2008-39-1

Basic information

• Product Name: N-Methylmethanamine 2,4-dichlorophenoxyacetate
• Synonyms: Dimethylammonium 2,4-dichlorophenoxyacetate;2,4-D DIMETHYLAMINE SALT;(2,4-DICHLOROPHENOXY)ACETIC ACID, DIMETHYLAMINE SALT;n-methylmethanamine 2,4-dichlorophenoxyacetate;WEEDICIDE AMINE(R);(2,4’dichlorophenoxy)-aceticacicompd.withn-methylmethanamine(1:1);(2,4-dichlorophenoxy)-aceticacicmpdwithdimethylamine(1:1)[qr];(2,4-dichlorophenoxy)-aceticacicmpdwithn-methylmethanamine(1:1)[qr]
• CAS NO: 2008-39-1
• Molecular Formula: C₂H₇N*C₈H₆Cl₂O₃
• Molecular Weight: 266.12
• EINECS: 217-915-8
• Product Categories: HERBICIDE;DA - DHPesticides&Metabolites;Alphabetic;D;Herbicides;Phenoxy structure
• Mol File: 2008-39-1.mol

Chemical Properties

• Melting Point: 85-87 °C
• Boiling Point: 345.6 °C at 760 mmHg
• Flash Point: 162.8 °C
• Appearance: Brown liquid
• Density: 1.4140 (rough estimate)
• Vapor Pressure: 2.31E-05mmHg at 25°C
• Refractive Index: 1.6140 (estimate)
• CAS DataBase Reference: N-Methylmethanamine 2,4-dichlorophenoxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylmethanamine 2,4-dichlorophenoxyacetate(2008-39-1)
• EPA Substance Registry System: N-Methylmethanamine 2,4-dichlorophenoxyacetate(2008-39-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53-43-41
• Safety Statements: 24/25-26-36/37/39-46-61
• RIDADR: 3345
• RTECS: AG8400000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2008-39-1(Hazardous Substances Data)

Usage

Air & Water Reactions

Water soluble.

Reactivity Profile

N-Methylmethanamine 2,4-dichlorophenoxyacetate neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

N-Methylmethanamine 2,4-dichlorophenoxyacetate is combustible.

InChI:InChI=1/C8H6Cl2O3.C2H7N/c9-5-1-2-7(6(10)3-5)13-4-8(11)12;1-3-2/h1-3H,4H2,(H,11,12);3H,1-2H3

Synthetic route

2,4-Dichlorophenoxyacetic acid (94-75-7) + dimethyl amine (124-40-3) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
Stage #1: 2,4-Dichlorophenoxyacetic acid With ethylenediaminetetraacetic acid In tert-butyl methyl ether Stage #2: dimethyl amine In tert-butyl methyl ether at 56℃; pH=8; Product distribution / selectivity;	100%
In water at 20℃; pH=7.1;
In water at 20℃;

methyl 2,4-dichlorophenoxyacetate (1928-38-7) + dimethyl amine (124-40-3) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
at 130℃;	98.88%
at 110℃; for 4h; Large scale;	3177.2 g

2-(N,N-dimethylamino)ethanol (108-01-0) + 2,4-Dichlorophenoxyacetic acid (94-75-7) + dimethyl amine (124-40-3) → 2,4-dichlorophenoxyacetic acid dimethylethanolamine (1004765-16-5) + 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
In water at 20℃;
In water at 20℃;

2,4-Dichlorophenoxyacetic acid (94-75-7) + dimethyl amine (124-40-3) + methylamine (74-89-5) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1) + 2,4-dichlorophenoxyacetic acid methylamine salt (51173-63-8)

