| Identification | Back Directory | [Name]
ISOCYANOBENZENE | [CAS]
931-54-4 | [Synonyms]
ISOCYANOBENZENE
Benzoisonitrile
PHENYLISOCYANIDE
Phenyl isonitrile
1-ISOCYANOBENZENE
Phenyl carbylamine
Benzene, isocyano-
PHENYL ISOCYANIDE (1-ISOCYANOBENZENE) | [EINECS(EC#)]
213-239-2 | [Molecular Formula]
C7H5N | [MDL Number]
MFCD05148520 | [MOL File]
931-54-4.mol | [Molecular Weight]
103.12 |
| Chemical Properties | Back Directory | [Boiling point ]
183.35°C (rough estimate) | [density ]
1.0248 (rough estimate) | [refractive index ]
1.6760 (estimate) | [solubility ]
Chloroform (Soluble), Methanol (Slightly) | [form ]
Oil to Thick Oil | [color ]
Very Dark Red to Black |
| Questions And Answer(Q&A) | Back Directory | [Preparation]
To a flask containing 7.9 gm (0.33 mole) of sodium hydride in 100 ml of tetrahydrofuran is slowly added a mixture of 9.3 gm (0.1 mole) of aniline and 25.3 gm (0.10 mole) of bromoform. After the addition, the reaction is stirred for 1-2 hr at room temperature, and water is added (100 ml) dropwise. Ether (200 ml) is added and the ether layer washed four times with 50-ml portions of water, three times with 20-ml portions of dilute hydrochloric acid, and then with water. The resulting ether layer is dried over sodium sulfate, concentrated, and the residue distilled to afford 4.7 gm (45%), b.p. 52-53°C (13 mm Hg).
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| Hazard Information | Back Directory | [Uses]
Isocyanobenzene is used in the study of the inhibition mechanism of reconstituted cytochrome p-450scc-linked monooxygenase system by antimycotic reagent and other inhibitors. | [Definition]
ChEBI: Phenyl isocyanide is an isocyanide. | [Precautions]
Should be used freshly distilled. Foul smelling liquid; should be stored and used in a fume hood. Contaminated equipment should be washed with 5% methanolic sulfuric acid.
| [References]
1. For general reviews on isocyanide chemistry, see: (a) Isonitrile Chemistry; Ugi, I., Ed.; Academic: New York, 1971. (b) Periasamy, M. P.; Walborsky, H. M. OPP 1979, 11, 295.
2. For applications in heterocyclic synthesis, see: Marcaccini, S.; Torroba, T. OPP 1993, 25, 141.
3. (a) Grundmann, C. CB 1958, 91, 1380. (b) Ugi, I.; Meyr, R. OS 1961, 41, 101. (c) Obrecht, R.; Herrmann, R.; Ugi, I. S 1985, 400.
4. Figueroa-Villar, J. D.; Carnieiro, C. L.; Cruz, E. R. H 1992, 34, 891
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