2,3-Dichlor-1,4-naphthochinone

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Names

[ CAS No. ]:
117-80-6

[ Name ]:
2,3-Dichlor-1,4-naphthochinone

[Synonym ]:
2,3-Dichlor-1,4-naphthochinone
1,4-Naphthalenedione, 2,3-dichloro-
2,3-dichloro-1,4-dihydronaphthalene-1,4-dione
2,3-dichloronaphthalene-1,4-dione
EINECS 204-210-5
MFCD00001677
2,3-Dichloro-1,4-naphthoquinone
2,3-dichloro-1,4-naphthalenedione

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
304.0±42.0 °C at 760 mmHg

[ Melting Point ]:
194-197 °C(lit.)

[ Molecular Formula ]:
C₁₀H₄Cl₂O₂

[ Molecular Weight ]:
227.044

[ Flash Point ]:
127.5±28.5 °C

[ Exact Mass ]:
225.958832

[ PSA ]:
34.14000

[ LogP ]:
2.35

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.634

[ Water Solubility ]:
0.008 g/L

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL7525000

CHEMICAL NAME :: 1,4-Naphthoquinone, 2,3-dichloro-

CAS REGISTRY NUMBER :: 117-80-6

LAST UPDATED :: 199710

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C10-H4-Cl2-O2

MOLECULAR WEIGHT :: 227.04

WISWESSER LINE NOTATION :: L66 BV EVJ CG DG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 160 mg/kg

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

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 16(5),52,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 440 mg/kg

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

REFERENCE :: 85GMAT "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982 Volume(issue)/page/year: -,47,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 26,570,1983

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 500 mg/kg

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

REFERENCE :: 85JFAN "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc. of Chemistry, 1983-86 Volume(issue)/page/year: A137,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 gm/kg/60D-C

TOXIC EFFECTS :: Liver - other changes Biochemical - Metabolism (Intermediary) - glycolytic

REFERENCE :: BECTA6 Bulletin of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1966- Volume(issue)/page/year: 35,23,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg/10D-I

TOXIC EFFECTS :: Liver - other changes Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 16(5),52,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1300 mg/kg/13W-I

TOXIC EFFECTS :: Liver - other changes Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 16(5),52,1972 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3300 mg/kg/78W-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - tumors

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB223-159

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 22 mg/kg

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - tumors

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB223-159 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.5 mg/m3 JAN 1993

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H410

[ Precautionary Statements ]:
P273-P305 + P351 + P338-P501

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

[ Hazard Codes ]:
Xn:Harmful;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R22;R36/38;R50/53

[ Safety Phrases ]:
S26-S60-S61

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
QL7525000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

[ HS Code ]:
29147090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

1,4-naphthoquinone
2-Chloro-1,4-naphthoquinone
BENZOHYDROQUINONE
1,4-Naphthalenedione,2,3-dichloro-2,3-dihydro-
9,10-Dimethoxyanthracene
1-Naphthalenol
Ethanone,1-(4-hydroxy-1-naphthalenyl)-
N-(4-hydroxynaphthalen-1-yl)-4-methylbenzenesulfonamide
Naphthionic acid
2,2,3,4,4-PENTACHLORO-1,2,3,4-TETRAHYDRONAPHTHALEN-1-ONE

DownStream

1,4-Naphthalenedione,2-chloro-3-(diethylamino)-
1,4-Naphthalenedione,2-chloro-3-[[3-(4-morpholinyl)propyl]amino]-
2-chloro-3-(4-methoxyanilino)naphthalene-1,4-dione
1,4-Naphthalenedione,2-[(4-methoxyphenyl)amino]-
2,5-dimethoxy-2,3,5-triphenylthiazolidin-4-one
p-Dimethylaminobenzaldehyde
Benzaldehyde
1,4-Naphthalenedione,2-chloro-3-(1H-indazol-6-ylamino)-
1,4-Naphthalenedione,2-chloro-3-(pentylamino)-
1,4-Naphthalenedione,2-chloro-3-(propylamino)-

Customs

[ HS Code ]: 2914700012

[ Summary ]:
2914700012 2,3-dichloronaphthalene-1,4-dione。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:0.0%。MFN tarrif:5.5%。general tariff:30.0%

Articles

Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors.

J. Med. Chem. 51 , 1706-18, (2008)

Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune supp...

The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors.

Bioorg. Med. Chem. 15 , 5340-50, (2007)

A series of 1,4-naphthoquinone derivatives diversely substituted at C-2, C-3, C-5 and C-8, prepared by reaction of amines, amino acids and alcohols with commercial 1,4-naphthoquinones, has been evalua...

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).

Bull. Environ. Contam. Toxicol. 41(2) , 164-71, (1988)

2,3-Dichlor-1,4-naphthochinone
2,3-Dichlor-1,4-dianilino-1,2,3,4-tetrahydro-naphthalin
2,3-Dichlor-1,4-naphthosemichinon
trans-2,3-Dichlor-1,4-dithian
5-Acetoxy-2,3-dichlor-1,4-dimethoxynaphthalin
2,3-Dichlor-2,5-di-t-pentyl-5-cyclohexen-1,4-dion