40843-73-0

Basic information

• Product Name: 4-(2,4-DICHLOROPHENOXY)PHENOL
• Synonyms: 4-(2,4-DICHLOROPHENOXY)PHENOL;2,4-dichlorophenoxyphenol;2,4-Dichloro 4'-Hydroxy Diphenyl Ether;p-(2,4-Dichlorophenoxy)phenol;Einecs 255-106-1;Phenol, 4-(2,4-dichlorophenoxy)-;4-dichlorophenoxy)-;4-(2,4-Dichlorophenoxy)
• CAS NO: 40843-73-0
• Molecular Formula: C₁₂H₈Cl₂O₂
• Molecular Weight: 255.1
• EINECS: 255-106-1
• Product Categories: API intermediates
• Mol File: 40843-73-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 354°C at 760mmHg
• Flash Point: 167.9°C
• Appearance: /
• Density: 1.398g/cm³
• Vapor Pressure: 1.69E-05mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(2,4-DICHLOROPHENOXY)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-DICHLOROPHENOXY)PHENOL(40843-73-0)
• EPA Substance Registry System: 4-(2,4-DICHLOROPHENOXY)PHENOL(40843-73-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 40843-73-0(Hazardous Substances Data)

Usage

General Description

4-(2,4-dichlorophenoxy)phenol, also known as 2,4-DCP, is a toxic chemical compound commonly used as a herbicide and fungicide. It is a white crystalline solid with a faint phenolic odor and is sparingly soluble in water. 2,4-DCP is primarily used in agricultural applications, but it can also be found in manufacturing processes and as a wood preservative. Studies have shown that 2,4-DCP can have negative effects on human health, including skin and eye irritation, respiratory issues, and potential long-term impacts on the endocrine system. Due to its toxicity, exposure to this chemical should be avoided, and proper protective measures should be taken when handling it.

InChI:InChI=1/C12H8Cl2O2/c13-8-1-6-12(11(14)7-8)16-10-4-2-9(15)3-5-10/h1-7,15H

Synthetic route

C12H7Cl2N2O(1+)*BF4(1-) → 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0)

Conditions	Yield
(i) Ac2O, (ii) aq. NaOH, MeOH; Multistep reaction;

1-bromo-2,4-dichlorobenzene (1193-72-2) + phenol (108-95-2) → 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0)

Conditions	Yield
Yield given. Multistep reaction;

2,4-dichloro-4'-aminodiphenyl ether (14861-17-7) → 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. HCl, AcOH, (ii) NaNO2, aq. HBF4 2: (i) Ac2O, (ii) aq. NaOH, MeOH View Scheme

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + (R,S)-2-chloropropionic acid (598-78-7) → diclofop (40843-25-2)

Conditions	Yield
With sodium hydroxide; phosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene; water	99.5%

Methyl 2-bromopropionate (5445-17-0) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → diclofop-methyl (51338-27-3)

Conditions	Yield
With potassium carbonate In acetone for 20h; Heating;	94%

ethyl (E)-4-bromopent-2-enoate (53662-67-2) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → Ethyl 4-[4(2,4-dichlorophenoxy)phenoxy](2)-pentenoate (72281-60-8)

Conditions	Yield
With sodium carbonate In N-methyl-acetamide	85.2%

3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (178043-45-3) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → 1,3-dichloro-5-((3,3-dichloroallyl)oxy)-2-(3-(4-(2,4-dichlorophenoxy)phenoxy)propoxy)benzene

Conditions	Yield
With potassium carbonate In acetonitrile for 1h; Reflux;	83%

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate (57057-80-4) → (+)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>-propionsaeure-ethylester (71283-67-5)

Conditions	Yield
With potassium carbonate In cyclohexane for 17h; Heating / reflux;	77%
With potassium carbonate In acetonitrile for 21h; Heating;

ethyl 4-bromo 2-pentenoate (71101-32-1) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → Ethyl 4-[4(2,4-dichlorophenoxy)phenoxy](2)-pentenoate (72281-60-8)

Conditions	Yield
With sodium carbonate

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + 2-Bromo-propionic acid 2-methoxy-ethyl ester → 2-[4-(2,4-Dichloro-phenoxy)-phenoxy]-propionic acid 2-methoxy-ethyl ester (65633-35-4)

Conditions	Yield
(i) K2CO3, DMF, (ii) /BRN= 6287738/; Multistep reaction;

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + propionyl chloride (79-03-8) → Propionic acid 4-(2,4-dichloro-phenoxy)-phenyl ester (62966-67-0)

