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

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1,2,4,5-Tetrachloro-3-nitrobenzene
Tecnazen.svg
Names
IUPAC name
1,2,4,5-Tetrachloro-3-nitrobenzene
Other names
    • Tecnazene
    • TCNB
    • 2,3,5,6-Tetrachloronitrobenzene
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 204-178-2
UNII
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 pictograms GHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Danger
H302, H317, H410
P273, P280, P301+312+330Script error: No such module "Preview warning".Category:GHS errors, P302+352
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).
Infobox references

1,2,4,5-Tetrachloro-3-nitrobenzene (tecnazene) is an organic compound with the formula HC
6
Cl
4
NO
2
. 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

  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. 3.0 3.1 3.2 3.3 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. https://discovery.ucl.ac.uk/id/eprint/10025215/. 
  5. "1,2,4,5-Tetrachloro-3-nitrobenzene Standard for quantitative NMR, TraceCERT 117-18-0". https://www.sigmaaldrich.com/US/en/product/sial/40384. 
  6. "Tecnazene Pestanal analytical standard 117-18-0". https://www.sigmaaldrich.com/US/en/product/sial/45672. 
  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. doi:10.1021/es800107k. PMID 18800534. Bibcode2008EnST...42.6587B.