1-phenyl-2-hydroxyethanone
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With β-D-glucose In aq. phosphate buffer at 35℃; for 24h; pH=7.5; Kinetics; Temperature; pH-value; Solvent; Reagent/catalyst; Enzymatic reaction; | 99.9% |
With cobalt(II) acetate; C31H31N2OP In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere; | 97% |
With hydrogen; chiral iridium(III) complex In methanol at 60℃; under 7600.51 Torr; for 15h; | 94% |
phenylglyoxal hydrate
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
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; | 99% |
styrene
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 20℃; for 2h; Sharpless asymmetric dihydroxylation; | 98% |
With potassium osmate(VI) dihydrate; cetyltrimethylammonim bromide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) In water at 20℃; for 48h; Sharpless dihydroxylation; optical yield given as %ee; | 98% |
With water; potassium carbonate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; potassium hexacyanoferrate(III) In tert-butyl alcohol for 6h; Reagent/catalyst; enantioselective reaction; | 98% |
(1R)-2-({[(1S)-2,2-dimethyl-1-phenylpropyl]amino}oxy)ethanol
A
(R)-1-phenyl-1,2-ethanediol
B
(1S)-α-(1,1-dimethylethyl)benzenemethanamine
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A n/a B 98% |
(R)-methyl mandelate
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 0.5h; | 97% |
With lithium aluminium tetrahydride | 74% |
Stage #1: (R)-methyl mandelate With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 20℃; for 12h; Elimination; Stage #2: With hydrogenchloride; ammonium chloride Hydrolysis; Further stages.; | 70% |
styrene oxide
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With E. coli/(recombinant Vigna radiata epoxide hydrolase VrEH3) whole cells In methanol; aq. phosphate buffer at 25℃; for 7h; pH=7.0; pH-value; Temperature; Microbiological reaction; enantioselective reaction; | 97% |
With tris paraperiodate; water In acetonitrile for 0.0833333h; Ambient temperature; | 90% |
With epoxide hydrolase from Vigna radiata; variant VrEH2M263V In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 1.5h; pH=7; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 90% |
styrene
A
styrene oxide
B
(R)-1-phenyl-1,2-ethanediol
C
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With styrene monooxygenase In Hexadecane for 24h; aq. buffer; optical yield given as %ee; | A 97% B n/a C n/a |
Conditions | Yield |
---|---|
Stage #1: styrene oxide With water; 4-nitro-benzoic acid; [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II) at 20℃; Acidic aqueous solution; Stage #2: With ammonia at 20℃; for 1h; | A 95.3% B 67.9% |
With Aspergillus niger epoxide hydrolases immobilized onto modified Eupergit C In aq. phosphate buffer; dimethyl sulfoxide at 25℃; for 4h; pH=6.5; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | A n/a B 48% |
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); water In dichloromethane; acetonitrile at 20℃; for 144h; Resolution of racemate; | A n/a B 47% |
1-phenyl-2-hydroxyethanone
A
(R)-1-phenyl-1,2-ethanediol
B
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With cobalt(II) acetate; C31H31N2OP In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Inert atmosphere; | A 95% B n/a |
With diisobutylaluminium hydride; (S)-1-methyl-2-<(piperidin-1-yl)-methyl>pyrrolidine; tin(ll) chloride In dichloromethane at -100℃; for 0.333333h; Product distribution; asymmetric reduction of prochiral hydroxy ketones; | |
With baker yeast Product distribution; Thermodynamic data; ee = 99.19percent, ΔΔG(excit.)298 = 3.26+/-0.06 kcal/mol; |
(R)-2-hydroxy-2-phenylethyl acetate
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With potassium carbonate In methanol for 4h; | 95% |
With potassium carbonate In methanol for 4h; | 94% |
(1R)-2-{[(S)-[(2-(methoxymethoxy)phenyl)(phenyl)methyl]amino]oxy}-1-phenylethanol
B
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A 95% B n/a |
Conditions | Yield |
---|---|
94% | |
94% | |
94% |
styrene oxide
A
(R)-1-phenyl-1,2-ethanediol
B
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With Escherichia coli Rosetta(DE3)/epoxide hydrolase from Glycine max wet cells In aq. phosphate buffer at 25℃; pH=7; Catalytic behavior; Microbiological reaction; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 93.8% B n/a |
With water at 37℃; rabbit liver microsomal epoxide hydrolase; Yields of byproduct given. Title compound not separated from byproducts; | |
With water In ethanol Beauveria sulfurescens; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(R)-2,2-dimethyl-4-phenyl-1,3-dioxolane
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
zirconium(IV) chloride In methanol at 35℃; for 3h; | 93% |
(R)-(-)-2-tert-butoxy-2-oxo-1-phenylethyl pyrrolidine-1-carboxylate
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 92% |
(2S,5R)-2-(2-chlorophenyl)-5-phenyl-3-tosyloxazolidin-4-one
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Inert atmosphere; | 92% |
(1R)-2-[({(1S)-1-[2-(methoxymethoxy)phenyl]ethyl}amino)oxy]-1-phenylethanol
A
(1S)-1-[2-(methoxymethoxy)phenyl]ethanamine
B
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A 91% B n/a |
(R)-(-)-1-phenylethane-1,2-diol dipropionate
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 25℃; for 3h; | 90% |
(R)-2-methylcarbonyloxy-1-phenylethyl acetate
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
zirconium(IV) chloride In methanol at 35℃; for 4h; | 90% |
With potassium carbonate In methanol at 20℃; for 4h; |
(4S,1'R,2'R)-N-(3)-[1'-(m-chlorobenzoyl)-2-hydroxy-2'-phenylethan-1'yl]-4-phenyl-5,5-dimethyloxazolidin-2-one
A
(R)-1-phenyl-1,2-ethanediol
B
(4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol for 0.166667h; | A 60% B 90% |
styrene
A
(R)-1-phenyl-1,2-ethanediol
B
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); methanesulfonamide; DHQD-PHAL-OPEG-OMe In water; tert-butyl alcohol at 0℃; for 24h; Title compound not separated from byproducts; | A 87% B n/a |
With osmium(VIII) oxide; lithium aluminium tetrahydride; MEQ-DHQD Thermodynamic data; Kinetics; 1) toluene, 2) THF, 30 min, RT; influence of the reaction temperature on the enantioselectivity of the asymmetric dihydroxylation of different olefins with other reagents, investigations of the ee-values; | |
With potassium dioxotetrahydroxoosmate(VI); iodine; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine In water; tert-butyl alcohol at 0℃; for 27h; Product distribution; Mechanism; electrolysis; various co-oxidants; asymmetric dihydroxylation; further cond.: chemical method; |
(R)-Styrene oxide
A
(R)-1-phenyl-1,2-ethanediol
B
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With Tris-HCl buffer; Sphingomonas sp. HXN-200 cell free extract In hexane at 25℃; for 4h; pH=7.5; Title compound not separated from byproducts; | A 87% B 13% |
With water; potassium hydroxide at 30℃; for 288h; Product distribution; Mechanism; other pH; | |
With sodium phosphate buffer; enzymatic extract of S. racemosum In dimethyl sulfoxide at 27℃; Rate constant; Mechanism; Product distribution; regioselectivity of the biohydrolysis; |
(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine under 11400.8 Torr; Stage #2: With dihydrogen peroxide Product distribution / selectivity; | 86% |
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine under 11400.8 Torr; Stage #2: With sodium hydroxide; dihydrogen peroxide Product distribution / selectivity; | 86% |
4-Phenyl-1,3-dioxolan-2-one
A
(R)-1-phenyl-1,2-ethanediol
B
(4S)-4-phenyl[1,3]dioxolan-2-one
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; Kinetics; pig liver esterase, phosphate buffer pH 7.4; | A 85% B n/a |
In dimethyl sulfoxide at 20℃; pig liver esterase, phosphate buffer pH 7.4; Yields of byproduct given; | A 85% B n/a |
(R)-Mandelic Acid
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether 1.) reflux, 5 h, 2.) RT, 12 h; | 85% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2.5h; Inert atmosphere; | 71% |
With lithium aluminium tetrahydride In diethyl ether for 6h; Reduction; Heating; | 70% |
(1R)-1-phenyl-2-({[(1S)-1-phenylpentyl]amino}oxy)ethanol
A
(R)-1-phenyl-1,2-ethanediol
B
(1S)-1-amino-1-phenylpentane
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A n/a B 85% |
(1R)-1-phenyl-2-({[(1S)-1-phenyl-2-propenyl]amino}oxy)ethanol
A
(R)-1-phenyl-1,2-ethanediol
B
(1S)-1-phenyl-2-propen-1-amine
Conditions | Yield |
---|---|
With zinc In tetrahydrofuran; water; acetic acid at 60℃; for 4h; | A n/a B 83% |
(1R)-1-phenyl-2-({[(1S)-1-phenylethyl]amino}oxy)ethanol
A
(S)-1-phenyl-ethylamine
B
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A 80% B n/a |
(R)-1-phenyl-2-(α,α-diphenylbenzyloxy)ethyl-3,4-di-O-benzyl-2-deoxy-6-O-(α,α-diphenylbenzyl)-L-glucoside
A
(R)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
In tetrahydrofuran; hydrogenchloride Hydrolysis; | A 2.37 g B 78% |
phenylethane 1,2-diol
A
(R)-1-phenyl-1,2-ethanediol
B
(S)-1-phenyl-1,2-ethanediol
Conditions | Yield |
---|---|
With cell free extract from Candida parapsilosis CICC 1627 In aq. phosphate buffer at 30℃; for 48h; pH=6.5; Reagent/catalyst; Microbiological reaction; enantioselective reaction; | A n/a B 78% |
With MCCD-HPS packed column In hydrogenchloride; acetonitrile pH=8.6; | |