Conditions	Yield
(i) aq. NaOH, toluene, (ii) /BRN= 385632/; Multistep reaction;

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + ethyl 2-phenyl-2-bromoacetate (2882-19-1) → [4-(2,4-Dichloro-phenoxy)-phenoxy]-phenyl-acetic acid (40843-41-2)

Conditions	Yield
(i) K2CO3, MeCOEt, (ii) aq. NaOH, MeOH; Multistep reaction;

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + 2-chloro-propanoic acid, ethyl ester (535-13-7) → D-(+)-2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid ethyl ester (51338-06-8)

Conditions	Yield
With potassium carbonate In butanone Heating;

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + ethyl 2-chloro-2-phenylacetate (10606-73-2, 99531-04-1, 116836-53-4, 4773-33-5) → [4-(2,4-Dichloro-phenoxy)-phenoxy]-phenyl-acetic acid (40843-41-2)

Conditions	Yield
(i) K2CO3, MeCOEt, (ii) aq. NaOH, MeOH; Multistep reaction;

3-(1,3-dioxolan-2-yl)-phenylbromide (17789-14-9) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → 3-[4-(2,4-Dichloro-phenoxy)-phenoxy]-benzaldehyde

Conditions	Yield
With pyridine; sodium hydride; copper(I) bromide 1.) DMF, 130 deg C, 15 min, 2.) DMF, reflux, 12 h; Multistep reaction;

Methyl 2-bromopropionate (5445-17-0) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → D-(+)-2-<4-(2,4-Dichlorphenoxy)-phenoxy>propionsaeuremethylester + L-(-)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>propionsaeuremethylester

Conditions	Yield
Yield given. Multistep reaction. Title compound not separated from byproducts;

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + 1-Azidomethoxy-4-chloro-2-chloromethyl-benzene (96239-02-0) → C20H14Cl3N3O3

Conditions	Yield
With potassium carbonate In ethanol 25 deg C, 1 h ; 65 deg C, 6 h; Yield given;

6-chloro-2,4-dimethoxypyrimidine (6320-15-6) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → 4-[4-(2,4-dichloro-phenoxy)-phenoxy]-2,6-dimethoxy-pyrimidine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Substitution;

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → diclofop (40843-25-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / K2CO3 / acetone / 20 h / Heating 2: 89 percent / 33percent NaOH / methanol / 2.5 h / Heating View Scheme

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → D-(+)-2-<4-(2,4-Dichlorphenoxy)-phenoxy>propionsaeure

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / K2CO3 / acetone / 20 h / Heating 2: 89 percent / 33percent NaOH / methanol / 2.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 21 h / Heating 2: 33percent NaOH / 1.) CH3OH, 2.5 h, reflux View Scheme

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → L-(-)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>propionsaeure (75021-71-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / K2CO3 / acetone / 20 h / Heating 2: 89 percent / 33percent NaOH / methanol / 2.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 94 percent / K2CO3 / acetone / 20 h / Heating 2: 3.0 g / 33percent NaOH / methanol / 2.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: K2CO3 / acetonitrile / 21 h / Heating 2: 33percent NaOH / 1.) CH3OH, 2.5 h, reflux View Scheme

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → L-(-)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>propionsaeuremethylester

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / K2CO3 / acetone / 20 h / Heating 2: 89 percent / 33percent NaOH / methanol / 2.5 h / Heating 4: 89 percent / diethyl ether View Scheme
Multi-step reaction with 3 steps 1: 94 percent / K2CO3 / acetone / 20 h / Heating 2: 3.0 g / 33percent NaOH / methanol / 2.5 h / Heating 3: 89 percent / diethyl ether View Scheme
Multi-step reaction with 3 steps 1: K2CO3 / acetonitrile / 21 h / Heating 2: 33percent NaOH / 1.) CH3OH, 2.5 h, reflux 3: 89 percent / diethyl ether View Scheme

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → 3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid cyano-{3-[4-(2,4-dichloro-phenoxy)-phenoxy]-phenyl}-methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH, 2.) CuBr, pyridine / 1.) DMF, 130 deg C, 15 min, 2.) DMF, reflux, 12 h 2: 67 percent / Bu4NBr / H2O; toluene / 6 h / 25 °C View Scheme

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → 4-Chloro-2-[4-(2,4-dichloro-phenoxy)-phenoxymethyl]-phenol (120676-92-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / ethanol / 25 deg C, 1 h ; 65 deg C, 6 h 2: 88 percent / H2 / Pd/C / ethyl acetate / 25 °C View Scheme

