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86-74-8 Usage

Introduction

Carbazole and its derivatives are a class of important nitrogen-containing heterocyclic compounds possessing various unique properties and biological activity. Carbazole is a colorless small scale crystal, insoluble in water and inorganic acid, slightly soluble in ethanol, ether, acetone, benzene (in high temperature), soluble in chloroform, glacial acetic acid, carbon disulfide, pyridine and furfural, etc. It has intense fluorescence and prolonged phosphorescence under ultraviolet light.

Extraction

Sulfuric acid method Dissolve crude anthracene in chlorobenzene or other solvents to remove soluble phenanthrenes, quinones, etc. Insoluble anthracene and carbazoles are then reacted with concentrated sulfuric acid, and then carbazole sulfate is generated departing from the anthracene. The carbazole sulfate is hydrolyzed, filtered and dried to obtain carbazole. Solvent-rectification method Dissolve crude anthracene with heavy benzene, and remove soluble phenanthrene, quinone and other substances. Insoluble anthracene and carbazole are rectified in a rectification tower to obtain a mixture containing 85 to 90% of carbazole with a yield of 65%. Pyridine solvent method Dissolve crude anthracene with heavy benzene, and remove soluble phenanthrene, quinone and other substances. Then pyridine is used as a solvent to filter off insoluble anthracene at 90°C, and the filtrate is then crystallized to obtain crude carbazole. The crude carbazole can be treated with chlorobenzene or other solvents to obtain carbazole with yield of 97 to 99%.

Production

a. Graebe-Ullmann: Diazotization from amino diphenylamine, and nitrogen gas heated off to generate carbazole. Reported by Graebe and Ullmann in 1896. b. Bucherer: Co-thermal reaction of aryl hydrazine and naphthol in the presence of sodium bisulfite. Reported by Bucherer in 1904. c. Borsche Drechsel: Hydrazone is synthesized by condensation of Benzoquinone and cyclohexanone, and the latter cyclized to tetrahydrocarbazole under acidic conditions and then catalyzed by dehydrogenation to generate carbazole. Reported by Drechsel and Borsche in 1868 and 1904 respectively. Thanks to the development of the catalytic dehydrogenation method, the Borsche method has become a carbazole synthetic route with simple operation, mild conditions, low cost and high yield, and has a high industrial production value. Because of its unique structure and physicochemical properties, carbazole has aroused great interest among researchers. In recent years, novel monoand poly-substituted carbazole derivatives have been found to have good anti-tumor and anti-convulsant activities, showing broad application prospects. The demand for carbazole and its derivatives has been increasing. In the last decade of the 20th century, a large number of novel precious metals and transition metal catalysts have been used in the synthesis of carbazoles and their derivatives, which greatly enriched the synthetic methods and lay the foundation of synthesizing more complex carbazole derivatives. Nowadays, not only carbazole, but tens of thousands of carbazole derivatives are synthesized by new methods, and are widely used in the pharmaceutical and dye industries.

Chemical Properties

Different sources of media describe the Chemical Properties of 86-74-8 differently. You can refer to the following data:
1. In the laboratory method, the ring-closure dehydrogenation of o-aminobiphenyl is made from ammonia or chlorobenzene. In the industrial production method, 90% of the world's carbazole is obtained from coal tar; it can also be synthesized from o-aminobiphenyl, and then purified by recrystallization from xylene. (1) Synthesis method: 1-phenyl-1,2,3-benzotriazole is prepared by using o-aminodiphenylamine as raw material and treated with nitrous acid. After heating, nitrogen is lost to form carbazole. (2) Sulfuric acid method: Dissolve the crude anthracene with chlorobenzene or other solvents. The phenanthrene, fluorene and other substances in the crude anthracene are separated from anthracene and carbazole due to insolubility. Anthracene and carbazole are added to sulfuric acid for reaction. Then it forms carbazole sulfate with sulfuric acid and separates from anthracene. After hydrolyzing carbazole sulfate, the finished product is obtained by filtration and drying. (3) Solvent-rectification method: The crude anthracene is dissolved in the heavy benzene (160~200℃) by-product of coking, and the phenanthrene, fluorene and other substances in the crude anthracene are separated from anthracene and carbazole. High-temperature rectification is carried out in the distillation tower, and after one rectification, a product containing 85% to 90% of carbazole can be obtained, and the yield is 65%.
2. white crystals or light brown powder

