Conditions | Yield |
---|---|
With hydrogenchloride; para-dodecylbenzenesulfonic acid In water at 160℃; for 1h; Temperature; Reagent/catalyst; | 99.6% |
With toluene-4-sulfonic acid In water at 106℃; for 3h; | 99.9% |
With hydrogenchloride; water for 3h; Reflux; | 98.3% |
Conditions | Yield |
---|---|
With (phthalocyaninato)iron(II); chlorine; acetic acid In water at 75℃; for 0.5h; Concentration; Time; | 99.8% |
With dihydrogen peroxide; chlorine In benzene at 100℃; for 1h; | 99% |
With iron(III) chloride; dimethylsulfide; chlorine In chloroform at 70℃; for 5h; Reagent/catalyst; Solvent; Temperature; | 99.4% |
Conditions | Yield |
---|---|
Stage #1: bromoacetic acid With water; potassium hydroxide at 110℃; for 2h; Green chemistry; Stage #2: 2,4-dichlorophenol With water; sodium hydroxide at 100 - 130℃; for 4.5h; Green chemistry; Stage #3: With sulfuric acid at 140℃; under 3000.3 Torr; for 2h; Green chemistry; | 99.8% |
Conditions | Yield |
---|---|
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry; | 99.7% |
With hydrogenchloride; sodium chlorate; acetic acid |
Conditions | Yield |
---|---|
Stage #1: chloroacetic acid With sodium hydroxide In water for 1h; Stage #2: 2,4-dichlorophenol With potassium hydroxide In water for 1h; Stage #3: With tetrabutylammomium bromide; potassium bromide In water at 130℃; for 2h; Reagent/catalyst; Temperature; | 99.6% |
Stage #1: chloroacetic acid With water; sodium carbonate at 100℃; for 1h; Green chemistry; Stage #2: 2,4-dichlorophenol With water; potassium hydroxide at 90 - 100℃; for 6h; Green chemistry; Stage #3: With hydrogenchloride In water at 150℃; under 4500.45 Torr; for 2h; Reagent/catalyst; Temperature; Green chemistry; | 99.7% |
With sodium hydroxide Irradiation; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide at 100℃; for 2h; | 99.5% |
With water; sodium hydroxide for 0.5h; Reflux; | 99.5% |
With water; sodium hydroxide for 0.5h; Reflux; | 99.6% |
methyl 2,4-dichlorophenoxyacetate
A
2,4-Dichlorophenoxyacetic acid
B
methylene chloride
Conditions | Yield |
---|---|
With hydrogenchloride; zinc(II) chloride In water at 140℃; for 4h; Reagent/catalyst; Temperature; | A 99.6% B 98.1% |
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Reagent/catalyst; Reflux; | 99.5% |
With sulfuric acid for 3h; Reflux; | 99.3% |
With hydrogenchloride In water for 6h; Reagent/catalyst; Reflux; | 222 g |
Conditions | Yield |
---|---|
With water; sodium hydroxide Reflux; | 99.5% |
With sulfuric acid at 90℃; for 2h; Large scale; | 2202.1 g |
With hydrogenchloride In water at 60℃; for 4h; Large scale; | 2200.7 g |
With hydrogenchloride; water at 60℃; for 4h; Large scale; | 2196.3 g |
With hydrogenchloride In water at 60℃; for 4h; | 219.49 g |
Conditions | Yield |
---|---|
With water; sodium hydroxide for 0.5h; Reflux; | 99.3% |
With toluene-4-sulfonic acid In water; butan-1-ol at 120℃; for 2h; | 99.3% |
Stage #1: Fernesta With sodium hydroxide at 100℃; for 23h; Stage #2: With sulfuric acid | 2200 kg |
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Reflux; | 99.3% |
With sulfuric acid for 3h; Reflux; | 221 g |
potassium salt of 2,4-dichlorophenol
bromoacetic acid
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
Stage #1: bromoacetic acid With D-sorbitol; sulfuric acid In toluene for 8h; Stage #2: potassium salt of 2,4-dichlorophenol for 4h; Stage #3: With tetrabutyl phosphonium bromide; acetic acid In water for 6h; Reflux; | 99.3% |
Conditions | Yield |
---|---|
Stage #1: chloroacetic acid With sodium ethanolate In ethanol Stage #2: phenol With sodium carbonate In ethanol; water at 110℃; Stage #3: With aluminum (III) chloride; sulfuryl dichloride In ethanol; water at 30 - 100℃; for 10h; Reagent/catalyst; Solvent; Temperature; | 99.2% |
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 |
Conditions | Yield |
---|---|
Stage #1: 2-Phenoxyethanol With dihydrogen peroxide; sodium hydroxide; manganese(ll) chloride In water at 160℃; for 12h; Stage #2: With chlorine; dimethylphenylsulfide; magnesium chloride pH=Ca. 10; Temperature; Reagent/catalyst; | 96.2% |
Stage #1: 2-Phenoxyethanol With silica gel; ozone In water at 120℃; for 12h; Stage #2: With sulfuryl dichloride; formamide In water at 80℃; Reagent/catalyst; | 217.4 g |
