(R)-(+)-2-Phenylglycinol supplier

Name
(R)-(+)-2-Phenylglycinol
EINECS 626-292-5
CAS No. 2549-14-6
Article Data46
CAS DataBase
Density 1.104 g/cm³
Solubility
Melting Point 59-65 °C(lit.)
Formula C₈H₁₁NO
Boiling Point 283.5 °C at 760 mmHg
Molecular Weight 137.181
Flash Point 125.3 °C
Transport Information UN 3259
Appearance
Safety 26-36/37/39-45
Risk Codes 22-34
Molecular Structure
Hazard Symbols C
Synonyms Benzenemethanol,a-(aminomethyl)-, (R)-;Benzylalcohol, a-(aminomethyl)-, (R)-(-)- (8CI);((R)-2-Hydroxy-2-phenylethyl)amine;(-)-(R)-2-Amino-1-phenylethanol;(-)-2-Amino-1-phenylethanol;(-)-Phenylethanolamine;(-)-a-(Aminomethyl)benzenemethanol;(-)-b-Hydroxyphenethylamine;(1R)-2-Amino-1-phenylethanol;(R)-(-)-1-Phenyl-2-aminoethanol;(R)-(-)-2-Amino-1-phenylethanol;(R)-1-Phenyl-2-aminoethanol;(R)-2-Amino-1-phenylethanol;(R)-a-(Aminomethyl)benzenemethanol;(aR)-a-(Aminomethyl)benzenemethanol;
PSA 46.25000
LogP 1.37900

Synthetic route

: 145920-96-3
(R)-2-nitro-1-phenylethanol

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol	100%

: <2R-(2α(R*),3aα,4α,7α,7aα)>-β-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)-oxy>-benzolethanamin

A: 2549-14-6
(R)-2-Amino-1-phenylethanol

B: 81925-10-2
<2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-2-methoxy-7,8,8-trimethyl-4,7-methanobenzofuran

Conditions

Conditions	Yield
With hydrogenchloride In methanol	A 97% B 93.5%

: 134625-72-2
(R)-2-azido-1-phenylethanol

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal	95%
With lithium aluminium tetrahydride In diethyl ether for 3h; Heating;	90%
With hydrogen; sodium hydroxide In aq. phosphate buffer; water at 30℃; under 7500.75 Torr; for 4h; pH=9; Green chemistry;	87%
With hydrogen; Lindlar's catalyst In ethyl acetate at 25℃; under 2327.2 Torr; for 7h;
With palladium 10% on activated carbon; hydrogen In methanol

: 613-89-8
2-Aminoacetophenone

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With C30H29N2OP; iron(II) acetate In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	94%
With Arthrobacter sp. TS-15 recombinant ephedrine dehydrogenase; NADH In aq. phosphate buffer at 25℃; pH=7.5; Kinetics; Green chemistry; Enzymatic reaction; enantioselective reaction;	n/a

: 10020-96-9
(R)-Mandelonitrile

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 3h; Ambient temperature;	92%
With lithium aluminium tetrahydride In diethyl ether
Multi-step reaction with 3 steps 1: 65 percent / pyridine / -20 °C 2: I2 / tetrahydrofuran 3: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: N-methylimidazole / tetrahydrofuran / 3 h / 20 °C 2: 88 percent / LiAlH4 / tetrahydrofuran / 4 h / 0 °C View Scheme

: 185035-43-2
(R)-(-)-2-benzylamino-1-(3-chlorophenyl)ethanol

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
	92%

: (R)-2-(2-hydroxy-2-phenylethyl)isoindoline-1,3-dione

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrazine In water at 60℃;	89%

: 604808-44-8
(R)-2-(diethylphosphoryloxy)-2-phenylacetonitrile

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;	88%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 4h;	88%

: 4358-86-5, 4410-31-5, 24008-63-7, 24008-62-6
(2R)-mandelamide

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating;	84%
With LiAlH In tetrahydrofuran 1.) reflux, 8 h, 2.) r.t., overnight;	78%
With lithium aluminium tetrahydride

