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2-Methyl-4-chlorophenoxyacetic acid

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2-Methyl-4-chlorophenoxyacetic acid Basic information

Product Name:
2-Methyl-4-chlorophenoxyacetic acid
Synonyms:
  • (4-CHLORO-O-TOLYOXY)ACETICACID
  • 4-CHLORO-2-METHYLCHLOROPHENOXYACETICACID
  • 2-Methyl-4-chlorphenoxyessigsure
  • Atlas MCPA
  • banleneplus
  • banvelm
  • basagran-m
  • BH MCPA
CAS:
94-74-6
MF:
C9H9ClO3
MW:
200.62
EINECS:
202-360-6
Product Categories:
  • Stain Blocker
  • HERBICIDE
  • Building Blocks
  • C9
  • Carbonyl Compounds
  • Carboxylic Acids
  • Agro-Products
  • Aromatics
  • Isotope Labelled Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • OLED
Mol File:
94-74-6.mol
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2-Methyl-4-chlorophenoxyacetic acid Chemical Properties

Melting point:
114-118 °C(lit.)
Boiling point:
288.02°C (rough estimate)
Density 
1.2799 (rough estimate)
refractive index 
1.5230 (estimate)
Flash point:
2 °C
storage temp. 
APPROX 4°C
solubility 
water: insoluble(lit.)
pka
3.14±0.10(Predicted)
form 
Solid
Water Solubility 
1.174g/L(25 ºC)
Merck 
14,5764
BRN 
2051752
CAS DataBase Reference
94-74-6(CAS DataBase Reference)
NIST Chemistry Reference
[(4-Chloro-o-tolyl)oxy]acetic acid(94-74-6)
EPA Substance Registry System
MCPA (94-74-6)
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Safety Information

Hazard Codes 
Xn,F,N
Risk Statements 
22-38-41-36-20/21/22-11-50/53
Safety Statements 
26-37-39-36-16-61-60-36/37
RIDADR 
UN 2765
WGK Germany 
2
RTECS 
AG1575000
HS Code 
29189900
Hazardous Substances Data
94-74-6(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 700 mg/kg (Rowe, Hymas)

MSDS

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2-Methyl-4-chlorophenoxyacetic acid Usage And Synthesis

Chemical Properties

White, crystalline solid. Free acid insoluble in water but sodium and amine salts are soluble.

Chemical Properties

MCPA is a colorless crystalline solid

Uses

Systemic postemergence herbicide used to control annual and perennial weeds in cereals, rice, flax, vines, peas, potatoes, asparagus, grassland and turf.

Uses

Labelled MCPA (C369470). Herbicide.

Definition

ChEBI: A chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2.

General Description

Colorless plates. Corrosive. Practically insoluble in water. Used as an herbicide.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Methyl-4-chlorophenoxyacetic acid is a chlorinated benzoic acid derivative. Reacts as a weak acid to neutralize bases, both organic (for example, the amines) and inorganic. May corrode iron, steel, and aluminum parts and containers if moist. Reacts with cyanide salts in the presence of moisture to generate gaseous hydrogen cyanide. May react if moist with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A variety of products is possible. Like other acids, may initiate polymerization reactions or catalyze other reactions. is a chlorinated carboxylic acid herbicide. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 2-Methyl-4-chlorophenoxyacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Agricultural Uses

Herbicide: A U.S. EPA restricted Use Pesticide (RUP) as MCPA, sodium salt. MCPA is a systemic post-emergence phenoxy herbicide used to control broadleaf annual and perennial weeds (including thistle and dock) in cereals, flax, rice, vines, peas, potatoes, grasslands, forestry applications, and on rights-of-way. It is very compatible with many other compounds and may be used in formulation with many other products, including bentazone, bromoxynil, 2,4-D, dicamba, fenoxaprop, MCPB, mecoprop, thifensulfuron, and tribenuron.

