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87-65-0 Usage

Chemical Properties

2,6-Dichlorophenol is a white crystalline solid having a strong odor similar to o-chlorophenol. Freely soluble in ethanol and ether, soluble in benzene and petroleum ether.

Uses

2,6-Dichlorophenol is produced as a by-product from the direct chlorination of phenol. It is used primarily as a starting material for the manufacture of trichlorophenols, tetrachlorophenols, and pentachlorophenols. It also acts as a sex pheromone for the Lone Star tick.

Preparation

2,6-Dichlorophenol has been prepared by the chlorination of phenol with chlorine gas in the presence of nitrobenzene and fuming sulfuric acid, by the decomposition of the diazotate of 2,6-dichloro-4-aminophenol, and by the decarboxylation of 3,5-dichloro-4-hydroxybenzoic acid in quinoline or dimethylaniline.

Definition

ChEBI: 2,6-dichlorophenol is a dichlorophenol with the chloro substituents at positions 2 and 6.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 2723, 1951 DOI: 10.1021/ja01150a084Organic Syntheses, Coll. Vol. 3, p. 267, 1955

General Description

2,6-dichlorophenol is a white crystalline solid with a strong odor. Odor threshold concentration: 0.003 mg/L at 86°F; 200 micrograms/liter at 68-72°F. Taste threshold concentration: 0.0002 mg/L. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,6-Dichlorophenol is incompatible with acid chlorides, acid anhydrides and oxidizing agents .

Fire Hazard

Flash point data for 2,6-Dichlorophenol are not available; however, 2,6-Dichlorophenol is probably combustible.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. A severe skin and eye irritant. When heated to decomposition it emits toxic fumes of Cl-. See also CHLOROPHENOLS.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid fumes, acid anhyrides and acid chlorides

Waste Disposal

Dissolve in a combustible solvent and incinerate in a furnace equipped with afterburner and scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

Check Digit Verification of cas no

The CAS Registry Mumber 87-65-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 87-65:
(4*8)+(3*7)+(2*6)+(1*5)=70
70 % 10 = 0
So 87-65-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H

87-65-0 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (A14411)  2,6-Dichlorophenol, 99%   

  • 87-65-0

  • 25g

  • 270.0CNY

  • Detail
  • Alfa Aesar

  • (A14411)  2,6-Dichlorophenol, 99%   

  • 87-65-0

  • 100g

  • 807.0CNY

  • Detail
  • Alfa Aesar

  • (A14411)  2,6-Dichlorophenol, 99%   

  • 87-65-0

  • 500g

  • 3226.0CNY

  • Detail
  • Sigma-Aldrich

  • (31102)  2,6-Dichlorophenol  PESTANAL®, analytical standard

  • 87-65-0

  • 31102-1G

  • 180.18CNY

  • Detail
  • Supelco

  • (40302)  2,6-Dichlorophenolsolution  certified reference material, 5000 μg/mL in methanol

  • 87-65-0

  • 000000000000040302

  • 533.52CNY

  • Detail

87-65-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-dichlorophenol

1.2 Other means of identification

Product number -
Other names 2,6-Dichlor-phenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:87-65-0 SDS

87-65-0Synthetic route

tert-butyl (2,6-dichlorophenoxy)dimethylsilane
188645-80-9

tert-butyl (2,6-dichlorophenoxy)dimethylsilane

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere;94%
2-monochlorophenol
95-57-8

2-monochlorophenol

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; sulfuryl dichloride In toluene at 25℃; for 24h; Inert atmosphere; regioselective reaction;91%
With 1,3-dichloro-5,5-dimethylhydantoin; diisopropylamine hydrochloride In toluene at 0℃; for 4h; Darkness; regioselective reaction;78%
With tetrachloromethane; tert-butylhypochlorite
3,5-dichloro-4-hydroxybenzoic acid
3336-41-2