Uses

Different sources of media describe the Uses of 86-74-8 differently. You can refer to the following data:
1. Important dye intermediate. Used in making photographic plates sensitive to ultraviolet light. Reagent for lignin, carbohydrates, and formaldehyde.
2. Carbazole and its derivatives are widely used as an intermediate in synthesis of pharmaceuticals, agrochemicals, dyes, pigments and other organic compounds.?carbazole is also used in luminescence chemistry as a photosensitizing and additional charge transport material. Carbazole structure is a motif in pharmaceuticals such as carvedilol used to treat high blood pressure and to prevent cardiac arrhythmias and angina.
3. Intermediate in production of dyes and UVsensitive photographic plates.

Definition

Different sources of media describe the Definition of 86-74-8 differently. You can refer to the following data:
1. A white crystalline compound used in the manufacture of dyestuffs.
2. carbazole: A white crystalline compoundfound with anthracene,C12H9N; m.p. 238°C; b.p. 335°C. It isused in the manufacture of dyestuffs.

Application

Carbazole can be used to produce dyes, pigments, photoconductors, photosensitive materials, special inks, etc. The pigment produced with it is permanent purple RL, which is widely used in the coloring of automobile topcoat and high temperature resistant plastics, and has the advantages of high temperature resistance and ultraviolet light resistance. The dyestuffs sulphur vat blue RNX and Haichang blue produced with it have excellent fastness indicators, especially the fastness to chlorine bleaching. The blue varieties include carbazole IDM, carbazole LR, carbazole LB, and carbazole L3B. , the black varieties have carbazole black D. It also produces carbazole bisoxazine violet, a blue-violet pigment used in coatings, printing inks, carbon paper, and more. Carbazole is used in the production of sulfide reduced blue RNX, direct lightfast blue FFRL, FFGL, etc. It can also make leather, N-vinylcarbazole plastics, pesticides and insecticides tetranitrocarbazole, chlorinated carbazole, and UV-sensitive photographic dry films. In addition, carbazole has been increasingly used in the development of emerging optoelectronic new materials. The use of carbazole can prepare organic nonlinear optics (NLO) materials, organic electroluminescence (OEL) materials, photorefractive materials, containing Bifunctional system of carbazole chromophore, carbazole-containing photorefractive small molecular glass, etc.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 761, 1973 DOI: 10.1016/S0040-4039(01)95705-3

General Description

White crystals, plates, leaflets or light tan powder. Sublimes readily. Exhibits strong fluorescence and long phosphorescence on exposure to ultraviolet light.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Carbazole is an extremely weak base. Carbazole is incompatible with strong oxidizing agents. Carbazole reacts with nitrogen oxides. Potassium hydroxide fusion yields a salt.

Hazard

Possible carcinogen.

Fire Hazard

Flash point data for Carbazole are not available; however, Carbazole is probably combustible.

Safety Profile

intraperitoneal route. A flammable liquid.

Solubility in organics

Very weak alkaline. Slightly soluble in ethanol, ether and benzene, soluble in quinoline, pyridine and acetone, slightly soluble in cold benzene, glacial acetic acid, chloroform, carbon disulfide and gasoline, soluble in concentrated sulfuric acid without decomposition, slightly soluble in petroleum ether, chlorinated hydrocarbons and acetic acid.

Purification Methods

Dissolve carbazole (60g) in conc H2SO4 (300mL), extract with three 200mL portions of *benzene, then stir this into 1600mL of an ice-water mixture. The precipitate is filtered off, washed with a little water, dried, recrystallised from *benzene and then from pyridine/*benzene [Feldman et al. J Am Chem Soc 73 4341 1951]. It has also been recrystallised from EtOH or toluene, sublimed in vacuum, zone-refined, and purified by TLC. [UV: Armarego in Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 158 1971, Beilstein 20/8 V 9.]