: 75735-33-0
(E)-2-oxo-2-phenylacetaldehyde O-methyl oxime

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With yeast Saccharomyces cerevisiae optical yield given as %ee;	77%

: 73908-23-3
(R)-2-bromo-1-phenylethanol

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With ammonia In water at 20℃; for 2h;	75%

: 69-96-5, 1078-17-7, 2584-74-9, 2584-75-0, 6254-48-4, 7352-06-9, 7687-36-7, 7695-56-9, 32946-42-2, 50897-27-3, 68296-26-4, 109120-55-0
dl-threo-phenylserine

: 56-40-6
glycine

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
Stage #1: dl-threo-phenylserine; glycine With manganese(ll) chloride In phosphate buffer at 25℃; for 24h; pH=5.5; Stage #2: With Pseudomonas putida L-threonine aldolase In phosphate buffer for 100h; pH=5.5; Further stages.;	57%

: 75735-33-0
(E)-2-oxo-2-phenylacetaldehyde O-methyl oxime

A: (R)-2-hydroxy-2-phenylacetaldehyde O-methyl oxime

B: 1287753-57-4
C9H13NO2

C: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
Stage #1: (E)-2-oxo-2-phenylacetaldehyde O-methyl oxime With borane-THF; C13H24BNO2 In tetrahydrofuran at 0 - 20℃; for 3.5h; Stage #2: With methanol at 20℃; for 24h;	A 31% B 13% C 3%
With borane-THF; C13H24BNO2 at 20℃; for 18h;

...Expand

: 613-89-8
2-Aminoacetophenone

A: C16H20N2O2

B: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

C: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide; isopropyl alcohol Electrochemical reaction;	A 9% B n/a C n/a

...Expand

: 7568-93-6
2-Amino-1-phenylethanol

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With MANDELIC ACID

: 74-90-8
hydrogen cyanide

: 100-52-7
benzaldehyde

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
(i) (enzymatic transformation), (ii) LiAlH4, Et2O; Multistep reaction;

: 613-90-1
benzoyl cyanide

A: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

B: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With sodium tetrahydroborate; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; cobalt(II) chloride 2.) methanol; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

: 144372-49-6
(2R)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine

A: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

B: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

: 86013-50-5
(R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With trifluoroacetic acid In water at 25℃; for 0.5h; Yield given;

: 144372-50-9
(R)-benzyl N-(2-hydroxy-2-phenylethyl)carbamate

A: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

B: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

: 120390-75-2
(R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-benzeneacetonitrile

A: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

B: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 4561-43-7
2-amino-1-phenylethanol hydrochloride

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 144372-51-0
Butyric acid (R)-2-butyrylamino-1-phenyl-ethyl ester

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating;	260 mg

: 144315-90-2
Butyric acid (S)-2-ethoxycarbonylamino-1-phenyl-ethyl ester

A: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

B: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

: 144315-91-3
Butyric acid (S)-2-benzyloxycarbonylamino-1-phenyl-ethyl ester

A: 56613-81-1
(S)-2-Amino-1-phenyl-1-ethanol

B: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water for 40h; Heating; Yields of byproduct given. Title compound not separated from byproducts;

: 149342-37-0
(R)-N-(2-hydroxy-2-phenylethyl)acetamide

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrogenchloride In methanol
With hydrogenchloride; water at 110℃; for 24h;	0.6 mg

: (2S)-N-ethoxycarbonyl-2-phenyl-2-hydroxyethylamine

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrogenchloride In methanol

: 149286-02-2
Thiophene-2-carboxylic acid ((R)-2-hydroxy-2-phenyl-ethyl)-amide

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrogenchloride In methanol

: 111059-46-2
(-)-N-benzoyl-2-hydroxy-2-phenylethylamine

: 2549-14-6
(R)-2-Amino-1-phenylethanol

Conditions

Conditions	Yield
With hydrogenchloride In methanol
With potassium hydroxide In ethanol; water at 80℃; for 8h; Substitution;

