116650-34-1

Basic information

• Product Name: (S)-3-Amino-1,2,3,4-tetrahydrocarbazole
• Synonyms: (S)-3-Amino-1,2,3,4-tetrahydrocarbazole;(S)-2,3,4,9-tetrahydro-1H-carbazol-3-amine;(S)-3-amino-1,2,3,4-terahydrocarbazole;(3S)-3-aMino-1,2,3,4-terahydrocarbazole;(3S)-3-AaMino-1,2,3,4-terahydrocarbazole
• CAS NO: 116650-34-1
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25
• Mol File: 116650-34-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 362.512 °C at 760 mmHg
• Flash Point: 200.5 °C
• Appearance: /
• Density: 1.192 g/cm³
• 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: (S)-3-Amino-1,2,3,4-tetrahydrocarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Amino-1,2,3,4-tetrahydrocarbazole(116650-34-1)
• EPA Substance Registry System: (S)-3-Amino-1,2,3,4-tetrahydrocarbazole(116650-34-1)

Safety Data

• Hazardous Substances Data: 116650-34-1(Hazardous Substances Data)

Usage

General Description

(S)-3-Amino-1,2,3,4-tetrahydrocarbazole is a chemical compound that belongs to the class of tetrahydrocarbazole derivatives. It is a heterocyclic compound containing a nitrogen atom in its ring structure. This chemical has been studied for its potential applications in various fields, including pharmaceuticals, organic synthesis, and materials science. It exhibits interesting properties due to its unique structure, and it is used as a building block in the synthesis of complex organic molecules. Additionally, its potential biological activities make it a subject of interest in drug discovery and development. The compound has also been investigated for its usefulness in the development of new materials, such as electronic and optical devices. Overall, (S)-3-Amino-1,2,3,4-tetrahydrocarbazole is a versatile chemical compound with a wide range of potential applications.

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/t8-/m0/s1

Upstream product

• 51145-61-0 1,2,3,4-tetrahydrocarbazol-3-one 
• 611-71-2 MANDELIC ACID 
• 61894-99-3 2,3,4,9-tetrahydro-1H-carbazol-3-yl-amine 
• 54621-12-4 1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane] 
• 100-63-0 phenylhydrazine 
• 17640-21-0 isopropyl methoxyacetate 
• 3938-96-3 ethyl 2-methoxyacetate 
• 128432-38-2 (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 104618-32-8 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 1344674-38-9 (S)-2-(9-(4-iodobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl)isoindoline-1,3-dione 
• 1344674-60-7 2-(4-(2-(4-iodobenzyl)-2-phenylhydrazono)cyclohexyl)isoindoline-1,3-dione 
• 1344675-16-6 (S)-9-(4-iodobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-amine 
• 179321-49-4 N-(tert-butoxycarbonyl)-4-aminocyclohexanone 

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 
• 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 
• 1374648-20-0 (R)-2-methoxy-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)acetamide 
• 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 
• 116649-85-5 ramatroban 
• 868984-45-6 (+/-)-benzyl 2,3,4,9-tetrahydro-1H-carbazol-3-yl-carbamate 
• 1414848-18-2 tert-butyl [9-(3-trifluoromethylbenzenesulfonyl)-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.

Cutting short the asymmetric synthesis of the ramatroban precursor by employing ω-transaminases

Starting from an adequate ketone precursor previous reports required three steps for the preparation of (R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine, a key intermediate for the synthesis of the antiallergic drug ramatroban. A single biocatalytic step was sufficient to prepare the target amine with >97% ee (HPLC) via reductive amination of the corresponding ketone using an ω-transaminase as biocatalyst. Since the ketone was barely soluble under the reaction conditions employed, it was provided as a solid and still the reaction went to completion within 4 h at 50 mM substrate concentration. Although 2-propylamine is regarded as an ideal amine donor, it turned out to be detrimental for the specific ketone precursor leading to the formation of various side products. These could be avoided by using (R)-1-phenylethylamine as the best suited amine donor. An alternative work-up was developed via freeze-drying of the reaction mixture, enabling the isolation of the desired (R)-amine in excellent yield (96%) and enantiopure form on a preparative scale (500 mg). No purification steps (e.g., column chromatography, crystallisation) were required.

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.