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123617

Sigma-Aldrich

Benzo[h]quinoline

97%

Synonym(s):

1-Naphthoquinoline, 7,8-Benzoquinoline

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About This Item

Empirical Formula (Hill Notation):
C13H9N
CAS Number:
230-27-3
Molecular Weight:
179.22
Beilstein:
120249
EC Number:
205-937-0
MDL number:
MFCD00004984
UNSPSC Code:
12352100
PubChem Substance ID:
24847579
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

bp

338 °C/719 mmHg (lit.)

mp

48-50 °C (lit.)

SMILES string

c1ccc2c(c1)ccc3cccnc23

InChI

1S/C13H9N/c1-2-6-12-10(4-1)7-8-11-5-3-9-14-13(11)12/h1-9H

InChI key

WZJYKHNJTSNBHV-UHFFFAOYSA-N

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Application

Benzo[h]quinoline was used to study the mutagenic activities of benzo[f]quinoline, benzo[h]quinolone and a number of their derivatives in strain TA 100 of Salmonella typhimurium. It was used in determination of nitrogen-containing polynuclear aromatic hydrocarbons in the gaseous products of the thermal degradation of polymers by HPLC- fluorescence detection. It was used as starting reagent for the synthesis of osmium and ruthenium complexes containing an N-heterocyclic carbene ligand.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4665
STBJ5277
STBH6133
STBG9472
STBG2041V

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M Wilhelm et al.
Journal of chromatography. A, 878(2), 171-181 (2000-06-24)
A method for the simultaneous determination of 22 nitrogen-containing polynuclear aromatic hydrocarbons (PAHs) (15 azaarenes and seven amino-PAHs) in the gaseous products of the thermal degradation of polymers is described. After desorption and clean-up using cation-exchange chromatography (PRS cartridge) the
E J LaVoie et al.
Japanese journal of cancer research : Gann, 78(2), 139-143 (1987-02-01)
The environmental occurrence and mutagenic activity of quinoline and benzoquinolines are well-documented. In this study, the relative carcinogenic activities of quinoline, benzo[f]quinoline, benzo[h]quinoline, and phenanthridine were evaluated in newborn mice. Mice were injected intraperitoneally on the first, eighth, and fifteenth
E J LaVoie et al.
Carcinogenesis, 4(9), 1133-1138 (1983-09-01)
Benzo[f]quinoline and benzo[h]quinoline are widespread environmental pollutants which have been found to be mutagenic. The metabolism of benzo[f]quinoline and benzo[h]quinoline was investigated using a liver homogenate from Aroclor-pretreated rats. The metabolites of benzo[f]quinoline which were identified were 7,8-dihydroxy-7,8-dihydrobenzo[f]quinoline, 9,10-dihydroxy-9,10-dihydrobenzo[f]quinoline, 7-hydroxybenzo[f]quinoline
Marko Weimar et al.
Organic & biomolecular chemistry, 11(1), 31-34 (2012-10-17)
The challenging coupling of 10-halobenzo[h]quinolines with ortho-substituted aryl boronic acids has been achieved using Pd(OAc)(2)/P(O)Ph(3) as the catalytic system. High yields were obtained for diversely functionalised substrates under mild reaction conditions.
E C Riesgo et al.
Inorganic chemistry, 40(14), 3413-3422 (2001-06-26)
The Friedländer condensation was employed to synthesize two series of 3,3'-polymethylene bridged ligands, L, based on 2-(2'-pyridyl)-benzo[h]quinoline and 2,2'-bibenzo[h]quinoline (BHQ) along with the fully aromatic naphtho[1,2-b]-1,10-phenanthroline. Complexes [Cu(L)(2)](+) were prepared as their perchlorate or hexafluorophosphate salts. The solution state structures
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