With halohydrin dehydro-dehalogenase from Alcaligenes sp. DS-S-7G; 2,6-Dichlorophenolindophenol; phenazine methosulfate Enzymatic reaction; Title compound not separated from byproducts.; |
(R)-1-phenyl-1,2-ethanediol
(R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide
Conditions | Yield |
---|---|
With thionyl chloride In tetrachloromethane Heating; | 100% |
With thionyl chloride Heating; | 79% |
With thionyl chloride In dichloromethane Yield given; |
(R)-1-phenyl-1,2-ethanediol
tert-butyldimethylsilyl chloride
(R)-2-(tert-butyldimethylsilyloxy)-1-phenylethan-1-ol
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere; | 100% |
With dmap; triethylamine In dichloromethane for 4h; Inert atmosphere; | 98% |
With dmap; triethylamine In dichloromethane at 20℃; for 2h; | 91% |
With dmap; triethylamine In dichloromethane at 20℃; for 2h; | 87% |
(R)-1-phenyl-1,2-ethanediol
methanesulfonyl chloride
(R)-phenyl-1,2-bis(methanesulfonyloxy)ethane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
With triethylamine In dichloromethane at 0 - 20℃; | |
With triethylamine In dichloromethane | |
Stage #1: (R)-1-phenyl-1,2-ethanediol With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: methanesulfonyl chloride In dichloromethane at 20℃; for 5h; |
(R)-1-phenyl-1,2-ethanediol
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 18h; | 99% |
With pyridine; 1-amino-3-(dimethylamino)propane In dichloromethane for 0.416667h; |
(R)-1-phenyl-1,2-ethanediol
ortho-diphenylphosphinobenzoic acid
(R)-2-hydroxy-2-phenylethyl 2-(diphenylphosphino)-benzoate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; Inert atmosphere; | 98% |
(R)-1-phenyl-1,2-ethanediol
(R)-Mandelic Acid
Conditions | Yield |
---|---|
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In acetone at 0℃; pH=8.3; chemoselective reaction; | 96% |
With recombinant alditol oxidase from Streptomyces coelicolor A3(2); catalase from bovine liver at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Temperature; pH-value; aq. phosphate buffer; Enzymatic reaction; enantioselective reaction; |
carbon dioxide
(R)-1-phenyl-1,2-ethanediol
(R)-1-phenyl-1,2-ethanediol carbonate
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 70℃; under 7500.75 Torr; for 18h; | 96% |
(R)-1-phenyl-1,2-ethanediol
p-toluenesulfonyl chloride
(R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With di(n-butyl)tin oxide; triethylamine In dichloromethane at 0 - 20℃; for 3h; | 92.2% |
With pyridine at 0 - 20℃; Inert atmosphere; | 78% |
With pyridine at -10℃; for 4h; | 76% |
(R)-1-phenyl-1,2-ethanediol
chloromethyldiphenylsilane
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere; | 90% |
(R)-1-phenyl-1,2-ethanediol
4-biphenylboronic acid
Conditions | Yield |
---|---|
In chloroform at 20℃; | 89% |
With 4 A molecular sieve In chloroform at 20℃; | 89% |
Structure of (R)-(-)-1-Phenyl-1,2-ethanediol (CAS NO.16355-00-3):
IUPAC Name: (1S)-1-Phenylethane-1,2-diol
Molecular Formula: C8H10O2
Molar mass: 138.1638 g/mol
Density: 1.17 g/cm3
Melting Point: 64-67 °C(lit.)
Flash Point: 145.8 °C
Index of Refraction: 1.572
Boiling Point: 273.5 °C at 760 mmHg
Vapour Pressure: 0.00278 mmHg at 25 °C
Water Solubility: soluble
Appearance: white to light yellow crystal powder
XLogP3-AA: 0.4
H-Bond Donor: 2
H-Bond Acceptor: 2
Canonical SMILES: C1=CC=C(C=C1)C(CO)O
Isomeric SMILES: C1=CC=C(C=C1)[C@@H](CO)O
InChI: InChI=1S/C8H10O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8-10H,6H2/t8-/m1/s1
InChIKey: PWMWNFMRSKOCEY-MRVPVSSYSA-N
Product categories: Chiral Compounds; Diols; Chiral Building Blocks; Synthetic Organic Chemistry; Simple Alcohols (Chiral)
Hazard Codes: Xi, T
Risk Statements: 23/24/25-36/37/38
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-45-36/37/39-26
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
Hazard Note: Irritant
(R)-(-)-1-Phenyl-1,2-ethanediol (CAS NO.16355-00-3) also can be called (1R)-1-phenylethane-1,2-diol ; (R)-(-)-alpha,beta-Dihydroxyethylbenzene ; (R)-(-)-Stryrene glycol and 1,2-ethanediol, 1-phenyl-, (1R)- . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first,should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, Get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's Inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Do not induce vomiting.If victim is conscious and alert, give 2-4 cupfuls of milk or water, and get medical aid immediately. In addition, (R)-(-)-1-Phenyl-1,2-ethanediol (CAS NO.16355-00-3) can be stable under normal temperature and pressure conditions. You must not take it with strong oxidants. And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases.
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