61894-99-3

Basic information

• Product Name: 3-Amino-1,2,3,4-tetrahydrocarbazol
• Synonyms: 3-amino-1,2,3,4-tetrahydrocarbazol;2,3,4,9-Tetrahydro-1H-carbazol-3-amine;3-aMino-1,2,3,4-tetrahydrocarbazole
• CAS NO: 61894-99-3
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25
• EINECS: 200-528-9
• Mol File: 61894-99-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 170-172 °C(Solv: ethanol (64-17-5))
• Boiling Point: 362.512 °C at 760 mmHg
• Flash Point: 200.5 °C
• Appearance: /
• Density: 1.192 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 17.54±0.40(Predicted)
• CAS DataBase Reference: 3-Amino-1,2,3,4-tetrahydrocarbazol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-1,2,3,4-tetrahydrocarbazol(61894-99-3)
• EPA Substance Registry System: 3-Amino-1,2,3,4-tetrahydrocarbazol(61894-99-3)

Safety Data

• Hazardous Substances Data: 61894-99-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 22, p. 191, 1985 DOI: 10.1002/jhet.5570220146

InChI:InChI=1/C12H14N2/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-4,8,14H,5-7,13H2

Upstream product

• 611-71-2 MANDELIC ACID 
• 179321-49-4 N-(tert-butoxycarbonyl)-4-aminocyclohexanone 
• 1392271-79-2 tert-butyl N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate 
• 97096-16-7 1,4-dioxaspiro[4.5]decan-8-amine 
• 100-63-0 phenylhydrazine 
• 180918-12-1 4-oximinocyclohexanone ethylene ketal 
• 54621-12-4 1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane] 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 1234493-21-0 3-(phthalimido)-1,2,3,4-tetrahydrocarbazole 
• 128432-38-2 (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol 
• 34154-31-9 3-hydroxy-1,2,3,4-tetrahydrocarbazole p-toluenesulphonate ester 
• 51145-61-0 1,2,3,4-tetrahydrocarbazol-3-one 

Downstream Products

• 60480-69-5 N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetamide 
• 116650-33-0 (3R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine 
• 1374648-20-0 (R)-2-methoxy-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetamide 
• 116650-34-1 (3S)-2,3,4,9-tetrahydro-1H-carbazol-3-amine 
• 116650-12-5 4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide 
• 1374648-21-1 (S)-benzyl 2,3,4,9-tetrahydro-1H-carbazol-3-yl-carbamate 
• 118699-38-0 (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide 
• 134525-56-7 (S)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide 
• 141307-19-9 (R)-methyl 3-[3-(4-fluorophenylsulfonamido)-3,4-dihydro-1H-carbazol-9(2H)-yl]propanoate 
• 134994-01-7 methyl 3-[3-(4-fluorophenylsulfonamido)-3,4-dihydro-1H-carbazol-9(2H)-yl]propanoate 
• 116650-36-3 (R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide 
• 116650-37-4 (S)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide 
• 116649-85-5 ramatroban 
• 868984-45-6 (+/-)-benzyl 2,3,4,9-tetrahydro-1H-carbazol-3-yl-carbamate 

Relevant articles and documents

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

N,N-Dimethyl-[9-(arylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amines as novel, potent and selective 5-HT6 receptor antagonists

The design, synthesis and SAR of novel tetrahydrocarbazole derivatives having 5-HT6 receptor antagonist activity is presented. The racemic compound 15e was found to possess desirable pharmacokinetic properties, adequate brain penetration and activity in animal models of cognition.

Fluorescence Studies with Tryptophan Analogues: Excited State Interactions Involving the Side Chain Amino Group

The fluorescence of a large set of tryptophan analogues, including several that are conformationally constrained, was studied.The constrained analogues include tetrahydrocarboline-3-carboxylic acid and 3-amino-3-carboxytetrahydrocarbazole.Steady state and time-resolved fluorescence measurements were made as a function of pH.The fluorescence quantum yields of the constrained analogues are higher than those for the unconstrained counterparts.The emission intensity of the constrained analogues, as well as 4-methyltryptophan, decreases with deprotonation of the side chain α-ammonium groups; this is in contrast to the increase in fluorescence of tryptophan with deprotonation of this group.These results are consistent with the existence of excited state proton transfer to carbon 4 of the indole ring as a quenching mechanism, which is sterically prohibited in the constrained analogues and 4-methyltryptophan.From quantum yield and lifetime data (most decays are nonexponential), the effective rate constant for nonradiative depopulation of the excited state was calculated.For tryptophan analogues having two side chain functional groups, there is a synergistic effect; the presence of two side chain groups causes more quenching than expected from the sum of the individual contributions.For analogues having an α-ammonium group, this synergism appears to be correlated with an induced change in the pKa of this group.Deprotonation of this α-ammonium group also caused a red shift in the emission of these compounds; this appears to be due to electrostatic repulsion between the α-NH3+ group and the excited indole dipole.