179914-05-7

Basic information

• Product Name: 1,2-Ethanediol, 1-(4-methylphenyl)-, (1R)-
• CAS NO: 179914-05-7
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• Mol File: 179914-05-7.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: 1,2-Ethanediol, 1-(4-methylphenyl)-, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol, 1-(4-methylphenyl)-, (1R)-(179914-05-7)
• EPA Substance Registry System: 1,2-Ethanediol, 1-(4-methylphenyl)-, (1R)-(179914-05-7)

Safety Data

• Hazardous Substances Data: 179914-05-7(Hazardous Substances Data)

Upstream product

• 13107-39-6 2-(4-methylphenyl)oxirane 
• 620986-95-0 1,2-bis(trichlorosilyl)-1-(4-methylphenyl)ethane 
• 104-87-0 4-methyl-benzaldehyde 
• 798567-54-1 tert-butyl benzothiazolidine-3-carboxylate 
• 148312-55-4 tert-butyl thiazolidine-3-carboxylate 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 647026-46-8 (R)-2-hydroxy-2-(4-methylphenyl)ethyl acetate 
• 13107-39-6 (R)-4-methylstyrene oxide 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 13107-39-6 (S)-4-methylstyrene oxide 
• 1505-50-6 3-(4-Methylphenyl)propanoic acid 
• 13603-62-8 1-(4-methylphenyl)-1,2-ethanediol 
• 100-52-7 benzaldehyde 
• 35675-44-6 4-methylphenylacetyl chloride 

Downstream Products

• 97642-98-3 (R)-1-(4'-methylphenyl)-2-aminoethanol 
• 18584-20-8 (R)-para-methylmandelic acid 
• 1402850-54-7 C₁₉H₂₁NO₃S 
• 1402850-55-8 C₁₉H₂₁NO₃S 
• 603123-92-8 4-((7S)-7-{[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]amino}-5,6,7,8-tetrahydro-2-naphthalenyl)benzoic acid hydrochloride 
• 603124-15-8 C₃₁H₃₅NO₅ 
• 603123-08-6 methyl 4-[(7S)-7-{(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(4-methylphenyl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-2-yl]benzoate 
• 13107-39-6 (R)-4-methylstyrene oxide 
• 851372-03-7 (R)-1-(4-methylphenyl)-2-(p-tolylsulfonyloxy)ethanol 

Relevant articles and documents

Structure-Guided Regulation in the Enantioselectivity of an Epoxide Hydrolase to Produce Enantiomeric Monosubstituted Epoxides and Vicinal Diols via Kinetic Resolution

Structure-guided microtuning of an Aspergillus usamii epoxide hydrolase was executed. One mutant, A214C/A250I, displayed a 12.6-fold enhanced enantiomeric ratio (E = 202) toward rac-styrene oxide, achieving its nearly perfect kinetic resolution at 0.8 M in pure water or 1.6 M in n-hexanol/water. Several other beneficial mutants also displayed significantly improved E values, offering promising biocatalysts to access 19 structurally diverse chiral monosubstituted epoxides (97.1 - ≥ 99% ees) and vicinal diols (56.2-98.0% eep) with high yields.

Syn-dihydroxylation of alkenes using a sterically demanding cyclic diacyl peroxide

The syn-dihydroxylation of alkenes is a highly valuable reaction in organic synthesis. Cyclic acyl peroxides (CAPs) have emerged recently as promising candidates to replace the commonly employed toxic metals for this purpose. Here, we demonstrate that the structurally demanding cyclic peroxide spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione (P4) can be effectively used for the syn-dihydroxylation of alkenes. Reagent P4 also shows an improved selectivity for dihydroxylation of alkenes bearing β-hydrogens as compared to other CAPs, where both diol and allyl alcohol products compete with each other. Furthermore, the use of enantiopure P4 (labeled P4′) demonstrates the potential of P4′ for a metal-free asymmetric syn-dihydroxylation of alkenes.

Exploiting Designed Oxidase-Peroxygenase Mutual Benefit System for Asymmetric Cascade Reactions

A unique P450 monooxygenase-peroxygenase mutual benefit system was designed as the core element in the construction of a biocatalytic cascade reaction sequence leading from 3-phenyl propionic acid to (R)-phenyl glycol. In this system, P450 monooxygenase (P450-BM3) and P450 peroxygenase (OleTJE) not only function as catalysts for the crucial initial reactions, they also ensure an internal in situ H2O2 recycle mechanism that avoids its accumulation and thus prevents possible toxic effects. By directed evolution of P450-BM3 as the catalyst in the enantioselective epoxidation of the styrene-intermediate, formed from 3-phenyl propionic acid, and the epoxide hydrolase ANEH for final hydrolytic ring opening, (R)-phenyl glycol and 9 derivatives thereof were synthesized from the respective carboxylic acids in one-pot processes with high enantioselectivity.