94-82-6

Basic information

• Product Name: 2,4-Dichlorophenoxybutyric acid
• Synonyms: 2,4-D Butyric;2,4-D butyric acid;2,4-dbutyricacid;2,4-DM;4-(2,4-dichlorophenoxy)-butyricaci;buratal;butanoicacid,4-(2,4-dichlorophenoxy)-;Butirex
• CAS NO: 94-82-6
• Molecular Formula: C₁₀H₁₀Cl₂O₃
• Molecular Weight: 249.09
• EINECS: 202-366-9
• Product Categories: Pharmaceutical Raw Materials;Organic acids
• Mol File: 94-82-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 118-120 °C(lit.)
• Boiling Point: 410.363 °C at 760 mmHg
• Flash Point: 201.98 °C
• Appearance: Off-white/Amorphous Powder
• Density: 1.3342 (estimate)
• Vapor Pressure: 8.07E-06mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: 0-6°C
• PKA: 4.56±0.10(Predicted)
• Water Solubility: 53mg/L(room temperature)
• Merck: 13,2855
• BRN: 1976809
• CAS DataBase Reference: 2,4-Dichlorophenoxybutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichlorophenoxybutyric acid(94-82-6)
• EPA Substance Registry System: 2,4-Dichlorophenoxybutyric acid(94-82-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 25-29-46-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: ES9100000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 94-82-6(Hazardous Substances Data)

Usage

Chemical Properties

White to light-brown crystalline solid. May be shipped as a concentrate to be mixed with water and used as a spray. Slight phenolic odor.

Uses

4-(2,4-Dichlorophenoxy)butanoic Acid is a herbicide.

Definition

ChEBI: A monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a 2,4-dichlorophenoxy group. A selective post-emergence herbicide.

General Description

Colorless crystals. Slightly corrosive to iron. A chlorinated phenoxy herbicide. Soluble in organic solvents.

Reactivity Profile

2,4-Dichlorophenoxybutyric acid is an organic acid. Neutralizes bases in exothermic reactions. Forms water soluble metal and amine salts. Hard water precipitates the calcium and magnesium salts from aqueous solutions of such salts.

Potential Exposure

2,4-DB is a chlorophenoxy/arylox- yalkanoic acid selective systemic herbicide used to control annual and perennial broadleaf weeds in many field crops such as alfalfa, peanuts, cereals and soybeans; used as a defoliant. In the plant, the compound changes to 2,4-D and inhibits growth at the tips of stems and roots.

Incompatibilities

2,4-DB is a weak organic acid. Keep away from oxidizers, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides, and epichlorohydrin. Corrosive to iron, aluminum, zinc, and possibly other metals, especially in the presence of moisture.

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guid- ance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office

InChI:InChI=1/C10H10Cl2O3/c1-2-8(10(13)14)15-9-4-3-6(11)5-7(9)12/h3-5,8H,2H2,1H3,(H,13,14)

Synthetic route

4-butanolide (96-48-0) + sodium 2,4-dichlorophenolate (3757-76-4) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
at 200℃;
With butan-1-ol at 160℃;

4-(2,4-dichlorophenoxy)butanenitrile (63867-25-4) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
With sulfuric acid; acetic acid
With potassium hydroxide

1-(3-bromopropoxy)-2,4-dichlorobenzene (6954-78-5) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous H2SO4; acetic acid View Scheme

(3-chloro-propyl)-(2,4-dichloro-phenyl)-ether (78483-28-0) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol 2: aq.-ethanolic KOH View Scheme

sodium 2,4-dichlorophenolate (3757-76-4) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol 2: ethanol 3: aq.-ethanolic KOH View Scheme

2,4-dichlorophenol (120-83-2) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate; potassium iodide / acetone / 0.5 h / 20 °C 1.2: 15 h / Reflux 2.1: sodium hydroxide / ethanol; water / 3 h / Reflux 2.2: 20 °C / pH 1 View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide 2: sodium hydroxide View Scheme

ethyl 4-(2,4-dichlorophenoxy)butanoate (42609-41-6) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Stage #1: ethyl 4-(2,4-dichlorophenoxy)butanoate With sodium hydroxide In ethanol; water for 3h; Reflux; Stage #2: With hydrogenchloride In ethanol; water at 20℃; pH=1;
With sodium hydroxide

