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Cas Database

239-01-0

239-01-0

Identification

  • Product Name:11H-Benzo[a]carbazole

  • CAS Number: 239-01-0

  • EINECS:

  • Molecular Weight:217.27

  • Molecular Formula: C16H11 N

  • HS Code:2933990090

  • Mol File:239-01-0.mol

Synonyms:1,2-Benzocarbazole;11-Azachrysofluorene; Benzo[a]carbazole; NSC 403640; NSC 60421

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Safety information and MSDS view more

  • Pictogram(s):T

  • Hazard Codes:T

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:11H-Benzo[a]carbazole
  • Packaging:50mg
  • Price:$ 70
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  • Manufacture/Brand:TCI Chemical
  • Product Description:11H-Benzo[a]carbazole >98.0%(GC)
  • Packaging:1g
  • Price:$ 165
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  • Manufacture/Brand:TCI Chemical
  • Product Description:11H-Benzo[a]carbazole >98.0%(GC)
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  • Price:$ 495
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:11H-Benzo[a]carbazole
  • Packaging:100 mg
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  • Manufacture/Brand:Crysdot
  • Product Description:11H-Benzo[a]carbazole 97%
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  • Manufacture/Brand:Crysdot
  • Product Description:11H-Benzo[a]carbazole 97%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:11H-BENZO[A]CARBAZOLE 98.00%
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  • Manufacture/Brand:Alichem
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Relevant articles and documentsAll total 66 Articles be found

-

Muth,Hanrahan

, p. 395 (1958)

-

-

Kametami et al.

, p. 786 (1968)

-

Efficient synthesis of 1,2,3,4-tetrahydro-11H-benzo[a]carbazole and its regioselective oxidation

Dufour, Fabien,Kirsch, Gilbert

, p. 1021 - 1022 (2006)

Carbazole derivative 4 was synthesized in an efficient three-step sequence and its further oxidation with dichlorodicyanoquinone gave selectively 4-oxo-1,2,3,4-tetrahydro-11H-benzo[a]carbazole 3. Georg Thieme Verlag Stuttgart.

A one-pot direct regioselective iodination of Fischer-Borsche product using periodic acid in PEG-400

Ghom, Monica H.,Naykode, Mahavir S.,Humne, Vivek T.,Lokhande, Pradeep D.

, p. 1029 - 1031 (2019)

A metal-free and greener approach for the one-pot direct iodination and dehydrogenation of dihydrobenzo[a]carbazoles has been developed using periodic acid in polyethylene glycol-400 (PEG-400) under mild condition. This method has been proven to be tolerate to a broad range of functional groups, with good to excellent yields include metal-free inexpensive catalyst, easy work-up, benign reaction condition and high regioselectivity. The solvent has been successfully recycled up to 5 times without any loss of activity in an aqueous medium.

Behavior of oxotetrahydrobenzo[b]- and [c]thiophenes and their α-hydroxymethylene derivatives in the fischer indole synthesis

Martarello, Laurent,Joseph, Delphine,Kirsch, Gilbert

, p. 367 - 379 (1996)

We described an approach to thienocarbazoles via a Fischer indole synthesis starting directly from oxotetrahydrobenzo[b]- and [c]thiophenes or from their α-hydroxymethylene derivatives with a Japp-Klingemann reaction to make the hydrazones which are cyclised under acidic conditions.

Chemoselective Borono-Catellani Arylation for Unsymmetrical Biaryls Synthesis

Wang, Peng,Chen, Shuqing,Zhou, Zhiyu,Cheng, Hong-Gang,Zhou, Qianghui

, p. 3323 - 3327 (2019)

Reported is the borono-Catellani arylation process for unsymmetrical biaryls synthesis, utilizing the readily available pinacol ester of arylboronic acids, aryl bromides, and olefins as the reactants. The distinct reactivity of arylboronic ester and aryl bromides secures the excellent chemoselectivity in the pivotal arylation step. The reaction is enabled by the cooperative catalysis of Pd(OAc)2 and the NBE derivative N7, with molecular oxygen as the terminal oxidant.