Multi-step reaction with 2 steps 1: aluminum oxide; chlorine / 0.5 h / -20 °C 2: oxygen / water / 90 - 130 °C / 5250.53 Torr View Scheme |
sodium monochloroacetic acid
sodium 2,4-dichlorophenolate
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
at 130℃; for 5h; | 90% |
Stage #1: sodium monochloroacetic acid; sodium 2,4-dichlorophenolate at 130℃; for 5h; Stage #2: With hydrogenchloride In water at 10℃; for 1h; | 204 g |
Stage #1: sodium monochloroacetic acid; sodium 2,4-dichlorophenolate at 150℃; for 5h; Stage #2: With hydrogenchloride In water at 10℃; for 1h; Temperature; Reagent/catalyst; Solvent; | 221 g |
sodium monochloroacetic acid
2,4-dichlorophenol
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 1h; Reflux; | 81.6% |
benzene
A
2,4-Dichlorophenoxyacetic acid
B
iodobenzene
C
2,4-dichlorophenyl 2,4-dichlorophenoxyacetate
D
2,4-dichlorophenoxymethyl 2,4-dichlorophenoxyacetate
Conditions | Yield |
---|---|
at 200℃; for 0.05h; Heating; | A 15% B 71% C 15% D 64% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium chlorate; acetic acid |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With sodium hydroxide |
sodium 2,4-dichlorophenolate
ethyl bromoacetate
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
With ethanol Erwaermen des Reaktionsgemisches mit wss. NaOH; |
DL-1-(2,4-Dichlor-phenoxy)-3-<2-(3,4-dimethoxyphenyl)-ethylamino>propan-2-ol
A
2,4-Dichlorophenoxyacetic acid
B
1-Amino-3-(2,4-dichloro-phenoxy)-propan-2-ol
C
3-(2,4-dichloro-phenoxy)-propane-1,2-diol
D
2-(3,4-dimethoxyphenyl)-ethylamine
E
4-{2-[3-(2,4-Dichloro-phenoxy)-2-hydroxy-propylamino]-ethyl}-2-methoxy-phenol
F
2,4-dichlorophenol
Conditions | Yield |
---|---|
biotransformation; |
sodium 2,4-dichlorophenolate
chloroacetic acid
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
In ethyl acetate |
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
With aq. buffer at 25℃; pH=7; Kinetics; Further Variations:; pH-values; Temperatures; Hydrolysis; |
iodine
acetic acid
2-phenoxyacetic acid
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
at 20 - 60℃; |
Conditions | Yield |
---|---|
at 20 - 60℃; |
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
With sodium hypochlorite; water |
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
With sodium hypochlorite; water |
Conditions | Yield |
---|---|
With thionyl chloride at 100℃; for 5h; Substitution; | 100% |
With thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride In chloroform for 4h; Chlorination; Heating; | 85% |
With thionyl chloride at 75℃; for 2h; | 80% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 100% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 86.4% |
2,4-Dichlorophenoxyacetic acid
dimethyl amine
2,4-dichlorophenoxyacetic acid dimethylamine
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℃; |
2,4-Dichlorophenoxyacetic acid
2-nitrophenylmethyl bromide
2,4-D 2-nitrobenzyl ester
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 73℃; | 100% |
methanol
2,4-Dichlorophenoxyacetic acid
2,4-dichlorophenoxyacetic acid dimethylamine
methyl 2,4-dichlorophenoxyacetate
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% |
Conditions | Yield |
---|---|
With aminosulfonic acid for 12h; Reflux; | 99% |
With tert.-butylnitrite at 40℃; for 48h; Green chemistry; | 90% |
With sulfuric acid at 70℃; | 86% |
With toluene-4-sulfonic acid Abdestillieren des entstehenden Wassers; |
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 99% |
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide | 99% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 30.6% |
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 99% |
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 99% |
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
Stage #1: 2,4-Dichlorophenoxyacetic acid With sodium hydroxide In water at 50℃; Stage #2: 1-n-hexadecylpyridinium halide In water at 20℃; for 0.5h; | 99% |
2,4-Dichlorophenoxyacetic acid
Conditions | Yield |
---|---|
Stage #1: 2,4-Dichlorophenoxyacetic acid With sodium hydroxide In water at 50℃; Stage #2: n-hexadecyltrimethylammonium halide In water at 20℃; for 0.5h; | 99% |
2,4-Dichlorophenoxyacetic acid
