L(+)-Leucinol Chemical Properties

Melting point:

56-58 °C

Boiling point:

208-210 °C(lit.)

alpha 

3 º (589nm, c=9, ethanol)

Density 

0.917 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4511(lit.)

Flash point:

195 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

12.88±0.10(Predicted)

form 

Liquid

Specific Gravity

0.917

color 

Clear colorless to slightly yellow light

optical activity

[α]20/D +4°, c = 9 in ethanol

Sensitive 

Air Sensitive

BRN 

1719240

CAS DataBase Reference

7533-40-6(CAS DataBase Reference)

NIST Chemistry Reference

1-Pentanol, 2-amino-4-methyl-, (S)-(7533-40-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-27

WGK Germany 

3

F 

2-10

HS Code 

29221990

MSDS

• Language:English Provider:L(+)-Leucinol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L(+)-Leucinol Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow

Uses

Starting material for the synthesis of aminopeptidase N and phospholipase A₂ inhibitors.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of (S)-2-amino-4-methylpentan-1-ol from L-leucine methyl ester hydrochloride was as follows: to a mixture of EtOH (1.8 L) containing L-leucine methyl ester hydrochloride (254 g, 1.4 mol), NaHCO3 (118 g, 1.4 mol, 1.0 eq.), and water (1.8 L) at 5°C, batchwise addition of NaBH4 (159 g, 4.2 mol, 3.0 eq.) at a rate commensurate with the reaction temperature, maintaining the reaction temperature at no more than 15°C (ca. 70 min.) After the addition of NaBH4 was complete, the ice bath was removed, and the reaction mixture was heated to reflux temperature and held overnight. Upon completion of the reaction, the mixture was cooled to room temperature. The resulting slurry was filtered with the aid of an ice bath and the solids were washed with EtOH (750 mL). The filtrates were combined and concentrated under reduced pressure to about 950 mL. the residue was diluted with EtOAc (2.5 L) and subsequently extracted with 1N NaOH solution (2 x 1 L). The aqueous layer was back-extracted with EtOAc (2 x 750mL). The organic phases were combined, dried over MgSO4 and concentrated under reduced pressure to afford (S)-1-(hydroxymethyl)-3-methylbutylamine as a light yellow oil (112 g, 65% yield). The product was characterized by 1H NMR (CDCl3): δ 0.88-0.93 (m, 6H), 1.17 (t, J = 7.7 Hz, 2H), 1.68-1.80 (m, 2H), 1.82 (br s, 2H), 2.86-2.91 (m, 1H), 3.22 (dd, J = 10.7,8.1 Hz, 1H), 3.56 ( dd, J = 10.3,3.6 Hz, 1H).

References

[1] Patent: US6353006, 2002, B1. Location in patent: Page column 31

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