2702-72-9

Basic information

• Product Name: Sodium 2,4-dichlorophenoxyacetate
• Synonyms: 2,4-dichlorophenoxyaceticacidsodium;2,4-d-sodium;Aceticacid,(2,4-dichlorophenoxy)-,sodiumsalt;Agrion;diconirt;diconirtd;dikonirt;dikonirtd
• CAS NO: 2702-72-9
• Molecular Formula: C₈H₅Cl₂O₃*Na
• Molecular Weight: 243.02
• EINECS: 220-290-4
• Product Categories: Pharmaceutical Raw Materials;Auxins;Biochemistry;Plant Growth Regulators
• Mol File: 2702-72-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 215°C
• Boiling Point: 345.6 °C at 760 mmHg
• Flash Point: 162.8 °C
• Appearance: clear brown to black liquid
• Vapor Pressure: 2.31E-05mmHg at 25°C
• Solubility: H2O: soluble
• Water Solubility: Soluble
• CAS DataBase Reference: Sodium 2,4-dichlorophenoxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium 2,4-dichlorophenoxyacetate(2702-72-9)
• EPA Substance Registry System: Sodium 2,4-dichlorophenoxyacetate(2702-72-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-41-43-51/53
• Safety Statements: 24/25-26-36/37/39-46-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: AG8925000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2702-72-9(Hazardous Substances Data)

Usage

Description

Sodium 2,4-dichlorophenoxyacetate, also known as 2,4-Dichlorophenoxy Acetic Acid Sodium Salt, is a chemical compound with a clear brown to black liquid appearance and a characteristic phenoxy odor. It is a salt form of 2,4-Dichlorophenoxyacetic Acid (D435680) and is classified as a herbicide. It is a crystalline solid that decomposes at 215°C and is slightly soluble in water. Its primary hazard is the threat to the environment, as it can easily penetrate the soil and contaminate groundwater and nearby waterways.

Uses

Used in Agriculture:
Sodium 2,4-dichlorophenoxyacetate is used as a herbicide for controlling the growth of unwanted plants in agricultural fields. It is particularly effective in controlling broadleaf weeds and some grassy weeds.
Used in Rubber Industry:
In the rubber industry, Sodium 2,4-dichlorophenoxyacetate is used to increase the latex output of old rubber trees. By applying this chemical, the productivity of mature rubber trees can be enhanced, leading to a higher yield of natural rubber.
Environmental Considerations:
Due to its potential environmental impact, immediate steps should be taken to limit the spread of Sodium 2,4-dichlorophenoxyacetate to the environment. This includes proper handling, storage, and disposal methods to minimize contamination of soil and water sources.

Air & Water Reactions

Completely soluble in water.

Reactivity Profile

Sodium 2,4-dichlorophenoxyacetate is incompatible with strong oxidizers.

Hazard

Irritant by inhalation.

Fire Hazard

Flash point data for Sodium 2,4-dichlorophenoxyacetate are not available. Sodium 2,4-dichlorophenoxyacetate is probably combustible.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by skin contact. An experimental teratogen. Human systemic effects by inhalation: anorexia, gastrointestinal, and liver changes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland Na2O.

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

Synthetic route

2-(2,4-dichlorophenoxy)ethanol (120-67-2) → 2,6-dichlorophenoxyacetic acid (575-90-6) + sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
With sodium hydroxide; oxygen; bismuth(III) nitrate; palladium on activated charcoal at 90℃; for 1.5h; Title compound not separated from byproducts;	A n/a B 95%

2,4-dichlorophenoxyacetic acid ammonium salt (2307-55-3) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
With sodium hydroxide

sodium monochloroacetic acid (3926-62-3) + sodium 2,4-dichlorophenolate (3757-76-4) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
at 80℃; Temperature;

chloroacetic acid (79-11-8) + 2,4-dichlorophenol (120-83-2) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
Stage #1: 2,4-dichlorophenol With sodium hydroxide In water at 80℃; for 1h; Large scale; Stage #2: chloroacetic acid With sodium hydroxide In water at 70 - 110℃; for 6h; Reagent/catalyst; Temperature; Large scale;

