| Identification | More | [Name]
L-(+)-Isoleucinol | [CAS]
24629-25-2 | [Synonyms]
2-AMINO-3-METHYL-1-PENTANOL
(2S,3S)-2-AMINO-3-METHYL-1-PENTANOL
(2S,3S)-2-AMINO-3-METHYL-PENTAN-1-OL
H-ILE-OL
H-ISOLEUCINOL
H-L-ILE-OL
(+)-L-ISOLEUCINOL
L(+)-ISOLEUCINOL
L-ISOLEUCINOL
(S)-(+)-2-AMINO-3-METHYL-1-PENTANOL
(S)-(+)-ISOLEUCINOL
(S,S)-2-AMINO-3-METHYL-1-PENTANOL
1-Pentanol, 2-amino-3-methyl-, [S-(R*,R*)]-
2-amino-3-methylpentan-1-ol
L-Ile-ol
(S)-(+)-ISOLEUCINOL/L-(+)-2-AMINO-3-METHYL-1-PENTANOL
1-PENTANOL, 2-AMINO-3-METHYL-, (2S,3S)-
(2S,3S)-2-Amino-3-methyl-1-pentanol, L-Isoleucinol
(2S,3S)-3-Methyl-2-amino-1-pentanol | [EINECS(EC#)]
246-371-4 | [Molecular Formula]
C6H15NO | [MDL Number]
MFCD00004731 | [Molecular Weight]
117.19 | [MOL File]
24629-25-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystalline solid or | [Melting point ]
36-39 °C(lit.)
| [alpha ]
4.5 º (c=1.6, EtOH) | [Boiling point ]
97 °C14 mm Hg(lit.)
| [density ]
0.9490 (rough estimate) | [refractive index ]
n20/D 1.4589(lit.)
| [Fp ]
213 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Viscous Liquid | [pka]
12.88±0.10(Predicted) | [color ]
White to light yellow | [Optical Rotation]
[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 Data | Back Directory | [Hazard Codes ]
C,Xi,Xn | [Risk Statements ]
R34:Causes burns.
R22:Harmful if swallowed.
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S22:Do not breathe dust . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29221990 |
| Hazard Information | Back Directory | [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 |
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