172164-19-1

Basic information

• Product Name: (1R,2R)-1,2-bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol
• Synonyms: (1R,2R)-1,2-bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol
• CAS NO: 172164-19-1
• Molecular Weight: 350.26
• Mol File: 172164-19-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2R)-1,2-bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-1,2-bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol(172164-19-1)
• EPA Substance Registry System: (1R,2R)-1,2-bis-(2-trifluoromethyl-phenyl)-ethane-1,2-diol(172164-19-1)

Safety Data

• Hazardous Substances Data: 172164-19-1(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 395-44-8 o-trifluoromethylbenzyl bromide 
• 447-61-0 2-Trifluoromethylbenzaldehyde 
• 128758-66-7 (E)-1,2-bis(2-(trifluoromethyl)phenyl)ethene 

Relevant articles and documents

Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol·SnCl4 complexes. Optimization, substrate scope and mechanistic investigations

We report a novel class of C2-symmetric chiral diols derived from the hydrobenzoin skeleton. The combination of these diols with SnCl 4 under Yamamoto's concept of Lewis acid assisted Bronsted acidity (LBA catalysis) leads to high levels of asymmetric induction in the allylboration of aldehydes by commercially available allylboronic acid pinacol ester 1a. The corresponding homoallylic alcohol products of synthetically useful aliphatic aldehydes are obtained in excellent yields with up to 98:2 er. This combined acid manifold is also efficient in catalyzing the diastereo- and enantioselective crotylboration of aldehydes, thus providing the propionate units in >95:5 dr and up to 98:2 er. The X-ray crystal structure of the optimal diol·SnCl4 complex, Vivol (4m)·SnCl 4, unambiguously shows the Bronsted acidic character of this LBA catalyst and its highly dissymmetrical environment. Further controls have ruled out a possible boron transesterification mechanism with the chiral diol and point to LBA catalyst-derived activation of the pinacol allylic boronates 1. Due to slow dissociation of the diol·SnCl4 complex, a small excess of diol is required in order to suppress a competing racemic cycle catalyzed by free SnCl4.

Heterodiene cycloadditoins of C2 symmetric 4,5-disubstituted ketene acetals: the nett asymmetric conjugate addition of recyclable acetic ester enolate equivalents to an activated enone

Heterodiene cycloadditions of 3-formylchromone 2 to a series of ketene acetals 1 derived from C2 symmetric 1,2-diarylethane-1,2-diols are diastereoselective.From (S,S)-1,2-di(o-tolyl)ethane-1,2-diol 6c the major cycloadduct 3c was isolated by crystallization and transformed by acid-catalysed methanolysis into (S)-methyl 4-oxo-3,4-dihydro-2H-1-benzopyran-2-ylacetate 5, together with the original 1,2-diol 6c which could be recycled.The structures of two cyclic carbonates 22a and 22c were determined by X-ray diffraction and used as models in seeking a mechanistic rationale for the stereoselective cycloadditions of the analogous ketene acetals 1a and 1c.