4-phenoxybutan-1-ol (1927-71-5) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride; 3,4-dichlorothiophene; chlorine / 0.5 h / 0 °C 2: platinum on activated charcoal / water / 80 - 85 °C / 8250.83 Torr View Scheme

2,4-dichlorophenoxybutanol → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
With platinum on activated charcoal In water at 80 - 85℃; under 8250.83 Torr; Reagent/catalyst; Pressure; Temperature;	249.85 g

4-bromoethylbutanoate (2969-81-5) + 2,4-dichlorophenol (120-83-2) → 4-(2,4-dichlorophenoxy)butyric acid (94-82-6)

Conditions	Yield
Stage #1: Ethyl 4-bromobutyrate; 2,4-dichlorophenol With potassium carbonate Williamson Ether Synthesis; Reflux; Stage #2: With water In tetrahydrofuran; methanol Alkaline conditions;

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + (2R,3R,4S,5S)-4-Amino-5-hydroxymethyl-2-{6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-tetrahydro-furan-3-ol (676558-83-1) → 3'-[4-(2,4-dichlorophenyloxy)butanamido]-3'-deoxy-N6-(1-naphthylmethyl)adenosine

Conditions	Yield
Multistep reaction;	95%

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + 4-amino-1-(3,3-diphenylpropyl)piperidine (163268-13-1) → 4-(2,4-Dichloro-phenoxy)-N-[1-(3,3-diphenyl-propyl)-piperidin-4-yl]-butyramide

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide for 19h;	81%

1,3-dimethylbarbituric acid (769-42-6) + 4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → C16H16Cl2N2O5

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	70%

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + 3-aminoadamantan-1-ol (702-82-9) → 4-(2,4-dichloro-phenoxy)-N-((1R,3S,5R,7S)-3-hydroxy-adamantan-1-yl)-butyramide

Conditions	Yield
Stage #1: 4-(2,4-dichlorophenoxy)butyric acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 3-aminoadamantan-1-ol With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 16h;	62%

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + camptothecin (7689-03-4) → 4-(2,4-dichloro-phenoxy)-butyric acid 4-ethyl-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-4-yl ester

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	47.3%

trans-(+-)-N,N'-dimethylcyclohexane-1,2-amine + 4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + 1,1'-carbonyldiimidazole (530-62-1) → trans-(+/-)-4-(2,4-dichlorophenoxy)-N-methyl-N-[2-(methylamino)cyclohexyl]butanamide monohydrochloride

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; diethyl ether	17%

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → 4-(2,4-dichloro-phenoxy)-butyryl chloride (31770-28-2)

Conditions	Yield
With thionyl chloride
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.25h;
With thionyl chloride In N,N-dimethyl-formamide Reflux;

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → 4-(2,4-dichloro-phenoxy)-butyric acid amide (51992-35-9)

Conditions	Yield
With thionyl chloride; benzene Eintragen des Reaktionsgemisches in wss. NH3;

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + N-chloromethyl-carbamic acid 2-chlorophenyl ester (64381-36-8) → 4-(2,4-Dichloro-phenoxy)-butyric acid (2-chloro-phenoxycarbonylamino)-methyl ester (64381-15-3)

Conditions	Yield
With triethylamine

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + Chloromethyl-carbamic acid 2,4-dichloro-phenyl ester (64381-41-5) → 4-(2,4-Dichloro-phenoxy)-butyric acid (2,4-dichloro-phenoxycarbonylamino)-methyl ester (64381-20-0)

Conditions	Yield
With triethylamine

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + Chloromethyl-carbamic acid 2,6-dichloro-phenyl ester (64381-42-6) → 4-(2,4-Dichloro-phenoxy)-butyric acid (2,6-dichloro-phenoxycarbonylamino)-methyl ester (64381-29-9)

Conditions	Yield
With triethylamine

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + Chloromethyl-carbamic acid 3,5-dimethyl-4-methylsulfanyl-phenyl ester (64381-44-8) → 4-(2,4-Dichloro-phenoxy)-butyric acid (3,5-dimethyl-4-methylsulfanyl-phenoxycarbonylamino)-methyl ester (64381-34-6)

Conditions	Yield
With triethylamine

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + (+/-)-cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine (67198-34-9, 67198-53-2, 67347-43-7, 99239-39-1, 116301-06-5, 121843-49-0, 121843-50-3, 121843-51-4, 142434-12-6) → 4-(2,4-Dichloro-phenoxy)-N-methyl-N-((1S,2R)-2-pyrrolidin-1-yl-cyclohexyl)-butyramide (99239-57-3, 99239-71-1, 130553-68-3)

