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2,6-Dinitrophenol

2,6-Dinitrophenol

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Also known as: 573-56-8, O-dinitrophenol, Phenol, 2,6-dinitro-, Beta-dinitrophenol, 2,6-dnp, Dinitro-2,6-phenol

Molecular Formula

C₆H₄N₂O₅

Molecular Weight

184.11 g/mol

InChI Key

JCRIDWXIBSEOEG-UHFFFAOYSA-N

FDA UNII

F4QM4I92KC

1 2D Structure

2,6-Dinitrophenol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,6-dinitrophenol

2.1.2 InChI

InChI=1S/C6H4N2O5/c9-6-4(7(10)11)2-1-3-5(6)8(12)13/h1-3,9H

2.1.3 InChI Key

JCRIDWXIBSEOEG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C(=C1)[N+](=O)[O-])O)[N+](=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

F4QM4I92KC

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 573-56-8

2. O-dinitrophenol

3. Phenol, 2,6-dinitro-

4. Beta-dinitrophenol

5. 2,6-dnp

6. Dinitro-2,6-phenol

7. 2,6-dinitrofenol

8. .beta.-dinitrophenol

9. Phenol, .beta.-dinitro-

10. Chebi:39357

11. F4qm4i92kc

12. Nsc-6215

13. Phenol, Beta-dinitro-

14. 2,6-dinitrofenol [czech]

15. 2,6-dinitro-phenol

16. Ccris 3104

17. Hsdb 6306

18. Nsc 6215

19. Einecs 209-357-9

20. Unii-f4qm4i92kc

21. Brn 1913410

22. 2,6-dinitro Phenol

23. Wln: Wnr Bq Cnw

24. Epitope Id:161741

25. 2,6-dinitrophenol, 95%

26. Schembl1077970

27. Chembl3278560

28. Dtxsid5022063

29. 2,6-dinitrophenol [mi]

30. Nsc6215

31. Stl355968

32. Zinc12358884

33. Akos000274520

34. As-40741

35. Db-020252

36. Bb 0259250

37. Ft-0610716

38. 2,6-dinitrophenol 10 Microg/ml In Acetonitrile

39. Q20856130

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₆H₄N₂O₅
Molecular Weight	184.11 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	0
Exact Mass	184.01202123 g/mol
Monoisotopic Mass	184.01202123 g/mol
Topological Polar Surface Area	112 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	198
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

/The investigators/ ... studied the pharmacokinetics of ... dinitrophenol isomers /incl 2,6-dinitrophenol/ and showed that elimination from the blood of mice, rabbits, guinea pigs, rats, and monkeys was complete within 30 hr.

National Research Council. Drinking Water & Health, Volume 4. Washington, DC: National Academy Press, 1981., p. 234

Dinitrophenol isomers are readily absorbed from the gastrointestinal tract and through the skin and lungs. The dinitrophenol isomers are not stored to any significant extent in the tissues of humans or lab animals following absorption, but are readily excreted, primarily via the urine. /Dinitrophenol/

National Research Council. Drinking Water & Health, Volume 4. Washington, DC: National Academy Press, 1981., p. 233

Absorption of dinitro compounds can take place with ease through the lungs, the gut, or the intact skin. The rate of absorption through skin is likely to be greater when the substances are applied in oily rather than aq soln. /Dinitro cmpd/

Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 134

... Dinitro compounds are persistent yellow dye-stuffs, staining exposed skin, hair, wool, fur, and feathers a distinct yellow or orange color which remains obvious for weeks or even months afterwards, despite the action of water and weather. Such staining provides evidence of at least external contact with the chemicals. /Dinitro cmpd/

Clarke, M. L., D. G. Harvey and D. J. Humphreys. Veterinary Toxicology. 2nd ed. London: Bailliere Tindall, 1981., p. 135

4.2 Metabolism/Metabolites

Metabolites of 2,6-Dinitrophenol: 2-amino-6-nitrophenol, 6-amino-2-nitrophenol, 2,6-diaminophenol /From table/

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for Dinitrophenols p.168 (August 1995) Toxic Profiles 64. Available from, as of September 16, 2010: https://www.atsdr.cdc.gov/toxprofiles/index.asp

4.3 Biological Half-Life

The half-lives for elimination of 2,6-dinitrophenol from the blood of mice and rats following a single large dose given intraperitoneally are 238 min and 210 min, respectively. /From table/

National Research Council. Drinking Water & Health, Volume 4. Washington, DC: National Academy Press, 1981., p. 234

4.4 Mechanism of Action

... /Of/ the six isomeric dinitrophenols, those with nitro groups in the 2,4- and 3,4-positions stimulate oxygen consumption, whereas those with nitro groups in the 2,5-position do not. ...

Hayes, Wayland J., Jr. Pesticides Studied in Man. Baltimore/London: Williams and Wilkins, 1982., p. 463

All nitrophenols inhibit the microbial growth of natural aquatic systems because they uncouple the metabolic process of oxidative phosphorylation. /Nitrophenols/

Callahan, M.A., M.W. Slimak, N.W. Gabel, et al. Water-Related Environmental Fate of 129 Priority Pollutants. Volume I. EPA-440/4 79-029a. Washington, DC: U.S. Environmental Protection Agency, December 1979., p. 90-5