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Sigma-Aldrich

2-(Chloromethyl)anthraquinone

98%

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About This Item

Empirical Formula (Hill Notation):
C15H9ClO2
CAS Number:
6374-87-4
Molecular Weight:
256.68
Beilstein:
1975355
MDL number:
MFCD00216612
UNSPSC Code:
12352100
PubChem Substance ID:
24867182
NACRES:
NA.22

Assay

98%

form

solid

mp

166-169 °C (lit.)

SMILES string

ClCc1ccc2C(=O)c3ccccc3C(=O)c2c1

InChI

1S/C15H9ClO2/c16-8-9-5-6-12-13(7-9)15(18)11-4-2-1-3-10(11)14(12)17/h1-7H,8H2

InChI key

NVUYDKYMEMGYFP-UHFFFAOYSA-N

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General description

2-(Chloromethyl)anthraquinone is an anthraquinone derivative. It was utilized as a substrate to synthesize Cibanone yellow R, a vat dye. Its electrochemical behavior has been studied over a wide pH range.

Application

2-(Chloromethyl)anthraquinone may be used in the following processes:
  • Synthesis of 2-[methylamino-N-(1′-methyl-4′-N,N-diethylaminobutyl)]anthraquinone diphosphate.
  • Synthesis of 2-(3,4-dicyano-phenyl)-2-(9,10-dioxo-9,10-dihydroantracen-2-yl-methyl)-malonic acid diethyl ester, starting reagent for the synthesis of tetra substituted metallophthalocyanines.
  • To alter the glassy carbon (GC) electrode surface in order to investigate the oxygen reduction reaction (ORR) in alkaline medium.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Electrocatalysis of oxygen reduction on glassy carbon electrodes modified with anthraquinone moieties.
Mooste M, et al.
Journal of Solid State Electrochemistry, 18(6), 1725-1733 (2014)
Synthesis, electrochemistry, spectroelectrochemistry and electrocolorimetry of phthalocyanine-anthraquinone hybrids.
Sezer B, et al.
Synt. Metals, 160(19), 2155-2166 (2010)
Sulphur dyes and sulphurised vat dyes.
Shah KH, et al.
Proceedings of the Indian Academy of Sciences - Section A, 30(1) (1949)
Electrochemical investigations of unexplored anthraquinones and their DNA binding.
Shah A, et al.
Journal of Electrochemical Science and Engineering, 3(1), 19-27 (2013)
Kevin K Schrader et al.
Applied and environmental microbiology, 69(9), 5319-5327 (2003-09-06)
Musty "off-flavor" in pond-cultured channel catfish (Ictalurus punctatus) costs the catfish production industry in the United States at least 30 million US dollars annually. The cyanobacterium Oscillatoria perornata (Skuja) is credited with being the major cause of musty off-flavor in
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