L-(+)-Isoleucinol Chemical Properties

Melting point:

36-39 °C(lit.)

Boiling point:

97 °C14 mm Hg(lit.)

alpha 

4.5 º (c=1.6, EtOH)

Density 

0.9490 (rough estimate)

refractive index 

n20/D 1.4589(lit.)

Flash point:

213 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

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

pka

12.88±0.10(Predicted)

form 

Viscous Liquid

color 

White to light yellow

optical activity

[α]20/D +4.0°, c = 1.6 in ethanol

InChI

InChI=1S/C6H15NO/c1-3-5(2)6(7)4-8/h5-6,8H,3-4,7H2,1-2H3/t5-,6+/m0/s1

InChIKey

VTQHAQXFSHDMHT-NTSWFWBYSA-N

SMILES

C(O)[C@@H](N)[C@@H](C)CC

CAS DataBase Reference

24629-25-2(CAS DataBase Reference)

NIST Chemistry Reference

(S)-(+)-Isoleucinol(24629-25-2)

Safety Information

Hazard Codes 

C,Xi,Xn

Risk Statements 

34-22-40

Safety Statements 

45-36/37/39-26-36-22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29221990

MSDS

• Language:English Provider:(2S,3S)-2-Amino-3-methyl-1-pentanol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

L-(+)-Isoleucinol Usage And Synthesis

Chemical Properties

white to light yellow crystalline solid or

Uses

peptide synthesis

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

The general procedure for the synthesis of L-isoleucinol from L-isoleucine is as follows: the synthesis of L-isoleucinol was carried out by reference to the literature method 61 with minor adjustments. Lithium aluminum hydride (7.2 g, 0.19 mol, 2.5 eq.) was suspended in anhydrous tetrahydrofuran (120 mL) under nitrogen protection with continuous stirring. Subsequently, L-isoleucine (10 g, 0.08 mol) was added in batches and the reaction suspension was heated to reflux for 20 hours. Upon completion of the reaction, it was cooled to room temperature, ethyl acetate was added slowly and the reaction mixture was carefully poured into concentrated sodium hydroxide solution. The organic layer was extracted with water and the organic phase was subsequently dried with sodium sulfate. Removal of the solvent under reduced pressure gave 4.5 g of L-isoleucinol as a yellow oil, which could be used in subsequent reactions without further purification. The product was characterized by 1H NMR (400 MHz, CDCl3) with the following chemical shifts: δ 0.75-0.90 (6H, m), 1.01-1.17 (1H, m), 1.22-1.36 (1H, m), 1.37-1.50 (1H, m), 2.48 (2H, br s), 2.50-2.65 (1H, m), 3.19 -3.29 (1H, m), 3.57 (1H, dd, J = 3.27,10.64Hz) ppm.

References

[1] Synthetic Communications, 1996, vol. 26, # 4, p. 703 - 706
[2] Russian Chemical Bulletin, 2008, vol. 57, # 9, p. 1981 - 1988
[3] Helvetica Chimica Acta, 2004, vol. 87, # 1, p. 90 - 105
[4] Journal of Organic Chemistry, 1993, vol. 58, # 13, p. 3568 - 3571
[5] Chemical Communications, 1997, # 12, p. 1087 - 1088

L-(+)-Isoleucinol(24629-25-2)Related Product Information

• (R)-TERT-LEUCINOL
• METHYLCYCLOPENTADIENE DIMER
• Ketorolac tromethamine
• Methyl acrylate
• Fosfomycin tromethamine
• Methyl acetate
• Kresoxim-methyl
• Lithium bis(trimethylsilyl)amide
• Dexketoprofen trometamol
• Mesityl oxide
• Methylparaben
• Methyl cyclopentenolone
• Bensulfuron methyl
• Thiophanate-methyl
• Hydrogenated Cottonseed Oil
• Tris(hydroxymethyl)aminomethane
• Methyl
• Parathion-methyl