Novel D-π-A benzocarbazole dyes with simple structures for efficient dye-sensitized solar cells

Han, Liang,Meng, Xiaozhou,Ke, Yong'an,Ye, Hongqiang,Cui, Yanhong

, p. 127 - 134 (2019)

Three benzocarbazole dyes were synthesized with N-butylbenzocarbazole as the electron donor, benzene, furan and thiophene as π-bridge, and cyanoacrylic acid as the electron acceptor. Their photophysical properties and photovoltaic performance were investigated and compared among three π-bridges. The incorporation of thiophene or furan unit favors intramolecular charge transfer through reducing the energy gap and improving the molecular conjugation due to their electron-rich properties and small volume compared with benzene unit. On the other hand, weakening coplanarity of dye with benzene bridge contributes to the antiaggregation and accordingly increase VOC, though decreases photo-generated current. Among three dyes, dye with furan bridge achieves the optimal photovoltaic performance 7.67% due to the highest JSC 15.45 mA cm?2.

COMPOSITION, ORGANIC OPTOELECTRONIC DEVICE, AND DISPLAY DEVICE

-

Paragraph 0163; 0166-0167; 0183; 0186-0187, (2021/03/13)

A composition including a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and a second compound represented by Chemical Formula 3, an organic optoelectronic device, and a display device are related. In Chemical Formula 1 to Chemical Formula 3, each substituent is the same as described in the specification.

Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

Steingruber, H. Sebastián,Mendioroz, Pamela,Volpe, María A.,Gerbino, Darío C.

, p. 4048 - 4058 (2021/08/03)

An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

Visible-light-driven Cadogan reaction

Qu, Zhonghua,Wang, Pu,Chen, Xing,Deng, Guo-Jun,Huang, Huawen

supporting information, p. 2582 - 2586 (2021/03/09)

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes

Qu, Zhonghua,Chen, Xing,Zhong, Shuai,Deng, Guo-Jun,Huang, Huawen

supporting information, p. 5349 - 5353 (2021/07/21)

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.

Pd-Catalyzed Reductive Cyclization of Nitroarenes with CO2 as the CO Source

Guan, Xinyu,Zhu, Haoran,Zhao, Yingwei,Driver, Tom G.

, p. 57 - 60 (2019/12/11)

A reductive amination process that constructs indoles, carbazoles or benzimidazoles from nitroarenes – irrespective of their electronic or steric nature – was developed that uses CO2 as the source of CO. The process is robust, tolerating common gaseous components of flue gas (H2S, SO2, NO and H2O) without adversely affecting the reductive cyclization.

Process route upstream and downstream products

Process route

2-(2-naphthyl)aniline
71221-26-6

2-(2-naphthyl)aniline

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

2,3-benzocarbazole
243-28-7

2,3-benzocarbazole

Conditions
Conditions Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate; Trimethylacetic acid; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 3h;
79%
10%
2-(2-nitrophenyl)naphthalene
94064-83-2

2-(2-nitrophenyl)naphthalene

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

2,3-benzocarbazole
243-28-7

2,3-benzocarbazole

Conditions
Conditions Yield
With Isopropylbenzene; triethyl phosphite; for 24h; Reflux;
46%
42%
naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

2-bromoaniline
615-36-1

2-bromoaniline

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

2,3-benzocarbazole
243-28-7

2,3-benzocarbazole

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / N,N-dimethyl-formamide; water / 24 h / 80 °C / Inert atmosphere
2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Trimethylacetic acid; copper diacetate / 1-methyl-pyrrolidin-2-one / 3 h / 120 °C
With bis-triphenylphosphine-palladium(II) chloride; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; copper diacetate; potassium carbonate; Trimethylacetic acid; In 1-methyl-pyrrolidin-2-one; water; N,N-dimethyl-formamide; 1: |Suzuki-Miyaura Coupling;
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

2,3-benzocarbazole
243-28-7

2,3-benzocarbazole

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 24 h / Reflux
2: triethyl phosphite; Isopropylbenzene / 24 h / Reflux
With tetrakis(triphenylphosphine) palladium(0); Isopropylbenzene; sodium carbonate; triethyl phosphite; In 1,4-dioxane; water;
naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

2,3-benzocarbazole
243-28-7

2,3-benzocarbazole

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 24 h / Reflux
2: triethyl phosphite; Isopropylbenzene / 24 h / Reflux
With tetrakis(triphenylphosphine) palladium(0); Isopropylbenzene; sodium carbonate; triethyl phosphite; In 1,4-dioxane; water;
2-(2'methylphenyl)-quinoline-3,4-dicarboxylic anhydride
144463-84-3