Trade name

ACME MCPA AMINE 4®; AGRITOX®; AGROXONE®; AGROZONE®; AGSCO®; ANICON KOMBI®; ANICON M®; BANLENE®; BLESEL MC®; BORDERMASTER®; BROMINAL M & PLUS®; CAMBILENE®; CHEYENNE®; CHIMAC OXY®; CHIPTOX®; CHWASTOX®; CORNOX M®; DAKOTA®; DED WEED®; DICOPUR-M®; DICOTEX®; DOW MCP AMINE WEED KILLER®; DYVEL®; EH1356 HERBICIDE®; EMCEPAN®; EMPAL®; ENVOY®; HEDAPUR M 52®; HEDAREX M®; HEDONAL M®; HERBICIDE M®; HORMOTUHO®; HORNOTUHO®; KILSEM®; 4 K-2 M®; KVK®; LEGUMEX DB®; LEUNA M®; LEYSPRAY®; LINORMONE®; M 40®; 2 M-4C®; 2 M-4KH®; MALERBANE®; MAYCLENE®; MEPHANAC®; MIDOX®; MXL®; OKULTIN®; PHENOXYLENE 50®; PHENOXYLENE PLUS®; PHENOXYLENE SUPER®; RAZOL DOCK KILLER®; RHOMENE®; RHONOX®; SHAMOX®; B-SELEKTONON M®; SEPPIC MMD®; TILLER®; TRIMEC®; U 46®; VACATE®; VESAKONTUHO®; WEEDAR®; WEEDAR MCPA CONCENTRATE®; WEEDONE MCPA ESTER®; WEED RHAP®; ZELAN®

Safety Profile

Suspected carcinogen. Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion. Human systemic effects by ingestion: blood pressure decrease and coma. Experimental teratogenic and reproductive effects. Mutation data reported. An herbicide. When heated to decomposition it emits toxic fumes of Cl-.

Potential Exposure

A potential danger to those involved in the manufacture, formulation, and application of this postemergence herbicide, used for control of broadleaf weeds in agricultural applications.

Environmental Fate

Biological. Cell-free extracts isolated from Pseudomonas sp. in a basal salt medium degraded MCPA to 4-chloro-o-cresol and glyoxylic acid (Gamar and Gaunt, 1971).
Soil. Residual activity in soil is limited to approximately 3–4 months (Hartley and Kidd, 1987).
Plant. The penetration, translocation and metabolism of radiolabeled MCPA in a cornland weed (Galium aparine) was studied by Leafe (1962). Carbon dioxide was identified as a metabolite but this could only account 7% of the applied MCPA. Though no
Photolytic. When MCPA in dilute aqueous solution was exposed to summer sunlight or an indoor photoreactor (l >290 nm), 2-methyl-4-chlorophenol formed as the major product as well as o-cresol and 4-chloro-2-formylphenol (Soderquist and Crosby, 1975). Clapés et al. (1986) studied the photodecomposition of aqueous solution of MCPA (120 ppm, pH 5.4, 25°C) in a photoreactor equipped with a high pressure mercury lamp. After three minutes of irradiation, 4-chloro-2-methylphenol formed as an intermediate which degraded to 2-methylphenol. Both compounds were not detected after 6 minutes of irradiation; however, 1,4-dihydroxy-2-methylbenzene and 2-methyl-2,5-cyclohexadiene-1,4- dione formed as major and minor photodecomposition products, respectively. The same experiment was conducted using simulated sunlight (l <300 nm) in the presence of riboflavin, a known photosensitizer. 4-Chloro-2-methylphenol and 4-chloro-2-methylbenzyl formate formed as major and minor photoproducts, respectively (Clapés et al., 1986). Ozone degraded MCPA in dilute aqueous solution with and without UV light (l >300 nm) (Benoit-Guyod et al., 1986).
Chemical/Physical. Reacts with alkalies forming water soluble salts (Hartley and Kidd, 1987). Ozonolysis of MCPA in the dark yielded the following benzenoid intermediates: 4-chloro-2-methylphenol, its formate ester, 5-chlorosalicyaldehyde, 5-chlo

Shipping

UN3345 Phenoxyacetic acid derivative pesticide, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Purification Methods

It is insoluble in H2O (solubility is 0.55g/L at 20o) and recrystallises from *C6H6 or chlorobenzene as plates [J.nsson et al. Acta Chem Scand 6 993 1952]. The S-benzylisothiouronium salt has m 164-165o, and the Cu2+ salt has m 247-249o(dec) [Armarego et al. Nature 183 1176 1959, UV: Duvaux & Grabe Acta Chem Scand 4 806 1950, IR: J.berg Acta Chem Scand 4 798 1950]. [Beilstein 6 IV 1991.] It is a plant growth substance and a herbicide.

Incompatibilities

A weak acid. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Incompatible with alkalis.

Waste Disposal

Incineration with added flammable solvent; incinerator equipped with fume scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office

2-Methyl-4-chlorophenoxyacetic acid Preparation Products And Raw materials

Raw materials

2-Methyl-4-chlorophenoxyacetic acidSupplier

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