3,4,3',4'-tetrachloroazobenzene is an organochlorine compound with the formula C12H6Cl4N2. It is a yellow solid that is insoluble in water but soluble in organic solvents. It is synthesized by the reaction of 3,4-dichloroaniline with sodium nitrite in the presence of hydrochloric acid. This compound has been studied extensively for its toxicological effects, particularly its carcinogenic potential. It has been shown to be a potent mutagen and has been linked to liver cancer in animal studies. 3,4,3',4'-tetrachloroazobenzene is also a known environmental contaminant and has been detected in soil, water, and air. It is believed to be released into the environment from industrial processes, such as the manufacture of pesticides and dyes. The environmental persistence and potential toxicity of 3,4,3',4'-tetrachloroazobenzene make it a compound of concern, leading to research efforts to understand its fate and effects in the environment.'
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3,4,3',4'-tetrachloroazobenzene: unwanted contaminant found in commercial synthesis of dichloroaniline or herbicides made from dichloroaniline; implicated in outbreak of acne in chemical workers; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
ID Source | ID |
---|---|
PubMed CID | 26423 |
SCHEMBL ID | 8759349 |
MeSH ID | M0060908 |
Synonym |
---|
tcab |
azobenzene, 3,3',4,4'-tetrachloro- |
3,4,3',4'-tetrachloroazobenzene |
diazene, bis(3,4-dichlorophenyl)- |
ccris 1273 |
brn 4871675 |
bis(3,4-dichlorophenyl)diazene |
14047-09-7 |
3,3',4,4'-tetrachloroazobenzene |
3,4,3',4'-tetrachloroazobenzene, (z)-isomer |
unii-pgg7w94gs9 |
pgg7w94gs9 , |
hsdb 8053 |
diazene,1,2-bis(3,4-dichlorophenyl)- |
diazene, bis(3,4-dichlorophenyl)-, (z)- |
64275-11-2 |
SCHEMBL8759349 |
SOBGIMQKWDUEPY-ISLYRVAYSA-N |
(e)-1,2-bis(3,4-dichlorophenyl)diazene # |
DTXSID6026086 |
3,3',4,4'-tetrachloro-azobenzene |
bis(3,4-dichlorophenyl)-diazene |
bis(3,4-dichlorophenyl)-(z)-diazene |
diazene, bis(3,4-dichlorophenyl)- (9ci) |
bis(3,4-dichlorophenyl)diazene, 9ci |
3,3',4,4'-tetrachloroazobenzene 100 microg/ml in acetonitrile |
tetrachloroazobenzene, 3,3',4,4'- |
3,3',4,4'-tetrachloroazobenzene [iarc] |
diazene, 1,2-bis(3,4-dichlorophenyl)- |
DTXSID80860129 |
Excerpt | Reference | Relevance |
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" Both TCAB and TCAOB were more toxic than all other chemicals that have been tested in the chick embryo with the exception of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)." | ( Embryotoxicity of 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in the chick embryo. Hsia, MT; Kreamer, BL; Schrankel, KR, 1982) | 0.26 |
Excerpt | Reference | Relevance |
---|---|---|
" The absolute oral bioavailability was determined to be 30%." | ( 3,3',4,4'-tetrachloroazobenzene absorption, disposition, and metabolism in male Fischer 344 rats. Kattnig, MJ; Liebler, DC; Mayersohn, M; McClure, T; Pillai, UA; Sipes, IG; Wang, DX; Ziegler, TL, 1996) | 0.29 |
Excerpt | Relevance | Reference |
---|---|---|
" In 2 groups of weanling rats the same dosage of TCAOB was able to reduce the relative thymus weight to 31% and 38% of the comparable control animals." | ( Thymic atrophy induced by acute exposure of 3,3',4,4'-tetrachloroazobenzene and 3,3',4,4'-tetrachloroazoxybenzene in rats. Burant, CF; Hsia, MT; Kreamer, BL; Schrankel, KR, 1982) | 0.26 |
"2 and 32 mg/kg), 39-45% of the dosed radioactivity was excreted into the urine and 53-56% was recovered in the feces within 48 hr." | ( 3,3',4,4'-tetrachloroazobenzene absorption, disposition, and metabolism in male Fischer 344 rats. Kattnig, MJ; Liebler, DC; Mayersohn, M; McClure, T; Pillai, UA; Sipes, IG; Wang, DX; Ziegler, TL, 1996) | 0.29 |
" Mean body weight gains of all dosed groups of females were significantly less than those of the vehicle controls." | ( Toxicology and carcinogenesis studies of 3,3',4,4'-tetrachloroazobenzene (TCAB) (CAS No. 14047-09-7) in Harlan Sprague-Dawley rats and B6C3F1 mice (gavage studies). , 2010) | 0.36 |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 17 (51.52) | 18.7374 |
1990's | 8 (24.24) | 18.2507 |
2000's | 2 (6.06) | 29.6817 |
2010's | 6 (18.18) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (17.44) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (2.86%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 34 (97.14%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |