1,2,4,5-Tetrachloro-3-nitrobenzene

1,2,4,5-Tetrachloro-3-nitrobenzene
Names
	IUPAC name 1,2,4,5-Tetrachloro-3-nitrobenzene
	Other names Tecnazene; TCNB; 2,3,5,6-Tetrachloronitrobenzene; ;
Identifiers
CAS Number	117-18-0;
3D model (JSmol)	Interactive image;
ChemSpider	21106573;
ECHA InfoCard	100.003.799
EC Number	204-178-2;
PubChem CID	8330;
UNII	02X6KNJ5EE;
CompTox Dashboard (EPA)	DTXSID0026098 ;
	InChI InChI=1S/C6HCl4NO2/c7-2-1-3(8)5(10)6(4(2)9)11(12)13/h1H Key: XQTLDIFVVHJORV-UHFFFAOYSA-N;
	SMILES C1=C(C(=C(C(=C1Cl)Cl)[N+](=O)[O-])Cl)Cl;
Properties
Chemical formula	C6HCl4NO2
Molar mass	260.88 g·mol−1
Appearance	Colorless[1]
Odor	Odorless
Density	1.862 g/cm3[2]
Melting point	99 °C (210 °F; 372 K)[3]
Boiling point	304 °C (579 °F; 577 K)[3] (decomposes)
Solubility in water	0.44 mg/L[3]
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H317, H410
Precautionary statements	P273, P280, P301+P312+P330, P302+P352
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	7.5 g/kg[3]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,2,4,5-Tetrachloro-3-nitrobenzene (tecnazene) is an organic compound with the formula HC₆Cl₄NO₂. It is a colorless solid. A related isomer is 1,2,3,4-tetrachloro-5-nitrobenzene.

It is used as a standard for quantitative analysis by nuclear magnetic resonance.[4][5]

1,2,4,5-Tetrachloro-3-nitrobenzene is also a fungicide used to prevent dry rot and sprouting on potatoes during storage.[6][7]

References

impure samples may appear yellow or pale-brown
Bhar, A.; Aune, J. P.; Benali-Cherif, N.; Benmenni, L.; Giorgi, M. (1995). "Three Polychloromononitrobenzenes: C₆H₃Cl₂NO₂, C₆H₂Cl₃NO₂ and C₆HCl₄NO₂". Acta Crystallographica Section C Crystal Structure Communications. 51 (2): 256–260. doi:10.1107/S0108270194002957.
Record of Tecnazen in the GESTIS Substance Database of the Institute for Occupational Safety and Health
Bayle, Elliott; Igoe, Niall; Fish, Paul V. (2017). "4-Cyano-2-methoxybenzenesulfonyl Chloride". Organic Syntheses. 94: 198–216. doi:10.15227/orgsyn.094.0198.
"1,2,4,5-Tetrachloro-3-nitrobenzene Standard for quantitative NMR, TraceCERT 117-18-0".
"Tecnazene Pestanal analytical standard 117-18-0".
Bhatt, Varsha D.; Soman, Rajiv S.; Miller, Matthew A.; Kasting, Gerald B. (2008). "Permeation of Tecnazene through Human Skin in Vitro as Assessed by HS-SPME and GC-MS". Environmental Science & Technology. 42 (17): 6587–6592. Bibcode:2008EnST...42.6587B. doi:10.1021/es800107k. PMID 18800534.

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[1] ure samples may appear yellow or pale-brown

[2] Bhar, A.; Aune, J. P.; Benali-Cherif, N.; Benmenni, L.; Giorgi, M. (1995). "Three Polychloromononitrobenzenes: C₆H₃Cl₂NO₂, C₆H₂Cl₃NO₂ and C₆HCl₄NO₂". Acta Crystallographica Section C Crystal Structure Communications. 51 (2): 256–260. doi:10.1107/S0108270194002957.

[GESTIS-3] Record of Tecnazen in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[4] Bayle, Elliott; Igoe, Niall; Fish, Paul V. (2017). "4-Cyano-2-methoxybenzenesulfonyl Chloride". Organic Syntheses. 94: 198–216. doi:10.15227/orgsyn.094.0198.

[5] "1,2,4,5-Tetrachloro-3-nitrobenzene Standard for quantitative NMR, TraceCERT 117-18-0".

[6] "Tecnazene Pestanal analytical standard 117-18-0".

[7] Bhatt, Varsha D.; Soman, Rajiv S.; Miller, Matthew A.; Kasting, Gerald B. (2008). "Permeation of Tecnazene through Human Skin in Vitro as Assessed by HS-SPME and GC-MS". Environmental Science & Technology. 42 (17): 6587–6592. Bibcode:2008EnST...42.6587B. doi:10.1021/es800107k. PMID 18800534.