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  • 35990 - 2,3-Dichloro-1,4-naphthoquinone


35990 Sigma-Aldrich


for spectrophotometric det. of hydrazides, ≥98.0%

Synonym: Dichlon

  • CAS Number 117-80-6

  • Empirical Formula (Hill Notation) C10H4Cl2O2

  • Molecular Weight 227.04

  •  Beilstein Registry Number 1073511

  •  EC Number 204-210-5

  •  MDL number MFCD00001677

  •  PubChem Substance ID 24862118



Related Categories Analytical Reagents, Analytical/Chromatography, Spectroscopy, UV/Vis Reagents, UV/Visible (UV/VIS) Spectroscopy More...
description   algaecide
assay   ≥98.0% (AT)
quality   for spectrophotometric det. of hydrazides
mp   192-195 °C
  194-197 °C(lit.)


Other Notes

Same product — same quality — now Sigma-Aldrich brand

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Safety & Documentation

Safety Information

Signal word 
Hazard statements 
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Personal Protective Equipment 
UN 2811 6.1/PG 3
WGK Germany 


Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers


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2, 3-Dichloro-1, 4-naphthoquinone Horst WP and Felix EL. Ind. and Eng. Chem. 35 (12), 1255-1259, (1943)

Spectrophotometric determination of hydrazides with 2, 3-dichloro-1, 4-napthoquinone. Plaizier JA, et.al. Anal. Chem. 48 (11), 1536-1538, (1976)

Spectrophotometric determination of isoniazid in presence of its hydrazones. Devani MB, et.al. J. Pharm. Sci. 67 (5), 661-663, (1978)

Irreversible inhibition of rat hepatic glutathione S-transferase isoenzymes by a series of structurally related quinones. Vos RM, Van Ommen B, Hoekstein MS, et al. Chem. Biol. Interact. 71(4), 381-92, (1989)


[Interaction of methimazole and quinones. Spectrophotometric determination of methimazole in blood]. Gallo N, Bianco P, Tapino R, et al. Minerva Med. 74(16), 875-7, (1983)


Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors. Sanjeev Kumar et al J. Med. Chem. 51, 1706-18, (2008)


Toxicology in the fast lane: application of high-throughput bioassays to detect modulation of key enzymes and receptors. Morisseau C, Merzlikin O, Lin A, et al. Environ. Health Perspect. 117(12), 1867-72, (2009)


2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: synthesis and biological evaluation as potential antiproliferative and antifungal agents. Vishnu K Tandon et al Eur. J. Med. Chem. 44, 1086-92, (2009)


A redox cycling mechanism of action for 2,3-dichloro-1,4-naphthoquinone with mitochondrial membranes and the role of sulfhydryl groups. Pritsos CA and Pardini RS Biochem. Pharmacol. 33(23), 3771-7, (1984)


Metabolic consequences of dietary 2,3-dichloro-1,4-naphthoquinone (CNQ) in the rat. Alteration in anti-oxidant enzyme activities. Pritsos CA, Aaronson LM, and Pardini RS Biochem. Pharmacol. 35(7), 1131-5, (1986)


A role for glutathione disulfide as a scavenger of oxygen radicals produced by 2,3-dichloro-1,4-naphthoquinone. Pritsos CA and Pardini RS Res. Commun. Chem. Pathol. Pharmacol. 42(2), 271-80, (1983)


The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors. Cláudia Valente et al Bioorg. Med. Chem. 15, 5340-50, (2007)


Involvement of superoxide in the interaction of 2,3-dichloro-1,4-naphthoquinone with mitochondrial membranes. Pritsos CA, Jensen DE, Pisani D, et al. Arch. Biochem. Biophys. 217(1), 98-109, (1982)


Development and validation of spectrophotometric methods for determination of fluoxetine, sertraline, and paroxetine in pharmaceutical dosage forms. Darwish IA J. AOAC Int. 88(1), 38-45, (2005)


Incorporation of a high potential quinone reveals that electron transfer in Photosystem I becomes highly asymmetric at low temperature. Mula S, Savitsky A, Möbius K, et al. Photochem. Photobiol. Sci. 11(6), 946-56, (2012)


Interaction of 2,3-dichloro-1,4-naphthoquinone with n-butylamine in halocarbon solvents. Neelgund GM and Budni ML Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 61(8), 1729-35, (2005)


New quinone-amino acid conjugates linked via a vinylic spacer. Alnabari M and Bittner S Amino Acids 20(4), 381-7, (2001)


Modulation of hepatic cytochrome P-450 and DT-diaphorase by oral and sub-cutaneous administration of the pro-oxidant fungicide dichlone (2,3-dichloro-1,4-naphthoquinone). Elliott AJ and Pardini RS Bull. Environ. Contam. Toxicol. 41(2), 164-71, (1988)


Spectroscopic and theoretical studies on the nucleophilic substitution of 2,3-dichloronaphthoquinone with para-substituted anilines in solid state via initial charge transfer complexation. Satheshkumar A and Elango KP Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 98, 378-83, (2012)


Study of a reaction between 2,3-dichloro-1,4-naphthoquinone and N,N'-diphenyl thiourea involving an EDA adduct as intermediate. Datta K and Mukherjee AK Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 60(7), 1641-7, (2004)


Charge transfer interaction of 4-acetamidophenol (paracetamol) with 2,3-dichloro-1,4-naphthoquinone: a study in aqueous ethanol medium by UV-vis spectroscopic and DFT methods. Saha A, Tiwary AS, and Mukherjee AK Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 71(3), 835-40, (2008)


Dichlone-induced oxidative stress in a model insect species, Spodoptera eridania. Ahmad S, Zaman K, MacGill RS, et al. Arch. Environ. Contam. Toxicol. 29(4), 442-8, (1995)


Inhibition of liver glycolysis in rats by dietary dichlone (2,3-dichloro-1,4-naphthoquinone). Pritsos CA, Pisani DE, and Pardini RS Bull. Environ. Contam. Toxicol. 35(1), 23-8, (1985)


Bacterial growth response to photoactive quinones. Vaughan PP, Novotny P, Haubrich N, et al. Photochem. Photobiol. 86(6), 1327-33, (2010)


[Reactions between dialkylamine drugs, 2,3-dichloro-1,4-naphthoquinone and acetaldehyde]. Kallmayer HJ and Thierfelder B Pharmazie 57(8), 530-4, (2002)


[Reactions of isopropyl-alkylamine with 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloro-1,4-naphthoquinone/acetaldehyde]. Kallmayer HJ and Thierfelder B Pharmazie 58(2), 104-7, (2003)


[Reactions of trialkylamine compounds with 2,3-dichloro-1,4-naphthoquinone]. Kallmayer HJ and Thierfelder B Pharmazie 57(9), 648-9, (2002)


[Preparation of water-soluble hydronaphthoquinone derivatives and its application to the determination of hydrogen peroxide in clinical chemistry]. Ohta S, Hatakeyama S, Aono C, et al. Yakugaku Zasshi 112(8), 585-91, (1992)


Merck 14,3045

Beil. 7,IV,2426

Corp MSDS 1 (1), 1146:A / FT-IR 1 (2), 80:D / FT-IR 2 (2), 2485:B / IR-Spectra (2), 785:A / IR-Spectra (3), 897:E / NMR-Reference 2 (2), 86:D / RegBook 1 (2), 1683:K / Sax 6, 953 / Structure Index 1, 267:D:1

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