Paraquat

Paraquat
Names


IUPAC name 1,1'-Dimethyl-4,4'-bipyridinium dichloride
Other names Paraquat dichloride; Methyl viologen dichloride; Crisquat; Dexuron; Esgram; Gramuron; Ortho Paraquat CL; Para-col; Pillarxone; Tota-col; Toxer Total; PP148; Cyclone; Gramixel; Gramoxone; Pathclear; AH 501.
Identifiers
CAS Number	1910-42-5^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:34905^N
ChEMBL	ChEMBL458019^Y
ChemSpider	15146^Y
ECHA InfoCard	100.016.015
IUPHAR/BPS	4552
PubChem	15938
UNII	2KZ83GSS73^Y
InChI InChI=1S/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;21H/q+2;;/p-2^Y Key: FIKAKWIAUPDISJ-UHFFFAOYSA-L^Y InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;21H/q+2;;/p-2/fC12H14N2.2Cl/h;21h/qm;2-1 InChI=1/C12H14N2.2ClH/c1-13-7-3-11(4-8-13)12-5-9-14(2)10-6-12;;/h3-10H,1-2H3;2*1H/q+2;;/p-2 Key: FIKAKWIAUPDISJ-NUQVWONBAF
SMILES C[n+]1ccc(cc1)c2cc[n+](cc2)C.[Cl-].[Cl-]
Properties
Chemical formula	C₁₂H₁₄Cl₂N₂
Molar mass	257.16 g·mol⁻¹
Appearance	Yellow solid
Odor	faint, ammonia-like
Density	1.25 g/cm³
Melting point	175 to 180 °C (347 to 356 °F; 448 to 453 K)
Boiling point	> 300 °C (572 °F; 573 K)
Solubility in water	High
Vapor pressure	<0.0000001 mmHg (20°C)
Hazards
Main hazards	Toxic, environmental hazard
Safety data sheet	Aldrich MSDS
GHS pictograms
GHS hazard statements	H301, H311, H315, H319, H330, H335, H372, H410
GHS precautionary statements	P260, P273, P280, P284, P301+310, P305+351+338
EU classification (DSD)	T+ N
R-phrases	R24/25, R26, R36/37/38, R48/25, R50/53
S-phrases	(S1/2), S22, S28, S36/37/39, S45, S60, S61
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	57 mg/kg (rat, oral) 120 mg/kg (mouse, oral) 25 mg/kg (dog, oral) 22 mg/kg (guinea pig, oral)
LC₅₀ (median concentration)	3 mg/m³ (mouse, 30 min respirable dust) 3 mg/m³ (guinea pig, 30 min respirable dust)
LC_Lo (lowest published)	1 mg/m³ (rat, respirable dust, 6 hr) 6400 mg/m³ (rat, nonrespirable dust, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 0.5 mg/m³ (resp) [skin]
REL (Recommended)	TWA 0.1 mg/m³ (resp) [skin]
IDLH (Immediate danger)	1 mg/m³
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

Paraquat (trivial name; /ˈpærəkwɑːt/) or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name) is the organic compound with the chemical formula [(C₆H₇N)₂]Cl₂. It is classified as a viologen, a family of redox-active heterocycles of similar structure. Paraquat was manufactured by Chevron. This salt is one of the most widely used herbicides. It is quick-acting and non-selective, killing green plant tissue on contact. It is also toxic to human beings and animals. It is linked to development of Parkinson's disease. The name is derived from the para positions of the quaternary nitrogens. Quantities are sometimes expressed by cation mass alone (paraquat cation, paraquat ion); other salts (with other anions besides chloride) exist. In fact, its redox activity, which produces superoxide anions, is why it is toxic.

Pyridine is coupled by treatment with sodium in ammonia followed by oxidation. The resulting 4,4'-bipyridine is then methylated with chloromethane to give the title compound:

...
Wikipedia