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| | 1,2,3,4-Tetrahydrocarbazole Basic information | | Synthesis |
| Product Name: | 1,2,3,4-Tetrahydrocarbazole | | Synonyms: | ,3,4,9-Tetrahydro-1H-carbazole;1H-Indole, 2,3-(1,4-butanediyl)-;2,3,4,9-tetrahydro-1h-carbazol;2,3-Tetramethylene-1H-indole;5,6,7,8-tetrahydro-carbazol;5,6,7,8-Tetrahydrocarbazole;Carbazole, 1,2,3,4-tetrahydro-;Carbazole, 5,6,7,8-tetrahydro- | | CAS: | 942-01-8 | | MF: | C12H13N | | MW: | 171.24 | | EINECS: | 213-385-7 | | Product Categories: | Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Building Blocks;Carbazoles;Heterocyclic Building Blocks | | Mol File: | 942-01-8.mol |  |
| | 1,2,3,4-Tetrahydrocarbazole Chemical Properties |
| Melting point | 118-120 °C (lit.) | | Boiling point | 325-330 °C (lit.) | | density | 1.1459 (rough estimate) | | refractive index | 1.6544 (estimate) | | Fp | 325-330°C | | storage temp. | Sealed in dry,Room Temperature | | form | powder to crystal | | pka | 17.84±0.20(Predicted) | | color | White to Orange to Green | | Water Solubility | Insoluble in water. Solubility in methanol (almost transparency). | | BRN | 133771 | | InChI | 1S/C12H13N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1,3,5,7,13H,2,4,6,8H2 | | InChIKey | XKLNOVWDVMWTOB-UHFFFAOYSA-N | | SMILES | C1CCc2c(C1)[nH]c3ccccc23 | | CAS DataBase Reference | 942-01-8(CAS DataBase Reference) | | NIST Chemistry Reference | 1H-Carbazole, 2,3,4,9-tetrahydro-(942-01-8) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 2 | | RTECS | FE6300000 | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| | 1,2,3,4-Tetrahydrocarbazole Usage And Synthesis |
| Synthesis |  In a 100 mL three-necked flask, phenylhydrazine hydrochloride (1.44 g, 10 mmol) was added in portions over 30 minutes to a 30 mL solution of cyclohexanone (1.00 g, 10 mmol) in acetic acid. The mixture was then refluxed for 8 hours until the reaction was complete. The reaction was cooled to room temperature and then poured into ice water. The solid was collected by filtration and recrystallized from methanol to give intermediate 1,2,3,4-tetrahydrocarbazole as a white solid, 1.44 g, yield 85%. | | Chemical Properties | beige crystalline powder | | Uses | It finds its application as a pharmaceutical intermediate and in the synthesis of aspidospermidine alkaloids. | | Uses | 1,2,3,4-Tetrahydrocarbazole can be used as a starting material to prepare:
- Spiro[cyclopentane-1,2′-indolin-3′-one] by photooxygenation.
- 9-Acyl-1,2,3,4-tetrahydrocarbazoles by N-acylation reactions.
- Carbazole via palladium-catalyzed asymmetric hydrogenation reaction.
| | Synthesis Reference(s) | Chemical and Pharmaceutical Bulletin, 14, p. 934, 1966 DOI: 10.1248/cpb.14.934 Tetrahedron Letters, 26, p. 161, 1985 DOI: 10.1016/S0040-4039(00)61869-5 |
| | 1,2,3,4-Tetrahydrocarbazole Preparation Products And Raw materials |
| Preparation Products | Ondansetron-->1,2,3,9-Tetrahydro-4(H)-carbazol-4-one-->9-[(5-chloro-1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-2,3,4,4a,9,9a-hexahydro-1H-carbazolium chloride-->9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE |
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