2976-74-1

Basic information

• Product Name: 2,3-DICHLOROPHENOXYACETIC ACID
• Synonyms: 2,3-D;2,3-DICHLOROPHENOXYACETIC ACID;2,3-Dichlorophenoxyacetic acid, 97+%;2,3-d (iso);2,3-d solution;2,3-Dichlorophenoxyacetic acid 98%;2,3-Dichlorophenoxyaceticacid98%;2,3-D solution, 2,3-Dichlorophenoxyacetic acid
• CAS NO: 2976-74-1
• Molecular Formula: C₈H₆Cl₂O₃
• Molecular Weight: 221.04
• EINECS: 221-022-9
• Product Categories: Phenoxyacetic Acids and Alcohols (substituted)
• Mol File: 2976-74-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 172-175 °C
• Boiling Point: 316.96°C (rough estimate)
• Flash Point: 164.5 °C
• Appearance: beige crystalline powder and needles
• Density: 1.4564 (rough estimate)
• Vapor Pressure: 1.9E-05mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: APPROX 4°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.96±0.10(Predicted)
• Water Solubility: 342.6mg/L(25 oC)
• BRN: 1963475
• CAS DataBase Reference: 2,3-DICHLOROPHENOXYACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DICHLOROPHENOXYACETIC ACID(2976-74-1)
• EPA Substance Registry System: 2,3-DICHLOROPHENOXYACETIC ACID(2976-74-1)

Safety Data

• Hazard Codes: Xi,C,T,F
• Statements: 36/37/38-23/24/25
• Safety Statements: 37/39-26-45-36/37/39-16-24/25
• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2976-74-1(Hazardous Substances Data)

Usage

Chemical Properties

BEIGE CRYSTALLINE POWDER AND NEEDLES

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

Synthetic route

2,3-dichlorophenol (576-24-9) + chloroacetic acid ethyl ester (105-39-5) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
Stage #1: 2,3-dichlorophenol; chloroacetic acid ethyl ester With potassium carbonate; potassium iodide In water; N,N-dimethyl-formamide at 100℃; for 0.0666667h; Microwave irradiation; Stage #2: With sodium hydroxide for 0.0833333h; Microwave irradiation;	91%

2,3-dichlorophenol (576-24-9) + chloroacetic acid (79-11-8) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
With sodium hydroxide In water at 110 - 120℃; for 3h;	77%
With sodium hydroxide Alkylation; Heating;
With sodium hydroxide

(2,3-dichloro-phenoxy)-acetic acid amide (67526-49-2) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
With sodium hydroxide

ethyl bromoacetate (105-36-2) + sodium-<2,3-dichloro-phenolate> → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
With ethanol anschliessend Erwaermen mit wss. Natronlauge;

2,3-dichlorophenol (576-24-9) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution; isopropyl alcohol 2: aq. NaOH solution View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / dimethyl sulfoxide 2: sodium hydroxide View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C 1.2: 12 h / 50 °C 2.1: lithium hydroxide / methanol; water / 12 h / 50 °C View Scheme

(dichloro-2,3 phenoxy)acetate d'ethyle (37536-92-8) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
alkaline hydrolysis;
Stage #1: (dichloro-2,3 phenoxy)acetate d'ethyle With sodium hydroxide Stage #2: With hydrogenchloride

2,3-dichlorophenol (576-24-9) + ethyl bromoacetate (105-36-2) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
Stage #1: 2,3-dichlorophenol; ethyl bromoacetate With potassium carbonate In dimethyl sulfoxide at 50℃; for 6h; Stage #2: With water; sodium hydroxide In acetone at 50℃; for 3h; Stage #3: With hydrogenchloride In water at 25℃; pH=1 - 2;

(2,3-dichlorophenoxy)-acetic acid, methyl ester (1928-56-9) → 2,3-dichlorophenoxyacetic acid (2976-74-1)

Conditions	Yield
With lithium hydroxide In methanol; water at 50℃; for 12h;

