(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL Chemical Properties

Melting point:

34-37 °C (lit.)

Boiling point:

307 °C (lit.)

Density 

1.0918 (rough estimate)

refractive index 

1.5464 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)

form 

Oil

pka

12.53±0.10(Predicted)

color 

Clear Colourless

optical activity

[α]20/D +4°, c = 1 in methylene chloride

Sensitive 

Air Sensitive

InChI

InChI=1S/C10H15NO2/c11-10(6-12)8-13-7-9-4-2-1-3-5-9/h1-5,10,12H,6-8,11H2/t10-/m1/s1

InChIKey

ZJUOMDNENVWMPL-SNVBAGLBSA-N

SMILES

C(O)[C@@H](N)COCC1=CC=CC=C1

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

3267

WGK Germany 

3

HazardClass 

8

HS Code 

29221990

MSDS

• Language:English Provider:SigmaAldrich

(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL Usage And Synthesis

Chemical Properties

Colorless to yellow liquid or low melting solid

Uses

(R)-(+)-2-Amino-3-benzyloxy-1-propanol is used as a reagent to synthesize beta-amino alcohols, compounds that are used as therapeutic agents to treat heart disease. (R)-(+)-2-Amino-3-benzyloxy-1-propanol is also used as a reagent to synthesize 15-membered macrolide antibiotics, drugs that are used to treat respiratory tract infections.

Synthesis

General procedure for the synthesis of O-benzyl-L-serinol from (S)-2-amino-3-(benzyloxy)propionic acid: O-benzyl-L-serine (15.0 g, 76.8 mmol) was slowly added to a tetrahydrofuran (THF, 150 mL) suspension of lithium aluminum hydride (4.37 g, 115.3 mmol) under reflux conditions. The reaction mixture was stirred at reflux temperature for 1.5 h. After cooling in an ice bath, distilled water (4.4 mL), 10% NaOH aqueous solution (4.4 mL), and distilled water (4.4 mL) were added sequentially. After stirring for 18 h at room temperature, the mixture was filtered and the filter cake was washed with THF. The filtrate was concentrated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent ratio CHCl3/MeOH/NH4OH = 10:1:0.1) to afford the target product, O-benzyl-L-serinol (6.43 g, 69% yield), as a colorless foamy substance. Its physical properties were as follows: [α]27D -5.0 (c 0.760, methanol); 1H NMR (CDCl3) δ 7.27-7.41 (m, 5H), 4.53 (s, 2H), 3.39-3.67 (m, 4H), 3.03-3.17 (m, 1H), 1.85 (br s, 3H); 13C NMR (CDCl3) δ 137.9, 128.2, 127.55, 127.50, 73.1, 72.5, 63.7, 52.3; MS (ESI) m/z 182.2 [M + H]+. The NMR data are in agreement with literature reports.

References

[1] Liebigs Annalen der Chemie, 1988, p. 851 - 854
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5787 - 5801
[3] Tetrahedron, 2002, vol. 58, # 46, p. 9387 - 9401
[4] Tetrahedron, 1975, vol. 31, p. 2629 - 2632
[5] Molecules, 2009, vol. 14, # 12, p. 5124 - 5143

(R)-2-AMINO-3-BENZYLOXY-1-PROPANOL(58577-87-0)Related Product Information

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