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4-Chlorophenol, also known as para-chlorophenol, is an organic compound with the chemical formula C6H4ClOH. It is a monochlorophenol substituted at the para position by a chlorine atom, and it exists as white or off-white crystals with a strong phenol odor. 4-Chlorophenol is slightly soluble to soluble in water, depending on the isomer, and is denser than water. It is noncombustible and is used as an intermediate in organic synthesis for various applications.

106-48-9

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106-48-9 Usage

Uses

Used in Liquid Crystals Industry:
4-Chlorophenol is used as an intermediate for the synthesis of liquid crystals, which are essential components in the production of display devices such as LCD screens.
Used in Antineoplastic Applications:
4-Chlorophenol is utilized as an antineoplastic agent, which means it has the potential to inhibit or prevent the growth of tumors and cancer cells.
Used in Biocide and Disinfectant Applications:
4-Chlorophenol serves as a biocide and disinfectant for various settings, including homes, hospitals, and farms. It helps in controlling the growth of harmful microorganisms and maintaining a hygienic environment.
Used in Pharmaceutical, Dye, and Plastic Industries:
4-Chlorophenol is used as a main raw material in the compounding for the pharmaceutical, dye, and plastic industries. Its versatile chemical properties make it a valuable component in the development of various products.
Used in Environmental Applications:
4-Chlorophenol was used in the visible-light-induced degradation of 4-chlorophenol in aqueous suspension of pure TiO2, which is a process aimed at reducing environmental pollution caused by 4-Chlorophenol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2145, 1985 DOI: 10.1021/jo00212a029Tetrahedron Letters, 24, p. 3117, 1983 DOI: 10.1016/S0040-4039(00)88111-3

Air & Water Reactions

Slightly soluble to soluble in water.

Reactivity Profile

CHLOROPHENOLS, SOLID are incompatible with acid chlorides, acid anhydrides and oxidizing agents. Also incompatible with iron . Liquefy and darken in color at temperatures above 108°F.

Hazard

Toxic by skin absorption, inhalation, or ingestion; strong irritant to tissue.

Health Hazard

Inhalation causes headache, dizziness, weak pulse. Ingestion causes irritation of mouth and stomach; headache, dizziness, weak pulse. Contact with eyes causes severe irritation and burning. Contact with skin causes irritation and burn; if absorbed, causes same symptoms as inhalation.

Fire Hazard

Special Hazards of Combustion Products: Toxic and irritating hydrogen chloride and chlorine gases may form in fires.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by inhalation and intraperitoneal routes. Moderately toxic by ingestion, skin contact, and subcutaneous routes. A severe skin and eye irritant. Human systemic effects by inhalation: excitement, irritability. Mutation data reported. Combustible when exposed to heat or flame. To fight fire, use water, spray, mist, fog, foam, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLOROPHENOLS and CHLORIDES.

Potential Exposure

Monochlorophenols are used in the manufacture of fungicides, slimicides, bactericides, pesticides, herbicides, disinfectants, wood and glue preservatives; in the production of phenolic resins; in the extraction of certain minerals from coal; as a denaturant for ethanol; as an antiseptic; as a disinfectant, and others.

Shipping

UN 2020 (solid); UN2021 (liquid) Chlorophenols, solid and liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Distil the phenol, then crystallise it from pet ether (b 40-60o) or hexane, and dry it under vacuum over P2O5 at room temperature. [Bernasconi & Paschalis J Am Chem Soc 108 2969 1986, Beilstein 6 IV 820.]

Incompatibilities

May form explosive mixture with air. Contact with oxidizing agents can cause fire and explosion hazard. Heat produces hydrogen chloride and chlorine. Corrosive to aluminum, copper and other chemically active metals.

Waste Disposal

Incinerate in admixture with flammable solvent in furnace equipped with afterburner and scrubber.