Check Digit Verification of cas no

The CAS Registry Mumber 86-74-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 86-74:
(4*8)+(3*6)+(2*7)+(1*4)=68
68 % 10 = 8
So 86-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H

86-74-8 Well-known Company Product Price

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  • CAS number
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  • Detail
  • TCI America

  • (C0032)  Carbazole  >97.0%(GC)

  • 86-74-8

  • 25g

  • 176.00CNY

  • Detail
  • TCI America

  • (C0032)  Carbazole  >97.0%(GC)

  • 86-74-8

  • 100g

  • 528.00CNY

  • Detail
  • TCI America

  • (C0032)  Carbazole  >97.0%(GC)

  • 86-74-8

  • 500g

  • 1,630.00CNY

  • Detail
  • Alfa Aesar

  • (A11448)  Carbazole, 95%   

  • 86-74-8

  • 50g

  • 224.0CNY

  • Detail
  • Alfa Aesar

  • (A11448)  Carbazole, 95%   

  • 86-74-8

  • 100g

  • 422.0CNY

  • Detail
  • Alfa Aesar

  • (A11448)  Carbazole, 95%   

  • 86-74-8

  • 500g

  • 1387.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1564)  Carbazole(Carprofen Related Compound A)  pharmaceutical secondary standard; traceable to USP

  • 86-74-8

  • PHR1564-200MG

  • 1,437.35CNY

  • Detail
  • Supelco

  • (48076)  Carbazolesolution  certified reference material, 2000 μg/mL in methylene chloride

  • 86-74-8

  • 000000000000048076

  • 449.28CNY

  • Detail
  • USP

  • (1096702)  Carprofen Related Compound A  United States Pharmacopeia (USP) Reference Standard

  • 86-74-8

  • 1096702-50MG

  • 14,578.20CNY

  • Detail

86-74-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 9H-carbazole

1.2 Other means of identification

Product number -
Other names diphenylenimine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:86-74-8 SDS

86-74-8Synthetic route

9-(methylsulfonyl)-9H-carbazole
2169-37-1

9-(methylsulfonyl)-9H-carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran; methanol for 24h; Reflux;100%
2-azidobiphenyl
7599-23-7

2-azidobiphenyl

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction;99%
With dirhodium(II) tetrakis(perfluorobutyrate) In toluene at 60℃; for 16h; Reactivity; Reagent/catalyst; Solvent; Temperature; Molecular sieve; Inert atmosphere;98%
With sulfur-modified Au-supported iron(0) nanoparticles In 1,4-dioxane at 110℃; for 12h; Inert atmosphere;93%
N-(tert-butoxycarbonyl)-2-(2'-chlorophenyl)aniline

N-(tert-butoxycarbonyl)-2-(2'-chlorophenyl)aniline

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With potassium amide In ammonia at -33℃; for 3h;99%
With potassium amide In ammonia at -33℃; for 3h; other N-(tert-butoxycarbonyl)-2-(chlorophenyl)anilines;99%
9-acetylcarbazole
574-39-0

9-acetylcarbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating;99%
With sulfuric acid In methanol at 60℃; for 0.25h;97%
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;71%
With sodium hydroxide; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; Pseudomonas aeruginosa; magnesium sulfate; potassium nitrate; sodium chloride; calcium chloride In water for 72h; pH 7.0;70%
Stage #1: 9-acetylcarbazole With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;
65%
N-phenyl-2-chloroaniline
1205-40-9

N-phenyl-2-chloroaniline

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With potassium carbonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; N-heterocyclic carbene palladium In N,N-dimethyl acetamide at 130℃;99%
With potassium tert-butylate; ammonia for 1h; UV-irradiation;93%
9-tosyl-9H-carbazole
3165-71-7

9-tosyl-9H-carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 4h; Reflux;98%
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 3h; Inert atmosphere;98%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 4h; Reflux;96%
2-nitrobiphenyl
86-00-0

2-nitrobiphenyl

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With 1,10-Phenanthroline; carbon monoxide; palladium diacetate In N,N-dimethyl-formamide at 140℃; under 3102.89 Torr; for 16h;97%
With triphenylphosphine for 0.0333333h; Cadogan reaction; Microwave irradiation;96%
With triphenylphosphine In 1,2-dichloro-benzene at 180℃; for 21h;91%
9-benzoyl-9H-carbazole
19264-68-7