2-(2'methylphenyl)-quinoline-3,4-dicarboxylic anhydride

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

11H-indeno[1,2-b]quinoline
243-51-6

11H-indeno[1,2-b]quinoline

2,3-benzocarbazole
243-28-7

2,3-benzocarbazole

benzo[c]carbazole
205-25-4

benzo[c]carbazole

Conditions
Conditions Yield
Mechanism; Product distribution; multistepreaction: flash vacuum pyrolysis;
85%
polystyrene

polystyrene

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

Benzo[k]fluoranthene
207-08-9

Benzo[k]fluoranthene

Tetracen
92-24-0

Tetracen

cyclopenta[c,d]pyrene
27208-37-3

cyclopenta[c,d]pyrene

Conditions
Conditions Yield
With air; at 900 ℃; Further byproducts given. Title compound not separated from byproducts; Formation of xenobiotics;
0.45 mg
0.21 mg
0.04 mg
0.03 mg
2-(2-nitrophenyl)naphthalene
94064-83-2

2-(2-nitrophenyl)naphthalene

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

Conditions
Conditions Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; triphenylphosphine; In 1,4-dioxane; at 55 ℃; for 60h; Inert atmosphere; Irradiation;
97%
With triphenylphosphine; In 1,2-dichloro-benzene; at 200 ℃;
92%
With triphenylphosphine; In 1,2-dichloro-benzene; at 220 ℃; for 12h;
88%
With 3,4,7,8-Tetramethyl-o-phenanthrolin; carbon monoxide; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 14h; Sealed tube;
88%
With triphenylphosphine; sodium iodide; In 1,4-dioxane; at 60 ℃; for 72h; Inert atmosphere; Irradiation;
83%
With phenylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 0.25h; regioselective reaction; Inert atmosphere;
75%
With triethyl phosphite; In 1,2-dichloro-benzene; at 150 ℃; for 15h;
69%
With triethyl phosphite; In 1,2-dichloro-benzene; at 150 ℃; for 15h;
69%
With triethyl phosphite; for 19h;
52%
With TPP; In 1,2-dichloro-benzene; at 150 ℃; for 24h;
5,6-dihydro-11H-benzo[a]carbazole
21064-49-3

5,6-dihydro-11H-benzo[a]carbazole

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

Conditions
Conditions Yield
With copper(II) choride dihydrate; In dimethyl sulfoxide; at 20 - 120 ℃; Reagent/catalyst;
91%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 1h; Heating;
90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 20 ℃; for 3h;
90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; at 20 ℃; for 3h;
90%
With palladium 10% on activated carbon; In para-xylene; for 24h; Inert atmosphere; Reflux;
90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; for 1h;
87%
palladium on activated charcoal; In xylene; for 1h; Heating;
81%
With iodine; In dimethyl sulfoxide; at 100 ℃; for 12h; Reagent/catalyst; Solvent; Temperature;
81%
palladium on activated charcoal; at 250 - 260 ℃; for 0.333333h;
78%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 20 ℃; for 3h; Inert atmosphere;
70%
With hydrogenchloride; 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate; oxygen; In water; acetonitrile; at 20 ℃; for 24h; Irradiation; Sealed tube;
69%
With palladium 10% on activated carbon; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h; Reflux;
65%
With palladium on activated charcoal; at 215 ℃; for 0.5h;
64%
With chloranil; In 5,5-dimethyl-1,3-cyclohexadiene; for 4h; Reflux; Inert atmosphere;
42%
With chloranil; In 5,5-dimethyl-1,3-cyclohexadiene; for 4h; Inert atmosphere; Reflux;
42%
With lead(II) oxide;
With palladium;
With chloranil; xylene;
With chloranil; toluene;
1-nitro-2-phenylnaphthalene
74886-75-2

1-nitro-2-phenylnaphthalene

11H-benzo[a]carbazole
239-01-0

11H-benzo[a]carbazole

Conditions
Conditions Yield
With triphenylphosphine; In 1,2-dichloro-benzene; at 200 ℃;
74%
With triphenylphosphine; In 1,2-dichloro-benzene; at 200 ℃;
74%

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