74892-78-7

Basic information

• Product Name: threo-2-bromo-1,2-diphenylethanol
• Synonyms: threo-2-bromo-1,2-diphenylethanol
• CAS NO: 74892-78-7
• Molecular Weight: 277.161
• Mol File: 74892-78-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: threo-2-bromo-1,2-diphenylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: threo-2-bromo-1,2-diphenylethanol(74892-78-7)
• EPA Substance Registry System: threo-2-bromo-1,2-diphenylethanol(74892-78-7)

Safety Data

• Hazardous Substances Data: 74892-78-7(Hazardous Substances Data)

Upstream product

• 1439-07-2 trans-Stilbene oxide 
• 1484-50-0 desyl bromide 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1689-71-0 cis-1,2-diphenyloxirane 

Downstream Products

• 947-91-1 Diphenylacetaldehyde 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 13027-48-0 rac-1,2-dibromo-1,2-diphenylethane 
• 13921-79-4 trans-(1-bromo-2-methoxyethane-1,2-diyl)dibenzene 
• 13921-79-4 erythro-1-bromo-2-methoxy-1,2-diphenylethane 
• 59982-09-1 erythro-1,2-diphenyl-1-bromo-2-fluoroethane 
• 59974-31-1 C₁₄H₁₂BrF 
• 19456-17-8 (4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one 
• 1439-07-2 trans-Stilbene oxide 

Relevant articles and documents

Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone

An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.

Regio- and stereoselective ring opening of 2,3-diaryl oxiranes by LiBr/Amberlyst 15: A new stereocontrolled access to 1,2-diaryl-2-bromo alcohols

(Chemical Equation Presented) Both symmetrical and non symmetrical trans-2,3-diaryloxiranes are regio- and stereoselectively opened by the LiBr/Amberlyst 15 system. In the case of symmetrical trans-stilbene oxide, the syn-versus anti-bromohydrins ratio ranged between 88/12 and 30/70, by varying the reaction temperature from 20 to -30°C. In the case of nonsymmetrical para -substituted trans-2,3-diaryloxiranes, the regioselectivity is determined by electronic effects. If one phenyl bears a strong electron-withdrawing group (as NO2 or CF3), the nucleophilic attack is totally on the β-carbon with respect to the substituted phenyl ring. With one phenyl bearing a strong electron-releasing group (OCH3), the regioselectivity is reversed. Ab initio calculation at the DFT/B3LYP/6- 31G* level, run on protonated epoxide structures, supports the formation of a cationic acyclic intermediate. Application of the method on ortho-methoxy and ortho-nitro 2,3-diaryloxiranes afforded the syn-bromohydrins in excellent yield, via regio- and stereoselective opening at either α- or β-carbon, respectively.

Single route to chiral syn- and anti-2-amino-1,2-diphenylethanols via a new stereodivergent opening of trans-1,2-diphenyloxirane

Oxiranyl ring opening of trans-stilbene oxide gave rise to anti- or syn-2-bromo-1,2-diphenylethanols, using either MgBr2·Et2O or MgBr2·Et2O, NaBr, and KBr with Amberlyst 15, respectively. Starting from optically pure (R,R)-trans-stilbene oxide, (1R,2R)- and (1R,2S)-2-amino-1,2-diphenylethanols were obtained in high yield and ee.