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MilliporeSigma

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/REAXYS Number:
120249
EC Number:
205-937-0
MDL number:
MFCD00004984
UNSPSC Code:
12352100
PubChem Substance ID:
24847579
NACRES:
NA.22

Key Documents

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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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1 of 4

This Item
T17000D223204448974
Benzo[h]quinoline 97%

Sigma-Aldrich

123617

Benzo[h]quinoline

Tetrahydroxy-1,4-quinone hydrate 99%

Sigma-Aldrich

T17000

Tetrahydroxy-1,4-quinone hydrate

Duroquinone 97%

Sigma-Aldrich

D223204

Duroquinone

p-Benzoquinone-d4 98 atom % D

Sigma-Aldrich

448974

p-Benzoquinone-d4

assay

97%

assay

99%

assay

97%

assay

99% (CP)

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

200

form

solid

form

-

form

powder

form

solid

bp

338 °C/719 mmHg (lit.)

bp

-

bp

-

bp

-

mp

48-50 °C (lit.)

mp

>300 °C (lit.)

mp

110-112 °C (lit.)

mp

113-115 °C (lit.)

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[1]. 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[2]. It was used as starting reagent for the synthesis of osmium and ruthenium complexes containing an N-heterocyclic carbene ligand[3].

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB2823
STBK4665
STBJ5277
STBH6133
STBG9472

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John B Sutherland et al.
Applied microbiology and biotechnology, 67(3), 405-411 (2005-04-28)
Cultures of Umbelopsis ramanniana (=Mucor ramannianus) were grown in fluid Sabouraud medium for 3 days, dosed with 0.23 mM benzo[f]quinoline, benzo[h]quinoline, or phenanthridine (benzo[c]quinoline), and incubated for another 18 days. Cultures were extracted and metabolites (66-75% of the UV absorbance)
Hanumantharao Paritala et al.
Bioorganic & medicinal chemistry letters, 19(6), 1584-1587 (2009-02-27)
G-quadruplexes are unusual structures formed from guanine-rich sequences of nucleic acids. G-quadruplexes have been postulated to play important roles in a number of biological systems including gene regulation and the inhibition of enzyme function. Recently, our laboratory reported on the
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
S Kumar et al.
Cancer research, 49(1), 20-24 (1989-01-01)
The mutagenic activities of benzo[f]quinoline, benzo[h]quinoline, and a number of their derivatives, including dihydrodiols, K-region oxides, diol epoxides, and tetrahydroepoxides, were assessed in strain TA 100 of Salmonella typhimurium. The dihydrodiol derivatives of benzo[f]quinoline and benzo[h]quinoline were also tested for
Osmium and Ruthenium Complexes Containing an N-Heterocyclic Carbene Ligand Derived from Benzo [h] quinoline.
Esteruelas MA, et al
Organometallics, 26(21), 5239-5245 (2007)
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