2,3-dichlorophenoxyacetic acid (2976-74-1) + camptothecin (7689-03-4) → camptothecin-20-O-2,3-dichlorophenoxyacetate (401478-45-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 20h;	86.5%

2,3-dichlorophenoxyacetic acid (2976-74-1) + 4-amino-6-benzyl-3-mercapto-1,2,4-triazine-5(4H)-one (22278-80-4) → 3-Benzyl-7-(2,3-dichloro-phenoxymethyl)-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-4-one

Conditions	Yield
With trichlorophosphate for 5h; Heating;	86%

2,3-dichlorophenoxyacetic acid (2976-74-1) + 4-amino-6-methyl-3-thio-1,2,4-triazin-5-one (22278-81-5) → 7-(2,3-dichloro-phenoxymethyl)-3-methyl-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-4-one

Conditions	Yield
With trichlorophosphate for 5h; Condensation; Cyclization; Heating;	78%

2,3-dichlorophenoxyacetic acid (2976-74-1) + 4-amino-3,4-dihydro-6-phenyl-3-thioxo-1,2,4-triazin-5(2H)-one (22278-82-6) → 7-(2,3-dichloro-phenoxymethyl)-3-phenyl-[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-4-one

Conditions	Yield
With trichlorophosphate for 5h; Condensation; Cyclization; Heating;	73%

2,3-dichlorophenoxyacetic acid (2976-74-1) + 1,3-cylohexanedione (504-02-9) → C14H12Cl2O4

Conditions	Yield
With triethylamine; 2-hydroxy-2-methylpropanenitrile; 1,1'-carbonyldiimidazole In dichloromethane at 25℃; for 12h;	72%

[2,2]bipyridinyl (366-18-7) + iron(III) chloride hexahydrate + 2,3-dichlorophenoxyacetic acid (2976-74-1) + acetonitrile (75-05-8) → bis(2,2'-bipyridine)dichlorobis(2-chloro-4-methyl-phenoxyacetato)oxodiiron(III) - 2,2'-bipyridine - acetonitrile (1/0.25/0.8)

Conditions	Yield
With NaOH In acetonitrile byproducts: NaCl, H2O; stoich., phenoxyalkanoic acid in CH3CN treated with NaOH, stirred for 30min, treated with FeCl3*6H2O in CH3CN and bipy in CH3CN dropwise, stirr ed for 30 min; concd., crystd. for 4 d, elem. anal.;	65%

methanol (67-56-1) + iron(III) chloride hexahydrate + 2,3-dichlorophenoxyacetic acid (2976-74-1) → hexakis(2,3-dichlorophenoxyacetato)tris(methanol)oxotriiron(III) chloride-methanol(1/3)

Conditions	Yield
With NaOH In methanol byproducts: NaCl, H2O; the acid was dissolved in MeOH and neutralized with NaOH, stirring for 30 min, 0.5 equiv. Fe-salt was dropwise added in MeOH; soln. was concd. and left to slowly evaporate for a week, elem. anal.;	30%

cis-N2-(4-amino-cyclohexyl)-N4,N4-dimethyl-quinazolin-2,4-diamine + 2,3-dichlorophenoxyacetic acid (2976-74-1) → 2-(2,3-dichlorophenoxy)-N-(cis-4-{[4-(dimethylamino)quinazolin-2-yl]amino}cyclohexyl)acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide)	27%

2,3-dichlorophenoxyacetic acid (2976-74-1) + 1,2-diamino-benzene (95-54-5) → 2-(2,3-Dichloro-phenoxymethyl)-1H-benzoimidazole (82326-51-0)

Conditions	Yield
With hydrogenchloride Heating;	10%

2-aminopyrimidine (109-12-6) + 2,3-dichlorophenoxyacetic acid (2976-74-1) → (2,3-Dichloro-phenoxy)-acetic acid; compound with pyrimidin-2-ylamine

Conditions	Yield
In ethanol at 110℃; for 0.333333h;

