6303-88-4

Basic information

• Product Name: 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE
• Synonyms: 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE;1,2,3,4-tetrahydro-N-methylcarbazole;1H-carbazole,2,3,4,9-tetrahydro-9-methyl-;9-methyl-1,2,3,4-tetrahydrocarbazole;9-methyltetrahydrocarbazole;carbazole,1,2,3,4-tetrahydro-9-methyl-;N-methyl-1,2,3,4-tetrahydrocarbazole;N-methyltetrahydrocarbazole
• CAS NO: 6303-88-4
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.26
• Mol File: 6303-88-4.mol

Chemical Properties

• Melting Point: 50 °C
• Boiling Point: 339.7 °C at 760 mmHg
• Flash Point: 159.2 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 0.000178mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE(6303-88-4)
• EPA Substance Registry System: 9-METHYL-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE(6303-88-4)

Safety Data

• Hazardous Substances Data: 6303-88-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H15N/c1-14-12-8-4-2-6-10(12)11-7-3-5-9-13(11)14/h2,4,6,8H,3,5,7,9H2,1H3

Upstream product

• 23061-00-9 N,N'-dimethyl-N-phenyl-N'-(1-cyclohexenyl)hydrazine 
• 38253-19-9 2-(N-methylanilino)cyclohexanone 
• 1484-12-4 N-methylcarbazole 

Downstream Products

• 23518-22-1 N-Methyl-1,2,3,4,5,6,7,8-octahydrocarbazol 
• 1484-12-4 N-methylcarbazole 
• 39581-69-6 9-methyl-6-nitro-2,3,4,9-tetrahydro-1H-carbazole 
• 1775-89-9 (±)-9-methyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 
• 1775-89-9 (+/-)-9-methyl-(4ar,9ac)-1,2,3,4,4a,9a-hexahydro-carbazole 
• 30451-38-8 1,9-dimethylcarbazole-3-carboxaldehyde 
• 78153-07-8 1,2,3,4-tetrahydro-9-methylcarbazole-7-carboxaldehyde 
• 1485-19-4 9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 87497-91-4 9-methyl-3-phenyl-4,4a,9,9a-tetrahydro-4a,9a-butano<1,2>oxazino<6,5-b>indole 
• 87497-93-6 8-methyl-2-phenyl-3,3a,8,8a-tetrahydro-3a,8a-butanopyrrolo<2,3-b>indole 1-oxide 
• 87497-92-5 6-methyl-2,11a-diphenyl-4,5a,6,10b,11,11a-hexahydro-5a,10b-butano-3H-imidazo<1',2':2,3><1,2>oxazino<6,5-b>indole 1-oxide 
• 87895-12-3 C₂₆H₃₁N₃O₄S 
• 27387-31-1 9-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 107663-60-5 9-methyldodecahydrocarbazole 

Relevant articles and documents

Concise Synthesis of Polycyclic Indoline Scaffolds through an InIII-Catalyzed Formal [4+2] Annulation of 2,3-Disubstituted Indoles with o-Aminobenzyl Alcohols

A concise indium(III)-catalyzed annulation of 2,3-disubstituted indoles with o-aminobenzyl alcohols is reported. The in situ generated aza-ortho-quinone methides (aza-oQMs) were efficiently trapped by diverse carbazoles in a formal [4+2] cycloaddition reaction catalyzed by indium(III) triflate, which provided rapid access to bridged polycyclic indoline alkaloid skeletons.

MECHANISM OF THE FISCHER REACTION. REARRANGEMENT OF CYCLOHEXANONE N-METHYLPHENYLHYDRAZONE AND N,N'-DIMETHYL-N'-(1-CYCLOHEXENYL)HYDRAZINE TO 9-METHYL-1,2,3,4-TETRAHYDROCARBAZOLE

The kinetics of the thermal and acid-catalyzed Fischer reaction of cyclohexanone N-methylphenylhydrazone and N,N'-dimethyl-N'-(1-cyclohexenyl)hydrazine were studied by a spectrophotometric method.Formation of the carbon-carbon bond proceeds by a -sigmatropic shift mechanism.This conclusion was confirmed by MINDO/3 calculations of the rearrangement of a model divinylhydrazine.

Light-induced Reactions of 2-(N-Alkyl-N-arylamino)cyclohexanones and Related Amino-cycloalkanones: Formation of 7-Azabicyclooctan-1-ols

On irradiation, 2-(N-alkyl-N-arylamino)cyclohexanones (aryl = Ph; alkyl = Me, benzyl, allyl, Et, CH2CH2Ph, or CH2CF3; or aryl = p-tolyl; alkyl = Me) (10) or (20), 4,4-dimethyl-2-(N-methylanilino)-cyclohexanone (24), and 2-(N-methylanilino)-5α-cholestan-3-one (26) underwent type-II cyclisation to afford azetidinol (7-azabicyclooctan-1-ol) derivatives.In general, fission to give the corresponding N-alkyl-N-arylamine and ketone was a minor photoreaction.When the alkyl group of the 2-(N-alkylanilino)cyclohexanone had the structure -CH(R)CH2R', a double 1,5-hydrogen transfer occurred leading to a low yield of a 2-anilinocyclohexanol (31a).Photolysis of 2-anilinocyclohexanone (32a) gave a little of the direct-fission product aniline (17a), and the alkylamino-ketones 2-(NN-diethylamino)- (32b) and 2-(N-pyrrolidino)-cyclohexanone (32c) underwent no significant photoreaction in methanol.The isolation of indan-1-one and N-trideuteriomethylaniline on irradiation of 2-(N-trideuteriomethylanilino)-indan-1-one (33b) in diethyl ether indicated that the photoreaction was a direct Cα-N bond fission and not a type-II fission.

2-(2,6-DIMETHYLPIPERIDINO)ACETONITRILE AS AN ACYL CARBANION EQUIVALENT

Reaction of lithio 2-(2,6-dimethylpiperidino)acetonitrile with alkyl halides affords monoalkylation products which are easily hydrolyzed under mild conditions to give the homogeneous aldehyde or its acetal in moderate yield.In the case of alkyl halides having an electron donating group on aromatic ring the cyclization products are obtained.