9-benzoyl-9H-carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating;97%
1,2,3,4-tetrahydrocarbazole
942-01-8

1,2,3,4-tetrahydrocarbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With copper(II) choride dihydrate In dimethyl sulfoxide at 100℃; for 7h;96%
With ethene; palladium 10% on activated carbon In acetonitrile at 100℃; for 96h; Sealed tube;92%
With vanadium(V) oxide; acetic acid at 118℃; for 24h; Time; Inert atmosphere;83%
N-([1,1′-biphenyl]-2-yl)picolinamide

N-([1,1′-biphenyl]-2-yl)picolinamide

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With manganese(IV) oxide; copper diacetate; acetic acid In N,N-dimethyl-formamide at 170℃; for 0.666667h; Kinetics; Temperature; Reagent/catalyst; Microwave irradiation; Sealed tube;96%
3-bromo-9H-carbazole
1592-95-6

3-bromo-9H-carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With hydrogen; triethylamine In ethanol; water at 140℃; under 37503.8 Torr; for 110h; Autoclave;96%
With triethylamine In acetonitrile at 20℃; for 15h; Irradiation; Inert atmosphere;77%
1-azido-2-iodo-benzene
54467-95-7

1-azido-2-iodo-benzene

phenylboronic acid
98-80-6

phenylboronic acid

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
Stage #1: 1-azido-2-iodo-benzene; phenylboronic acid With potassium carbonate In 1,4-dioxane at 110℃; for 8h; Inert atmosphere;
Stage #2: In 1,4-dioxane; water Inert atmosphere; Reflux;
96%
diphenylamine
122-39-4

diphenylamine

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With air; potassium carbonate; Trimethylacetic acid; palladium diacetate at 110℃; for 14h;95%
With oxygen; palladium diacetate In acetic acid at 80℃; under 760.051 Torr; for 24h;91%
With copper diacetate; palladium diacetate In N,N-dimethyl-formamide at 130℃; for 1h; Sealed tube; Microwave irradiation;84%
sulfoxyde de phenothiazine
1207-71-2

sulfoxyde de phenothiazine

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With sodium; lithium In tetrahydrofuran for 24h; Heating;95%
C18H22BNO2
1451894-46-4

C18H22BNO2

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With copper diacetate; potassium carbonate In toluene at 110℃; for 1h; Reagent/catalyst; Temperature; Solvent;95%
N-([1,1'-biphenyl]-2-yl)-1,1-diphenyl-λ4-sulfanimine

N-([1,1'-biphenyl]-2-yl)-1,1-diphenyl-λ4-sulfanimine

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Wavelength; Temperature; Solvent; Inert atmosphere; Irradiation;95%
bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}

bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}

2-azidobiphenyl
7599-23-7

2-azidobiphenyl

A

Rh2(α,α,α′,α′-tetramethyl-1,3-benzenedipropionate)2(carbazole)

Rh2(α,α,α′,α′-tetramethyl-1,3-benzenedipropionate)2(carbazole)

B

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
In toluene at 60℃; for 16h; Molecular sieve;A 88.3%
B 94.1%
2-azidobiphenyl
7599-23-7

2-azidobiphenyl

A

N-(2-biphenyl)aniline
35887-50-4

N-(2-biphenyl)aniline

B

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With boron trifluoride In benzene for 0.166667h; Ambient temperature;A 3%
B 94%
di-9-carbazolyldichlorosilane

di-9-carbazolyldichlorosilane

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With water at 20℃; for 1h;94%
2-bromodiphenylamine
61613-22-7

2-bromodiphenylamine

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate In N,N-dimethyl acetamide at 130℃;94%
With potassium tert-butylate; ammonia for 0.5h; UV-irradiation;93%
With rubidium carbonate; tri(cyclohexylmethyl)acetic acid; palladium dichloride at 60℃; for 24h; Inert atmosphere; Schlenk technique;74%
With 6-methoxy quinoline; palladium diacetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 48h; Sealed tube;50%
With sodium carbonate; palladium diacetate In N,N-dimethyl-formamide for 15h; Cyclization; Heating;41%
5,6,7,8,8a,9-hexahydro-4bH-carbazole
1775-86-6

