Identification | More | [Name]
(S)-(-)-Methyl 2-chloropropionate | [CAS]
73246-45-4 | [Synonyms]
(-)-METHYL (S)-2-CHLOROPROPIONATE METHYL (S)-(-)-2-CHLOROPROPIONATE S-2-CHLOROPROPANOIC ACID METHYL ESTER (S)-(-)-2-CHLOROPROPIONIC ACID METHYL ESTER (S)-2-CHLOROPROPIONIC ACID METHYL ESTER (S)-(+)-METHYL 2-CHLOROPROPIONATE 2-chloro-,methylester,(s)-propanoicaci Methyl 2-chloropropanoate Methyl L-chloropropionate L(-)-2-Chloropropionate methyl ester (2S)-2-Chloropropanoic acid methyl ester (S)-2-Chloropropionic acid methyl | [EINECS(EC#)]
412-470-8 | [Molecular Formula]
C4H7ClO2 | [MDL Number]
MFCD00062941 | [Molecular Weight]
122.55 | [MOL File]
73246-45-4.mol |
Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R10:Flammable. R36:Irritating to the eyes. R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . | [RIDADR ]
UN 2933 3/PG 3
| [WGK Germany ]
1
| [F ]
19 | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29159000 |
Hazard Information | Back Directory | [Uses]
(-)-Methyl α-Chloropropionate is used in the preparation of TIPTP which is a therapeutic agent for rheumatoid arthritis. | [Uses]
Chiral starting material. | [Synthesis]
Step I, preparation of Vilmerier reagent: 71.4 g (0.6 mol) of thionyl chloride was added to a 250 mL four-necked flask, cooled to 5~10°C in an ice-water bath, and 50.4 g (0.69 mol) of dry N,N-dimethylformamide was slowly added, the reaction was exothermic obviously, and mechanically stirred for 2 h to obtain a colorless Vilmerier reagent solution. Step II, Synthesis of methyl (S)-2-chloropropionate: a small amount of dioxane was added to the Vilmerier reagent solution obtained in Step I via a constant pressure dropping funnel at 20~30°C to form a mixed solution. Subsequently, 62.4 g (0.6 mol) of (R)-lactic acid methyl ester was slowly added dropwise to the mixed solution, and the reaction was markedly exothermic and gas was generated. After the dropwise addition, the reaction was continued with stirring and heated to 55°C for 6 h to obtain a solution of methyl (S)-2-chloropropionate. After the reaction was completed, the reaction mixture was cooled. Step III, post-treatment: the (S)-2-chloropropionic acid methyl ester solution obtained in Step II was washed, desolventized and distilled to obtain the product (S)-2-chloropropionic acid methyl ester 54.4 g, with 86% yield and 87% optical purity. | [References]
[1] Patent: CN103232344, 2016, B. Location in patent: Paragraph 0036-0039 |
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