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94-82-6

Basic Information
CAS No.: 94-82-6
Name: 2,4-Dichlorophenoxybutyric acid
Article Data: 17
Molecular Structure:
Molecular Structure of 94-82-6 (2,4-Dichlorophenoxybutyric acid)
Formula: C10H10Cl2O3
Molecular Weight: 249.094
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;
EINECS: 202-366-9
Density: 1.373 g/cm3
Melting Point: 118-120 °C(lit.)
Boiling Point: 410.363 °C at 760 mmHg
Flash Point: 201.98 °C
Solubility: 53mg/L(room temperature)
Appearance: Colorless crystals
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 22-51/53
Safety: 25-29-46-61
Transport Information: UN 3077 9/PG 3
PSA: 46.53000
LogP: 3.23700
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;
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    Molecular Formula C10H10Cl2O3 Molecular Weight 249.09 CAS Registry Number 94-82-6 EINECS 202-366-9 Name2,4-Dichlorophe…

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    CAS Number: 94-82-6 Molecular Formula: C10H10Cl2O3 Molecular Weight: 249.09 EINECS: 202-366-9 Melting Point: 118-120 oC

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Chemistry

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

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.

Consensus Reports

EPA Genetic Toxicology Program.

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.

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.