Conditions	Yield
In water

phenol (108-95-2) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydrogencarbonate / toluene / 0.5 h / 90 °C 2: chlorine; titanium(IV) oxide; 2-ethylthiazole / 0.5 h / 50 °C 3: 3 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene / 0.5 h / 90 °C / Large scale 2: sulfuryl dichloride / 40 °C / Large scale 3: 4 h / 110 °C / Large scale View Scheme

n-pentyl phenoxyacetate (74525-52-3) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine; titanium(IV) oxide; 2-ethylthiazole / 0.5 h / 50 °C 2: 3 h / 100 °C View Scheme

n-pentyl 2,4-dichlorophenoxyacetate (1917-92-6) + dimethyl amine (124-40-3) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
at 100℃; for 3h;	319.87 g

methyl 2-phenoxyacetate (2065-23-8) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuryl dichloride / 40 °C / Large scale 2: 4 h / 110 °C / Large scale View Scheme

n-propyl phenoxyacetate (6212-47-1) → 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride; chlorine; phenyl mesityl sulfide / 0.5 h / -20 °C 2: 130 °C View Scheme

methanol (67-56-1) + 2,4-Dichlorophenoxyacetic acid (94-75-7) + 2,4-dichlorophenoxyacetic acid dimethylamine (2008-39-1) + (BF3)-MeOH complex → methyl 2,4-dichlorophenoxyacetate (1928-38-7)

Conditions	Yield
Stage #1: 2,4-dichlorophenoxyacetic acid dimethylamine In sodium hydroxide at 80℃; for 0.333333h; pH=14; Hydrolysis; Stage #2: methanol; 2,4-Dichlorophenoxyacetic acid; (BF3)-MeOH complex In diethyl ether pH=2; Esterification; Heating;	99.2%

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 124-40-3 dimethyl amine 
• 74-89-5 methylamine 
• 108-95-2 phenol 
• 74525-52-3 n-pentyl phenoxyacetate 
• 1917-92-6 n-pentyl 2,4-dichlorophenoxyacetate 
• 1928-38-7 methyl 2,4-dichlorophenoxyacetate 
• 2065-23-8 methyl 2-phenoxyacetate 
• 6212-47-1 n-propyl phenoxyacetate 

Downstream Products

• 1928-38-7 methyl 2,4-dichlorophenoxyacetate 

Relevant articles and documents

Preparation method of 2,4-dichlorophenoxyacetic acid and salt thereof

The invention provides a preparation method of 2,4-dichlorophenoxyacetic acid and a salt thereof, wherein the preparation method includes the following steps: S1) carrying out a reaction of phenol andchloracetic ester under alkaline conditions to obtain phenoxyacetic ester; S2) carrying out selective chlorination reaction of the phenoxyacetic ester with a chlorinating agent under the action of acatalyst A and a catalyst B to obtain 2,4-dichlorophenoxyacetic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thioethers, thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S3) carrying out hydrolysis reaction of 2,4-dichlorophenoxyacetic ester under acidic conditions to obtain 2,4-dichlorophenoxyacetic acid; or after 2,4-dichlorophenoxyaceticester is obtained, carrying out an alkaline hydrolysis reaction with an alkaline compound to obtain 2,4-dichlorophenoxyacetate. The production and use of 2,4-dichlorophenol with unpleasant odor are avoided, the production of dioxins is eliminated, the yield of products is improved, and the output of three wastes is greatly reduced.

Preparation method of phenoxycarboxylate herbicide

The invention provides a preparation method of a phenoxycarboxylate herbicide, wherein the preparation method includes the steps: S1, carrying out condensation reaction of phenol or o-cresol with chlorocarboxylic ester under the action of alkaline substances to obtain phenoxycarboxylic ester, wherein chlorocarboxylic ester has the general formula of ClR1COOR, R1 is C1-3 alkylene or alkylidene, R is C1-10 alkyl of or C3-10 cycloalkyl; and S2, under the action of a first catalyst and a second catalyst, carrying out selective chlorination of the phenoxycarboxylic ester with a chlorinating agent to obtain the chlorophenoxycarboxylic ester represented by the formula I, R3 is H, Cl or CH3, the first catalyst is selected from Lewis acid, and the second catalyst is selected from C5-22 thioether, thiazole, isothiazole or thiophene compounds; and S3, mixing chlorophenoxycarboxylic ester with an alkaline compound, and carrying out alkaline hydrolysis to obtain the phenoxycarboxylate herbicide. The preparation method can improve the product quality and production operation environment, and has low quantity of three wastes.

