84367-31-7
(R)-(+)-4-chloro 3-hydroxybutyronitrile
CAS: 84367-31-7
Molecular Formula: C4H6ClNO
84367-31-7 - Names and Identifiers
84367-31-7 - Physico-chemical Properties
| Molecular Formula | C4H6ClNO |
| Molar Mass | 119.55 |
| Density | 1.250g/mLat 20°C(lit.) |
| Boling Point | 110°C1mm Hg(lit.) |
| Specific Rotation(α) | 11 º (neat) |
| Flash Point | >230°F |
| Vapor Presure | 0.0343mmHg at 25°C |
| Appearance | clear liquid |
| Color | Colorless to Light yellow |
| BRN | 1700586 |
| pKa | 12.67±0.20(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Refractive Index | n20/D 1.474(lit.) |
| MDL | MFCD00273362 |
| Physical and Chemical Properties | Colorless to light yellow liquid, stored in a closed container at room temperature. Boiling point 76-80°C/0.1mmHg. |
| Use | (-)-carnitine and (-)-γ-amino-β-hydroxybutyric acid can be prepared with this synthetic monomer. |
84367-31-7 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-21 |
| HS Code | 29269090 |
84367-31-7 - Reference Information
| Introduction | (R)-4-chloro-3-hydroxy-butyronitrile is an organic intermediate, it can be prepared by reacting R-epichlorohydrin and hydrocyanic acid. It has been reported in the literature to be useful in the preparation of L-carnitine. L-carnitine, also known as carnitine, vitamin BT, L-carnitine, chemical name for beta-hydroxy-gamma-trimethylammonium butyric acid, L-carnitine molecular formula for C7Hl5NO3, molecular weight of 161.20, is a white lens or white transparent fine powder, with a special smell, easy to absorb moisture. In 1905, a team of Russian scientists led by Gulewitsch first discovered carnitine from meat extracts. |
| preparation | (1) 19.19g(0.174mol)(R)-(-)-chloroglycerol, 50ml of dichloromethane was put into a 22.74 ml three-necked flask, and g (0.1910 ml) of dichlorosulfoxide was slowly added dropwise in an ice bath. Reaction 1h, 40ml of water was added, the organic layer was washed twice with saturated saline, the aqueous layer was washed twice with ethyl acetate, and the organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 27.23G of a colorless liquid. That is, the cyclic sulfinate intermediate was directly used in the next step without purification, and the yield was 100%. (2) add 10g(0.064mol) cyclic sulfinate, 30ml methanol to ML three-necked flask, add 5.21g(0.08mol)KCN at room temperature, stir for 10min, it was then raised to 50 °c and stirred vigorously for 12h. Concentrate under reduced pressure, add 15ml of ethyl acetate and slowly add 20% H2SO4 solution dropwise. After stirring for 5H, dilute NaCO3 solution was added and washed twice, washed twice with water, washed once with saturated brine, the aqueous layer was washed with ethyl acetate, and the organic layer was combined and dried with anhydrous sodium sulfate. A fraction of 89-90 ° C./<1mmHg was collected by distillation under reduced pressure to give 6.51G of a colorless liquid, I .e., a chlorobutylnitrile intermediate in a yield of 85%. |
| Use | a variety of chiral pharmaceutical intermediates. |
Last Update：2024-04-09 21:54:55
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