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| | Chloroacetic anhydride Basic information |
| | Chloroacetic anhydride Chemical Properties |
| Melting point | 51 °C | | Boiling point | 203 °C | | density | 1.449 | | vapor pressure | <0.75 mm Hg ( 20 °C) | | refractive index | 1.4730 (estimate) | | Fp | >230 °F | | storage temp. | Hygroscopic, -20°C Freezer, Under inert atmosphere | | solubility | Freely soluble in ether, chloroform. Slightly soluble in benzene. Insoluble in cold ligroin | | form | Crystals, Chunks or Low Melting Mass | | color | brown | | Sensitive | Moisture Sensitive | | Merck | 14,2113 | | BRN | 774533 | | Stability: | Moisture Sensitive | | InChIKey | PNVPNXKRAUBJGW-UHFFFAOYSA-N | | CAS DataBase Reference | 541-88-8(CAS DataBase Reference) | | EPA Substance Registry System | Acetic acid, chloro-, anhydride (541-88-8) |
| | Chloroacetic anhydride Usage And Synthesis |
| Chemical Properties | brownish semi-transparent crystals, chunks or low | | Uses | In N-acetylation of amino acids in alkaline solution; preparation of cellulose chloroacetates. | | Uses | Chloroacetic anhydride has been used in the synthesis of 3,3-bis(sulfonato)-4,4-bis(chloroacetamido)azobenzene (BSBCA), a water-soluble, thiol-reactive and photo-switchable cross-linker, D,L-7-azatryptophan, 2-methyl-[3,4-di-O-acetyl-6-O-(chloroacetyl)-1,2-dideoxy-α-D-glucopyrano]-[2,1:4,5]-2-oxazoline. | | Preparation | chloroacetic anhydride Synthesis: Powdered s odium monochloroacetate(113.3g, 1.138 mol) was added slowly for a period of 15 min at room temperature (which slowly raises to 60°C) to a stirred solution of commercially available chloroaceyl chloride (127.5g, 1mol) in dry benzene (136mL) was refluxed for 9h. Salts were filtered off, the filtrate was cooled to room temperature, diluted with n-hexane and further cooled to 0°C. The solid separated was then filtered, washed with dry hexane and dried to yield chloroacetic anhydride as white crystalline compound in 60% yield (80g); mp=46-49°C [Lit. mp=46°C]. Alternatively, the benzene layer was directly subjected to high vacuum distillation.The product collected at 109-10°C at 10mm vacuum on cooling chloroacetic anhydride in lump form in 70 % yield (93g). It was observed that, the latter method gives anhydride in lump form while the former method gives in crystalline form. | | Purification Methods | Crystallise the it from *benzene. [Eglinton et al. J Chem Soc 1860 1954, Beilstein 2 IV 487.] |
| | Chloroacetic anhydride Preparation Products And Raw materials |
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