Preparation method of chlorophenoxycarboxamide salt

The invention provides a preparation method of chlorophenoxycarboxamide salt, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B has the following structural formula of R1'-S-R2'; and S2) carrying out ammonolysis reaction of chlorophenoxycarboxylic ester and amine to obtain chlorophenoxycarboxamide salt. By redesigning of the process route and fine screening of the catalysts and the chlorinating agent, the method reduces energy consumption, improves chlorination selectivity and avoids loss of effective components.The yield of the obtained chlorophenoxycarboxamide salt can reach 98.5% or more. At the same time, the production of high-salt wastewater is completely eradicated, the dust hazard caused by drying and use of chlorophenoxycarboxylic acid is avoided, energy is saved and equipment investment is reduced.

AQUEOUS HERBICIDAL CONCENTRATES

Aqueous based pesticide compositions having a high concentration of a water-soluble salt of a herbicide and a water-insoluble pesticide are provided herein. These compositions are, among other things, transparent, homogeneous, stable upon storage in various thermal environments, and upon dilution in water form a stable emulsion.

PROCESS FOR PREPARATION OF HERBICIDAL SALTS

A process for the preparation of solid amine salts of aromatic substituted carboxylic acid herbicides by reaction of the aromatic substituted carboxylic acid herbicide with an amine comprising reacting the aromatic substituted carboxylic acid herbicide in an ether solvent with an amine to form the amine salt and collecting the amine salt of the aromatic substituted carboxylic acid herbicide as a precipitate from the ether solvent reaction mixture wherein the ether is a dialiphatic ether comprising at least one primary aliphatic group.

AUXIN HERBICIDE COMPOSITION

An aqueous liquid herbicide composition comprising a solution of at least one of 2,4-D and dicamba in the form of the monomethylamine salt and at least one of 2,4-D and dicamba in the form of the dimethylamine salt wherein the molar ratio of monomethylamine to dimethylamine is in the range of from 1:20 to 4:6.

HIGH-STRENGTH, HERBICIDAL COMPOSITIONS OF GLYPHOSATE AND 2,4-D SALTS

The mixture of certain amine salts of glyphosate and 2,4-D allows the preparation of high-strength liquid compositions containing up to greater than 450 gae/L of total active ingredient loading if the pH is adjusted to 6.0 to 8.0. Compositions are particularly well-suited for application to crops that are resistant or tolerant to both glyphosate and 2,4-D.

High-strength, low-temperature stable herbicidal formulations of 2,4-dichlorophenoxy acetic acid salts

This invention relates to a high-strength herbicidal formulation containing high concentrations of 2,4-D salt mixtures. The 2,4-D salt mixtures can include the DMA salt and the DMEA and/or the DEEA salt of 2,4-D. Selected combinations of the 2,4-D salt mixtures exhibit significantly greater low temperature stability at high concentrations.

High-strength, low-temperature stable herbicidal formulations of 2,4-Dichlorophenoxy acetic acid salts

This invention relates to a high-strength herbicidal formulation containing high concentrations of 2,4-D salt mixtures. The 2,4-D salt mixtures can include the DMA salt and the DMEA and/or the DEEA salt of 2,4-D. Selected combinations of the 2,4-D salt mixtures exhibit significantly greater low temperature stability at high concentrations.

Dialkylammonium-2,4-dichlorophenoxyacetates as plant growth regulators and the method of making same

Various dialkylammonium-2,4-dichlorophenoxyacetates having the formula STR1 wherein R1 and R 2 are radicals each selected from the group consisting of methyl and ethyl, are useful as plant growth regulators. Mono-substituted alkylamines are not suitable for processing into compounds of this invention. The compounds of the invention exhibit excellent water solubility characteristics and possess an exceptionally high and unexpected degree of effectiveness as a general weed killer on lawns, pasture lands, ponds, lakes, canals, ditches, etc. Methods of using and preparing these compounds are disclosed.