484066-24-2

Basic information

• Product Name: (S)-Me₃CN(a)CHCHN(b)[CH(Ph)Me]B-NC(N(a)-B)
• CAS NO: 484066-24-2
• Molecular Weight: 253.155
• Mol File: 484066-24-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-Me₃CN(a)CHCHN(b)[CH(Ph)Me]B-NC(N(a)-B)(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Me₃CN(a)CHCHN(b)[CH(Ph)Me]B-NC(N(a)-B)(484066-24-2)
• EPA Substance Registry System: (S)-Me₃CN(a)CHCHN(b)[CH(Ph)Me]B-NC(N(a)-B)(484066-24-2)

Safety Data

• Hazardous Substances Data: 484066-24-2(Hazardous Substances Data)

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 506-64-9 silver(I) cyanide 
• 484066-18-4 (S)-Me₃CN(a)CHCHN(b)[CH(Ph)Me]BBr(N(a)-B) 
• 484066-16-2 tert-Butyl-[2-[(E)-(S)-1-phenyl-ethylimino]-eth-(E)-ylidene]-amine 

Relevant articles and documents

Chiral 2,3-dihydro-1H-1,3,2-diazaboroles

A series of differently substituted chiral 2,3-dihydro-1H-1,3,2-diazaboroles has been prepared by various methods. 2-Bromo-1-tert-butyl-3-[(S)-1-phenylethyl]-2,3-dihydro-1H-1,3,2-diazaborole (3a), 2-bromo-1,3-di[(S)-l-phenylethyl]-2,3-dihydro-1H-1,3,2-diazaborole (3b) and 2-bromo-1,3-di[(S)-1-cyclohexylethyl]-2,3-dihydro-1H-1,3,2-diazaborole (3c) were formed from the reaction of the corresponding 1,4-diazabutadienes and boron tribromide and the subsequent reduction of the resulting borolium salts [R1Na = CH-CH= Nb(R2)BBr2] Br(Na-B) [2a: R1 = tBu, R2 = CH(Me)Ph; 2b: R1 = R2 = CH(Me)Ph; 2c: R1 = R2 = CH(Me)(cC6H11)] with sodium amalgam. Treatment of (S)-3a with LiAlH4 or methyllithium afforded 1-tert-butyl-2-hydro-3-[(S)-1-phenylethyl]-2,3-dihydro-1H-1,3,2-diazaborole [(S)-6] and 1-tert-butyl-2-methyl-3-[(S)-1-phenylethyl]-2-3-dihydro-1H-1,3,2-diazaborole [(S)-7], respectively. Aminolysis of the BBr bond of (S)-3a by tertbutylamine or (S)-1-phenylethylamine gave the corresponding 2-tert-butylamino- and 2-[1-phenylethylamino]-2,3-dihydro-1H-1,3,2-diazaboroles (S)-8 and (S,S)-9, respectively. Similarly, (S,S)-3b and (S,S)-3c were reacted with tert-butylamine to furnish the 2-tert-butylamino-2,3-dihydro-1H-1,3,2-diazaborole derivatives (S,S)-11 and (S,S)-12, respectively. The 2-trimethylstannyl-2,3-dihydro-1H-1,3,2-diazaboroles (S,S)-10 and (S,S)-14 were accessible from 3b or 3c and trimethylstannyllithium. The transformation of achiral 2-bromo-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaborole into the chiral (S)-2-[1-phenylethylamino] and (S)-2-[1-cyclohexyl-ethylamino] derivatives (S)-15 and (S)-16 was effected by aminolysis with enantiomerically pure (S)-1-phenylethylamine or (S)-1-cyclohexylethylamine. The novel compounds were characterized by 1H, 11B, 13C, and 119Sn NMR spectroscopy as well as mass spectrometry and determination of the optical rotation. The molecular structure of compound 3c was confirmed by X-ray structural analysis. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.