asymmetry is only induced as moderate enantiomeric excess values, providing an enantioface differentiation, between the bis- and mono(boronate)esters. Alternatively, the method based on the catalytic asymmetric dihydroboration/oxidation of alkynes as diphenylacetylene can provide 1,2-diphenyl-1,2-ethanediol (hydrobenzoin) with a selectivity of 68% mainly as the erythro isomer.

Catalytic asymmetric hydroboration/amination and alkylamination with rhodium complexes of 1,1′-(2-diarylphosphino-1-naphthyl)isoquinoline

Catecholboronate esters formed by asymmetric hydroboration of arylalkenes are not directly converted to amines by reaction with hydroxylamine-O-sulfonic acid. Prior conversion to a trialkylborane by reaction with ZnEt2 or MeMgCl permits a subsequent amination reaction to occur with essentially complete retention of configuration, leading to a range of primary α-arylalkylamines in up to 97% enantiomeric excess (ee). Secondary, but not tertiary amines may be formed by a related pathway when in situ generated alkylchloramines are employed as the aminating agent. The catalytic asymmetric hydroboration, β-alkylation and amination steps may be combined in a single stage. Overall, this provides a practical procedure for the synthesis of enantiomerically enriched arylamines, exemplified inter alia by the synthesis of (S)-1,2,3,4-tetrahydro-1-naphthylamine in 95-97% ee and of (R)-N-(cyclohexyl)-1′-(4-methoxyphenyl)ethylamine in 93 % ee.