1-n-butyl-1-methylpyrrolidinium (2,4-dichlorophenoxy)acetate
Conditions | Yield |
---|---|
Stage #1: 1-n-butyl-1-methylpyrrolidinium halide With Dowex-Monosphere 550A (OH) anion exchange resin Stage #2: 2,4-Dichlorophenoxyacetic acid for 0.166667h; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With NaOH In water 2,4-dichlorophenoxyacetic acid dissolved in H2O with addition of solid NaOH with heating to about 60°C (equimolar amt. of NaOH and acid);pH was brought to 7 (NaOH); filtered; aq. soln. of Pb(NO3)2 added with vigorously stirring (metal:acid=1:2); ppt. filtered off after 24 h; dried (air) at room temp.; crushed in mortar; elem. anal.; | 98.5% |
1-hydroxy-pyrrolidine-2,5-dione
2,4-Dichlorophenoxyacetic acid
(2,4-Dichloro-phenoxy)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In ethyl acetate | 98% |
With dicyclohexyl-carbodiimide | |
With dicyclohexyl-carbodiimide In 1,4-dioxane for 0.5h; |
2,4-Dichlorophenoxyacetic acid
1-n-propoxymethyl-1-methylpiperidinium (2,4-dichlorophenoxy)acetate
Conditions | Yield |
---|---|
Stage #1: 1-n-propoxymethyl-1-methylpiperidinium halide With Dowex-Monosphere 550A (OH) anion exchange resin Stage #2: 2,4-Dichlorophenoxyacetic acid for 0.166667h; | 98% |
2,4-Dichlorophenoxyacetic acid
4-n-butyl-4-methylmorpholinium (2,4-dichlorophenoxy)acetate
Conditions | Yield |
---|---|
Stage #1: 4-n-butyl-4-methylmorpholinium halide With Dowex-Monosphere 550A (OH) anion exchange resin Stage #2: 2,4-Dichlorophenoxyacetic acid for 0.166667h; | 98% |
IUPAC Name: 2-(2,4-Dichlorophenoxy)acetic acid
Molecular Formula: C8H6Cl2O3
Molecular Weight: 221.04g/mol
EINECS: 202-361-1
Melting Point: 137-141 ºC
Freely Rotating Bonds: 3
Polar Surface Area: 35.53 Å2
Index of Refraction: 1.572
Molar Refractivity: 48.91 cm3
Molar Volume: 148.4 cm3
Polarizability: 19.39 ×10-24cm3
Surface Tension: 51.2 dyne/cm
Density: 1.488 g/cm3
Flash Point: 162.8 °C
Enthalpy of Vaporization: 62.24 kJ/mol
Boiling Point: 345.6 °C at 760 mmHg
Vapour Pressure: 2.31E-05 mmHg at 25°C
The Cas Register Number of 2,4-D Acid is 94-75-7 .The chemical synonyms of 2,4-D Acid (CAS No. 94-75-7) are Rarechem al bo 0361 ; Verton(r) ; Weedar(r) ; (2,4-Dichloor-fenoxy)-azijnzuur ; (2,4-Dichlorophenoxy)-aceticaci ; (2,4-Dichlorophenyloxy)acetic acid ; (2,4-Dichlorphenoxy)acetic acid ; (2,4-Dichlor-phenoxy)-essigsaeure .Product categories of 2,4-D Acid (CAS No. 94-75-7) are Pharmaceutical raw materials ; Acetics acid and esters ; Organic acids ; Plant growth regulator ; Analytical chemistry ; Auxins ; Biochemistry ; Chlorinated compounds (environmental endocrine disruptors) ; Environmental endocrine disruptors ; Plant growth regulators ; Aromatics ; Da - dhmethod specific ; Pesticidespesticides&Metabolites ; Alphabetic ; D ; Endocrine disruptors (draft)Method specific ; EPA ; Herbicides ; Oeko-tex standard 100 ; Phenoxy structure .The molecular structure of 2,4-D Acid (CAS No. 94-75-7) is.
1. | ratLD50:1500mg/kg | World Review of Pest Control. Vol. 9, Pg. 119, 1970. | ||
2. | ratLD50:375mg/kg | Farm Chemicals Handbook. Vol. -, Pg. C174, 1991. | ||
3. | rabbitLDLo:800mg/kg | Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 12, Pg. 26, 1951. | ||
4. | mouseLD50:347mg/kg | Roczniki Panstwowego Zakladu Higieny. Vol. 31, Pg. 373, 1980. |
Hazard Codes: Xn Xi T F
Risk Statements: 22-37-41-43-52/53-39/23/24/25-23/24/25-36/37/38-11
R22: Harmful if swallowed.
R37: Irritating to respiratory system
R41: Risk of serious damage to the eyes.
R43: May cause sensitization by skin contact.
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R11: Highly flammable.
Safety Statements: 24/25-26-36/37/39-46-61-2-45-36/37-27-16
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S46: If swallowed, seek medical advice immediately and show this container or label.
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
S2: Keep out of the reach of children.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37: Wear suitable protective clothing and gloves.
S27: Take off immediately all contaminated clothing.
S16: Keep away from sources of ignition.
RIDADR: UN 3077 9/PG 3
WGK Germany: 2
RTECS: AG6825000
HazardClass: 6.1
PackingGroup: III
HS Code: 29189090
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