5,6,7,8,8a,9-hexahydro-4bH-carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With 4-tert-Butylcatechol In chloroform; water at 20℃; for 18h;94%
9-benzyl-9H-carbazole
19402-87-0

9-benzyl-9H-carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With potassium tert-butylate; oxygen; dimethyl sulfoxide at 25℃; for 0.166667h;93%
With aluminium trichloride In various solvent(s) for 3h; Ambient temperature;85%
With aluminium trichloride; methoxybenzene85%
1-diphenylmethyl-4-<2-(9-carbazolyl)ethyl>pyridinium bromide
113142-41-9

1-diphenylmethyl-4-<2-(9-carbazolyl)ethyl>pyridinium bromide

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With 2,3,5-trimethyl-pyridine In ethanol for 29h; Heating;93%
With sodium In pyridine; acetonitrile for 4.5h; Heating;78%
1-(9H-carbazol-9-yl)-2,2-dimethylpropan-1-one
70950-05-9

1-(9H-carbazol-9-yl)-2,2-dimethylpropan-1-one

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at 40 - 45℃;93%
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - 45℃; for 2h; Inert atmosphere;93%
2,2'-dihydroxybiphenyl
1806-29-7

2,2'-dihydroxybiphenyl

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With ammonium hydroxide; 10 wt% Pd(OH)2 on carbon; sodium formate; trifluoroacetic acid In m-xylene at 140℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere;92%
With ammonium hydroxide; ammonium sulfite monohydrate at 200℃; for 288h; Autoclave;12%
With ammonia; water at 260℃;
2-azidobiphenyl
7599-23-7

2-azidobiphenyl

A

9H-carbazole
86-74-8

9H-carbazole

B

2-phenylaniline
90-41-5

2-phenylaniline

Conditions
ConditionsYield
With dimethylsulfide at 155℃;A 92%
B 6%
With aluminium trichloride In dichloromethane Ambient temperature;A 83%
B 2%
With aluminium trichloride In dichloromethane Ambient temperature;A 83%
B n/a
With tetrabutylammonium tricarbonylnitrosylferrate In 1,2-dichloro-ethane at 100℃; for 16h; Inert atmosphere; Schlenk technique;
2-azidobiphenyl
7599-23-7

2-azidobiphenyl

benzene
71-43-2

benzene

A

N-(2-biphenyl)aniline
35887-50-4

N-(2-biphenyl)aniline

B

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 60℃;A 3%
B 92%
trans-9-(2-Acetoxyvinyl)carbazole
269408-20-0

trans-9-(2-Acetoxyvinyl)carbazole

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 20℃; for 27h;92%
[(P((C6H5)3))Pd((C6H4)2NH)]2

[(P((C6H5)3))Pd((C6H4)2NH)]2

A

tetrakis(triphenylphosphine) palladium(0)
14221-01-3

tetrakis(triphenylphosphine) palladium(0)

B

9H-carbazole
86-74-8

9H-carbazole

Conditions
ConditionsYield
1 h, room temp.;A n/a
B 92%
9H-carbazole
86-74-8

9H-carbazole

methyl iodide
74-88-4

methyl iodide

N-methylcarbazole
1484-12-4

N-methylcarbazole

Conditions
ConditionsYield
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: methyl iodide In N,N-dimethyl-formamide
100%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;96%
With sodium hydroxide In N,N-dimethyl-formamide at 2℃; for 4h;95%
9H-carbazole
86-74-8

9H-carbazole

N-ethylcarbazole
86-28-2

N-ethylcarbazole

Conditions
ConditionsYield
100%
98.1%
93.1%
With sodium amide; toluene und Erwaermen des Reaktionsgemisches mit Aethylbromid;
Multi-step reaction with 2 steps
1: potassium hydroxide; decalin / 170 °C
2: nickel; methanol / 80 °C / 11032.6 Torr / Hydrogenation
View Scheme
9H-carbazole
86-74-8

