Dinitro-ortho-cresol

{{DISPLAYTITLE:Dinitro-''ortho''-cresol}} {{Chembox | Name = Dinitro-''ortho''-cresol | ImageFile = 2-Methyl-3,5-dinitrophenol.svg | ImageSize = 150px | PIN = 2-Methyl-3,5-dinitrophenol | OtherNames = {{bulletedlist|3,5-Dinitro-''ortho''-cresol| 3,5-Dinitro-''o''-cresol| DNOC| 2-Methyl-3,5-dinitrophenol | 3,5-Dinitro-2-hydroxytoluene | DNC }} | Section1 = {{Chembox Identifiers | CASNo = 497-56-3 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 68131 | ChemSpiderID = 61439 | SMILES = [O-][N+](=O)c1cc(O)c(c([N+]([O-])=O)c1)C | InChI = 1S/C7H6N2O5/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10/h2-3,10H,1H3 }} | Section2 = {{Chembox Properties | C=7 | H=6 | N=2 | O=5 | Appearance = Yellow solid<ref name=PGCH/> | Odor = Odorless<ref name=PGCH/> | Density = 1.58 g/cm³ | MeltingPtC = 86.5 | BoilingPtC = 312 | Solubility = 0.01% (20°C)<ref name=PGCH/> | VaporPressure = 0.00005 mmHg (20°C)<ref name=PGCH/> }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = noncombustible | FlashPt_ref = <ref name=PGCH/> | AutoignitionPt = | PEL = TWA 0.2 mg/m³ [skin]<ref name=PGCH>{{PGCH|0234}}</ref> | REL = TWA 0.2 mg/m³ [skin]<ref name=PGCH/> | IDLH = 5 mg/m³<ref name=PGCH/> | LD50 = 7 mg/kg (oral, rat)<br/>50 mg/kg (oral, cat)<br/>21 mg/kg (oral, mouse)<br/>24.6 mg/kg (oral, rabbit)<br/>24.6 mg/kg (oral, guinea pig)<br/>31 mg/kg (oral, rat)<ref>{{cite web |url = https://www.cdc.gov/niosh/idlh/534521.html |title = Dinitro-o-cresol |work = Immediately Dangerous to Life or Health Concentrations (IDLH)|publisher = National Institute for Occupational Safety and Health (NIOSH) |date = 4 December 2014 |accessdate = 17 March 2015}}</ref> }} }}

'''Dinitro-''ortho''-cresol''' ('''DNOC''') is an organic compound with the structural formula CH₃C₆H₂(NO₂)₂OH. It is a yellow solid that is only slightly soluble in water. It is extremely toxic to humans and was previously used as a herbicide and insecticide.

==Preparation== This compound is prepared by disulfonation of ''o''-cresol. The resulting disulfonate is then treated with nitric acid to give DNOC. A variety of related derivatives are known including those where the methyl group is replaced by ''sec''-butyl (dinoseb), ''tert''-butyl (dinoterb), and 1-methylheptyl (dinocap). These are prepared by the direct nitration of the alkyphenols.<ref name=Booth>{{cite encyclopedia|author=Gerald Booth|title=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411}}</ref>

==Applications and safety== DNOC is an uncoupler, which means that it interferes with adenosine triphosphate (ATP) production,<ref>{{cite journal | last1 = Parker | first1 = V. H. | last2 = Barnes | first2 = J. M. | last3 = Denz | first3 = F. A. | title = Some Observations on the Toxic Properties of 3:5-Dinitro-Ortho-Cresol | doi = 10.1136/oem.8.4.226 | year = 1951 | pages = 226 | volume = 8 | journal = Occupational and Environmental Medicine | url= | issue=4| pmc = 1037342 | pmid=14878957}}</ref><ref>{{cite journal | pmid = 14839311 | last1 = Harvey | first1 = DG | year = 1951 | pages = 13–6 | issue = 4722 | last2 = Bidstrup | volume = 2 | first2 = PL | journal = British Medical Journal | last3 = Bonnell | first3 = JA | title = Poisoning by dinitro-ortho-cresol; some observations on the effects of dinitro-ortho-cresol administered by mouth to human volunteers | pmc = 2069381 | doi=10.1136/bmj.2.4722.13}}</ref> making it extremely toxic to humans.<ref name="epa">{{cite web |title=4,6-DINITRO-o-CRESOL (DNOC) (including salts) |url=https://www.epa.gov/sites/default/files/2016-09/documents/4-6-dinitro-o-cresol.pdf |website=Environmental Protection Agency |access-date=14 December 2023}}</ref>

DNOC was one of the earliest pesticides developed, being used as an insecticide since the 1890s and a herbicide since the 1930s.<ref>{{cite journal |last1=Biegaǹska |first1=Jolanta |title=Neutralization of 4,6-Dinitro- o -cresol Waste Pesticide by Means of Detonative Combustion |journal=Environmental Science & Technology |date=1 February 2005 |volume=39 |issue=4 |pages=1190–1196 |doi=10.1021/es035327p}}</ref> It was banned for use as a pesticide in the United States in 1991.<ref name="epa"/>

Symptoms of dinitro-''ortho''-cresol poisoning, due to ingestion or other forms of exposure, include confusion, fever, headache, shortness of breath, and sweating.<ref>{{Cite web|url=http://www.rightdiagnosis.com/c/chemical_poisoning_dinitrocresol/intro.htm|title=Chemical poisoning -- Dinitrocresol Symptoms, Diagnosis, Treatments and Causes - RightDiagnosis.com|website=www.rightdiagnosis.com}}</ref>

==References== {{reflist}}

==External links== * [https://www.who.int/entity/ipcs/publications/ehc/en/ehc220.pdf World Health Organization] * [https://www.cdc.gov/niosh/npg/npgd0234.html CDC - NIOSH Pocket Guide to Chemical Hazards]

Category:Uncouplers Category:Cresols Category:Nitrotoluene derivatives Category:Nitrophenol derivatives