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| | 2-hydroxy-3-(o-tolyloxy)propyl carbamate Basic information |
| Product Name: | 2-hydroxy-3-(o-tolyloxy)propyl carbamate | | Synonyms: | 2-hydroxy-3-(o-tolyloxy)propyl carbamate;3-(2-Methylphenoxy)-1,2-propanediol 1-carbamate;Tolseram;[2-hydroxy-3-(2-methylphenoxy)propyl] carbamate;carbamic acid [2-hydroxy-3-(2-methylphenoxy)propyl] ester;1,2-Propanediol, 3-(2-methylphenoxy)-, 1-carbamate;Mephenesin carbamate | | CAS: | 533-06-2 | | MF: | C11H15NO4 | | MW: | 225.24 | | EINECS: | 2085531 | | Product Categories: | | | Mol File: | 533-06-2.mol |  |
| | 2-hydroxy-3-(o-tolyloxy)propyl carbamate Chemical Properties |
| Melting point | about 93°; mp 80-84° | | Boiling point | 366.75°C (rough estimate) | | density | 1.2102 (rough estimate) | | refractive index | 1.5080 (estimate) |
| Toxicity | LD50 in mice (mM/kg): 2.77 i.p.; 7.67 orally (Dresel, Slater) |
| | 2-hydroxy-3-(o-tolyloxy)propyl carbamate Usage And Synthesis |
| Originator | Tolseram,Squibb,US,1954 | | Definition | ChEBI: Mephenesin carbamate is an aromatic ether. | | Manufacturing Process | A solution of 32 g (0.30 mol) phosgene in 200 ml benzene is added dropwise at 30°C to a stirred solution of 53.5 g (0.32 mol) 3-o-toloxy-1,2-propanediol in 400 ml benzene. The mixture is stirred for an hour after the addition is completed, and a solution of 39 g of dimethylaniline in 100 ml benzene is then added, and stirring continued for a half-hour. Ice water (about one-third volume) is then added, and the benzene layer formed is separated and stirred with 500 mi concentrated ammonia at 5°C for six hours. The precipitated solid (weighing about 55 g) is recovered and recrystallized from water. The product thus obtained in a yield of about 53 g is 3-(o-toloxy)-2-hydroxypropyl carbamate: it is a crystalline solid melting at about 93°C, and having a lower water-solubility and higher oil-solubility than 3-o-toloxy-1,2-propanediol. | | Therapeutic Function | Muscle relaxant | | Synthesis Reference(s) | Journal of the American Chemical Society, 72, p. 3710, 1950 DOI: 10.1021/ja01164a107 |
| | 2-hydroxy-3-(o-tolyloxy)propyl carbamate Preparation Products And Raw materials |
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