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

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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.

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.799 Edit this at Wikidata
EC Number
  • 204-178-2
UNII
  • InChI=1S/C6HCl4NO2/c7-2-1-3(8)5(10)6(4(2)9)11(12)13/h1H
    Key: XQTLDIFVVHJORV-UHFFFAOYSA-N
  • C1=C(C(=C(C(=C1Cl)Cl)[N+](=O)[O-])Cl)Cl
Properties
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)
0.44 mg/L[3]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H317, H410
P273, P280, P301+P312+P330, P302+P352
Lethal dose or concentration (LD, LC):
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).

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

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  1. ^ impure 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.
  3. ^ a b c d 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.
 

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