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2,4-Dichlorophenoxybutyric acid
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Name

2,4-Dichlorophenoxybutyric acid

 EINECS 202-366-9
CAS No. 94-82-6 Density 1.373 g/cm3
PSA 46.53000 LogP 3.23700
Solubility 53mg/L(room temperature) Melting Point 118-120 °C(lit.)
Formula C10H10Cl2O3 Boiling Point 410.363 °C at 760 mmHg
Molecular Weight 249.094 Flash Point 201.98 °C
Transport Information UN 3077 9/PG 3 Appearance Colorless crystals
Safety 25-29-46-61 Risk Codes 22-51/53
Molecular Structure Molecular Structure of 94-82-6 (2,4-Dichlorophenoxybutyric acid) Hazard Symbols HarmfulXn,DangerousN
Synonyms

Butyricacid, 4-(2,4-dichlorophenoxy)- (8CI);2,4-DB;2,4-DM;4-(2,4-Dichlorophenoxy)butanoic acid;4-(2,4-Dichlorophenoxy)butyric acid;Buratal;Butyrac;Butyrac 118;Legumex;Legumex D;NSC 70337;Sys 67 Buratal;g-(2,4-Dichlorophenoxy)butyric acid;

Article Data 17

2,4-Dichlorophenoxybutyric acid Synthetic route

96-48-0

4-butanolide

3757-76-4

sodium 2,4-dichlorophenolate

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
at 200℃;
With butan-1-ol at 160℃;
63867-25-4

4-(2,4-dichlorophenoxy)butanenitrile

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
With sulfuric acid; acetic acid
With potassium hydroxide
6954-78-5

1-(3-bromopropoxy)-2,4-dichlorobenzene

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aqueous H2SO4; acetic acid
View Scheme
78483-28-0

(3-chloro-propyl)-(2,4-dichloro-phenyl)-ether

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol
2: aq.-ethanolic KOH
View Scheme
3757-76-4

sodium 2,4-dichlorophenolate

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol
2: ethanol
3: aq.-ethanolic KOH
View Scheme
120-83-2

2,4-dichlorophenol

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
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
42609-41-6

ethyl 4-(2,4-dichlorophenoxy)butanoate

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
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
1927-71-5

4-phenoxybutan-1-ol

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
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

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

Conditions
ConditionsYield
With platinum on activated charcoal In water at 80 - 85℃; under 8250.83 Torr; Reagent/catalyst; Pressure; Temperature;249.85 g
2969-81-5

4-bromoethylbutanoate

120-83-2

2,4-dichlorophenol

94-82-6

4-(2,4-dichlorophenoxy)butyric acid

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

2,4-Dichlorophenoxybutyric acid Chemical Properties

Molecular Structure of 4-(2,4-Dichlorophenoxy)butyric acid (94-82-6):

EINECS: 202-366-9
IUPAC Name: 4-(2,4-Dichlorophenoxy)butanoic acid 
Molecular Formula: C10H10Cl2O3
Molecular Weight: 249.090600 g/mol
XLogP3: 3.5
H-Bond Donor: 1
H-Bond Acceptor: 3
Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)OCCCC(=O)O
InChI: InChI=1S/C10H10Cl2O3/c11-7-3-4-9(8(12)6-7)15-5-1-2-10(13)14/h3-4,6H,1-2,5H2,(H,13,14)
InChIKey: YIVXMZJTEQBPQO-UHFFFAOYSA-N
Index of Refraction: 1.554
Molar Refractivity: 58.18 cm3
Molar Volume: 181.4 cm3
Surface Tension: 47.6 dyne/cm
Density: 1.372 g/cm3
Flash Point: 202 °C
Melting Point: 118-120 °C(lit.)
Boiling Point: 410.4 °C at 760 mmHg
Enthalpy of Vaporization: 69.87 kJ/mol
Vapour Pressure: 1.8E-07 mmHg at 25 °C
Water Solubility: 57.46 mg/L at 25 °C
Storage Temp.: 0-6 °C
BRN: 1976809

2,4-Dichlorophenoxybutyric acid Toxicity Data With Reference

1.    

dnr-esc 5 mg/disc

     NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB80-133226 .
2.    

dnr-bcs 5 mg/disc

     NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB80-133226 .
3.    

orl-rat LD50:700 mg/kg

     RREVAH    Residue Reviews. 10 (1965),97.
4.    

skn-rat LD50:800 mg/kg

     WRPCA2    World Review of Pest Control. 9 (1970),119.

2,4-Dichlorophenoxybutyric acid Consensus Reports

EPA Genetic Toxicology Program.

2,4-Dichlorophenoxybutyric acid Safety Profile

Safety Information of 4-(2,4-Dichlorophenoxy)butyric acid (94-82-6):
Hazard Codes: Xn ,N
Risk Statements: 22-51/53
22: Harmful if swallowed
51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 25-29-46-61
25: Avoid contact with eyes
29: Do not empty into drains
46: If swallowed, seek medical advice immediately and show this container or label
61: Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: ES9100000
HazardClass: 6.1(b)
PackingGroup: III
Moderately toxic by ingestion and skin contact. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. An herbicide. When heated to decomposition it emits toxic fumes of Cl−.

2,4-Dichlorophenoxybutyric acid Specification

  4-(2,4-Dichlorophenoxy)butyric acid (94-82-6) is colorless crystals, known as  2,4-D butyric acid ; 2,4-DB ; 2,4-DM ; 4-(2,4-Dichlorophenoxy)butanoic acid ; 4-(2,4-Dichlorophenoxy)butyric acid ; 4-06-00-00927 (Beilstein Handbook Reference) ; Buratal ; Butirex ; Butormone ; Butoxon ; Butoxone ; Butoxone amine ; Butoxone ester ; Butyrac ; Butyrac 118 ; Butyrac 200 ; Butyrac ester ; CCRIS 1021 ; Caswell No. 316 ; EPA Pesticide Chemical Code 030801 ; HSDB 6603 ; Kyselina 4-(2,4-dichlorfenoxy)maselna ; Kyselina 4-(2,4-dichlorfenoxy)maselna [Czech] ; Legumex D ; NSC 70337 ; Sys 67 Buratal ; gamma-(2,4-Dichlorophenoxy)butyric acid ; 2,4-(Dichlorophenoxy)butyric acid ; Butanoic acid, 4-(2,4-dichlorophenoxy)- ; Butanoic acid, 4-(2,4-dichlorophenoxy)- (9CI) ; Butyric acid, 4-(2,4-dichlorophenoxy)- . 4-(2,4-Dichlorophenoxy)butyric acid (94-82-6) is a selective systemic phenoxy herbicide used to control many annual and perennial broadleaf weeds in alfalfa, peanuts, soybeans, and other crops. It is classified in toxicity class III.

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