9H-carbazole

benzyl chloride
100-44-7

benzyl chloride

9-benzyl-9H-carbazole
19402-87-0

9-benzyl-9H-carbazole

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran for 48h; Heating;100%
With potassium hydroxide; PEG-400-Et2 In water; benzene at 30℃; for 3h;97%
With tetrabutylammomium bromide; potassium carbonate for 0.0666667h; Irradiation;95%
9H-carbazole
86-74-8

9H-carbazole

allyl bromide
106-95-6

allyl bromide

9-allyl-9H-carbazole
3998-04-7

9-allyl-9H-carbazole

Conditions
ConditionsYield
Stage #1: 9H-carbazole With potassium hydroxide In dimethyl sulfoxide at 50℃; for 0.5h;
Stage #2: allyl bromide In dimethyl sulfoxide for 0.25h;
100%
Stage #1: 9H-carbazole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.333333h;
Stage #2: allyl bromide In dimethyl sulfoxide at 35℃; for 0.5h; Solvent; Sonication;
98%
With caesium carbonate In N,N-dimethyl-formamide at 26℃; for 8h;97%
9H-carbazole
86-74-8

9H-carbazole

tert-butyl alcohol
75-65-0

tert-butyl alcohol

1,3,6,8-tetra-tert-butyl-9H-carbazole
34601-54-2

1,3,6,8-tetra-tert-butyl-9H-carbazole

Conditions
ConditionsYield
With trifluoroacetic acid Heating;100%
9H-carbazole
86-74-8

9H-carbazole

N-chlorocarbazole
105598-33-2

N-chlorocarbazole

Conditions
ConditionsYield
With sodium hypochlorite In dichloromethane for 48h;100%
With sodium hypochlorite In dichloromethane; water for 48h; Yield given;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

9H-carbazole
86-74-8

9H-carbazole

N-(tert-butyl)-9H-carbazole-9-carboxylate

N-(tert-butyl)-9H-carbazole-9-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile for 1.75h;100%
Stage #1: 9H-carbazole With hydrogenchloride In water at -5 - 0℃; for 0.5h;
Stage #2: di-tert-butyl dicarbonate In water at -5 - 0℃; for 1h;
91.2%
1-bromo-octane
111-83-1

1-bromo-octane

9H-carbazole
86-74-8

9H-carbazole

9-octylcarbazole
4041-19-4

9-octylcarbazole

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In toluene at 120℃;100%
With sodium hydroxide; triethylamine hydrochloride In water; dimethyl sulfoxide at 80℃; for 8h;97.4%
With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 24h; Inert atmosphere; Reflux;96%
Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

9H-carbazole
86-74-8

9H-carbazole

d t-butyl 2-(carbazol-9-yl)-2-butene-1,4-dicarboxylate
1292841-09-8

d t-butyl 2-(carbazol-9-yl)-2-butene-1,4-dicarboxylate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 4h; optical yield given as %de;100%
9H-carbazole
86-74-8

9H-carbazole

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(carbazol-9-yl)-2-butene-1,4-dicarboxylate
1292841-08-7

diethyl 2-(carbazol-9-yl)-2-butene-1,4-dicarboxylate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 4h; optical yield given as %de;100%
9H-carbazole
86-74-8

9H-carbazole

bis(5-bromomethyl-1,3-phenylene)-32-crown-10
201213-73-2

bis(5-bromomethyl-1,3-phenylene)-32-crown-10

bis[5-(N-carbazylmethyl)-1,3-phenylene]-32-crown-10
1303559-34-3

bis[5-(N-carbazylmethyl)-1,3-phenylene]-32-crown-10

Conditions
ConditionsYield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Reflux;
Stage #2: bis(5-bromomethyl-1,3-phenylene)-32-crown-10 In tetrahydrofuran at 20℃; for 24.5h; Inert atmosphere; Reflux;
100%
C18H10FNO3
1373227-46-3

C18H10FNO3

9H-carbazole
86-74-8

9H-carbazole

C30H18N2O3
1373227-47-4

C30H18N2O3

Conditions
ConditionsYield
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃;
Stage #2: C18H10FNO3 In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;
100%
4-(3-bromopropyl)-12-[3-{N-(1,8-naphthalimidyl)}propyl]-[2.2]paracyclophane