2,3-dichlorophenoxyacetic acid (2976-74-1) + (+/-)-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) → 2-(2,3-Dichloro-phenoxy)-N-methyl-N-((1R,2S)-2-pyrrolidin-1-yl-cyclohexyl)-acetamide (99239-25-5, 99239-72-2, 130553-53-6)

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

2,3-dichlorophenoxyacetic acid (2976-74-1) → (2,3-dichlotophenoxy)acetic acid-4-sulfonic acid

Conditions	Yield
With sulfuric acid In water at 20℃;

2,3-dichlorophenoxyacetic acid (2976-74-1) + ethanolamine (141-43-5) → 2-(2,3-dichlorophenoxy)-N-(2-hydroxyethyl)acetamide (87762-15-0)

Conditions	Yield
With 1,1'-carbonyldiimidazole 1) r.t, THF, 30 min, 2) - 50 deg C, THF; Yield given. Multistep reaction;

2,3-dichlorophenoxyacetic acid (2976-74-1) + Triphenylphosphine oxide (791-28-6) → C18H15OP*C8H6Cl2O3

Conditions	Yield
In ethanol at 110℃; for 0.333333h;

chloral hydrate (302-17-0) + 2,3-dichlorophenoxyacetic acid (2976-74-1) → {5-[1-(3-carboxymethoxy-4,5-dichloro-phenyl)-2,2,2-trichloro-ethyl]-2,3-dichloro-phenoxy}-acetic acid

Conditions	Yield
With sulfuric acid Condensation;

2,3-dichlorophenoxyacetic acid (2976-74-1) → (2,3-dichlorophenoxy)acetyl chloride (85630-84-8)

Conditions	Yield
With thionyl chloride
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
With thionyl chloride for 4h; Reflux;

2,3-dichlorophenoxyacetic acid (2976-74-1) → N-(3-methylcarbamoylphenyl)-2,3-dichlorophenoxyacetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: (COCl)2; DMF / CH2Cl2 / 1 h / 20 °C 2: pyridine / CH2Cl2 / 20 °C View Scheme

2,3-dichlorophenoxyacetic acid (2976-74-1) → geranyl (2,3-dichlorophenoxy)acetate

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: 78 percent / benzene / 0.5 h View Scheme

2,3-dichlorophenoxyacetic acid (2976-74-1) → 3-methyl-2ξ,4E-decadienyl (2,3-dichlorophenoxy)acetate

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: 78 percent / benzene / 0.5 h View Scheme

2,3-dichlorophenoxyacetic acid (2976-74-1) → (3,4-dichlorophenoxy)acetic acid-6-sulfonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / H2O / 20 °C 2: sulfuric acid / H2O / 20 °C View Scheme

2,3-dichlorophenoxyacetic acid (2976-74-1) → 2-<(2,3-dichlorophenyl)amino>ethanol (87762-19-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) N,N'-carbonyldiimidazole / 1) r.t, THF, 30 min, 2) - 50 deg C, THF 2: 1) KH, 18-crown-6, 2) H2O / 1) THF, -20 to 0 deg C, 1 h, 2) THF View Scheme

2,3-dichlorophenoxyacetic acid (2976-74-1) + 2-Fluorobenzoyl chloride (393-52-2) → 4-(2-fluorobenzoyl)-2,3-dichlorophenoxy acetic acid (62967-02-6)

Conditions	Yield
With hydrogenchloride; carbon disulfide; aluminium trichloride In water

copper(II) choride dihydrate + 2,3-dichlorophenoxyacetic acid (2976-74-1) → Cu((2,3-dichlorophenoxy)acetate)2(H2O)2

Conditions	Yield
With CH3ONa In methanol treatment of ligand with NaOMe, then with CuCl2;

[2,2]bipyridinyl (366-18-7) + copper(II) choride dihydrate + 2,3-dichlorophenoxyacetic acid (2976-74-1) → [Cu((2,3-dichlorophenoxy)acetate)(2,2'-bipyridine)2]Cl

