| Identification | Back Directory | [Name]
2-hydroxy-3-(o-tolyloxy)propyl carbamate | [CAS]
533-06-2 | [Synonyms]
Tolseram
Mephenesin carbamate
2-hydroxy-3-(o-tolyloxy)propyl carbamate
3-(2-Methylphenoxy)-1,2-propanediol 1-carbamate
[2-hydroxy-3-(2-methylphenoxy)propyl] carbamate
1,2-Propanediol, 3-(2-methylphenoxy)-, 1-carbamate
carbamic acid [2-hydroxy-3-(2-methylphenoxy)propyl] ester | [EINECS(EC#)]
208-553-1 | [Molecular Formula]
C11H15NO4 | [MOL File]
533-06-2.mol | [Molecular Weight]
225.24 |
| Chemical Properties | Back Directory | [Melting point ]
about 93°; mp 80-84° | [Boiling point ]
366.75°C (rough estimate) | [density ]
1.2102 (rough estimate) | [refractive index ]
1.5080 (estimate) |
| Hazard Information | Back Directory | [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 |
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