4-(3-bromopropyl)-12-[3-{N-(1,8-naphthalimidyl)}propyl]-[2.2]paracyclophane

9H-carbazole
86-74-8

9H-carbazole

4-{3-(N-carbazolyl)propyl}-12-[3-{N-(1,8-naphthalimidyl)}-propyl][2.2]paracyclophane

4-{3-(N-carbazolyl)propyl}-12-[3-{N-(1,8-naphthalimidyl)}-propyl][2.2]paracyclophane

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 48h; Reflux;100%
9H-carbazole
86-74-8

9H-carbazole

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

ethyl 2-(9H-carbazol-9-yl)propanoate
65962-23-4

ethyl 2-(9H-carbazol-9-yl)propanoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 20℃; for 3h; Inert atmosphere;100%
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 0℃; Schlenk technique; Inert atmosphere;
Stage #2: Ethyl 2-bromopropionate In N,N-dimethyl-formamide at 0 - 20℃; Schlenk technique; Inert atmosphere;
((5R,6S,9R)-2-(2,6-diisopropylphenyl)-6-isopropyl-3,3,9-trimethyl-2-azaspiro[4.5]decan-1-ylidene)AgCl

((5R,6S,9R)-2-(2,6-diisopropylphenyl)-6-isopropyl-3,3,9-trimethyl-2-azaspiro[4.5]decan-1-ylidene)AgCl

9H-carbazole
86-74-8

9H-carbazole

((5R,6S,9R)-2-(2,6-diisopropylphenyl)-6-isopropyl-3,3,9-trimethyl-2-azaspiro[4.5]decan-1-ylidene)Ag(carbazole)

((5R,6S,9R)-2-(2,6-diisopropylphenyl)-6-isopropyl-3,3,9-trimethyl-2-azaspiro[4.5]decan-1-ylidene)Ag(carbazole)

Conditions
ConditionsYield
With sodium t-butanolate In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox; Darkness;100%
9H-carbazole
86-74-8

9H-carbazole

2'-aminobiphenyl-2,3-diol
148519-91-9

2'-aminobiphenyl-2,3-diol

Conditions
ConditionsYield
With Escherichia coli JM109 In dimethyl sulfoxide at 30℃; for 18h; L-medium; Enzymatic reaction;99.1%
2-Chloroquinoline
612-62-4

2-Chloroquinoline

9H-carbazole
86-74-8

9H-carbazole

 2-(N-carbazolyl)quinoline
102183-59-5

2-(N-carbazolyl)quinoline

Conditions
ConditionsYield
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 2-Chloroquinoline With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 108 - 112℃; for 0.25h; Inert atmosphere;
99%
With [(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Ni(styrene)2]; lithium tert-butoxide In 1,4-dioxane at 110℃; for 2h; Inert atmosphere;94%
With iodine; copper; potassium carbonate
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

9H-carbazole
86-74-8

9H-carbazole

9-(4-chlorophenyl)-9H-carbazole
19264-71-2

9-(4-chlorophenyl)-9H-carbazole

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 1,2-dimethoxyethane; water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;99%
With Cu(HOC6H3(O)CHNCH2CH2NCHC6H3(O)OH); sodium hydroxide at 120℃; for 8h;90%
With copper(l) iodide; cesium fluoride; N,N`-dimethylethylenediamine In tetrahydrofuran at 25℃; for 18 - 24h; Inert atmosphere;88%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

9H-carbazole
86-74-8

9H-carbazole

N-(4-bromophenyl)carbazole
57102-42-8

N-(4-bromophenyl)carbazole

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 1,2-dimethoxyethane; water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;99%
With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 42h; Inert atmosphere;96%
With copper(I) oxide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere; Schlenk technique;95%
ethyl bromide
74-96-4

ethyl bromide

9H-carbazole
86-74-8

9H-carbazole

N-ethylcarbazole
86-28-2

N-ethylcarbazole

Conditions
ConditionsYield
Stage #1: 9H-carbazole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.333333h;
Stage #2: ethyl bromide In dimethyl sulfoxide at 35℃; for 0.05h; Solvent; Sonication;
99%
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.666667h; Cooling with ice;95%
With potassium hydroxide; PEG-400-Et2 In water; benzene at 30℃; for 2h;92%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

