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20989-17-7

Basic Information
CAS No.: 20989-17-7
Name: (S)-(+)-2-Phenylglycinol
Article Data: 156
Molecular Structure:
Molecular Structure of 20989-17-7 ((S)-(+)-2-Phenylglycinol)
Formula: C8H11NO
Molecular Weight: 137.181
Synonyms: S(+)-2-phenylglycinol;Benzeneethanol, beta-amino-, (S)-;(2S)-2-amino-2-phenyl-ethanol;L-phenylglycinol;(S)-(+)-2-Amino-2-phenylethanol;L-(+)-alpha-Phenylglycinol;L-2-Phenylglycinol;(S)-(+)-2-Pheny;(S)-(+)-Phenylglycinol;(S)-(-)-2-Phenylalanine;(S)-2-Phenylglycinol;L-(+)-2-Phenylglycinol;(S)-Phenylglycinol;(S)-2-Phenylglycinol hydrochloride;
EINECS: 260-287-5
Density: 1.104 g/cm3
Melting Point: 76-79 °C
Boiling Point: 261 °C at 760 mmHg
Flash Point: 125.3 °C
Solubility: Soluble in chloroform, dimethylsulfoxide and methanol. Limited solubility in water.
Appearance: white to light yellow crystal powder
Hazard Symbols: CorrosiveC, ToxicT
Risk Codes: 34-36/37/38-23/24/25
Safety: 22-24/25-45-36/37/39-26
PSA: 46.25000
LogP: 1.37900
Synthetic route
118958-06-8

N-<(2R,4E)-2-Methyl-4-hexenoyl>-S-phenylglycinol

A

20989-17-7

(2S)-2-phenylglycinol

B

93553-73-2

(2R,4E)-2-Methyl-4-hexenoic acid

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane at 70 - 80℃; for 3h;A 92%
B 99%
2935-35-5

(S)-2-phenylglycine

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;97%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;97%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;95%
117049-14-6

tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
In acetonitrile at 300℃; under 75007.5 Torr;93%
6591-61-3, 24461-61-8, 26682-99-5, 37760-98-8

(S)-Phenylglycine methyl ester

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Reflux;88%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.5h; Reflux;88%
Stage #1: (S)-Phenylglycine methyl ester With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 0.25h;
Stage #2: With methanol In tetrahydrofuran at 65℃; stereospecific reaction;
73%
With sodium tetrahydroborate In methanol at 20℃; for 1h;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h; Cooling with ice; Inert atmosphere;
99395-88-7

(S)-4-phenyl-2-oxazolidinone

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With 3-azapentane-1,5-diamine at 140℃; for 18h;85%
15028-39-4

L-2-phenylglycine methyl ester hydrochloride

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol 1) RT, 9h, b) 5.5h, reflux, c) RT, 8h;83%
With sodium tetrahydroborate In ethanol; water for 5.5h; Heating;
Stage #1: L-2-phenylglycine methyl ester hydrochloride With triethylamine In methanol; diethyl ether at -10℃; for 1h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;
4.4 g
217650-36-7

N-(2-methoxymethoxy-1-phenyl-ethyl)-acetamide

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
In methanol Hydrolysis; Acid hydrolysis;81%
130406-31-4

benzyl (S)-(2-hydroxy-1-phenylethyl)carbamate

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol for 0.25h;80%

A

56613-80-0

(R)-Phenylglycinol

B

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
With hydrogenchloride; (S)-(+)-3,3′-bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate In dichloromethane; water at 21.84℃; pH=2.32; Centrifugal contactor separators; Resolution of racemate; optical yield given as %ee;A n/a
B 36%
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up;
With 3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In tetrachloromethane at 6℃; pH=3; aq. buffer; enantioselective reaction;
2935-35-5

(S)-2-phenylglycine

A

(2S)-(-)-2-amino-2-phenylethanol N-borane

B

20989-17-7

(2S)-2-phenylglycinol

Conditions
ConditionsYield
Stage #1: (S)-2-phenylglycine With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran; diethyl ether at 0 - 20℃; for 20h; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 2h;
A 27%
B 33%
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Chemistry

Molecular Structure of (S)-(+)-2-Phenylglycinol (CAS NO.20989-17-7):

IUPAC Name: (2S)-2-amino-2-phenylethanol 
Empirical Formula: C8H11NO
Molecular Weight: 137.179
H bond acceptors: 2
H bond donors: 3
Freely Rotating Bonds: 4
Polar Surface Area: 12.47 Å2
Index of Refraction: 1.572
Molar Refractivity: 40.87 cm3
Molar Volume: 124.1 cm3
Surface Tension: 48.8 dyne/cm
Density: 1.104 g/cm3
Flash Point: 125.3 °C
Enthalpy of Vaporization: 52.69 kJ/mol
Boiling Point: 261 °C at 760 mmHg
Vapour Pressure: 0.00601 mmHg at 25°C
Melting point: 76-79 °C
Storage temp: Store at 0-5°C
Sensitive: Air Sensitive
InChI
InChI=1/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m1/s1
Smiles
c1(ccccc1)[C@@H](CO)N
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container. Corrosives area. Store under nitrogen.
Product Categories: Pharmaceutical Intermediates; Alcohols and Derivatives; chiral; Chiral Reagent; Phenylglycine [Phg]; Amino Acids 13C, 2H, 15N; Amino Alcohols (Chiral); Asymmetric Synthesis; Chiral Building Blocks; Synthetic Organic Chemistry; Amino alcohols; Amino Acids & Derivatives

Safety Profile

Risk Statements: 34-36/37/38-23/24/25
R34:Causes burns. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-24/25-45-36/37/39-26
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Hazard Codes: CorrosiveC,ToxicT
WGK Germany: 3
F: 2-10

Specification

 (S)-(+)-2-Phenylglycinol , with CAS number of 20989-17-7, can be called (R)/(S)-Phenylglycinol ; 2-Amino-2-pheynlethanol ; Benzeneethanol, beta-amino-, (S)- ; (2S)-2-amino-2-phenyl-ethanol ; (S)-(+)-2-Amino-2-phenylethanol ; (S)-(+)-2-Pheny ; S-(+)-2-Phenylglycinol (>=99%) ; (S)-(-)-2-Phenylalanine ; L-(+)-2-Phenylglycinol ; (S)-(+)-2-Amino-2-Phenylethanol; (S)-(+)-2- . It is a white to light yellow crystal powde.