phenol (108-95-2) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / benzene / 0.5 h / 110 °C 2: sulfuryl dichloride; titanium tetrachloride; 3,4-dichlorothiophene / 0.5 h / 70 °C 3: sodium hydroxide / 4 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: calcium hydroxide / toluene / 0.5 h / 80 °C 2: thionyl chloride; lead acetate; 2,3,4-trichlorothiophene / 0.5 h / 20 °C 3: sodium hydrogencarbonate / water / 2 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide / benzene / 0.5 h / 110 °C 2: sulfuryl dichloride / 0.5 h / 100 °C 3: sodium carbonate / water / 4 h / 60 °C View Scheme

n-decyl phenoxyacetate → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; lead acetate; 2,3,4-trichlorothiophene / 0.5 h / 20 °C 2: sodium hydrogencarbonate / water / 2 h / 80 °C View Scheme

2,4-dichlorophenoxyacetic acid n-decyl ester (67821-08-3) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
With sodium hydrogencarbonate In water at 80℃; for 2h;	242.67 g

n-heptyl phenoxyacetate → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuryl dichloride; titanium tetrachloride; 3,4-dichlorothiophene / 0.5 h / 70 °C 2: sodium hydroxide / 4 h / 60 °C View Scheme

n-heptyl 2,4-dichlorophenoxyacetate (1917-96-0) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
With sodium hydroxide at 60℃; for 4h;	241.32 g

2,4-Dichlorophenoxyacetic acid (94-75-7) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
With sodium hydrogencarbonate for 0.5h;

isopropyl 2-phenoxyacetate (49566-35-0) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuryl dichloride / 0.5 h / 100 °C 2: sodium carbonate / water / 4 h / 60 °C View Scheme

Amchem Weed Killer 650 (94-11-1) → sodium 2,4-dichlorophenoxyacetate (2702-72-9)

Conditions	Yield
With sodium carbonate In water at 60℃; for 4h;	241.94 g

sodium 2,4-dichlorophenoxyacetate (2702-72-9) → 2,4-Dichlorophenoxyacetic acid (94-75-7)

Conditions	Yield
With hydrogenchloride In water	98.3%
With hydrogenchloride In water at 0 - 150℃; pH=1 - 2; Reagent/catalyst; Temperature; Large scale;	221 kg

chlormequat chloride (999-81-5) + sodium 2,4-dichlorophenoxyacetate (2702-72-9) → 2-chloroethyltrimethylammonium 2-(2,4-dichlorophenoxy)acetate (1432795-72-6)

Conditions	Yield
In water at 20℃; for 3h;	95%

sodium 2,4-dichlorophenoxyacetate (2702-72-9) + bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9) → benzene (57357-22-9)

Conditions	Yield
In acetonitrile for 24h; Ambient temperature;	62%

sodium 2,4-dichlorophenoxyacetate (2702-72-9) + 5-bromosalicyclaldehyde (1761-61-1) → 6-Bromo-3-(2,4-dichloro-phenoxy)-chromen-2-one

Conditions	Yield
With acetic anhydride Heating;	24.8%

Chloromethyl-(3-chloro-phenyl)-carbamic acid 2-chloro-ethyl ester (39073-65-9) + sodium 2,4-dichlorophenoxyacetate (2702-72-9) → (2,4-Dichloro-phenoxy)-acetic acid [(2-chloro-ethoxycarbonyl)-(3-chloro-phenyl)-amino]-methyl ester (50887-91-7)

Conditions	Yield
In acetonitrile Heating;

sodium 2,4-dichlorophenoxyacetate (2702-72-9) → 2,4-dichlorophenoxymethyl 2,4-dichlorophenoxyacetate (83143-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / acetonitrile / 24 h / Ambient temperature 2: 40 percent / I2 / CH2Cl2 / 6 h / Heating View Scheme

Upstream product

• 120-67-2 2-(2,4-dichlorophenoxy)ethanol 
• 49566-35-0 isopropyl 2-phenoxyacetate 
• 94-11-1 Amchem Weed Killer 650 
• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 1917-96-0 n-heptyl 2,4-dichlorophenoxyacetate 
• 79239-83-1 n-heptyl phenoxyacetate 
• 67821-08-3 2,4-dichlorophenoxyacetic acid n-decyl ester 
• 108-95-2 phenol 
• 79-11-8 chloroacetic acid 
• 120-83-2 2,4-dichlorophenol 
• 3926-62-3 sodium monochloroacetic acid 
• 3757-76-4 sodium 2,4-dichlorophenolate 
• 2307-55-3 2,4-dichlorophenoxyacetic acid ammonium salt 

