1775-86-6

Basic information

• Product Name: 2,3,4,4a,9,9a-hexahydro-1H-carbazole
• Synonyms: 2,3,4,4a,9,9a-hexahydro-1H-carbazole;1H-Carbazole, 2,3,4,4a,9,9a-hexahydro-
• CAS NO: 1775-86-6
• Molecular Formula: C₁₂H₁₅N
• Molecular Weight: 173.2542
• EINECS: 217-206-3
• Mol File: 1775-86-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 99 °C
• Boiling Point: 279.7°Cat760mmHg
• Flash Point: 127.4°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.00397mmHg at 25°C
• Refractive Index: 1.557
• PKA: 6.42±0.20(Predicted)
• CAS DataBase Reference: 2,3,4,4a,9,9a-hexahydro-1H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,4a,9,9a-hexahydro-1H-carbazole(1775-86-6)
• EPA Substance Registry System: 2,3,4,4a,9,9a-hexahydro-1H-carbazole(1775-86-6)

Safety Data

• Hazardous Substances Data: 1775-86-6(Hazardous Substances Data)

Usage

General Description

2,3,4,4a,9,9a-hexahydro-1H-carbazole is a chemical compound with the molecular formula C12H15N. It is a bicyclic heterocyclic compound that is commonly used in the production of a variety of organic compounds, including pharmaceuticals, dyes, and agrochemicals. It is a colorless liquid with a faint odor and is insoluble in water but soluble in organic solvents. 2,3,4,4a,9,9a-hexahydro-1H-carbazole is also known for its potential applications in the field of advanced material science and is being investigated for its use in organic electronic devices such as OLEDs and organic solar cells. Additionally, it is used as a precursor in the synthesis of other heterocyclic compounds and is an important building block in the chemical industry.

InChI:InChI=1/C12H15N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1,3,5,7,10,12-13H,2,4,6,8H2

Upstream product

• 86-74-8 9H-carbazole 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 4828-96-0 cis-2,3,4,4a,9,9a-hexahydro-1H-carbazole 
• 721968-93-0 3-methoxyphenyl allyl carbonate 
• 108-94-1 cyclohexanone 
• 59-88-1 phenylhydrazine hydrochloride 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 916902-76-6 4-tert-butyl-2-phenyloxazol-5-yl acetate 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 100-63-0 phenylhydrazine 
• 4806-81-9 o-cyclohexylaniline 
• 46175-80-8 2‘,3‘,4‘,5‘-tetrahydro-[1,1‘-biphenyl]-2-amine 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 

Downstream Products

• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 86-74-8 9H-carbazole 
• 916902-85-7 (+)-(2R,3R)-cis-5,6,7,8,8a,9-hexahydro-4bH-carbazole 
• 1448544-30-6 C₁₈H₁₈BrNO₂S 
• 206647-27-0 4-oxo-1,2,3,4-tetrahydrocarbazole 
• 570431-99-1 1-benzyl-3-(2,3-dihydro-1H-indol-1-yl)-4-(9H-carbazol-9-yl)-1H-pyrrole-2,5-dione 
• 570432-00-7 1-benzyl-3-(1H-indol-1-yl)-4-(9H-carbazol-9-yl)-1H-pyrrole-2,5-dione 
• 570431-98-0 1-benzyl-3-bromo-4-(9H-carbazol-9-yl)-1H-pyrrole-2,5-dione 
• 570431-97-9 1-benzyl-3-(1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)-4-bromo-1H-pyrrole-2,5-dione 

Relevant articles and documents

Diboron-mediated palladium-catalyzed asymmetric transfer hydrogenation using the proton of alcohols as hydrogen source

The developments of hydrogen sources stand at the forefront of asymmetric reduction. In contrast to the well-studied alcohols as hydrogen sources via β-hydride elimination, the direct utilization of the proton of alcohols as a hydrogen source for activator-mediated asymmetric reduction is rarely explored. Herein we report the proton of alcohols as a hydrogen source in diboron-mediated palladium-catalyzed asymmetric transfer hydrogenation of 1,3-diketones and indoles, providing a series of chiral β-hydroxy ketones and indolines with excellent yields and enantioselectivities. This strategy would be useful for the synthesis of chiral deuterium-labelled compounds due to the ready availability of deuterium-labelled alcohols. Mechanistic investigations and DFT calculations revealed that active chiral Pd-H species was generated from the proton of alcohols by activating of tetrahydroxydiboron, hydrogen transfer was the rate-determining step, and the reaction preferred Pd(0)-catalyzed mechanism. [Figure not available: see fulltext.]

Dearomatization-Rearomatization Strategy for Synthesizing Carbazoles with 2,2′-Biphenols and Ammonia by Dual C(Ar)-OH Bond Cleavages

Carbazole is an essential building block in various pharmaceuticals, agrochemicals, natural products, and materials. For future sustainability, it is highly desirable to synthesize carbazole derivatives directly from renewable resources or cheap raw materials. Phenolic compounds are a class of degradation products of lignin. On the other hand, ammonia is a very cheap industrial inorganic chemical. Herein, an efficient dearomatization-rearomatization strategy has been developed to directly cross-couple 2,2′-biphenols with ammonia by dual C(Ar)-OH bond cleavages. This strategy provides a greener pathway to synthesize valuable carbazole derivatives from phenols.

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.