(R)-(-)-1-Phenyl-1,2-ethanediol

Base Information

• Chemical Name: (R)-(-)-1-Phenyl-1,2-ethanediol
• CAS No.: 16355-00-3
• Molecular Formula: C8H10O2
• Molecular Weight: 138.166
• Hs Code.: 29062900
• European Community (EC) Number: 640-490-9
• UNII: 2LZM4B71KF
• Nikkaji Number: J65.123K
• Wikidata: Q27254904
• Mol file: 16355-00-3.mol

Synonyms:1,2-Ethanediol, 1-phenyl-, (R)-(-)- (8CI);(-)-(1R)-1-Phenyl-1,2-ethanediol;(-)-1-Phenylethane-1,2-diol;(-)-1-Phenylethylene glycol;(-)-Phenyl glycol;(-)-Styrene glycol;(R)-(-)-1-Phenylethane-1,2-diol;(R)-2-Phenyl-1,2-ethanediol;1R-Phenyl-1,2-ethanediol;

Chemical Property of (R)-(-)-1-Phenyl-1,2-ethanediol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00278mmHg at 25°C
• Melting Point: 64-67 °C(lit.)
• Refractive Index: -40 ° (C=3, H2O)
• Boiling Point: 273.5 °C at 760 mmHg
• PKA: 13.61±0.20(Predicted)
• Flash Point: 145.8 °C
• PSA: 40.46000
• Density: 1.17 g/cm³
• LogP: 0.71230
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 138.068079557
• Heavy Atom Count: 10
• Complexity: 87.3

Purity/Quality:

99% ^*data from raw suppliers

(R)-StyreneGlycol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,T
• Hazard Codes: Xi,T
• Statements: 23/24/25-36/37/38
• Safety Statements: 24/25-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CO)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](CO)O
• Uses: (R)-(-)-1-Phenyl-1,2-ethanediol is an intermediate for the synthesis of enantiopure substituted 1,4-Dioxanes. Extremely valuable and versatile alcohol used as a chiral building block in organic synthesis. Intermediate for the synthesis of chiral phosphine catalysts for asymmetric hydrogenations.

Technology Process of (R)-(-)-1-Phenyl-1,2-ethanediol

There total 188 articles about (R)-(-)-1-Phenyl-1,2-ethanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

1-phenyl-2-hydroxyethanone (582-24-1) → (R)-1-phenyl-1,2-ethanediol (16355-00-3)

Guidance literature:

With β-D-glucose; In aq. phosphate buffer; at 35 ℃; for 24h; pH=7.5; Temperature; pH-value; Solvent; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1016/j.procbio.2015.08.002

Reference yield: 99.0%

phenylglyoxal hydrate (1074-12-0) → (R)-1-phenyl-1,2-ethanediol (16355-00-3)

Guidance literature:

With D-glucose; D-glucose dehydrogenase; β-nicotinamide adenine dinucleotide 2'-phosphate reduced tetra(cyclohexylammonium) salt; carbonyl reductase from Pichia pastoris GS₁₁₅; sodium hydroxide; In aq. phosphate buffer; dimethyl sulfoxide; at 20 ℃; for 12h; pH=6.5; Enzymatic reaction;

DOI:10.1016/j.tet.2013.02.085

Reference yield: 98.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → (R)-1-phenyl-1,2-ethanediol (16355-00-3)

Guidance literature:

With 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(03)00023-5

upstream raw materials:

2-chloro-benzaldehyde

(R)-methyl mandelate

styrene

styrene oxide

Downstream raw materials:

(R)-Styrene oxide

(R)-(-)-1-phenyl-2-(pyrrolidin-1-yl)ethanol

2-methoxy-2-methyl-4-phenyl-1,3-dioxolane

(R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide

Refernces

• 1、 Uccello-Barretta, Gloria,Balzano, Federica,Quintavalli, Cristiana,Salvadori, Piero. "Different enantioselective interaction pathways induced by derivatized quinines". . p. 3596 - 3602. Retrieved 2000.
• 2、 Horsman, Geoffrey P.,Lechner, Anna,Ohnishi, Yasuo,Moore, Bradley S.,Shen, Ben. "Predictive model for epoxide hydrolase-generated stereochemistry in the biosynthesis of nine-membered enediyne antitumor antibiotics". . p. 5217 - 5224. Retrieved 2013.
• 3、 Bolm, Carsten,Gerlach, Arne. "Asymmetric Dihydroxylation with MeO-Polyethyleneglycol-Bound Ligands". . p. 741 - 743. Retrieved 1997.
• 4、 Zhang, Jian-Dong,Zhao, Jian-Wei,Gao, Li-Li,Zhao, Jing,Chang, Hong-Hong,Wei, Wen-Long. "One-Pot Three-Step Consecutive Transformation of L-α-Amino Acids to (R)- and (S)-Vicinal 1,2-Diols via Combined Chemical and Biocatalytic Process". . p. 5032 - 5037. Retrieved 2019.
• 5、 Letko, Christopher S.,Heiden, Zachariah M.,Rauchfuss, Thomas B.. "Activation and deactivation of Cp*Ir(TsDPEN) hydrogenation catalysts in water". . p. 4927 - 4930. Retrieved 2009.
• 6、 Zhou, Xiaotian,Zhang, Rongzhen,Xu, Yan,Liang, Hongbo,Jiang, Jiawei,Xiao, Rong. "Coupled (R)-carbonyl reductase and glucose dehydrogenase catalyzes (R)-1-phenyl-1,2-ethanediol biosynthesis with excellent stereochemical selectivity". . p. 1807 - 1813. Retrieved 2015.
• 7、 Rink, Rick,Lutje Spelberg, Jeffrey H.,Pieters, Roland J.,Kingma, Jaap,Nardini, Marco,Kellogg, Richard M.,Dijkstra, Bauke W.,Janssen, Dick B.. "Mutation of tyrosine residues involved in the alkylation half reaction of epoxide hydrolase from Agrobacterium radiobacter AD1 results in improved enantioselectivity [7]". . p. 7417 - 7418. Retrieved 1999.
• 8、 Ji, He-Yuan,Wang, Bin,Pan, Li,Li, Yue-Sheng. "Lewis pairs for ring-opening alternating copolymerization of cyclic anhydrides and epoxides". . p. 641 - 648. Retrieved 2018.
• 9、 Xue, Xiuru,Chen, Pu,Xu, Peng,Wang, Yanhua. "Highly efficient and recyclable chiral Pt nanoparticle catalyst for enantioselective hydrogenation of activated ketones". . p. 55 - 58. Retrieved 2018.
• 10、 Li, Bin,Nie, Yao,Mu, Xiao Qing,Xu, Yan. "De novo construction of multi-enzyme system for one-pot deracemization of (R,S)-1-phenyl-1,2-ethanediol by stereoinversion of (S)-enantiomer to the corresponding counterpart". . p. 21 - 28. Retrieved 2016.