Name | Chloromethyl pivalate |
Synonyms | hloromethyl pivalate Chloromethyl pivalate Methanol, chloro-, pivalate Pivalic acid Methyl chloride Chloromethyl 2,2-dimethylpropanoate Chloromethyl Pivalate [Amino-Protecting Agent] Chloromethyl Pivalate , (2,2-Dimethylpropanoic acid chlormetyl ester) Chloromethyl Trimethylacetate2,2-Dimethylpropionic Acid Chloromethyl EsterPivalic Acid Chloromethyl EsterTrimethylacetic Acid Chloromethyl Ester |
CAS | 18997-19-8 |
EINECS | 242-735-1 |
InChI | InChI=1/C6H11ClO2/c1-6(2,3)5(8)9-4-7/h4H2,1-3H3 |
InChIKey | GGRHYQCXXYLUTL-UHFFFAOYSA-N |
Molecular Formula | C6H11ClO2 |
Molar Mass | 150.6 |
Density | 1.045 g/mL at 25 °C (lit.) |
Boling Point | 146-148 °C (lit.) |
Flash Point | 104°F |
Water Solubility | Miscible with most organic solvents. Immiscible with water. |
Vapor Presure | 5.45mmHg at 25°C |
Appearance | Liquid |
Specific Gravity | 1.038 |
Color | Clear colorless to slightly yellow |
BRN | 1560838 |
Storage Condition | Inert atmosphere,2-8°C |
Refractive Index | n20/D 1.417(lit.) |
Physical and Chemical Properties | density 1.045 boiling point 70-72 ° C. (50 torr) refractive index 1.416-1.418 flash point 40 ° C. |
Use | For pharmaceutical intermediates, is the second generation of oral cephalosporin antibiotics ceftazidime Ester and cephalosporin Ester raw materials |
Risk Codes | R10 - Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S16 - Keep away from sources of ignition. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S41 - In case of fire and / or explosion do not breathe fumes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
UN IDs | UN 3272 3/PG 3 |
WGK Germany | 3 |
TSCA | Yes |
HS Code | 29159000 |
Hazard Class | 3 |
Packing Group | III |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Introduction | methyl chloride pivalate is an organic intermediate, which can be prepared from trimethylacetic acid and chloromethyl sulfonate as raw materials in one step. It has been reported in the literature that it can be used for the preparation of drug substances such as telopenem Ester and Adefovir dipivoxil. |
preparation method | trimethylacetic acid (5.68mmol) was dissolved in dichloromethane (15ml) and water (17ml) at room temperature. Sodium bicarbonate (28.45mmol) and tetrabutylammonium hydrogen sulfate (0.56mmol) were added slowly with vigorous stirring, and chloromethyl chlorosulfonate (8.5mmol) was added dropwise at 0 °c, stir at room temperature for 24h. After completion of the reaction, 100ml of ethyl acetate was added to the reaction mixture, which was then washed with a saturated aqueous ammonium chloride solution, the aqueous phase was extracted with ethyl acetate, and the organic phases were combined. The organic phase was washed successively with distilled water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain methyl chloride pivalate. |
Use | organic intermediates. for pharmaceutical intermediates, is the second generation of oral cephalosporin antibiotics ceftazidime Ester and cephalosporin Ester raw materials used as pharmaceutical intermediates; is the third generation of oral cephalosporin antibiotics cefetamet pivoxil and cephalosporin Ester raw materials. |
production method | results from chloromethylation of pivaloyl chloride. Pivaloyl chloride and paraformaldehyde were added to the reaction pot and stirred. Anhydrous Zinc chloride was added and the reaction was carried out for 21h at 90-100 °c. Then, distillation was carried out under reduced pressure, and the fraction of 71-75 ° C. (6.67kPa) was collected to obtain a final product. |