3,5-dichloro-4-hydroxybenzoic acid

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With copper(I) oxide In quinoline at 220℃; for 6h; Autoclave;86%
With quinoline at 190℃;
With methyllithium; calcium carbonate
2,6-dichlorobenzaldehyde
83-38-5

2,6-dichlorobenzaldehyde

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2,6-dichlorobenzoic acid
50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 52h; Heating;A 4 % Chromat.
B 86%
2-monochlorophenol
95-57-8

2-monochlorophenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With iron(III) chloride; diphenyl sulfide; boric acid at 40 - 80℃;A 13.31%
B 85.43%
With chloroamine In water pH=9.0; Product distribution; Further Variations:; Reagents; pH-values;A 23%
B 77%
With N-chlorobis(2-chloroethyl)amine; silica gel In tetrachloromethane at 25℃; Yield given. Yields of byproduct given;
With 2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one In tetrachloromethane; N,N-dimethyl-formamide at 20℃; for 360h; other reagent; Yield given. Yields of byproduct given;
With aluminum (III) chloride; sulfuryl dichloride In neat (no solvent) at 25 - 55℃; for 3h; Reagent/catalyst; Temperature; regioselective reaction;A 5.7 %Chromat.
B 92.1 %Chromat.
2,2,6,6-tetrachlorocyclohexanone
3776-30-5

2,2,6,6-tetrachlorocyclohexanone

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With triethylamine In toluene at 80℃; for 2.5h; Reagent/catalyst; Solvent; Time;84.4%
With triethylamine In N,N-dimethyl-formamide at 100℃; for 4h; Dehydrochlorination;30%
1,3-dichloro-2-(2-propenyloxy)benzene
6267-90-9

1,3-dichloro-2-(2-propenyloxy)benzene

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;75%
2,6-dichlorophenylboronic acid
73852-17-2

2,6-dichlorophenylboronic acid

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With ozone In ethanol; water at 20 - 30℃; for 0.583333h;73%
C11H12Cl2O

C11H12Cl2O

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;70%
phenol
108-95-2

phenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

4-chloro-phenol
106-48-9

4-chloro-phenol

C

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride; sodium chlorate In water; acetic acid at 20℃; for 72h;A 4%
B 16%
C 65%
phenol
108-95-2

phenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2-monochlorophenol
95-57-8

2-monochlorophenol

C

4-chloro-phenol
106-48-9

4-chloro-phenol

D

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

E

2,4,6-Trichlorophenol
88-06-2

2,4,6-Trichlorophenol

Conditions
ConditionsYield
With aluminium trichloride; diphenyl sulfide; chlorine In neat (no solvent) at 35℃; for 1.5h; Product distribution; others 2-alkylphenols; var. chlorinating agent, temp., and time;A 0.5%
B 18.4%
C 58.6%
D 7.7%
E 0.5%
With N,N'-dichloropiperazine; silica gel In tetrachloromethane at 25℃; Product distribution; further reagents;
With tert-butylhypochlorite; tris(3-pyridiniumprop-1-yl)benzene-1,3,5-tricarboxylatetrichloride In acetonitrile Product distribution; Mechanism; other tentacle reagents and variations of concentration;
With tert-butylhypochlorite; cetylpyridinium chloride In water Product distribution; other reagents and solvent;
With sulfuryl dichloride; 2-aminopyridine In toluene at 70℃; for 1h; Product distribution; chlorination catalyzed by var. amines under var. conditions;A n/a
B 32.3 % Chromat.
C 60.3 % Chromat.
D n/a
E n/a
phenol
108-95-2

phenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2-monochlorophenol
95-57-8