: 24424-99-5
di-tert-butyl dicarbonate

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 86013-50-5
(R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
	100%
In tetrahydrofuran at 20℃;	100%
With triethylamine In dichloromethane at 20℃; for 3h;	99%
In tetrahydrofuran at 20℃; for 3h;	89.1%
In chloroform at 0℃; for 0.5h;

: 1448350-40-0
tert-butyl N-{2-[4-(isothiocyanatomethyl)benzamido]phenyl}carbamate

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 1448350-47-7
(R)-tert-butyl N-(2-(4-((3-(2-hydroxy-2-phenylethyl)thioureido)methyl)benzamido)phenyl)carbamate

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 16h;	100%
In tetrahydrofuran at 20℃; for 18h;

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 107-02-8
acrolein

: C22H26N2O2

Conditions

Conditions	Yield
In chloroform at 20℃; for 0.166667h; Solvent;	100%

: C44H48N4O4(2+)*2Cl(1-)

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: C60H66N6O4(2+)*2Cl(1-)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 20h; Inert atmosphere;	100%

: 81865-10-3
2-(4-aminophenyl)ethyl chloride

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 391901-45-4
YM-208876

Conditions

Conditions	Yield
With triethylamine In methanol at 60 - 65℃; for 8h; Temperature;	97.6%

: 108-30-5
succinic acid anhydride

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 1417721-52-8
C12H15NO4

Conditions

Conditions	Yield
In dichloromethane	97%
In dichloromethane	97%

: 110-52-1
1,4-dibromo-butane

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 87069-57-6
(R)-(-)-1-phenyl-2-(pyrrolidin-1-yl)ethanol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In toluene at 105 - 118℃; Dean-Stark; Inert atmosphere;	97%

: 55175-50-3
1-(ethoxycarbonylmethyl)benzimidazole

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: (R)-N-(2-hydroxy-1-phenylethyl)-2-(1H-benzo[d]-imidazol-1-yl) acetamide

Conditions

Conditions	Yield
In toluene at 180℃; for 0.166667h; Microwave irradiation;	96%

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 2-(2-aminothiazol-5-yl)-N-[4-(2-chloroethyl)phenyl]acetamide

: mirabegron

Conditions

Conditions	Yield
With triethylamine In methanol at 60 - 65℃; for 8h; Solvent;	96%

: 120-57-0
piperonal

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 179930-11-1
(R)-E-β-((1, 3-benzodioxol-5-ylmethylene)amino)benzene-ethanol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; Large scale;	95.4%

: 40138-16-7
2-formylbenzene boronic acid

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: (C6H4CHNCH2CH(C6H5)O)2B2O

Conditions

Conditions	Yield
In chloroform byproducts: H2O; B compd. stirred with aminoalcohol in CHCl3 at room temp. for 10 min; solvent removed under reduced pressure;	95%
In chloroform for 0.166667h;	95%

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 108-59-8
malonic acid dimethyl ester

: N,N'-bis[(R)-1-phenyl-2-hydroxyethyl]propane-1,3-diamide

Conditions

Conditions	Yield
With lithium methanolate In n-heptane at 100℃; for 3h;	94%

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 658700-09-5
N-(4-fluoro-3-nitro-phenyl)-N-methyl-benzamide

: 863409-16-9
N-[4-((R)-2-hydroxy-2-phenyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20 - 85℃; for 24h;	93.4%

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 530-62-1
1,1'-carbonyldiimidazole

: 54705-41-8
(5R)-5-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 16h;	92%

: 27339-38-4
3-formyl-furan-2-ylboronic acid

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: (OC4H2CHNCH2CH(C6H5)O)2B2O

Conditions

Conditions	Yield
In chloroform byproducts: H2O; B compd. stirred with aminoalcohol in CHCl3 at room temp. for 10 min; solvent removed under reduced pressure;	92%
In chloroform for 0.166667h;	92%

: N-(quinolin-8-yl)but‐3‐enamide

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 3-(((R)-2-hydroxy-2-phenylethyl)amino)-N-(quinolin-8-yl)butanamide

Conditions

Conditions	Yield
With cesium acetate at 100℃; for 24h; Schlenk technique; chemoselective reaction;	92%

