2,3,4,9-tetrahydro-1H-carbazole

• ChemBase ID: 71703
• Molecular Formular: C12H13N
• Molecular Mass: 171.23832
• Monoisotopic Mass: 171.10479942
• SMILES: c1ccc2[nH]c3c(c2c1)CCCC3
• Canonical SMILES: C1CCc2c(C1)[nH]c1c2cccc1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3,4,9-tetrahydro-1H-carbazole
• IUPAC Traditional name: 2,3,4,9-tetrahydro-1H-carbazole
• Synonyms: 2,3,4,9-Tetrahydro-1H-carbazole; 1,2,3,4-Tetrahydrocarbazole; 1,2,3,4-Tetrahydrocarbazole; 1,2,3,4-四氢咔唑

Database IDs

• CAS Number: 942-01-8
• EC Number: 213-385-7
• MDL Number: MFCD00004959
• Beilstein Number: 133771
• PubChem SID: 24899946; 162037139
• PubChem CID: 13664

CALCULATED PROPERTIES

• Acid pKa: 17.278738
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 3.2883556
• LogD (pH = 7.4): 3.2883556
• Log P: 3.2883556
• Molar Refractivity: 54.6582 cm^3
• Polarizability: 22.121792 Å^3
• Polar Surface Area: 15.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 118-120 °C(lit.); 118-120°C
• Boiling Point: 325-330 °C(lit.); 325-330°C

Safety Information

• Storage Warning: IRRITANT
• RTECS: FE6300000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%; 99%
• Empirical Formula (Hill Notation): C12H13N

DETAILS

MP Biomedicals - 05218972

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T12408

Packaging
25 g in glass bottle

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):