Conditions	Yield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → 4-(2,4-Dichloro-phenoxy)-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + 2-<(1S,2S(?))-6,6-dimethyl-norpinan-2-yl>-ethanol → 4-(2,4-dichloro-phenoxy)-butyric acid-{2-[(1S,2S)-6,6-dimethyl-norpinan-2-yl]-ethyl ester} (5423-01-8)

Conditions	Yield
With sulfuric acid; xylene Entfernen des entstehenden Wassers;

(E)-(RS)-3-[1-(allyloxyimino)butyl]4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-enecarboxylic acid + decaethylene glycol (5579-66-8) + 4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → C46H71Cl2NO17

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → 4-(2,4-Dichlorophenoxy)butyric acid ethoxycarbonyl-ethylsulfanylcarbonyloxy-methyl ester

oxalyl dichloride (79-37-8) + 5-(3,3-dichloro-allyloxy)-N-hydroxy-2-methoxy-benzamidine (796119-00-1) + 4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → 3-[5-(3,3-dichloro-allyloxy)-2-methoxy-phenyl]-5-[3-(2,4-dichloro-phenoxy)-propyl]-[1,2,4]oxadiazole

Conditions	Yield
In pyridine; dichloromethane; water; N,N-dimethyl-formamide

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + cobalt(II) nitrate → cobalt(II) γ-(2,4-dichlorophenoxy)butyrate hydrate

Conditions	Yield
With NaOH In water addn. of an aq. NaOH soln. to the ligand, stirring until getting a neutral or weakly acidic reaction, filtration, addn. of the filtrate to a soln. of Co(NO3)2 in water, keeping the resultant pptn. under the mother liquor for 24 h; filtration under suction, washing with water, drying in air, elem. anal.;

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) → cobalt(II) γ-(2,4-dichlorophenoxy)butyrate

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / water 2: neat (no solvent) View Scheme

4-(2,4-dichlorophenoxy)butyric acid (94-82-6) + C8H9N2O3PolS → C18H17Cl2N2O5PolS

Conditions	Yield
Stage #1: C8H9N2O3PolS With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h; polystyrene resin; Stage #2: 4-(2,4-dichlorophenoxy)butyric acid With diisopropyl-carbodiimide In dichloromethane at 20℃; polystyrene resin;

Upstream product

• 96-48-0 4-butanolide 
• 3757-76-4 sodium 2,4-dichlorophenolate 
• 63867-25-4 4-(2,4-dichlorophenoxy)butanenitrile 
• 6954-78-5 1-bromo-3-(2,4-dichlorophenoxy)propane 
• 78483-28-0 (3-chloro-propyl)-(2,4-dichloro-phenyl)-ether 
• 120-83-2 2,4-dichlorophenol 
• 42609-41-6 ethyl 4-(2,4-dichlorophenoxy)butanoate 
• 1927-71-5 4-phenoxybutan-1-ol 
• 2969-81-5 Ethyl 4-bromobutyrate 

Downstream Products

• 31770-28-2 4-(2,4-dichloro-phenoxy)-butyryl chloride 
• 51992-35-9 4-(2,4-dichloro-phenoxy)-butyric acid amide 
• 5423-01-8 4-(2,4-dichloro-phenoxy)-butyric acid-{2-[(1S,2S)-6,6-dimethyl-norpinan-2-yl]-ethyl ester} 
• 99239-57-3 4-(2,4-Dichloro-phenoxy)-N-methyl-N-((1S,2R)-2-pyrrolidin-1-yl-cyclohexyl)-butyramide 
• 64381-29-9 4-(2,4-Dichloro-phenoxy)-butyric acid (2,6-dichloro-phenoxycarbonylamino)-methyl ester 
• 64381-20-0 4-(2,4-Dichloro-phenoxy)-butyric acid (2,4-dichloro-phenoxycarbonylamino)-methyl ester 
• 64381-15-3 4-(2,4-Dichloro-phenoxy)-butyric acid (2-chloro-phenoxycarbonylamino)-methyl ester 

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Combination of herbicides and safeners

A herbicidally active composition comprises a mixture of A. a herbicidally effective amount of one or more compounds of the formula (I), ?and B. an antidote-effective amount of one or more compounds of the formulae (II) to (IV),