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1,2,3,4-Tetrahydrocarbazole

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1,2,3,4-Tetrahydrocarbazole manufacturers

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 Structure
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
pka17.84±0.20(Predicted)
color White to Orange to Green
Water Solubility Insoluble in water. Solubility in methanol (almost transparency).
BRN 133771
InChI1S/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
InChIKeyXKLNOVWDVMWTOB-UHFFFAOYSA-N
SMILESC1CCc2c(C1)[nH]c3ccccc23
CAS DataBase Reference942-01-8(CAS DataBase Reference)
NIST Chemistry Reference1H-Carbazole, 2,3,4,9-tetrahydro-(942-01-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 2
RTECS FE6300000
HS Code 29339900
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
1,2,3,4-Tetrahydrocarbazole English
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1,2,3,4-Tetrahydrocarbazole Usage And Synthesis
Synthesis

Synthetic Route of 1,2,3,4-Tetrahydrocarbazole

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 Propertiesbeige crystalline powder
UsesIt finds its application as a pharmaceutical intermediate and in the synthesis of aspidospermidine alkaloids.
Uses1,2,3,4-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
Tag:1,2,3,4-Tetrahydrocarbazole(942-01-8) Related Product Information
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