Conditions	Yield
With NaOCH3 In methanol elem. anal.;

Upstream product

• 576-24-9 2,3-dichlorophenol 
• 37536-92-8 (dichloro-2,3 phenoxy)acetate d'ethyle 
• 1928-56-9 (2,3-dichlorophenoxy)-acetic acid, methyl ester 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 
• 67526-49-2 (2,3-dichloro-phenoxy)-acetic acid amide 

Downstream Products

• 904702-58-5 O,O-dimethyl α-(2,3-dichlorophenoxyacetoxy)-3-nitrobenzylphosphonate 
• 1258077-56-3 C₂₃H₁₇Cl₂FN₄O₂S 
• 183150-11-0 tetrakis(2,3-dichlorophenoxyacetato)bis(methanol)dicopper(II) 
• 87762-19-4 2-<(2,3-dichlorophenyl)amino>ethanol 
• 85630-84-8 (2,3-dichlorophenoxy)acetyl chloride 

Relevant articles and documents

Eco-friendly microwave synthesis of Mg(II) phenoxy carboxylic acid coordination compounds with specific motifs driven by multiple hydrogen bonding

Four novel Mg(ii) coordination compounds [Mg(CPA)2(H2O)4] 1, [Mg(H2O)6]·(MCPA)22, [Mg(DCPA)(H2O)5]·(DCPA) 3 and [Mg(TCPA)2(H2O)4]·2H2O 4 were designed by the strategy of hydrogen bonding driven self-assembly (HCPA = 2-chlorophenoxyacetic acid, HMCPA = 2-methyl-4-chlorophenoxyacetic acid, HDCPA = 2,3-dichlorophenoxyacetic acid and HTCPA = 2,4,6-trichlorophenoxyacetic acid). Single-crystal X-ray diffraction demonstrated that each coordination compound had its own specific motif driven by multiple hydrogen bonding: rectangle motif (compound 1), butterfly motif (compound 2), head and tail connected double heart-rectangle motif (compound 3) and alternative one side shared hexagon-rectangle motif (compound 4). The hydrogen bonding effects (O-H?Cl and O-H?O) on thermostability of the title compounds were well proved by TG analysis. The antibacterial activity of 1-4 has been explored, and all of them showed antibacterial efficiency against colibacillus at certain concentrations. The number of chlorides in the ligands seemed to affect the efficiency of the complexes while their position had no obvious effect. In addition, all the title compounds were evaluated for plant growth regulation by using the lettuce seedling growth bioassay. The results showed that these kinds of compounds had potential to serve as natural plant growth regulators because of their higher allelopathic activity. This research firstly applied the effective microwave method to synthesize Mg(ii) phenoxy carboxylic acid coordination compounds. The design strategy of hydrogen-bonding-driven self-assembly presented here gave a novel insight into the further structural prediction and biofunction achievement of Mg(ii) supramolecular assemblies.

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Synthesis and biological activity of 1-(Substituted phenoxyacetoxy)- 1-(pyridin-2-yl or thien-2-yl)methylphosphonates

A series of novel O,O-dimethyl 1-(substituted phenoxyacetoxy)-1-(pyridin-2-yl or thien-2-yl)methylphosphonates 6a-n and 7a-d were synthesized. Their structures were confirmed by IR, 1H NMR, mass spectroscopy, and elemental analyses. The results of preliminary bioassays show that some of the title compounds exhibit moderate to good herbicidal and fungicidal activities. For example, the title compounds 6a, 6c, 6l, 6m, and 7d possess 90-100% inhibition against most of the tested plants at the dosage of 1500 g ai/ha, whereas the title compounds 6b, 6g-h and 6n possess 92-100% inhibition against Fusarium oxysporum, Phyricularia grisea, Botrytis cinereapers, Gibberella zeae, Sclerotinia sclerotiorum, and Cercospora beticola at the concentration of 50mg/L.