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Carbazole information


Carbazole
Names
Preferred IUPAC name
9H-Carbazole[1]
Other names
9-azafluorene
dibenzopyrrole
diphenylenimine
diphenyleneimide
USAF EK-600
Identifiers
CAS Number
  • 86-74-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
3956
ChEBI
  • CHEBI:27543 checkY
ChEMBL
  • ChEMBL243580 checkY
ChemSpider
  • 6593 checkY
DrugBank
  • DB07301 checkY
ECHA InfoCard 100.001.542 Edit this at Wikidata
EC Number
  • 201-696-0
Gmelin Reference
102490
KEGG
  • C08060 checkY
PubChem CID
  • 6854
RTECS number
  • FE3150000
UNII
  • 0P2197HHHN checkY
CompTox Dashboard (EPA)
  • DTXSID4020248 Edit this at Wikidata
InChI
  • InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H checkY
    Key: UJOBWOGCFQCDNV-UHFFFAOYSA-N checkY
  • InChI=1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
    Key: UJOBWOGCFQCDNV-UHFFFAOYAV
SMILES
  • c1ccc2c(c1)c3ccccc3[nH]2
Properties
Chemical formula
C12H9N
Molar mass 167.211 g·mol−1
Density 1.301 g cm−3
Melting point 246.3 °C (475.3 °F; 519.5 K)[2]
Boiling point 354.69 °C (670.44 °F; 627.84 K)[2]
Magnetic susceptibility (χ)
−117.4 × 10−6 cm3 mol−1
Hazards
GHS labelling:
Pictograms
GHS08: Health hazardGHS09: Environmental hazard
Signal word
Warning
Hazard statements
H341, H351, H400, H411, H413
Precautionary statements
P201, P202, P273, P281, P308+P313, P391, P405, P501
Flash point 220 °C (428 °F; 493 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole structure, but in which a second benzene ring is fused onto the five-membered ring at the 2–3 position of indole (equivalent to the 9a–4a double bond in carbazole, respectively).

Carbazole is a constituent of tobacco smoke.[3]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ a b c Lide, David R. (2007). CRC Handbook of Chemistry and Physics, 88th Edition. CRC Press. pp. 3–86. ISBN 978-0-8493-0488-0.
  3. ^ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". Int. J. Environ. Res. Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. PMC 3084482. PMID 21556207.

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Carbazole

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Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side...

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Carbazole alkaloids

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The carbazole alkaloids are natural products of the indole alkaloid type, derived from carbazole. Carbazole alkaloids with unsubstituted benzene rings...

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Bucherer carbazole synthesis

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The Bucherer carbazole synthesis is a chemical reaction used to synthesize carbazoles from naphthols and aryl hydrazines using sodium bisulfite. The reaction...

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Heterocyclic compound

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heterocycles for this third family of compounds are acridine, dibenzothiophene, carbazole, and dibenzofuran, respectively. Heterocyclic organic compounds can be...

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Hemiaminal

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formaldehyde with carbazole, which is weakly basic, proceed similarly: Again, this carbinol converts readily to the methylene-linked bis(carbazole). Hemiaminal...

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Carprofen

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Carprofen is a nonsteroidal anti-inflammatory drug (NSAID) of the carbazole and propionic acid class that was previously for use in humans and animals...

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Liquid organic hydrogen carriers

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Liquid organic hydrogen carriers (LOHC) are organic compounds that can absorb and release hydrogen through chemical reactions. LOHCs can therefore be used...

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Polychlorinated carbazoles

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Polychlorinated carbazoles (PCCZ) are a group of chlorinated organic compounds. They are derivatives of carbazole and nitrogen analogues of polychlorinated...

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Polyvinylcarbazole

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Polyvinylcarbazole (PVK) is a temperature-resistant thermoplastic polymer produced by radical polymerization from the monomer N-vinylcarbazole. It is a...

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Pigment violet 23

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member of the dioxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-N-ethylcarbazole...

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Curry tree

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tree leaves, stems, bark, and seeds include cinnamaldehyde, and numerous carbazole alkaloids, including mahanimbine, girinimbine, and mahanine. Nutritionally...

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OLED

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high efficiency. An example of using exciplex is grafting Oxadiazole and carbazole side units in red diketopyrrolopyrrole-doped Copolymer main chain shows...

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Acetylene

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vinylcarbazole are produced industrially by vinylation of 2-pyrrolidone and carbazole. The hydration of acetylene is a vinylation reaction, but the resulting...

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Pseudomonas resinovorans

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commonly found in the lubricating oils of wood mills. It is able to degrade carbazole, and as such, may be used in bioremediation. Based on 16S rRNA analysis...

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Pseudomonas

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use cyanide as a nitrogen source. P. resinovorans, which can degrade carbazole. P. aeruginosa, P. putida, P. desmolyticum, and P. nitroreducens can degrade...

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Phenols

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Reaction of naphtols and hydrazines and sodium bisulfite in the Bucherer carbazole synthesis. Many phenols of commercial interest are prepared by elaboration...

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Anthracene

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major source of this material. Common impurities are phenanthrene and carbazole. The mineral form of anthracene is called freitalite and is related to...

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Slime mold

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colored red by arcyriaflavins A–C, which contain an unusual indolo[2,3-a]carbazole alkaloid ring. By 2022, more than 100 pigments had been isolated from...

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IARC group 2B

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Butyl methacrylate Butylated hydroxyanisole β-Butyrolactone Caffeic acid Carbazole Carbon black Carbon nanotubes, multi-walled MWCNT-7 Carbon tetrachloride...

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Carbon nanotube

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Single-Walled Carbon Nanotubes with Specific Chiral Indices by Poly( N -decyl-2,7-carbazole)". Journal of the American Chemical Society. 133 (4): 652–655. doi:10...

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Hans Theodor Bucherer

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and gave name to several chemical reactions, for example the Bucherer carbazole synthesis, the Bucherer reaction, and the Bucherer–Bergs reaction Bucherer...

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Chinglish

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meanings of guanchang "(make) a sausage; (give) an enema". A weak 'pyridaben carbazole' sound is found on translated instructions for a photographic light, "Install...

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Ring forming reaction

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Azide-alkyne Huisgen cycloaddition Bischler–Napieralski reaction Bucherer carbazole synthesis Danheiser annulation Dieckmann condensation Diels–Alder reaction...

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Electronic waste

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ethers (PBDEs), polychlorinated biphenyls (PCBs) and polyhalogenated carbazoles (PHCZs) in soil from an e-waste disposal site in Hangzhou (which has been...

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Nocardioides aromaticivorans

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Nocardioides aromaticivorans has the ability to degrade dibenzofuran and carbazole. Kubota, M; Kawahara, K; Sekiya, K; Uchida, T; Hattori, Y; Futamata, H;...

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Indole alkaloid

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Pyrroloindole alkaloids Indole-3-carbinol Indole-3-acetic acid Tryptamines Carbazoles Isoprenoid: hemiterpenoids: ergot alkaloids monoterpenoids. Strictosidine...

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