172585-06-7

Basic information

• Product Name: (S,S)-(+)-1,2-bis(2-methylphenyl)ethane-1,2-diol
• Synonyms: (S,S)-(+)-1,2-bis(2-methylphenyl)ethane-1,2-diol
• CAS NO: 172585-06-7
• Molecular Weight: 242.318
• Mol File: 172585-06-7.mol

Chemical Properties

• CAS DataBase Reference: (S,S)-(+)-1,2-bis(2-methylphenyl)ethane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-(+)-1,2-bis(2-methylphenyl)ethane-1,2-diol(172585-06-7)
• EPA Substance Registry System: (S,S)-(+)-1,2-bis(2-methylphenyl)ethane-1,2-diol(172585-06-7)

Safety Data

• Hazardous Substances Data: 172585-06-7(Hazardous Substances Data)

Upstream product

• 36888-18-3 (E)-2,2'-dimethylstilbene 
• 529-20-4 2-methylphenyl aldehyde 
• 89-92-9 2-methylbenzyl bromide 
• 191283-14-4 3,4,4a,5,6,7-hexahydro-5,5-dimethyl-4'S,5'S-bis(2-methylphenyl)spiro[8H-2-benzopyran-3,2'-[1,3]-dioxolan]-8-one 
• 253446-53-6 3,4,4a,5,6,7-hexahydro-5,5-dimethyl-4'S,5'S-bis(2-methylphenyl)spiro[8H-2-benzopyran-3,2'-[1,3]-dioxolan]-8-ol 
• 92431-56-6 (2-methylbenzyl) phosphonic acid diisopropyl ester 
• 191283-22-4 (S,S,S)-1,2-bis(2-methylphenyl)-2-hydroxyethyl (2-formyl-6,6-dimethyl-2-cyclohexen-1-yl)acetate 
• 67-56-1 methanol 
• 692-48-8 (E)-2,2,5,5-tetramethylhex-3-ene 

Downstream Products

• 172277-06-4 (4S,5S)-2-Bromomethyl-4,5-di-o-tolyl-[1,3]dioxolane 
• 302842-98-4 (5S,6S)-5,6-Di-o-tolyl-[1,4]dioxan-2-one 
• 172276-99-2 (4aR,4'S,5'S)-4',5'-bis(2-methylphenyl)-4,4a-dihydrospiro<3H,10H-pyrano<4,3-b><1>benzopyran-3,2'-<1,3>dioxolan>-10-one 

Relevant articles and documents

Truly catalytic and enantioselective pinacol coupling of aryl aldehydes mediated by chiral Ti(III) complexes

A variety of chiral Ti(IV) complexes were reduced in situ with zinc in acetonitrile. The resulting chiral Ti(III) complexes were found to catalyze the pinacol coupling reaction stereoselectively. The best results were obtained from the Ti-SALEN complex, which was found to be an efficient catalyst at 10 mol % concentration. Various aromatic aldehydes were coupled to obtain chiral hydrobenzoin derivatives with high diastereoselectivity and enantioselectivity. A plausible mechanism is proposed that rationalizes the stereochemical outcome of the reaction.

Enantioselective pinacol coupling reaction of aromatic aldehydes catalyzed by chiral vanadium complexes

The asymmetric pinacol coupling of aromatic aldehydes by chiral salan-vanadium complexes as effective catalysts is reported. Chiral 1,2-diols were obtained with high diastereoselectivities (up to 90/10) and moderate to high enantioselectivities (up to 82%

Enantioselective pinacol coupling of aryl aldehydes catalyzed by chiral Salan-Mo(IV) complexes

(Chemical Equation Presented) Reported herein is the asymmetric pinacol coupling of aromatic aldehydes with chiral Salan-Mo(VI) dioxo complex as an effective precatalyst. Chiral diols were obtained with high diastereoselectivity and enantioselectivity up

Catalytic enantioselective and catalyst-controlled diastereofacial- selective additions of allyl- and crotylboronates to aldehydes using chiral Bronsted acids

(Chemical Equation Presented) Towards the ideal: A chiral diol-SnCl 4 complex is applied to the allylboration of aldehydes (see scheme). This approach highlights the use of chiral Bronsted acid catalysis in the development of an ideal method for the allylation of aldehydes which would display high diastereo- and enantioselectivity, wide substrate scope, and high practicality (ease of use, low cost, and low environmental impact).

Enantioselective pinacol coupling of aldehydes mediated and catalyzed by chiral titanium complexes

equation presented Starting from easily available chiral Schiff bases, a straightforward synthesis of air-stable titanium(IV) complexes was devised. Asymmetric pinacol coupling of aromatic aldehydes mediated and catalyzed by the corresponding low valent complexes afforded the chiral diols with high yields and enantioselectivities up to 91%. ? Universite catholique de Louvain. ? Universite Paris-Sud.

Anti-selective glycolate aldol additions with an oxapyrone boron enolate

The boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2-diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92%

Stereo- and enantioselective routes to functionalised cyclohexenes via heterodiene cycloadditions of 6-oxocyclohexene-1-carbaldehydes with ketene acetals

Various substituted cyclohexenes related to α-cyclocitral have been prepared using the heterodiene cycloadditions of 2-formyl-4,4-dimethyl-2- cyclohexen-1-one 4 with ketene acetals as the pivotal step. The key intermediates are accessible in homochiral form via an auxiliary-based sequence in which a C2-symmetric ketene acetal derived from 1,2-bis(2- methylphenyl)ethane-1,2-diol 2a serves as the 2π component. The diol 2a can be recovered in optically pure form.

The use of homochiral 2-methylene-4,5-diaryl-1,3-dioxolanes as recyclable acetic ester enolate equivalents: asymetric synthesis of terpenoids

The α-cyclocitral derivatives 5 and 10 are accessible in homochiral form via an auxiliary-based sequence using the heterodiene cycloaddition of a 2-methylene-4,5-diaryl-1,3-dioxolane 1 to 2-formyl-4,4-dimethyl-2-cyclohexen-1-one 2 as the key step.

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.