143394-10-9

Basic information

• Product Name: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol
• Synonyms: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol
• CAS NO: 143394-10-9
• Molecular Weight: 166.22
• Mol File: 143394-10-9.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol(143394-10-9)
• EPA Substance Registry System: (S,S)-α,α'-dimethyl-1,4-benzenedimethanol(143394-10-9)

Safety Data

• Hazardous Substances Data: 143394-10-9(Hazardous Substances Data)

Upstream product

• 108124-68-1 α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 108-22-5 Isopropenyl acetate 
• 6781-43-7 1,4-bis(1-hydroxyethyl)benzene 
• 627-93-0 hexanedioic acid dimethyl ester 
• 1009-61-6 1,4-Diacetylbenzene 
• 912334-66-8 C₁₈H₂₆O₄ 
• 143329-80-0 (R,R)-α,α'-dimethyl-1,4-benzenedimethanol diacetate 
• 105-05-5 1,4-diethylbenzene 
• 935-14-8 1,4-diethynylbenzene 
• 101219-72-1 (S)-1-(4-ethylphenyl)ethan-1-ol 

Relevant articles and documents

Chiral polyesters by dynamic kinetic resolution polymerization

(Figure Presented) Problem resolved: Enzymatic polymerization was combined with an in situ Rucatalyzed racemization process. The reaction mixture comprises a racemic mixture of a chiral diol and dimethyl adipate. Because of the high stereoselectivity of the enzyme Candida antarctica lipase B (CALB), the S-configured stereocenters of the chiral diol are practically nonreactive. Polycondensation was achieved by concurrent racemization of the S- into the R-configured centers.

One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis

A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF3SO3H and a fluorinated chiral diamine Ru(ii) complex in aqueous CF3CH2OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.

Mechanistic basis for the enantioselectivity of the anaerobic hydroxylation of alkylaromatic compounds by ethylbenzene dehydrogenase

The enantioselectivity of reactions catalyzed by ethylbenzene dehydrogenase, a molybdenum enzyme that catalyzes the oxygen-independent hydroxylation of many alkylaromatic and alkylheterocyclic compounds to secondary alcohols, was studied by chiral chromatography and theoretical modeling. Chromatographic analyses of 22 substrates revealed that this enzyme exhibits remarkably high reaction enantioselectivity toward (S)-secondary alcohols (18 substrates converted with > 99% ee). Theoretical QM:MM modeling was used to elucidate the structure of the catalytically active form of the enzyme and to study the reaction mechanism and factors determining its high degree of enantioselectivity. This analysis showed that the enzyme imposes strong stereoselectivity on the reaction by discriminating the hydrogen atom abstracted from the substrate. Activation of the pro(S) hydrogen atom was calculated to be 500 times faster than of the pro(R) hydrogen atom. The actual hydroxylation step (i.e., hydroxyl group rebound reaction to a carbocation intermediate) does not appear to be enantioselective enough to explain the experimental data (the calculated rate ratios were in the range of only 2-50 for pro(S): pro(R)-oriented OH rebound).