2-monochlorophenol

C

4-chloro-phenol
106-48-9

4-chloro-phenol

D

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With chloroamine In water pH=9.0; Product distribution; Further Variations:; Reagents; pH-values;A 9.6%
B 50.5%
C 23%
D 16.3%
With oxygen; silica gel; copper dichloride at 200℃; Formation of xenobiotics;A 0.004%
B 4.761%
C 1.149%
D 0.393%
With oxygen; silica gel; copper dichloride at 225℃; Formation of xenobiotics; Further byproducts.;A 0.008%
B 3.892%
C 0.998%
D 0.394%
2,6-dichlorophenyl dimethylcarbamate
14863-58-2

2,6-dichlorophenyl dimethylcarbamate

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With hydrazine hydrate at 60℃; for 2h; Sealed tube; regioselective reaction;50%
phenol
108-95-2

phenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride; potassium permanganate In acetonitrile at 60℃;A 44%
B 44%
With alkaline sodium hypochlorite solution
With chlorine
2,6-dichloroanisole
1984-65-2

2,6-dichloroanisole

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With sodium methylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃;33%
1,2,3-trichlorobenzene
87-61-6

1,2,3-trichlorobenzene

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2,3-dichloroanisole
1984-59-4

2,3-dichloroanisole

C

2,6-dichloroanisole
1984-65-2

2,6-dichloroanisole

Conditions
ConditionsYield
With potassium hydroxide; Tris(3,6-dioxaheptyl)amine at 135℃; for 2h;A 23%
B 756 g
C 496 g
2-nitropropane
79-46-9

2-nitropropane

2,6-dichloro-4-dimethylaminomethyl-phenol
56733-60-9

2,6-dichloro-4-dimethylaminomethyl-phenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

3,5-dichloro-4-hydroxybenzaldehyde
2314-36-5

3,5-dichloro-4-hydroxybenzaldehyde

C

2,6-Dichlor-4-(2-methyl-2-nitropropyl)phenol
85628-45-1

2,6-Dichlor-4-(2-methyl-2-nitropropyl)phenol

Conditions
ConditionsYield
potassium fluoride; tetrabutyl-ammonium chloride for 30h; Heating;A n/a
B n/a
C 12%
2-monochlorophenol
95-57-8

2-monochlorophenol

A

dioxin
262-12-4

dioxin

B

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

C

1-chlorodibenzo-p-dioxin
39227-53-7

1-chlorodibenzo-p-dioxin

D

4,6-dichlorodibenzofuran

4,6-dichlorodibenzofuran

Conditions
ConditionsYield
With oxygen at 600℃; for 0.000555556h; Product distribution; Further Variations:; Temperatures;A 1.32%
B 0.59%
C 0.92%
D 9.43%
2-monochlorophenol
95-57-8

2-monochlorophenol

A

dioxin
262-12-4

dioxin

B

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

C

1-chlorodibenzo-p-dioxin
39227-53-7

1-chlorodibenzo-p-dioxin

D

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With oxygen; silica gel; copper dichloride at 400℃; Product distribution; Further Variations:; Temperatures;A 0.6915%
B 0.219%
C 0.7511%
D 0.238%
With oxygen; silica gel; copper dichloride at 350℃; Formation of xenobiotics; Further byproducts.;A 0.0672%
B 0.229%
C 0.3293%
D 0.282%
2-monochlorophenol
95-57-8

2-monochlorophenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

C

2,4,6-Trichlorophenol
88-06-2

2,4,6-Trichlorophenol

Conditions
ConditionsYield
With oxygen; silica gel; copper dichloride at 300℃; Formation of xenobiotics;A 0.282%
B 0.379%
C 0.128%
With N-chloro-succinimide at 80℃; for 10h; regioselective reaction;A 8 %Chromat.
B 55 %Chromat.
C 18 %Chromat.
2-monochlorophenol
95-57-8

2-monochlorophenol

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

1-chlorodibenzo-p-dioxin
39227-53-7

1-chlorodibenzo-p-dioxin

C

2,4-dichlorophenol
120-83-2

2,4-dichlorophenol

D

2,4,6-Trichlorophenol
88-06-2

2,4,6-Trichlorophenol

Conditions
ConditionsYield
With oxygen; silica gel; copper dichloride at 325℃; Formation of xenobiotics;A 0.257%
B 0.0024%
C 0.312%
D 0.053%
quinoline
91-22-5

quinoline

3,5-dichloro-4-hydroxybenzoic acid
3336-41-2

3,5-dichloro-4-hydroxybenzoic acid

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
at 190 - 200℃;
at 190℃;
tert-butylhypochlorite
507-40-4

tert-butylhypochlorite

2-monochlorophenol
95-57-8

2-monochlorophenol

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

4-bromo-2,6-dichloro-phenol
3217-15-0

4-bromo-2,6-dichloro-phenol

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With palladium on activated charcoal; sodium acetate; benzene Hydrogenation.Reagens 4: Cyclohexan;
With sodium sulfite In water at 130℃; Sealed tube; Microwave irradiation; Green chemistry;63 mg
4-tert-butyl-2,6-dichloro-phenol
34593-75-4

4-tert-butyl-2,6-dichloro-phenol

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With aluminium trichloride; xylene
4-amino-2,6-dichlorophenol
5930-28-9

4-amino-2,6-dichlorophenol

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With sulfuric acid Diazotization.Kochen des Diazoniumsulfats mit Wasser und Soda;
2,6-dichloro-4-tert-pentyl-phenol
75908-77-9

2,6-dichloro-4-tert-pentyl-phenol

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With aluminium trichloride; xylene at 65 - 95℃;
With boron trifluoride; xylene at 60℃;
3,5-dichloro-4-hydroxybenzoic acid
3336-41-2

3,5-dichloro-4-hydroxybenzoic acid

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
at 190℃;
methanol
67-56-1

methanol

sodium methylate
124-41-4

sodium methylate

1,2,3-trichlorobenzene
87-61-6

1,2,3-trichlorobenzene

A

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

B

2,3-dichloroanisole
1984-59-4

2,3-dichloroanisole

C

2,3-dichlorophenol
576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
at 180℃; im Rohr;
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2-(2,6-dichlorophenoxy)ethanol
42001-44-5

2-(2,6-dichlorophenoxy)ethanol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;100%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2,6-dichlorophenyl trifluoromethanesulphonate
133280-47-4

2,6-dichlorophenyl trifluoromethanesulphonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃;100%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

phenylboronic acid
98-80-6

phenylboronic acid

(1,1';3',1''-terphenyl)-2'-ol
2432-11-3

(1,1';3',1''-terphenyl)-2'-ol

Conditions
ConditionsYield
With palladium diacetate; dicyclohexylphenylphosphine In water; 1,2-dichloro-ethane at 40 - 70℃; for 3h; Reagent/catalyst; Solvent; Temperature; Concentration; Suzuki Coupling; Inert atmosphere; Sealed tube;99.3%
With C28H44N2PPd; potassium carbonate In ethanol; water at 60℃; for 6h; Suzuki coupling;96%
With reduced graphene oxide/Pd-Fe3O4(at)polypyrrole nanocomposite In water at 70℃; for 3h; Suzuki Coupling; Sonication;65%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

4-(4-nitrophenyl)-1-piperazinecarbonyl chloride
177489-12-2

4-(4-nitrophenyl)-1-piperazinecarbonyl chloride

C17H15Cl2N3O4
1092069-78-7

C17H15Cl2N3O4

Conditions
ConditionsYield
Stage #1: 2,6-Dichlorophenol With sodium hydride In tetrahydrofuran for 0.25h; Molecular sieve;
Stage #2: 4-(4-nitrophenyl)-1-piperazinecarbonyl chloride In tetrahydrofuran at 20℃; for 18.5h; Heating / reflux;
99%
Stage #1: 2,6-Dichlorophenol With sodium hydride In tetrahydrofuran for 0.25h;
Stage #2: 4-(4-nitrophenyl)-1-piperazinecarbonyl chloride In tetrahydrofuran at 20℃; for 19h; Heating / reflux;
99%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

