| Identification | More | [Name]
(S)-4-Chloro-3-hydroxybutyronitrile | [CAS]
127913-44-4 | [Synonyms]
4-CHLORO-3-HYDROXY-BUTYRONITRILE
(S)-(-)-4-CHLORO-3-HYDROXYBUTYRONITRILE
(S)-4-CHLORO-3-HYDROXYBUTYRONITRILE
(S)-(-)-4-CHLORO-3-HYDROXYBUTYRONITRILE, 97% (97% EE/GLC)
(S)-4-CHLORO-3-HYDROXYBUTYRONITRILE 98+% | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C4H6ClNO | [MDL Number]
MFCD00273363 | [Molecular Weight]
119.55 | [MOL File]
127913-44-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [Boiling point ]
110 °C/1 mmHg(lit.) | [density ]
1.250 g/mL at 20 °C(lit.) | [refractive index ]
n20/D 1.474(lit.) | [Fp ]
110 °C | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Oil | [pka]
12.67±0.20(Predicted) | [color ]
Clear Colourless | [Optical Rotation]
Consistent with structure | [InChI]
InChI=1S/C4H6ClNO/c5-3-4(7)1-2-6/h4,7H,1,3H2/t4-/m0/s1 | [InChIKey]
LHBPNZDUNCZWFL-BYPYZUCNSA-N | [SMILES]
C(#N)C[C@H](O)CCl | [CAS DataBase Reference]
127913-44-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to light yellow liqui | [Uses]
(3S)-4-Chloro-3-hydroxybutyronitrile is used in various organic precursor syntheses. It is used in the synthesis of hydroxypyrrolidinones to by used as carbapenem precursors. Also used in the preparat
ion of atorvastatin (A791750) precursors. Impurity in the synthesis of Rosuvastatin (R700500), a selective, competitive HMG-CoA reductase inhibitor. Antilipemic. | [Synthesis]
1. 75 L of water was added to the reactor followed by (S)-epichlorohydrin (99.3% ee). Under stirring conditions, 4.76 kg of 25% aqueous sodium cyanide and 3.30 kg of 50% aqueous citric acid were slowly added dropwise for 1 h. 2. The pH was maintained between 7.9 and 8 during the reaction, and the temperature was controlled at 22-25°C for 50 min. 3. After completion of the reaction, stirring was continued for 10 h. Then 0.7 kg of sodium chloride was added and stirred until it was The reaction mixture was extracted with 20 L of ethyl acetate and the organic layer was separated. 5. 0.2 kg of anhydrous sodium sulfate was added to the ethyl acetate layer, stirred for 30 min and filtered. 6. The ethyl acetate was removed by evaporation under reduced pressure, and the residue was distilled through a membrane distiller at 110°C/1 mbar to give 1.77 kg of (S)-4-chloro-3-hydroxybutanenitrile (Yield 91.3%, chemical purity 99.1%). 7. and 99.1% chemical purity).7. The optical purity of the product was determined to be 99.3% ee by GC analysis.8. The experiments were repeated under different reaction conditions according to the same method and the results are summarized in Table 1. | [References]
[1] Synthesis, 2004, # 16, p. 2629 - 2632
[2] Patent: WO2005/87715, 2005, A1. Location in patent: Page/Page column 9-10
[3] Patent: WO2005/87715, 2005, A1. Location in patent: Page/Page column 10
[4] Patent: WO2005/87715, 2005, A1. Location in patent: Page/Page column 10 |
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