ChemicalBook CAS DataBase List 3-Chloropropiononitrile

3-Chloropropiononitrile synthesis

10synthesis methods

Product Name:3-Chloropropiononitrile
CAS Number:542-76-7
Molecular formula:C3H4ClN
Molecular Weight:89.52

3-Chloropropionitrile [542-76-7], 3-chloropropanenitrile, b-chloropropionitrile, ClCH2 CH2CN, Mr 89.53, mp-51℃, bp 175 –176℃ (101.3 kPa), n20D 1.4360, d204 1.1573, is a colorless liquid miscible with acetone, benzene, ethanol and diethyl ether. It can be obtained by hydrochlorination of acrylonitrile with hydrochloric acid [49] and is used as an organic intermediate in the synthesis of the H2-receptor famotidine.

98-88-4 Synthesis

98-88-4
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109-78-4 Synthesis

109-78-4
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542-76-7
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5325-95-1
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Yield:542-76-7 75%

Reaction Conditions:

with 1-pyrrolidinecarboxaldehyde at 80; for 5.5 h;Reagent/catalyst;Temperature;

Steps:

General procedure: Entry 1: According to general procedure Ill (chapter 2.1.3) a 100 mL flask with strong stir bar was charged with 3-hydroxypropannitrile 145 (14.1 mL, 14.66 g, 200 mmol, 1.0 equiv) and FPyr (7.9 mL, 8.10 g, 80.0 mmol, 40mo1%) and heated to 80 °C. Within 1.25 h benzoyl chloride (23.9 mL, 28.97 g,204 mmol, 1.02 equiv) was added dropwise and the reaction mixture was stirred for further 4.25 h at80 °C. After 4 h of stirring ‘H-N MR of a small aliquot of the reaction mixture (ca. 10 mg) showed fullconsumption of the starting material 145 and a chloride 245 to ester 345 ratio of 82:18. Then thereaction solution was allowed to cool down to ambient temperature accompanied by benzoic acidprecipitating. Distillation at 10 mbar through a micro distillation apparatus without dispenser delivered the chloride 245 as a colorless oil (13.75 g) with a boiling range of 66-80 °C (oil bath temperature 100-150 °C). As ‘H-N MR showed 2 mol% formiate 745 (referred to 245), the desired chloroalkane 245 was obtained in 75% yield (150.2 mmol).

References:

UNIVERSITAET DES SAARLANDES;HUY, Peter Helmut WO2016/202894, 2016, A1 Location in patent:Page/Page column 53; 132; 142; 143

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107-13-1 Synthesis