N-[l-(-)-2-tosyloxypropionyl]isoxazolidine + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → N-[(+/-)-2-[4-(2,4-dichlorophenoxy)phenoxy]propionyl]isoxazolidine

Conditions	Yield
With potassium carbonate In acetonitrile; benzene

ethyl acetate n-hexane + t-butyl 2(R)-hydroxypropionate (59854-10-3) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + diethylazodicarboxylate (1972-28-7) → tert-butyl (2R)-(+)-2-[4'-(2",4"-dichlorophenoxy)phenoxy]propionate

Conditions	Yield
With triphenylphosphine In tetrahydrofuran

2-chloro-propionic acid methyl ester (17639-93-9) + 4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) → diclofop (40843-25-2)

Conditions	Yield
With sodium hydroxide In methanol; 5,5-dimethyl-1,3-cyclohexadiene; water

4-(2',4'-dichlorophenoxy)-phenol (40843-73-0) + methyl 2-{[(4-methylphenyl)sulfonyl]oxy}propanoate (66648-29-1) → diclofop-methyl (51338-27-3)

Conditions	Yield
With potassium carbonate In acetonitrile

Upstream product

• 1193-72-2 1-bromo-2,4-dichlorobenzene 
• 108-95-2 phenol 
• 14861-17-7 2,4-dichloro-4'-aminodiphenyl ether 

Downstream Products

• 72281-60-8 Ethyl 4-[4(2,4-dichlorophenoxy)phenoxy]⁽²⁾-pentenoate 
• 40843-41-2 [4-(2,4-Dichloro-phenoxy)-phenoxy]-phenyl-acetic acid 
• 71283-67-5 (+)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>-propionsaeure-ethylester 
• 51338-27-3 diclofop-methyl 
• 40843-25-2 diclofop 
• 120676-92-8 4-Chloro-2-[4-(2,4-dichloro-phenoxy)-phenoxymethyl]-phenol 
• 71283-65-3 L-(-)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>propionsaeuremethylester 
• 75021-71-5 L-(-)-2-<4-(2.4-Dichlorphenoxy)-phenoxy>propionsaeure 
• 71283-65-3 D-(+)-2-<4-(2,4-Dichlorphenoxy)-phenoxy>propionsaeuremethylester 
• 51338-06-8 D-(+)-2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid ethyl ester 
• 62966-67-0 Propionic acid 4-(2,4-dichloro-phenoxy)-phenyl ester 
• 65633-35-4 2-[4-(2,4-Dichloro-phenoxy)-phenoxy]-propionic acid 2-methoxy-ethyl ester 

Relevant articles and documents

Evaluation of the Elbs Persulfate Oxidation Reaction for the Preparation of Aryloxyphenoxypropionate Herbicides

A new, simple method for the preparation of several 4-(aryloxy)phenols (2a-d) and alkyl 2-(4-hydroxyphenoxy)propionates (3a,b) is described.These compounds are key precursors for the synthesis of important aryloxyphenoxypropionate herbicides (1a-d).The method uses the Elbs persulfate oxidation to convert phenol into 4-hydroxyphenyl sulfate (5).The free hydroxy group is then reacted with various aryl halides and alkyl 2-halopropionates.Mild hydrolysis of the sulfate group with boiling acetic acid then gives the products (2a-d) and (3a,b), generally in modest to good yield.

4-Phenoxy-phenoxy-alkane-carboxylic acid derivatives and process for their manufacture

Novel 4-phenoxy-phenoxy-alkane-carboxylic acid derivatives of the formula I STR1 in which R1 stands for hydrogen, methylthio, cyclopentyl, cyclohexyl, phenyl, methylcyclohexyl, ethylcyclohexyl, or R1 and R3 together stand for a --CH=CH--CH=CH-- bridge or--unless at least one of the substituents R2 to R8 stands for hydrogen, or if R9 stands for a radical having at least 2 carbon atoms--for chlorine, R2 and R3, independent of one another, each stands for hydrogen, chlorine or alkyl of 1 to 4 carbon atoms, R4 stands for hydrogen, chlorine, alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, methylcyclohexyl or R3 and R4 together stand for a --CH=CH--CH=CH-- bridge, R5, R6 and R7, independent of one another, each stands for hydrogen or alkyl of 1 to 4 carbon atoms, R8 stands for hydrogen, alkyl of 1 to 4 carbon atoms or allyl, R9 stands for alkyl of 1 to 10 carbon atoms or phenyl and X stands for hydrogen, the cation of a physiologically acceptable inorganic or organic base of a hydrocarbon radical of 1 to 10 carbon atoms, having a strong action on the lipide and cholesterine metabolism and a process for their manufacture.