9H-carbazole
86-74-8

9H-carbazole

N-(4-cyanophenyl)carbazole
57103-17-0

N-(4-cyanophenyl)carbazole

Conditions
ConditionsYield
With copper(l) iodide; trans-1,2-Diaminocyclohexane; potassium carbonate In dimethyl sulfoxide at 140℃; Inert atmosphere;99%
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate In toluene at 100℃; for 12h;97%
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); caesium carbonate In toluene at 100℃; for 24h; Glovebox; Inert atmosphere;92%
9H-carbazole
86-74-8

9H-carbazole

4-benzyloxybenzyl chloride
836-42-0

4-benzyloxybenzyl chloride

9-(4-Benzyloxy-benzyl)-9H-carbazole
205578-45-6

9-(4-Benzyloxy-benzyl)-9H-carbazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide Ambient temperature;99%
bromobenzene
108-86-1

bromobenzene

9H-carbazole
86-74-8

9H-carbazole

N-phenylcarbazole
1150-62-5

N-phenylcarbazole

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether In o-xylene at 20 - 120℃; for 2h; Product distribution / selectivity;99%
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: bromobenzene With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 108 - 112℃; for 0.5h; Inert atmosphere;
99%
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 3h; Inert atmosphere;98%
3,5-dimethylphenyl iodide
22445-41-6

3,5-dimethylphenyl iodide

9H-carbazole
86-74-8

9H-carbazole

9-(3,5-dimethylphenyl)-9H-carbazole

9-(3,5-dimethylphenyl)-9H-carbazole

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane; dodecane at 110℃; for 24h;99%
With copper(I) oxide; potassium phosphate; N1,N2-bis(furan-2-ylmethyl)oxalamide In acetonitrile at 80℃;94%
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 1,2-dimethoxyethane; water at 95℃; for 20h; Catalytic behavior; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;91%
9H-carbazole
86-74-8

9H-carbazole

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

N-methylcarbazole
1484-12-4

N-methylcarbazole

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 7h; Product distribution; Further Variations:; Temperatures; Solvents; Pressures; Reagents; reaction times; microwave irradiation;99%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 94 - 95℃; for 24h;97%
With 1,4-diaza-bicyclo[2.2.2]octane at 90 - 95℃; for 24h;97%
1-bromo-hexane
111-25-1

1-bromo-hexane

9H-carbazole
86-74-8

9H-carbazole

N-hexylcarbazole
4041-21-8

N-hexylcarbazole

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 80℃; for 14h;99%
With potassium hydroxide In acetone Reflux;99%
Stage #1: 9H-carbazole With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.666667h;
Stage #2: 1-bromo-hexane In N,N-dimethyl-formamide at 20℃; for 9h;
98%

86-74-8Relevant articles and documents

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Huang, Wen-Bin,Yang, Meng,He, Liang-Nian

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The selective N-alkylation of indole substrates remains an ongoing research challenge for the relative attenuated nucleophilicity toward nitrogen. Herein, we developed the hydroxymethylation of indole derivatives to afford N-alkylated indole products with

Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles

Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing

, p. 143 - 148 (2020/12/18)

The synthesis of carbazoles based on the electrochemical Pd-catalyzed intramolecular C—H amination of 2-amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily. Compared with previous methods, this protocol affords a simple and sustainable avenue for the construction of carbazoles.

Quinoline Ligands Improve the Classic Direct C?H Functionalisation/Intramolecular Cyclisation of Diaryl Ethers to Dibenzofurans

Mackey, Katrina,Jones, David J.,Pardo, Leticia M.,McGlacken, Gerard P.

supporting information, p. 495 - 498 (2021/01/12)

The C?H functionalisation approach to the synthesis of dibenzofurans is hampered by a number of problems. Herein we describe the evolution of a cheap, bench stable quinoline ligand, which obviates most of the current limitations and allows for a high yielding synthesis of a range of valuable dibenzofurans. Dibenzofurans are important motifs in natural products and compounds with wide biological activity.

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