1,2,3,4-Tetrahydrocarbazole

• Catalog No.: B23657
• CAS Number: 942-01-8
• M. F.: C12H13N
• M. W.: 171.23832
• Purity: 99%

SYNONYMS

• Title: 1,2,3,4-四氢咔唑
• IUPAC name: 2,3,4,9-tetrahydro-1H-carbazole
• IUPAC Traditional name: 2,3,4,9-tetrahydro-1H-carbazole

DATABASE IDS

• EC Number: 213-385-7
• MDL Number: MFCD00004959
• Beilstein Number: 133771
• CAS Number: 942-01-8

PROPERTIES

• Purity: 99%
• Boiling Point: 325-330°C
• Melting Point: 118-120°C
• GHS Hazard statements: H315-H319-H335-H303
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• RTECS: FE6300000
• Safety Statements: 26-37
• TSCA Listed: 否

REFERENCES

• Deprotonation with excess superbasic n-BuLi/KO-t-Bu to give the N,ɑ-dianion has been studied in a variety of ether solvents. Formation of substantial amounts of the ɑ-ethyl derivative was observed with Et₂O and THF, and also, remarkably, with various alkyl methyl ethers; e.g. in n-BuOMe, the ɑ-ethyl product was obtained in 60% yield. The ethyl group originates from the interaction of the solvent with the strong base, confirmed by the detection of ethylene in the absence of the tetrahydrocarbazole substrate: J. Org. Chem., 60, 8334 (1995). ɑ-Ethylation also occurred with 2-ethylindole, but not with 2-methyl- or 2-isopropyl analogues.
• Photooxygenation with singlet oxygen, followed by reduction of the expected hydroperoxide to the allylic alcohol, is accompanied by ring contraction to a spiro ketone. The same product is formed in high yield on treatment of the spiroketone with mineral acid: J. Org. Chem., 61, 810 (1996):