Diquat dibromide

Diquat dibromide

Names
IUPAC name 6,7-Dihydrodipyrido[1,2-a:2′,1′-c]pyrazinediium dibromide
Other names 1,1′-Ethylene-2,2′-bipyridyldiylium dibromide
Identifiers
CAS Number	85-00-7 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1599022 N
ChemSpider	6536 Y
ECHA InfoCard	100.001.436
KEGG	C18577 Y
PubChem CID	6794
UNII	A9A615U4MP Y
InChI InChI=1S/C12H12N2.2BrH/c1-3-7-13-9-10-14-8-4-2-6-12(14)11(13)5-1;;/h1-8H,9-10H2;2*1H/q+2;;/p-2 Y Key: ODPOAESBSUKMHD-UHFFFAOYSA-L Y InChI=1/C12H12N2.2BrH/c1-3-7-13-9-10-14-8-4-2-6-12(14)11(13)5-1;;/h1-8H,9-10H2;2*1H/q+2;;/p-2 Key: ODPOAESBSUKMHD-NUQVWONBAO
SMILES C1[n+]2ccccc2-c3cccc[n+]3C1.[Br-].[Br-]
Properties
Chemical formula	C12H12Br2N2
Molar mass	344.05 g·mol−1
Appearance	Yellow crystals
Density	1.22–1.27 g/cm3
Melting point	335 °C (635 °F; 608 K)
Boiling point	Decomposes
Solubility in water	70% (20 °C)
Vapor pressure	<6997133322387415000♠0.00001 mmHg (20 °C)
Hazards
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 0.5 mg/m3
IDLH (Immediate danger)	N.D.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Diquat is a contact herbicide that produces desiccation and defoliation most often available as the dibromide, diquat dibromide. Brand names for this formulation include Aquacide, Dextrone, Preeglone, Deiquat, Spectracide, Detrone, Reglone, Reglon, Reglox, Tribune, Ortho-Diquat, Weedtrine-D, Weedol 2 and, in combination with glyphosate, Resolva.

Diquat is a non-selective herbicide that acts quickly to damage only those parts of the plant to which it is applied. It has been used in pre-harvest crop desiccation. It bonds strongly to mineral and organic particles in soil and water where it remains without significant degradation for years. However, bound to clays diquat is biologically inactive at concentrations typically observed in agricultural soils.

Diquat dibromide is moderately toxic. It may be fatal to humans if swallowed, inhaled, or absorbed through the skin in large quantities.

Pyridine is oxidatively coupled to 2,2′-bipyridine over a heated Raney nickel catalyst. The ethylene bridge is formed by the reaction with 1,2-dibromoethane: