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Paraquat dichloride

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Name

Paraquat dichloride

EINECS 217-615-7
CAS No. 1910-42-5 Density 1.25
PSA 7.76000 LogP -4.98940
Solubility soluble in water Melting Point > 300 °C(lit.)
Formula C12H14Cl2N2 Boiling Point 175oC
Molecular Weight 257.163 Flash Point N/A
Transport Information UN 2811 6.1/PG 1 Appearance off-white powder
Safety 22-28-36/37/39-45-60-61-28A Risk Codes 24/25-26-36/37/38-48/25-50/53
Molecular Structure Molecular Structure of 1910-42-5 (Paraquat dichloride) Hazard Symbols VeryT+,DangerousN
Synonyms

1,1'-Dimethyl-4,4'-bipyridiniumdichloride (6CI,7CI);1,1'-Dimethyl-4,4'-dipyridinium dichloride;AH 501;AH 501 (herbicide);Cekuquat;Cyclone Max;Dimethylviologen chloride;Galokson;Gramixel;Gramoxone;Gramoxone D;Gramoxone Max;Gramoxone S;N,N'-Dimethyl-4,4'-bipyridinium dichloride;OK 622;4,4'-Bipyridinium,1,1'-dimethyl-, chloride (1:2);

Article Data 36

Paraquat dichloride Synthetic route

1983-60-4

methyl vilogen diiodide

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
With silver(I) chloride In water95%
With Amberlite IRA-400
553-26-4

4,4'-bipyridine

79-11-8

chloroacetic acid

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 24h;94%
at 140℃; for 4h;2.43 g
553-26-4

4,4'-bipyridine

74-88-4

methyl iodide

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
In acetonitrile at 60℃; for 12h;92.3%
553-26-4

4,4'-bipyridine

77-78-1

dimethyl sulfate

1910-42-5

paraquat dichloride

553-26-4

4,4'-bipyridine

74-87-3

methylene chloride

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
In water at 130℃; for 8h;
at 20℃; for 1h;
26985-31-9

methyl viologen cation radical

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
With ruthenium(III) In water Rate constant;
With water; titanium(IV) oxide; isopropyl alcohol Equilibrium constant; Irradiation;
1910-42-5, 79028-21-0

methyl viologen radical cation chloride

98-95-3

nitrobenzene

A

98-95-3, 12169-65-2

nitrobenzene radical anion

B

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
With isopropyl alcohol In water at 23℃; Equilibrium constant; Mechanism; Rate constant; Irradiation; pulse radiolytic study, effect of pH;
45709-30-6

4-cyano-1-methylpyridinium chloride

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
With sodium hydrogencarbonate; titanium(IV) oxide In ethanol Irradiation;

cucurbit[7]uril methylviologen dichloride 1:1 inclusion complex

A

1910-42-5

paraquat dichloride

B

259886-50-5

cucurbituril

Conditions
ConditionsYield
With Tris buffer; sodium chloride In water at 25℃; pH=7.2; Equilibrium constant; Further Variations:; Reagents;
553-26-4

4,4'-bipyridine

1910-42-5

paraquat dichloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / dimethylformamide / 1.) in an ice bath, 1 h, 2.) RT, 24 h
2: Amberlite IRA-400
View Scheme

Paraquat dichloride Chemical Properties

The Molecular Structure of Methyl viologen (CAS NO.1910-42-5):

Empirical Formula: C12H14Cl2N2
Molecular Weight: 257.159 
IUPAC Name: 1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium dichloride 
Appearance: off-white powder
Nominal Mass: 256 Da
Average Mass: 257.159 Da
Monoisotopic Mass: 256.053404 Da 
log P (octanol-water): -2.710 (none) EST
Water Solubility: 7.00E+05 mg/L at 20°C
Atmospheric OH Rate Constant: 2.12E-11 cm3/molecule-sec at 25°C  
Storage temp: 0-6°C
Water Solubility: soluble
Stability: Stable. Incompatible with strong oxidizing agents
InChI
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
Smiles
c1(c2cc[n+](C)cc2)cc[n+](C)cc1.[ClH-].[ClH-] 
Synonyms:  Dimethyldipyridyl chloride ; Efoxon ; Dextrone x(r) ; 'lgc' (1622) ; Gramoxone ; Gramoxone(r) ; Herbaxon ; Arial gramoxone(r) 
Product Categories: HERBICIDE;Functional Materials;Photochromic Compounds;Pyridinium Compounds;Viologens (Photochromic, Related Compounds);PA - PENPesticides&Metabolites;500 Series Drinking Water Methods;Alpha sort;EPA;Herbicides;Method 549Pesticides&Metabolites;N-PAlphabetic;P;Quaternary amonium salts

Paraquat dichloride History

 Methyl viologen (CAS NO.1910-42-5) was first produced for commercial purposes in 1961 by Syngenta,and is today among the most commonly used herbicides. The European Union allowed paraquat in 2004. Sweden, supported by Austria, Denmark, and Finland, brought the European Union commission to court. On 11 July 2007 the court annulled the directive authorising Paraquat as an active plant protection substance.

Paraquat dichloride Uses

 Methyl viologen (CAS NO.1910-42-5) is  used as a quaternary ammonium herbicide, it is one of the most widely used herbicides in the world. Methyl viologen (CAS NO.1910-42-5) is also often used in science to catalyze the formation of reactive oxygen species (ROS). Methyl viologen (CAS NO.1910-42-5) will under go redox cycling in vivo, being reduced by an electron donor such NADPH, before being oxidized by an electron receptor such as dioxygen to produce superoxide, a major ROS.

Paraquat dichloride Production

 Methyl viologen (CAS NO.1910-42-5) is coupled with sodium in anhydrous ammonia to give 4,4'-bipyridine, which is then methylated with chloromethane to give the desired compound PARAQUAT:

Paraquat dichloride Toxicity Data With Reference

1.    

mmo-omi 20 ppm

    MUREAV    Mutation Research. 138 (1984),39.
2.    

orl-rat LD50:150 mg/kg

    FMCHA2    Farm Chemicals Handbook .(Meister Publishing,Willoughy, OH.: )1983,C118.
3.    

orl-man LDLo:171 mg/kg:PUL,GIT

    JTCTDW    Journal of Toxicology, Clinical Toxicology. 26 (1988),35.
4.    

orl-man LDLo:1690 mg/kg:PUL,GIT

    JTCTDW    Journal of Toxicology, Clinical Toxicology. 26 (1988),35.
5.    

orl-man LDLo:343 mg/kg :GIT,SYS

    JTCTDW    Journal of Toxicology, Clinical Toxicology. 26 (1988),35.
6.    

orl-rat LD50: 100 mg/kg

    IYKEDH    Iyakuhin Kenkyu. Study of Medical Supplies. 10 (1979),520.
7.    

ipr-rat LD50:14,800 µg/kg

    VHTODE    Veterinary and Human Toxicology. 22 (1980),395.
8.    

orl-mus LD50:120 mg/kg

    GEPHDP    General Pharmacology. 14 (1983),541.
9.    

orl-gpg LD50:40 mg/kg

    GEPHDP    General Pharmacology. 14 (1983),541.

Paraquat dichloride Consensus Reports

EPA Genetic Toxicology Program.

Paraquat dichloride Safety Profile

Poison by ingestion and intraperitoneal routes. Mutation data reported. Human systemic effects: changes in structure or function of esophagus, diarrhea, edema, fibrosis of lung, fibrosis, focal (pneumoconiosis), hemorrhage, jaundice, renal damage, renal function tests depressed, respiratory depression, ulceration or bleeding from stomach, vomiting. Death from anoxia may result. When heated to decomposition it emits toxic fumes of NOx. See also PARAQUAT DICHLORIDE. Pure paraquat ingested is highly toxic to mammals and humans potentially leading to acute respiratory distress syndrome (ARDS), and there are no specific antidotes. Even a single swig, immediately spat out, can cause death from fibrous tissue developing in the lungs leading to asphyxiation.
Hazard Codes: VeryT+DangerousN
Risk Statements: 24/25-26-36/37/38-48/25-50/53 
R24/25: Toxic in contact with skin and if swallowed 
R26: Very toxic by inhalation
R36/37/38: Irritating to eyes, respiratory system and skin
R48/25: Toxic: danger of serious damage to health by prolonged exposure if swallowed 
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 22-28-36/37/39-45-60-61-28A 
S22: Do not breathe dust
S28: After contact with skin, wash immediately with plenty of soap-suds
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
S28: After contact with skin, wash immediately with plenty of soap-suds
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
RTECS: DW2275000
HazardClass: 6.1(a)
PackingGroup: II

Paraquat dichloride Standards and Recommendations

OSHA PEL: Respirable Dust: TWA 0.1 mg/m3 (skin)
ACGIH TLV: TWA 0.1 mg/m3

Paraquat dichloride Analytical Methods

For occupational chemical analysis use NIOSH: Paraquat 5003.

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