Chloromethyl 1-methylethyl carbonate
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Chloromethyl 1-methylethyl carbonate
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CAS No:
35180-01-9
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Formula:
C5H9ClO3
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Chemical Name:
Chloromethyl 1-methylethyl carbonate
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Synonyms:
Carbonic acid,chloromethyl 1-methylethyl ester;Chloromethyl 1-methylethyl carbonate;Isopropoxycarbonyloxymethyl chloride;Chloromethyl isopropyl carbonate;[(Isopropyloxycarbonyl)oxy]methyl chloride;Isopropyl chloromethyl carbonate;Chloromethyl propan-2-yl carbonate
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CAS No:
Characteristics
35.5
2
Colorless and transparent liquid
1.1±0.1 g/cm3
66 °C @ Press: 16 Torr
50.0±21.6 °C
1.420
Safety Information
Ⅲ
2924
3,8
24/25
P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
H315
Chloromethyl 1-methylethyl carbonate Use and Manufacturing
To cold solution (about 10 °C.) in chloro methyl chloroformate (65 mL) in diethyl ether (1.4 L), isopropanol (56 mL) was added followed by pyridine (60 mL) dropwise. After addition, the cold bath was removed and the reaction mixture was stirred for 18 h. The reaction mixture was poured into a separatory funnel containing cold water (100 mL). The ether layer was separated and washed with water (100 mL × 2) then dried over Na2SO4. Chloromethyl isopropyl carbonate (107 g, 95percent) was finished by evaporation of the solvent. Chloromethyl isobutyl carbonate, chloromethyl neopentyl carbonate, chloromethyl tert-butyl carbonate and chloromethyl 3-pentyl carbonate are synthesized in a similar manner.Propanol (73.14 mmole, 5.6 mL) was added to a solution of CHLOROMETHYL CHLOROFORMATE (73.85 mmole, 6.5 mL) in ether (100 mL). The reaction mixture was cooled to 0°C and pyridine (74.18 mmole, 6 mL) was dropwise added with stirring. Thereafter, the reaction mixture was stirred at ambient temperature for 20 hours. The formed solids were filtered and the filtrate was washed with citric acid (1percent aqueous), water, sodium bicarbonate solution (1percent) and brine. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 10.26 g (92percent) of a colorless oil. MS (ES+): m/e 152 (M+H).Propan-2-ol (785 mg, 13.19 mmol) was added to a solution of chloromethyl chloroformate (1.7 g, 13.19 mmol) in dry ethyl ether (2OmL) . The reaction mixture was cooled to 0A mixture of isopropanol (2.79 g, 46.5 mmol), triethylamine (4.94 g, 48.8 mmol) and dichloromethane (10.0 ml) was added drop wise to the stirred and cooled (0 C) solution of chloromethyl choroformate (6.0 g, 46.5 mmol) in dichoromethane (30 ml) during 30 min. The mixture was stirred at this temperature for another 30 min then the precipitate was filtered off. The filtrate was washed twice with saturated NAHC03 solution and water. The solvent was evaporated and the residue purified by distillation to obtain 2.84 g (4LAPOS;-.) of Carbonic acid chloromethyl ester isopropyl ester. NMR 1H (CDC13, 400 MHz) 5.75 (s, 2H), 5.00 (m, 1H), 1. 39 (d, 6H). *Procedure described in Synthetic communications, (1990) 20 (18), pp2865-2885
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Chloromethyl 1-methylethyl carbonate
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