C12H15BCl2O3

C12H15BCl2O3

Conditions
ConditionsYield
In [D3]acetonitrile at 20℃; Inert atmosphere;99%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2,6-dichloro-4-nitrophenol
618-80-4

2,6-dichloro-4-nitrophenol

Conditions
ConditionsYield
With Zn(NO3)2*2N2O4 In dichloromethane at 20℃; for 0.0833333h;98%
With tetra(n-butyl)ammonium dichromate(VI); sodium nitrite In dichloromethane for 23h; Reflux; chemoselective reaction;98%
With Tetraethylene glycol; silica gel; dinitrogen tetraoxide In dichloromethane at 20℃; for 0.0833333h;97%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

A

2,6-Dichlorophenyl sulfate
92545-10-3

2,6-Dichlorophenyl sulfate

B

3,5-Dichloro-4-sulfooxy-benzenesulfonic acid

3,5-Dichloro-4-sulfooxy-benzenesulfonic acid

Conditions
ConditionsYield
With sulfur trioxide In nitromethane-d3 at -30℃; for 0.0333333h; Product distribution; various solvents, times, temperatures, amounts of SO3;A 98%
B 2%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

2,6-dichlorophenyl 3-phenylpropanoate

2,6-dichlorophenyl 3-phenylpropanoate

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 5℃; for 1h;98%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

3-chloro-1-(4-fluorophenyl)-1-propanol
31736-75-1

3-chloro-1-(4-fluorophenyl)-1-propanol

1-(4-fluorophenyl)-1-(2,6-dichlorophenoxy)-3-chloropropane
1037716-90-7

1-(4-fluorophenyl)-1-(2,6-dichlorophenoxy)-3-chloropropane

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; Inert atmosphere;98%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

3-chloro-1-(p-tolyl)propan-1-ol
22422-27-1

3-chloro-1-(p-tolyl)propan-1-ol

1-(4-methylphenyl)-1-(2,6-dichlorophenoxy)-3-chloropropane
1037716-99-6

1-(4-methylphenyl)-1-(2,6-dichlorophenoxy)-3-chloropropane

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; Inert atmosphere;98%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl (2,6-dichlorophenoxy)dimethylsilane
188645-80-9

tert-butyl (2,6-dichlorophenoxy)dimethylsilane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;98%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;98%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2,6-dichloro-4-iodophenol
34074-22-1

2,6-dichloro-4-iodophenol

Conditions
ConditionsYield
Stage #1: 2,6-Dichlorophenol With ethylenediamine; sodium iodide In ethanol; water for 0.25h;
Stage #2: With iodine In ethanol; water at 20℃;
97%
With dihydrogen peroxide; iodine In water for 0.75h; Sonication;97%
With dihydrogen peroxide; iodine In water at 50℃; for 24h; regioselective reaction;95%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

4-bromo-2,6-dichloro-phenol
3217-15-0

4-bromo-2,6-dichloro-phenol

Conditions
ConditionsYield
With bromine In acetonitrile at 0℃; for 6h;97%
With bromine In acetonitrile at 0℃; for 2h;95.5%
With bromine In acetonitrile at 0℃; for 2h;94%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2,6-dichloroanisole
1984-65-2

2,6-dichloroanisole

Conditions
ConditionsYield
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 2h; Microwave irradiation; Green chemistry;97%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

(2-benzoylamino-phenyl)-acetic acid methyl ester
3559-26-0

(2-benzoylamino-phenyl)-acetic acid methyl ester

C22H17Cl2NO3

C22H17Cl2NO3

Conditions
ConditionsYield
Stage #1: (2-benzoylamino-phenyl)-acetic acid methyl ester With thionyl chloride for 3h; Reflux;
Stage #2: 2,6-Dichlorophenol With potassium carbonate In toluene for 3h; Reagent/catalyst; Cooling with ice; Reflux;
97%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

