Dinoseb

Not to be confused with dinoterb.
Dinoseb
Names
Preferred IUPAC name
2-(Butan-2-yl)-4,6-dinitrophenol
Other names
2-(sec-Butyl)-4,6-dinitrophenol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.692 Edit this at Wikidata
EC Number
  • 201-861-7
KEGG
UNII
UN number 2779 2902
  • InChI=1S/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3 checkY
    Key: OWZPCEFYPSAJFR-UHFFFAOYSA-N checkY
  • InChI=1/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3
    Key: OWZPCEFYPSAJFR-UHFFFAOYAU
  • [O-][N+](=O)c1cc(cc(c1O)C(CC)C)[N+]([O-])=O
Properties
C10H12N2O5
Molar mass 240.215 g·mol−1
Density 1.35 g/cm3
Melting point 38–42 °C (100–108 °F; 311–315 K)
Acidity (pKa) 4.4[1]
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazardGHS05: Corrosive
Danger
H300, H311, H315, H317, H318, H360, H410[2]
P201, P273, P280, P302+P352, P305+P351+P338, P310[2]
Safety data sheet (SDS) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dinoseb is a common industry name for 6-sec-butyl-2,4-dinitrophenol, a herbicide in the dinitrophenol family. It is a crystalline orange solid which does not readily dissolve in water. Dinoseb is banned as an herbicide in the European Union (EU) and the United States because of its toxicity.

It also finds use as a polymerisation inhibitor, where it is often referred to as DNBP. It is used to prevent the thermally induced polymerisation of styrene and other unsaturated monomers when they are being purified by distillation.

  1. ^ Szeto, Sunny Y.; Price, Patricia M. (September 1991). "Persistence of pesticide residues in mineral and organic soils in the Fraser Valley of British Columbia". Journal of Agricultural and Food Chemistry. 39 (9): 1679–1684. doi:10.1021/jf00009a027.
  2. ^ a b c Sigma-Aldrich Co., Dinoseb. Retrieved on 2020-03-24.