- (R)-(-)-1-Phenyl-1,2-ethanediol
- (R)-(-)-1-Phenyl-1,2-ethanediol 2-tosylate
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Cas Database |
| Name |
(R)-(-)-1-Phenyl-1,2-ethanediol |
EINECS | 202-258-1 |
| CAS No. | 16355-00-3 | Density | 1.17 g/cm3 |
| PSA | 40.46000 | LogP | 0.71230 |
| Solubility | Soluble in water | Melting Point |
64-67 °C(lit.) |
| Formula | C8H10O2 | Boiling Point | 273.5 °C at 760 mmHg |
| Molecular Weight | 138.166 | Flash Point | 145.8 °C |
| Transport Information | N/A | Appearance | white to light yellow crystal powder |
| Safety | 24/25-45-36/37/39-26 | Risk Codes | 23/24/25-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi, T
|
| 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; |
Article Data | 304 |
(R)-(-)-1-Phenyl-1,2-ethanediol Synthetic route
- 582-24-1
1-phenyl-2-hydroxyethanone
- 16355-00-3
(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% |
- 1074-12-0
phenylglyoxal hydrate
- 16355-00-3
(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% |
- 292638-84-7
styrene
- 16355-00-3
(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% |
- 757195-36-1
(1R)-2-({[(1S)-2,2-dimethyl-1-phenylpropyl]amino}oxy)ethanol
A
- 16355-00-3
(R)-1-phenyl-1,2-ethanediol
B
- 82729-98-4
(1S)-α-(1,1-dimethylethyl)benzenemethanamine
| Conditions | Yield |
|---|---|
| With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h; | A n/a B 98% |
- 20698-91-3
(R)-methyl mandelate
- 16355-00-3
(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% |
- 96-09-3
styrene oxide
- 16355-00-3
(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% |
- 292638-84-7
styrene
A
- 96-09-3
styrene oxide
B
- 16355-00-3
(R)-1-phenyl-1,2-ethanediol
C
- 25779-13-9
(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% |
- 582-24-1
1-phenyl-2-hydroxyethanone
A
- 16355-00-3
(R)-1-phenyl-1,2-ethanediol
B
- 25779-13-9
(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; |
- 147256-18-6
(R)-2-hydroxy-2-phenylethyl acetate
- 16355-00-3
(R)-1-phenyl-1,2-ethanediol
| Conditions | Yield |
|---|---|
| With potassium carbonate In methanol for 4h; | 95% |
| With potassium carbonate In methanol for 4h; | 94% |
(R)-(-)-1-Phenyl-1,2-ethanediol Chemical Properties
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)
(R)-(-)-1-Phenyl-1,2-ethanediol Safety Profile
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 Specification
(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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