(R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione
245728-73-8

(R)-2-(4-hydroxybutan-2-yl)isoindoline-1,3-dione

(R)-2-(4-(2,6-dichlorophenoxy)butan-2-yl)isoindoline-1,3-dione
1429187-74-5

(R)-2-(4-(2,6-dichlorophenoxy)butan-2-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;96%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 17h;96%
vinyl acetate
108-05-4

vinyl acetate

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2,6-dichlorophenyl acetate
28165-71-1

2,6-dichlorophenyl acetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 70 - 140℃; for 0.183333h; Microwave irradiation;96%
triethylsilane
617-86-7

triethylsilane

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

(2,6-dichlorophenoxy)triethylsilane

(2,6-dichlorophenoxy)triethylsilane

Conditions
ConditionsYield
With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 3h; Irradiation;96%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

acetic anhydride
108-24-7

acetic anhydride

2,6-dichlorophenyl acetate
28165-71-1

2,6-dichlorophenyl acetate

Conditions
ConditionsYield
aluminium dodecatungsten phosphate at 20℃; for 0.25h;95%
With o-benzenedisulfonimide at 20℃; for 4h;95%
With pentaaminechlorocobalt(III) dichloride; phosphoric acid In neat (no solvent) at 75℃; for 0.166667h; Reagent/catalyst; Green chemistry; chemoselective reaction;90%
In 1,4-dioxane; water at 25℃; Rate constant; Anion, pH 7.50;
With pyridine
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

methyl 2-(2-(2-bromopropionamido)phenyl)acetate

methyl 2-(2-(2-bromopropionamido)phenyl)acetate

[2-(2,6-dichloroanilino)phenyl]acetic acid
15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 60 - 100℃; for 8h; Temperature; Reagent/catalyst;95%
iodobenzene
591-50-4

iodobenzene

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2,6-dichlorodiphenyl ether
28419-69-4

2,6-dichlorodiphenyl ether

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) at 90℃; for 5h; Green chemistry;95%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

acetyl chloride
75-36-5

acetyl chloride

2,6-dichlorophenyl acetate
28165-71-1

2,6-dichlorophenyl acetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;94.1%
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;94%
With triethylamine In dichloromethane at 20℃; for 2.5h;94%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

allyl bromide
106-95-6

allyl bromide

1,3-dichloro-2-(2-propenyloxy)benzene
6267-90-9

1,3-dichloro-2-(2-propenyloxy)benzene

Conditions
ConditionsYield
Stage #1: 2,6-Dichlorophenol With potassium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere;
Stage #2: allyl bromide In dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere; regioselective reaction;
94%
With potassium carbonate; butanone
With potassium carbonate
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

4-(1-hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2,6-dichlorophenol

4-(1-hydroxy-1-methoxycarbonyl-2,2,2-trifluoroethyl)-2,6-dichlorophenol

Conditions
ConditionsYield
With triethylamine In benzene for 6h; Ambient temperature;94%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide
14301-31-6

2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide

2-(2,6-dichloro-phenoxy)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide
223686-74-6

2-(2,6-dichloro-phenoxy)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 6h; Heating;94%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2-(3-bromopropyl)isoindole-1,3-dione
5460-29-7

2-(3-bromopropyl)isoindole-1,3-dione

2-(3-(2,6-dichlorophenoxy)propyl)isoindoline-1,3-dione
1148000-14-9

2-(3-(2,6-dichlorophenoxy)propyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; caesium carbonate In tetrahydrofuran at 20 - 50℃; for 16h;94%
With tetra-(n-butyl)ammonium iodide; caesium carbonate In tetrahydrofuran at 20 - 50℃; for 16h;94%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;
With potassium carbonate In N,N-dimethyl-formamide at 100℃;
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

