3,4,5,6-Tetrachlorobenzene-1,2-diol

Names

[ Name ]:
3,4,5,6-Tetrachlorobenzene-1,2-diol

[Synonym ]:
1,2-Benzenediol, 3,4,5,6-tetrachloro-
MFCD00002190
3,4,5,6-Tetrachloro-1,2-benzenediol (9CI)
3,4,5,6-tetrachlorobenzene-1,2-diol
3,4,5,6-Tetrachloro-1,2-benzenediol
TETRACHLOROCATECHOL

Biological Activity

[Description]:

Tetrachlorocatechol is a metabolite of pentachlorophenol. Tetrachlorocatechol is one of the most toxic chlorinated catechol produced by the chlorobleaching of pulp and frequently found in the kraft pulp mill effluents[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. G. Renner, et al. Acute toxicities of pentachlorophenol, pentachloroanisole, tetrachlorohydroquinone, tetrachlorocatechol, tetrachlororesorcinol, tetrachlorodimethoxybenzenes and tetrachlorobenzenediol diacetates administered to mice, Toxicological & Environmental Chemistry, 11:1, 37-50.

[2]. Mukherjee, et al. Evaluation of Acute Toxicity Levels and Ethological Responses Under Tetrachlorocatechol Exposure in Common Carp, Cyprinus carpio (Linnaeus). Proc Zool Soc 67, 108–113 (2014).

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
309.1±37.0 °C at 760 mmHg

[ Melting Point ]:
184-186°C (dec.)

[ Molecular Formula ]:
C₆H₂Cl₄O₂

[ Molecular Weight ]:
247.891

[ Flash Point ]:
140.7±26.5 °C

[ Exact Mass ]:
245.880890

[ PSA ]:
40.46000

[ LogP ]:
4.74

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.662

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UX2449000

CHEMICAL NAME :: Pyrocatechol, tetrachloro-

CAS REGISTRY NUMBER :: 1198-55-6

BEILSTEIN REFERENCE NO. :: 1876366

LAST UPDATED :: 199710

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C6-H2-Cl4-O2

MOLECULAR WEIGHT :: 247.88

WISWESSER LINE NOTATION :: QR BQ CG DG EG FG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,526,1986

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,526,1986 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 318 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - tremor Behavioral - muscle weakness

REFERENCE :: TECSDY Toxicological and Environmental Chemistry. (Gordon & Breach Science Pub. Inc., 1 Park Ave., New York, NY 10016) V.3(3/4)- 1981- Volume(issue)/page/year: 11,37,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 136 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 40,63,1978

Safety Information

[ Symbol ]:

GHS05, GHS07, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H318-H400

[ Precautionary Statements ]:
P273-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/22

[ Safety Phrases ]:
S26-S36/37/39-S39

[ RIDADR ]:
2811

[ RTECS ]:
UX2449000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2908199090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2908199090

[ Summary ]:
HS: 2908199090. derivatives of polyphenols or phenol-alcohols containing only halogen substituents and their salts. VAT:17.0%. tax rebate rate:9.0%. supervision conditions:None. MFN tariff:5.5%. general tariff:30.0%

Articles

Polyhalogenated benzo- and naphthoquinones are potent inhibitors of plant and bacterial ureases.

FEBS Lett. 555(2) , 367-70, (2003)

Polyhalogenated benzo- and naphthoquinones were found to be potent inhibitors of pure ureases from Bacillus pasteurii and Canavalia ensiformis. They also inhibited ureases in whole cells of Helicobact...

Oxidative double dehalogenation of tetrachlorocatechol by a bio-inspired CuII complex: formation of chloranilic acid.

Chemistry 14(18) , 5567-76, (2008)

Copper(II) complexes of the potentially tripodal N,N,O ligand 3,3-bis(1-methylimidazol-2-yl)propionate (L1) and its conjugate acid HL1 have been synthesised and structurally and spectroscopically char...

Synergistic cytotoxic effect of tetrachlorocatechol and sodium azide in Escherichia coli: toxicity, metabolism, and mechanistic aspects.

Environ. Toxicol. Chem. 28(7) , 1380-9, (2009)

Pentachlorophenol (PCP) is used in industrial and domestic applications, including as a biocide and a wood preservative. Metabolism of PCP undergoes oxidative dechlorination, forming tetrachlorocatech...

Related Compounds

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