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L-Alaninol

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L-Alaninol Basic information

Product Name:
L-Alaninol
Synonyms:
  • H-L-ALA-OL
  • H-ALANINOL
  • H-ALA-OL
  • H-ALA-OL S-(+)-2 AMINO-PROPANOL
  • 2-AMINOPROPANOL
  • L-(+)-ALANINOL
  • L-ALANINOL
  • L-ALANILOL
CAS:
2749-11-3
MF:
C3H9NO
MW:
75.11
EINECS:
220-388-7
Product Categories:
  • Amino Alcohols
  • Alcohols and Derivatives
  • Alanine [Ala, A]
  • Amino Alcohols (Chiral)
  • Chiral Building Blocks
  • Synthetic Organic Chemistry
  • Pharmaceutical Intermediates
  • Pharmaceutical Raw Materials
  • Chiral Compound
  • Amino alcohols
  • API
  • buildingblock
Mol File:
2749-11-3.mol
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L-Alaninol Chemical Properties

Melting point:
-2°C
Boiling point:
72-73 °C11 mm Hg(lit.)
alpha 
21.8 º (c=2,ethanol)
Density 
0.965 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.450
Flash point:
145 °F
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
Water Solubility 
Completely miscible in water
solubility 
Chloroform, Methanol (Slightly)
pka
12.88±0.10(Predicted)
form 
Oily Liquid
color 
Clear colorless to yellow
Specific Gravity
0.96
optical activity
[α]20/D +18°, neat
Sensitive 
Hygroscopic
BRN 
1718865
CAS DataBase Reference
2749-11-3(CAS DataBase Reference)
NIST Chemistry Reference
1-Propanol, 2-amino-, (S)-(2749-11-3)
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Safety Information

Hazard Codes 
C,Xi
Risk Statements 
34-36/37/38
Safety Statements 
26-36/37/39-45-36
RIDADR 
UN 2735 8/PG 2
WGK Germany 
3
10-23
HazardClass 
8
PackingGroup 
III
HS Code 
29221990

MSDS

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L-Alaninol Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

S-(+)-2-Amino-1-propanol is an aliphatic amino alcohol shown to induce an antiproliferative effect in B16 melanoma cells. S-(+)-2-Amino-1-propanol is used in the preparation of oxazolines which are of ten used as ligands in homogeneous catalysis.

Uses

(S)-(+)-2-Amino-1-propanol (L-Alaninol) may be used in the preparation of unsymmetrical tridentate Schiff base ligands via condensation with carbonyl compounds. It may also be used as a chiral auxillary for the preparation of tert-butyl 4-N-[(2-hydroxy-1-(S)-methyl)ethylamino]-2-methylene-4-(S)-phenyl-butyrate.

Definition

ChEBI: An amino alcohol that is L-alanine in which the carboxy group has been reduced to the corresponding alcohol.

Biochem/physiol Actions

Pseudomonas sp. strain KIE171 was able to grow with L-alaninol [S-(+)-2-amino-1-propanol] as the sole carbon source[1]. W?sch et al. found that mutant KIE171-BI transformed isopropylamine to L-alaninol, mutant KIE171-BII failed to do so.

Synthesis

Simply produce L-alaninol in high yield and good reproducibility by directly reducing an inorganic acid salt of an L-alanine ester with NaBH4. 3.0 mol of NaBH 4 was added and dissolved in 560 ml of cold water, and L-alanine ethyl ester hydrochloride 1. A solution of 0 mol dissolved in 560 ml of ethanol was added. The mixture was added dropwise at 20 ° C. over 5 hours and further aged at 20 to 28 ° C. to complete the reaction. After the reaction, excess NaBH 4 was decomposed with acetone, 1000 ml of ethyl acetate was introduced, and the precipitated inorganic substance was separated by filtration. The lower aqueous layer portion of the filtrate was extracted with 600 ml of ethyl acetate; the ethyl acetate layer was distilled under reduced pressure to remove the solvent and then vacuum distilled to yield L-alaninol.

Purification Methods

Purify it as for S-2-amino-3-methylbutan-1-ol below. [Beilstein 4 IV 1615.]

References

[1] Susana I de Azevedo W?sch. “Transformation of isopropylamine to L-alaninol by Pseudomonas sp. strain KIE171 involves N-glutamylated intermediates.”Applied and Environmental Microbiology (2002): 68.

L-Alaninol Preparation Products And Raw materials

Preparation Products

Raw materials

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