Category
Small Molecule Semiconductor Building Blocks; Electroluminescence Materials; Other Electronic Materials; Polymers
Description
Carbazole appears as white crystals, plates, leaflets or light tan powder. Sublimes readily. Exhibits strong fluorescence and long phosphorescence on exposure to ultraviolet light. (NTP, 1992)
Molecular Weight
167.21g/mol
Canonical SMILES
C1=CC=C2C(=C1)C3=CC=CC=C3N2
InChI
InChI=1S/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H
InChI Key
UJOBWOGCFQCDNV-UHFFFAOYSA-N
Boiling Point
671 °F at 760 mm Hg (NTP, 1992);354.7 °C;354.6 °C
Melting Point
473 to 475 °F (NTP, 1992);246.2 °C;245 °C
Flash Point
220.0 °C (428.0 °F) - closed cup
Density
1.1 at 64 °F (NTP, 1992);1.10 at 18 °C/4 °C
Solubility
less than 1 mg/mL at 66° F (NTP, 1992);1.08e-05 M;In water, 1.80 mg/L at 25 °C;In water, 1.20 mg/L at 20 °C;1 gram dissolves in 3 mL quinoline, 6 mL pyridine, 9 mL acetone, 2 mL acetone at 50 °C, 35 mL ether, 120 mL benzene, 135 mL absolute alcohol; slightly soluble in petroleum ether, chlorinated hydrocarbons, acetic acid; dissolves in concentrated sulfuric acid without decomposition;Slightly soluble in pyrimidine, carbon disulfide; soluble in hot chloroform, toluene
Application
Carbazole is a versatile compound available as white crystals or a light brown powder, primarily employed as a vital intermediate in dye production. It plays a crucial role in enhancing UV sensitivity in photographic plates and serves as a reagent for detecting lignin, carbohydrates, and formaldehyde. Beyond its fundamental applications, carbazole is integral to manufacturing a variety of dyes and pigments, including permanent purple RL, which is favored for its exceptional heat and UV resistance in automobile topcoats and high-temperature plastics. Dye varieties like sulphur vat blue RNX and Haichang blue crafted from carbazole are renowned for their remarkable fastness, particularly against chlorine bleaching. The compound is also pivotal in synthesizing black pigments like carbazole black D and other pigments such as carbazole bisoxazine violet. In addition to these traditional uses, carbazole is increasingly significant in crafting innovative optoelectronic materials, organic nonlinear optics, and electroluminescent materials. Although it exhibits weak alkalinity and varies in solubility across different solvents, carbazole's adaptability makes it indispensable in its various roles across industries.
Color/Form
Crystals from alcohol, benzene, toluene, glacial acetic acid;White crystals;White crystals, plates, leaflets or light tan powder
Covalently-Bonded Unit Count
1
Exact Mass
167.073499g/mol
Heat of Vaporization
65.7 kJ/mol at 540 K
Log P
3.72 (LogP);log Kow = 3.72
MeSH Entry Terms
9-azafluorene;9H-carbazole;carbazole;dibenzo(b,d)pyrrole;dibenzopyrrole;diphenylenimine
Monoisotopic Mass
167.073499g/mol
Other Experimental
Exhibits strong fluorescence and long phosphorescence on exposure to UV light;Sublimes readily;Potassium hydroxide fusion yields n-potassium salt;An approximated pKa value for carbazole, between those of indole and pyrrole (-2.4 and -3.8), indicates that the environmental chemistry of carbazole will involve only the free base.;Henry's Law constant = 1.16X10-7 atm-cu m/mole at 25 °C;Hydroxyl radical reaction rate constant = 4.0X10-11 cu cm/molecule-sec at 25 °C
Stability
Stable under recommended storage conditions.
Vapor Pressure
400 mm Hg at 613 °F (NTP, 1992);7.50e-07 mmHg;1.5X10-6 mm Hg at 25 °C (extrapolated)