(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol supplier

Name
(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol
EINECS 248-867-6
CAS No. 28143-91-1
Article Data45
CAS DataBase
Density 1.206 g/cm³
Solubility
Melting Point 110 °C
Formula C₉H₁₃NO₂
Boiling Point 360.6 °C at 760 mmHg
Molecular Weight 167.208
Flash Point 171.9 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,3-Propanediol,2-amino-1-phenyl-, L-threo-(+)- (8CI);1,3-Propanediol, 2-amino-1-phenyl-,[S-(R*,R*)]-;(1S,2S)-(+)-1-Phenyl-2-amino-1,3-propanediol;(1S,2S)-2-Amino-1-phenyl-1,3-propanediol;(2S,3S)-3-Phenylpropane-2-amine-1,3-diol;(S,S)-2-Amino-1-phenyl-1,3-propanediol;L-(+)-threo-1-Phenyl-2-amino-1,3-propanediol;
PSA 66.48000
LogP 0.73990

Synthetic route

: 119677-35-9
(2R,3S)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

: 3306-06-7, 5285-86-9, 28143-91-1, 36391-67-0, 36391-68-1, 46032-98-8, 55057-81-3, 105452-39-9, 119364-52-2
(+/-)-threo-2-amino-1-phenyl-1,3-propanediol

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

Conditions

Conditions	Yield
With L-Tartaric acid
With L-(-)-O,O'-dibenzoyltartaric acid
With (1S)-(+)-3-bromocamphor-10-sulfonic acid
With D-Glutamic acid

: 91247-54-0
1-Phenyl-2-acetamido-1,3-propandiol

A: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

B: 46032-98-8
(1R,2R)-2-amino-1-phenylpropane-1,3-diol

C: 105452-39-9
(1R,2S)-(+)-2-amino-1-phenyl-1,3-propanediol

D: 119364-52-2
(1S,2R)-2-amino-1-phenylpropane-1,3-diol

Conditions

Conditions	Yield
hydrolysis;

...Expand

: 125219-10-5
((1S,2S)-2-Hydroxy-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester

A: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

B: 100-06-1
1-(4-methoxyphenyl)ethanone

Conditions

Conditions	Yield
Irradiation; mild conditions;

(1S,2S)-2-amino-1-<4-amino-phenyl>-propane-1,3-diol: (1S,2S)-2-amino-1-<4-amino-phenyl>-propane-1,3-diol

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

Conditions

Conditions	Yield
With hypophosphorous acid; sodium nitrite

(5S)-2,2-dimethyl-4c-phenyl-<1,3>dioxan-5r-ylamine: (5S)-2,2-dimethyl-4c-phenyl-<1,3>dioxan-5r-ylamine

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

Conditions

Conditions	Yield
With mineral acid

(+-)-2,2-dimethyl-4c-phenyl-<1,3>dioxan-5r-ylamine: (+-)-2,2-dimethyl-4c-phenyl-<1,3>dioxan-5r-ylamine

A: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

B: 46032-98-8
(1R,2R)-2-amino-1-phenylpropane-1,3-diol

Conditions

Conditions	Yield
With (1S)-(+)-3-bromocamphor-10-sulfonic acid; ethyl acetate

: 167082-56-6
tert-butyl [(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h;

: 50-00-0
formaldehyd

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: C30H39N3O6

Conditions

Conditions	Yield
In methanol at 20℃; for 16h;	100%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 501-53-1
benzyl chloroformate

: 127102-27-6
benzyl L-threo-1,3-dihydroxy-1-phenylpropan-2-yl-carbamate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water Ambient temperature;	99%
With triethylamine In methanol for 1h; Ambient temperature;	91%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 586-75-4
4-chlorobenzoyl chloride

: (1S,2S)-2-(4'-bromobenzoylamino)-1-phenyl-propane-1,3-diol

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	99%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 82911-69-1
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

: 1072502-00-1
C24H23NO4

Conditions

Conditions	Yield
In 1,4-dioxane; water at 20℃; for 16h;	99%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 84010-78-6
(1S,2S)-1-phenyl-2-amino-1,3-di(trimethylsilanyloxy)-propane

Conditions

Conditions	Yield
With sodium hydrogencarbonate 8 h, 140 degC then allowed to reach room temperature;	98.1%

: 50-00-0
formaldehyd

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 58210-04-1, 67250-22-0, 108147-10-0, 108147-47-3
(+)-(1S,2S)-2-(dimethylamino)-1-phenylpropane-1,3-diol