: 1201482-21-4
(R)-2-(2-(4-chlorobenzylamino)-2-oxoethyl)pent-4-enoic acid

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 1201482-32-7
C22H25ClN2O3

Conditions

Conditions	Yield
Stage #1: (R)-2-(2-(4-chlorobenzylamino)-2-oxoethyl)pent-4-enoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: (R)-2-Amino-1-phenylethanol With dmap In N,N-dimethyl-formamide at 0 - 20℃;	91%

: 38274-14-5
2,2'-bis-(bromomethyl)-1,1'-biphenyl

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: (R)-2-(5H-dibenzo[c,e]azepin-6(7H)-yl)-1-phenylethanol

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 24h; Reflux;	91%

: 29684-56-8
Burgess Reagent

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: (S)-1,1-Dioxo-3-phenyl-1λ6-[1,2,5]thiadiazolidine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 6h;	90%
at 0 - 25℃; for 6h;	90%

: 1120-71-4
1,3-propanesultone

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: 3-{[(2R)-2-hydroxy-2-phenylethyl]amino}-2-propanesulfonic acid

Conditions

Conditions	Yield
In toluene; acetonitrile for 4h; Heating / reflux;	90%

: 1223105-85-8
3-(3,5-ditrifluoromethylphenylamino)-4-methoxybutane-3-en-1,2-dione

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: C20H14F6N2O3

Conditions

Conditions	Yield
In methanol at 20℃; for 24h; Inert atmosphere;	90%

: 24424-99-5
di-tert-butyl dicarbonate

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: [(R)-2-phenyl-propyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	89.1%

: 486-73-7
1-isoquinolinecarboxylic acid

: 2549-14-6
(R)-2-Amino-1-phenylethanol

: (R)-(-)-N-(2-hydroxy-2-phenylethyl)isoquinoline-1-carboxamide

Conditions

Conditions	Yield
Stage #1: 1-isoquinolinecarboxylic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 20 - 22℃; for 2h; Stage #2: (R)-2-Amino-1-phenylethanol With triethylamine In tetrahydrofuran at 0 - 22℃;	89%
Stage #1: 1-isoquinolinecarboxylic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: (R)-2-Amino-1-phenylethanol With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	89%

(R)-(+)-2-Phenylglycinol Specification

The systematic name of Benzenemethanol, a-(aminomethyl)-, (aR)- is (1R)-2-amino-1-phenylethanol. With the CAS registry number 2549-14-6, it is also named as (R)-α-(aminomethyl)benzyl alcohol. The product's categories are Pharmacetical; Benzene Series; Amino Acid Derivatives. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.46; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 12.47 Å²; (7)Index of Refraction: 1.572; (8)Molar Refractivity: 40.87 cm³; (9)Molar Volume: 124.1 cm³; (10)Polarizability: 16.2×10^-24 cm³; (11)Surface Tension: 48.8 dyne/cm; (12)Density: 1.104 g/cm³; (13)Flash Point: 125.3 °C ; (14)Enthalpy of Vaporization: 55.18 kJ/mol; (15)Boiling Point: 283.5 °C at 760 mmHg; (16)Vapour Pressure: 0.00148 mmHg at 25°C.

Preparation of Benzenemethanol, a-(aminomethyl)-, (aR)-: It can be obtained by D-mandelamide. This reaction needs reagent LiAlH₄.

Uses of Benzenemethanol, a-(aminomethyl)-, (aR)-: It can react with pyridine-2-carboximidic acid methyl ester to get (R)-(-)-5-Phenyl-2-(2-pyridinyl)-2-oxazolin. This reaction needs reagent conc. HCl at temperature of 60 °C. The reaction time is 12 hours. The yield is 78%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. And it can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:O[C@H](c1ccccc1)CN
2. InChI:InChI=1/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m0/s1
3. InChIKey:ULSIYEODSMZIPX-QMMMGPOBBV

Product Name

(R)-(+)-2-Phenylglycinol

Synthetic route

(R)-(+)-2-Phenylglycinol Specification

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