Downstream Products

• 94-75-7 2,4-Dichlorophenoxyacetic acid 
• 1432795-72-6 2-chloroethyltrimethylammonium 2-(2,4-dichlorophenoxy)acetate 
• 83143-98-0 2,4-dichlorophenoxymethyl 2,4-dichlorophenoxyacetate 
• 57357-22-9 benzene 
• 50887-91-7 (2,4-Dichloro-phenoxy)-acetic acid [(2-chloro-ethoxycarbonyl)-(3-chloro-phenyl)-amino]-methyl ester 

Relevant articles and documents

Synthesis, characterization, biological screenings and molecular docking study of Organotin(IV) derivatives of 2,4-dichlorophenoxyacetic acid

New tri- and diorganotin (IV) derivatives of 2,4-dichlorophenoxyacetic acid with general formula: R3SnL and R2SnL2: {Me3SnL (1), Bu3SnL (2), Me2SnL2 (3), Bu2SnL2 (4) and Oct2SnL2 (5), L = 2,4-dichlorophenoxyacetate} have been synthesized and characterized in solid state by elemental and FT-IR analysis, whereas in solution state by 1H and 13C NMR spectroscopy. Compound 1 was also characterized by single crystal X-ray crystallography. The FT-IR data of compounds 1–5 confirm the bidentate binding mode of ligand with penta and hexa-coordinated arrangements around the Sn(IV) centre in solid state. The value of C–Sn–C angle for complexes 1 and 3 calculated from NMR (1H and 13C) data using Lockart's equation were 114.7° and 114.9°, respectively which falls in the range of 5-coordinated geometry. The DNA binding of synthesized compounds were studied via UV–Vis spectroscopy and viscometry resulting in an intercalative mode of interaction. Molecular docking analysis of the studied compounds also supports the results of the UV–vis and viscometry. Moreover, interaction of the synthesized compounds with a cationic surfactant i.e., cetyltrimethyl ammonium bromide (CTAB) has been studied by conductometric method. Enzyme inhibition activity against α-amylase and α-glucosidase was carried out and compound 3 was found to possess maximum inhibition (88.1% and 91.3%, respectively). The theoretical study also enforce the experimental data for enzyme inhibition of the compound 3 (docking score = ?12.4096) by forming seven hydrogen bonds and two pi-H linkages with the Glu 276, Ala 278, Phe 300, Arg 312, Tyr 313, Asp 349, Asn 412, Phe 430 and Arg 439 residues of the binding pocket of the α-glucosidase. The potency of the compound 3 might be due to the presence of the strong electron withdrawing chloro group. IC50 value of the brine shrimp activity revealed that triorganotin (IV) derivatives (1 and 2) were more toxic than their diorganotin (IV) analogues. Moreover, compound 2 has the MIC values of 12.5 μg/mL and 6.25 μg/mL against S. Aureus and M. Leuteus bacterial strains, respectively.

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 and production system for 2,4-dichlorophenoxyacetic acid

The invention provides a preparation method for 2,4-dichlorophenoxyacetic acid. The preparation method comprises the following steps: a) reacting 2,4-dichlorophenol with an alkali to obtain 2,4-dichlorophenolate and reacting haloacetic acid with an alkali so as to obtain haloacetate; B) reacting the 2,4-dichlorophenolate with the haloacetate so as to obtain 2,4-dichlorophenoxyacetate; and C) mixing the 2,4-dichlorophenoxyacetate with acid and carrying out crystallization in a tubular crystallizer so as to obtain 2,4-dichlorophenoxyacetic acid. According to the invention, the 2,4-dichlorophenolate and the haloacetate are separately prepared at first and then subjected to a reaction so as to produce the 2,4-dichlorophenoxyacetate; then the 2,4-dichlorophenoxyacetate is mixed with acid; and finally, crystallization in the tubular crystallizer is carried out. With such a specific continuous crystallization manner, the prepared 2,4-dichlorophenoxyacetic acid is large in particle size and high in purity and yield; and dust is not produced during drying and usage, so environment friendliness is achieved.