4,5-dichloro-2-chloromethyl-pyridazin-3(2H)-one
51356-03-7

4,5-dichloro-2-chloromethyl-pyridazin-3(2H)-one

4-chloro-5-(2,6-dichlorophenoxy)-2-[(2,6-dichlorophenoxy)-methyl]pyridazin-3(2H)-one
1174278-25-1

4-chloro-5-(2,6-dichlorophenoxy)-2-[(2,6-dichlorophenoxy)-methyl]pyridazin-3(2H)-one

Conditions
ConditionsYield
With potassium carbonate In methanol for 5h; Reflux;94%
2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

pentaphenylantimony
2170-05-0

pentaphenylantimony

2,6-dichlorophenoxytetraphenylstiborane
171977-33-6

2,6-dichlorophenoxytetraphenylstiborane

Conditions
ConditionsYield
In toluene room temperature;93%
phosgene
75-44-5

phosgene

2,6-Dichlorophenol
87-65-0

2,6-Dichlorophenol

2,6-Dichlorophenyl chloroformate
374568-08-8

2,6-Dichlorophenyl chloroformate

Conditions
ConditionsYield
With N,N-dimethyl-aniline In toluene Inert atmosphere;93%

87-65-0Relevant articles and documents

The use of polymeric sulfides as catalysts for the para-regioselective chlorination of phenol and 2-chlorophenol

Smith, Keith,Hegazy, Amany S.,El-Hiti, Gamal A.

, p. 1 - 12 (2019/11/20)

Various poly(alkylene sulfide)s have been synthesized and used as catalysts to enhance the para-regioselectivity in chlorination of phenol and 2-chlorophenol using freshly distilled sulfuryl chloride in the presence of AlCl3 as an activator. Poly(alkylene sulfide)s having alternating spacers, one having three methylene groups and the second having three, six or nine methylene groups were the most para-regioselective catalysts in chlorination of both phenol and 2-chlorophenol. For example, chlorination of phenol and 2-chlorophenol in the presence of optimal examples of such poly(alkylene sulfide)s gave 4-chlorophenol and 2,4-dichlorophenol as the major products in 94.8 and 95.4% yields, respectively, compared with 75.4 and 55.0% yields in the absence of catalysts. In addition, double chlorination of phenol in the presence of poly(alkylene sulfide)s gave 2,4-dichlrophenol in up to 97.1% yield compared with only 58.6% in the absence of catalysts.

Method for producing high purity 2, 4 - dichlorophenol

-

Paragraph 0107-0115, (2019/07/04)

The invention provides a method for producing high purity 2, 4 - dichlorophenol, including: (1) heating and melting the raw materials, the mixed catalyst is added in the raw material, wherein the feedstock is phenol, O-phenol or [...] in at least one of, the mixed catalyst is phenyl sulfide, mixture of ferric chloride and trifluoromethanesulfonic acid; (2) to maintain the temperature of the material is 40 - 100 °C, to the material to carry out chlorination chlorinating agent is filled in the catalytic reaction to obtain 2, 4 - dichlorophenol crude product, the chlorinating agent is chlorine or sulfuryl chloride in at least one of; (3) to said 2, 4 - dichlorophenol crude melt crystallization, to obtain 2, 4 - dichlorophenol product. In this invention the states the chlorizating agent can be a chloride, can also be chlorine, the two can achieve higher conversion rate of raw materials, the application in the catalytic chlorination reaction the crude product obtained without rectification, only through the melt crystallization to obtain the purity 99% of the 2, 4 - dichlorophenol product.

Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications

Xiong, Xiaodong,Yeung, Ying-Yeung

, p. 4033 - 4043 (2018/05/22)

An ortho-selective ammonium chloride salt-catalyzed direct C-H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated BINOLs are useful synthons for the synthesis of a wide range of unsymmetrical 3-aryl BINOLs that are not easily accessible. In addition, the same catalytic system can facilitate the ortho-selective selenylation of phenols.

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