Conditions

Conditions	Yield
With formic acid	98%
With formic acid for 24h; Cooling with ice; Reflux;	88%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 220096-47-9
1,2-bis[di(3',5'-diformylphenyl)phosphanyl]benzene

: (+)-1,2-bis[bis[3',5'-bis(N-methyliden-(1S,2S)-2-amino-1-phenypropane-1,3-diol)phenyl]phosphanyl]benzene

Conditions

Conditions	Yield
With trimethyl orthoformate In methanol for 20h; Ambient temperature;	98%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 108-94-1
cyclohexanone

: (2S,3S)-3-hydroxymethyl-2-phenyl-1-oxa-4-azaspiro[4.5]decane

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	98%

: 1271-42-7
ferrocenecarboxylic acid

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: (C5H5)Fe(C5H4CONHCH(CH2OH)(CH(C6H5)(OH)))

Conditions

Conditions	Yield
With oxalyl dichloride; triethylamine In not given 1) (COCl)2; 2) ligand, (C2H5)3N;	98%

: 69739-34-0
t-butyldimethylsiyl triflate

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 191418-28-7
2-(tert-butyldimethylsilanyloxy)-1-(t-butyldimethylsilanyloxymethyl)-2-phenylethylamine

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In dichloromethane at 23℃; for 16h; Inert atmosphere;	98%

: 383-63-1
ethyl trifluoroacetate,

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 175690-17-2
(1S,2S)-1-phenyl-2-trifluoroacetamidopropan-1,3-diol

Conditions

Conditions	Yield
In methanol at 0℃; for 15h;	97%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 70-34-8
2,4-Dinitrofluorobenzene

: 194539-30-5
(1S,2S)-2-(2,4-Dinitro-phenylamino)-1-phenyl-propane-1,3-diol

Conditions

Conditions	Yield
	97%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 98-88-4
benzoyl chloride

: 72002-77-8
(1S,2S)-2-(Benzoylamino)-1-phenyl-1,3-propanediol

Conditions

Conditions	Yield
With potassium hydroxide In diethyl ether	96%

: 108-77-0
1,3,5-trichloro-2,4,6-triazine

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 2-chloro-4,6-bis{[(2S,3S)-1,3-dihydroxy-3-phenylprop-2-yl]amino}-1,3,5-triazine

Conditions

Conditions	Yield
With potassium carbonate In tetrahydrofuran at -78 - 20℃;	96%
With potassium carbonate; 18-crown-6 ether In toluene at 0 - 25℃; for 48h;	86%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 874-60-2
4-methyl-benzoyl chloride

: (1S,2S)-2-(4'-methylbenzoylamino)-1-phenyl-propane-1,3-diol

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	96%

: 1121-60-4
pyridine-2-carbaldehyde

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: (+)-(1S,2S)-1-Phenyl-2-<(2-pyridinylmethylen)amino>-1,3-propandiol

Conditions

Conditions	Yield
With calcium sulfate In methanol at 50℃; for 1h;	95%

: 7142-72-5
N-benzyloxamic acid ethyl ester

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: N-benzyl-N'-[(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]oxalamide

Conditions

Conditions	Yield
In toluene at 20℃; for 2h; Reflux; Inert atmosphere;	95%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 75-36-5
acetyl chloride

: 173094-51-4
acetate de (S)-2-acetamido-(S)-3-hydroxy-3-phenylpropyle

Conditions

Conditions	Yield
With triethylamine In dichloromethane -5 deg C, 1h; -5 deg C to RT;	94%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 5333-86-8
ethyl benzimidate hydrochloride

: 95341-86-9
(+)-(4,5-dihydro-2,5-diphenyloxazol-4-yl)methanol

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 15h; Ambient temperature;	94%
In ethanol Condensation;

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 93-97-0
benzoic acid anhydride

: 72002-77-8
(1S,2S)-2-(Benzoylamino)-1-phenyl-1,3-propanediol

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 16h;	94%
With triethylamine In tetrahydrofuran at 20℃;

: 17261-28-8
ortho-diphenylphosphinobenzoic acid

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: (-)-tris-O1,N2,O3-<2-(diphenylphosphino)benzoyl>-L-(+)-threo-2-amino-1-phenyl-1,3-propanediol

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 14h; Ambient temperature;	93.3%

: 85-44-9
phthalic anhydride

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 123537-84-8
(1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol

Conditions

Conditions	Yield
In xylene for 2h; Heating;	93%
at 160℃;	88%
at 160℃; under 0.5 Torr;	70%
at 160℃; under 0.5 Torr; for 0.25h;	70%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 174069-00-2
3α,12α-dihydroxy-5β-cholan-24-oic acid 2,5-dioxopyrrolidin-1-yl ester

: (1S,2S)-1-phenyl-2-deoxycholicacetamidopropane-1,3-diol

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 1.5h;	92%

: 14777-29-8, 85273-25-2
methyl acetimidate

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 53732-41-5
(4S,5S)-4-Hydroxymethyl-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazole

Conditions

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	91%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 100-47-0
benzonitrile

: 95341-86-9
(+)-(4,5-dihydro-2,5-diphenyloxazol-4-yl)methanol

Conditions

Conditions	Yield
potassium carbonate In ethylene glycol; glycerol at 115℃;	91%
In ethylene glycol; glycerol at 110℃; for 20h;	74.7%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 879-18-5
naphthalene-1-carbonic acid chloride

: (1S,2S)-2-(1'-naphthoylamino)-1-phenyl-propane-1,3-diol

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 16h;	91%

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 952234-39-8
(1S,2S)-2-azido-1-phenyl-1,3-propanediol

Conditions

Conditions	Yield
With potassium carbonate; copper(II) sulfate In methanol at 20℃; for 4h;	91%
With imidazole-1-sulfonyl azide hydrochloride

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 100-52-7
benzaldehyde

: 195144-29-7
(1S,2S)-(+)-2-(benzylideneamino)-1-phenylpropane-1,3-diol

Conditions

Conditions	Yield
In ethanol for 12h; Heating;	90%
With ethanol
With copper(II) sulfate In methanol for 3h; Heating;

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 98-59-9
p-toluenesulfonyl chloride

: 130854-92-1
(1S,2S)-N-(4-methylphenylsulphonyl)-2-amino-1-phenyl-1,3-propanediol

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 24h;	90%
With triethylamine In N,N-dimethyl-formamide for 18h; Ambient temperature;
With triethylamine In N,N-dimethyl-formamide

: 28143-91-1
(1S,2S)-2-amino-1-phenyl-1,3-diol

: 70090-26-5
cholic acid N-succinimidyl ester

: (1S,2S)-1-phenyl-2-cholicacetamidopropane-1,3-diol

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 1.5h;	90%

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Chemical Properties

IUPAC Name: 2-amino-1-phenylpropane-1,3-diol
The MF of (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1): C₉H₁₃NO₂
The MW of (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1): 167.21
EINECS: 248-867-6
mp: 110 °C
alpha: 35 °(c=1, 1N HCl)
refractive index: 26.5 ° (C=1, MeOH)
Molar Refractivity: 47 cm³
Molar Volume: 138.5 cm³
Polarizability: 18.63 10^-24 cm³
Surface Tension: 57.8 dyne/cm
Density: 1.206 g/cm³
Flash Point: 171.9 °C
Enthalpy of Vaporization: 63.98 kJ/mol
Boiling Point: 360.6 °C at 760 mmHg
Vapour Pressure: 7.87E-06 mmHg at 25°C
Appearance: white to light yellow crystal powder
Categories: Propanes/propenes;chiral;Amino Alcohols (Chiral);Chiral Building Blocks;Asymmetric Synthesis;for Resolution of Acids;Optical Resolution;Synthetic Organic Chemistry
Synonyms: S-BASE;LBS;Levo-Amin-odiol;threo-2-amino-1-phenyl-1,3-propanediol;L(+)-THREO-2-AMINO-1-PHENYL-1,1,3-PROPANEDIOL;L-(+)-THREO-2-AMINO-1-PHENYL-1,3-PROPANEDIOL;L-THREO-(+)-PHENYL-2-AMINO-1,3-PROPANDIOL;L-(+)-THREO-1-PHENYL-2-AMINO-1,3-PROPANEDIOL
The Structure of (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1):

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Uses

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1) is used as pharmaceutical intermediates.
(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol(28143-91-1) is used in pharmaceutical industry.

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Safety Profile

Hazard Codes:

Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37/39: Wear suitable gloves and eye/face protection
WGK Germany: 3

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Specification

1. First Aid Measures
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Eyes:
Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.

Product Name

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol

Synthetic route

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Chemical Properties

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Uses

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Safety Profile

(1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol Specification

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