36684-65-8

Basic information

• Product Name: 6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE 9&
• Synonyms: 6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE 9&;6-CHLORO-1,2,3,4-TETRAHYDROCARBAZOLE, 98 %;1,2,3,4-Tetrahydro-6-chlorocarbazole;NSC 298291
• CAS NO: 36684-65-8
• Molecular Formula: C₁₂H₁₂ClN
• Molecular Weight: 205.68338
• Product Categories: Building Blocks;Carbazoles;CarbazolesHeterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 36684-65-8.mol
• Article Data: 41

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 358.8°Cat760mmHg
• Flash Point: 202.1°C
• Appearance: /
• Density: 1.280
• Vapor Pressure: 5.15E-05mmHg at 25°C
• Refractive Index: 1.672
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: slightly sol. in Methanol
• PKA: 16.93±0.20(Predicted)
• CAS DataBase Reference: 6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE 9&(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE 9&(36684-65-8)
• EPA Substance Registry System: 6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE 9&(36684-65-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 36684-65-8(Hazardous Substances Data)

Usage

General Description

6-Chloro-1,2,3,4-tetrahydrocarbazole 9 is a chemical compound with the molecular formula C13H13ClN. It is a derivative of carbazole, a tricyclic aromatic compound, and is characterized by the presence of a chloro group at the 6-position on the carbazole ring. 6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE 9& has potential applications in pharmaceutical and material science research, as well as in the synthesis of organic molecules. Its unique structure and reactivity make it a valuable intermediate in the production of various compounds with diverse properties and applications. Additionally, its potential biological and pharmacological activities make it a target for further investigation and potential drug development.

InChI:InChI=1/C12H12ClN/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h5-7,14H,1-4H2

Upstream product

• 100116-43-6 2-((4-chlorophenyl)amino)cyclohexan-1-one 
• 106-47-8 4-chloro-aniline 
• 533-60-8 cyclohexanone-2-ol 
• 822-87-7 2-Chlorocyclohexanone 
• 931-17-9 1,2-Cyclohexanediol 
• 108-94-1 cyclohexanone 
• 4340-77-6 4-chloroazobenzene 
• 955-98-6 1,2-bis(4-methylphenyl)diazene oxide 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 110-52-1 1,4-dibromo-butane 
• 17422-32-1 5-chloro-1H-indole 
• 1417717-04-4 tert-butyl 2-(4-chlorophenyl)hydrazine-1-carboxylate 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 
• 1073353-99-7 2-(5-chloro-2-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 859084-76-7 (6-chloro-1,2,3,4-tetrahydro-9H-carbazol-9-yl) (phenyl) methanone 
• 216856-80-3 (4aS,9aS)-6-chloro-2,3,4,4a,9,9a-hexahydro-1H-carbazole 
• 121593-97-3 Benzyl-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-amine 
• 1446264-40-9 6-chloro-N-(2-nitrophenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine 
• 1446264-39-6 6-chloro-N-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine 
• 1446264-53-4 4-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-ylamino)benzonitrile 
• 1424131-25-8 C₂₀H₁₈ClNO₂ 
• 1424131-36-1 4a-benzyl-6-chloro-2,3,4,4a-tetrahydro-1H-carbazole 
• 88368-11-0 6-Chloro-1,2,3,9-tetrahydro-4H-carbazol-4-one 
• 1314043-60-1 (R)-1-benzyl-5-(6-chloro-3,4-dihydro-1H-carbazol-9(2H)-yl)pyrrolidin-2-one 
• 686279-38-9 2-chloro-4-hydroxy-5-phenyl-8,9,10,11-tetrahydropyrido[3,2,1-jk]carbazol-6-one 
• 14192-67-7 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 86-74-8 9H-carbazole 
• 216856-80-3 6-chloro-1,2,3,4,4a,9a-hexahydro-carbazole 

Relevant articles and documents

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

SBA-15-Pr-SO3H catalyzed one-pot synthesis of indole derivatives via Fischer indole pathway

In this work, an efficient, user-friendly, and simple procedure was reported for the preparation of indole derivatives catalyzed by the heterogeneous SBA-15-Pr-SO3H via Fischer indole pathway. The title compounds were synthesized from various arylhydrazines and ketones in the presence of 3 mol% of the catalyst in the refluxing ethanol.

Design, synthesis, in vivo and in vitro studies of 1,2,3,4-tetrahydro-9H-carbazole derivatives, highly selective and potent butyrylcholinesterase inhibitors

Abstract: Inhibition of butyrylcholinesterase (BChE) might be a useful therapeutic target for Alzheimer’s disease (AD). A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit (> 100?μM), they were selective potent BChE inhibitors. 1-(2-(6-fluoro-1,2,3,4-tetrahydro-9H-carbazole-9-yl)ethyl)piperidin-1-ium chloride (15?g) had the most potent anti-BChE activity (IC50 value = 0.11?μM), the highest BChE selectivity and mixed-type inhibition. Pharmacokinetic properties were accordant to Lipinski rule and compound 15g demonstrated neuroprotective and inhibition of β-secretase (BACE1) activities. Furthermore, in vivo study of compound 15g in Morris water maze task has confirmed memory improvement in scopolamine-induced impairment. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD. Graphical abstract: A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit, they were selective potent BChE inhibitors. Compound 15g had the most potent anti-BChE activity. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD.[Figure not available: see fulltext.]