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

Description

(S)-3-Amino-1,2,3,4-tetrahydrocarbazole is a heterocyclic chemical compound belonging to the tetrahydrocarbazole derivatives. It features a nitrogen atom in its ring structure, which endows it with unique properties and makes it a versatile building block in the synthesis of complex organic molecules. (S)-3-Amino-1,2,3,4-tetrahydrocarbazole has garnered attention for its potential applications across various fields, including pharmaceuticals, organic synthesis, and materials science, due to its interesting properties and potential biological activities.

Uses

Used in Pharmaceutical Industry:
(S)-3-Amino-1,2,3,4-tetrahydrocarbazole is used as a key intermediate in the synthesis of pharmaceutical compounds for its potential biological activities, contributing to drug discovery and development.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-3-Amino-1,2,3,4-tetrahydrocarbazole serves as a valuable building block for creating complex organic molecules, facilitating the development of novel chemical entities.
Used in Materials Science:
(S)-3-Amino-1,2,3,4-tetrahydrocarbazole is utilized in the development of new materials for its potential to contribute to the advancement of electronic and optical devices, showcasing its versatility in applications beyond traditional chemical uses.

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 
• 34154-31-9 3-hydroxy-1,2,3,4-tetrahydrocarbazole p-toluenesulphonate ester 
• 128432-38-2 (+/-)-2,3,4,9-tetrahydro-1H-carbazol-3-ol 
• 611-71-2 MANDELIC ACID 
• 1234493-21-0 3-(phthalimido)-1,2,3,4-tetrahydrocarbazole 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 100-63-0 phenylhydrazine 
• 54621-12-4 1,2,4,9-tetrahydrospiro[3H-carbazole-3,2*-[1,3]doxolane] 
• 180918-12-1 4-oximinocyclohexanone ethylene ketal 
• 97096-16-7 1,4-dioxaspiro[4.5]decan-8-amine 
• 1392271-79-2 tert-butyl N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)carbamate 
• 179321-49-4 N-(tert-butoxycarbonyl)-4-aminocyclohexanone 
• 1344675-16-6 (S)-9-(4-iodobenzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-amine 
• 1344674-60-7 2-(4-(2-(4-iodobenzyl)-2-phenylhydrazono)cyclohexyl)isoindoline-1,3-dione 

Downstream Products

• 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 
• 116650-12-5 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 
• 1414848-18-2 tert-butyl [9-(3-trifluoromethylbenzenesulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]carbamate 
• 1609031-05-1 (E)-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)-3-(3,4,5-trimethoxyphenyl)acrylamide 

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.