Check Digit Verification of cas no

The CAS Registry Mumber 106-48-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 106-48:
(5*1)+(4*0)+(3*6)+(2*4)+(1*8)=39
39 % 10 = 9
So 106-48-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H9ClO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2H2,1H3

106-48-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A15602)  4-Chlorophenol, 99%   

  • 106-48-9

  • 100g

  • 281.0CNY

  • Detail
  • Alfa Aesar

  • (A15602)  4-Chlorophenol, 99%   

  • 106-48-9

  • 250g

  • 460.0CNY

  • Detail
  • Alfa Aesar

  • (A15602)  4-Chlorophenol, 99%   

  • 106-48-9

  • 1000g

  • 1482.0CNY

  • Detail
  • Alfa Aesar

  • (A15602)  4-Chlorophenol, 99%   

  • 106-48-9

  • 5000g

  • 2602.0CNY

  • Detail
  • Sigma-Aldrich

  • (35826)  4-Chlorophenol  PESTANAL®, analytical standard

  • 106-48-9

  • 35826-1G

  • 179.01CNY

  • Detail
  • USP

  • (1496802)  Parachlorophenol  United States Pharmacopeia (USP) Reference Standard

  • 106-48-9

  • 1496802-500MG

  • 4,588.74CNY

  • Detail
  • Sigma-Aldrich

  • (25865)  4-Chlorophenolsolution  725 mg/L in H2O, for AOX determination (according to DIN 38409-H14)

  • 106-48-9

  • 25865-50ML

  • 403.65CNY

  • Detail

106-48-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-chlorophenol

1.2 Other means of identification

Product number -
Other names p-Chlorophenol

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:106-48-9 SDS

106-48-9Synthetic route

4-chloromethoxybenzene
623-12-1

4-chloromethoxybenzene

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With sodium; diphenyldisulfane In 1-methyl-pyrrolidin-2-one for 0.5h; Heating;100%
With calcium hydride; diphenyldisulfane In 1-methyl-pyrrolidin-2-one at 220℃; for 0.5h;99%
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;96%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

(4-Chlorophenoxy)dimethylsulfoxonium Tetrafluoroborate
73040-88-7

(4-Chlorophenoxy)dimethylsulfoxonium Tetrafluoroborate

A

n-butyl 4-chlorophenyl ether
51241-35-1

n-butyl 4-chlorophenyl ether

B

[(18)O]dimethyl sulfone

[(18)O]dimethyl sulfone

C

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With 18O-labeled water In 1,2-dimethoxyethane at -11 - 25℃; Product distribution; Mechanism;A 5%
B 100%
C 79%
1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

A

2-monochlorophenol
95-57-8

2-monochlorophenol

B

diphenyl sulfide
139-66-2

diphenyl sulfide

C

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With hydrogenchloride; phenol In dichloromethane at 0 - 25℃;A n/a
B 100%
C n/a
1-methoxyl-4-(phenylsulfinyl)benzene
951-92-8

1-methoxyl-4-(phenylsulfinyl)benzene

A

2-monochlorophenol
95-57-8

2-monochlorophenol

B

1-methoxy-4-(phenylsulfanyl)benzene
5633-57-8

1-methoxy-4-(phenylsulfanyl)benzene

C

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With hydrogenchloride; phenol In dichloromethane at 0 - 25℃;A n/a
B 100%
C n/a
ammonium thiocyanate

ammonium thiocyanate

4-chlorophenyl 1-chloroethylcarbonate
117971-97-8

4-chlorophenyl 1-chloroethylcarbonate

A

4-chlorophenyl 1-thiocyanoethylcarbonate
117972-05-1

4-chlorophenyl 1-thiocyanoethylcarbonate

B

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
In formamide at 50℃; for 20h;A 100%
B n/a
1-<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene
126644-72-2

1-<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 20℃; for 0.3h;99%
With sodium phosphate dodecahydrate In N,N-dimethyl-formamide at 20℃; for 0.3h;98%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 8h;96%
With P(MeNCH2CH2)3N In dimethyl sulfoxide at 80℃; for 24h; desilylation;94%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;99%
With water In tetrahydrofuran at 100℃; for 12h;99%
With dihydrogen peroxide In acetonitrile at 30 - 35℃; for 0.0833333h; Schlenk technique;98%
4-chlorophenoxytrimethylsilane
17005-59-3

4-chlorophenoxytrimethylsilane

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h;99%
With nano magnetic sulfated zirconia (Fe3O4 at ZrO2/SO42-) In neat (no solvent) at 20℃; for 0.75h; Green chemistry;91%
With K5 In acetonitrile at 20℃; for 1.25h;5 % Chromat.
With (NH4)8[CeW10O36]*20H2O In acetonitrile at 20℃; for 0.5h;55 %Chromat.
1-<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene
126644-72-2

1-<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene

Cs2CO3

Cs2CO3

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 20℃; for 1h;99%
1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;99%
Stage #1: 1-Chloro-4-iodobenzene With copper(l) iodide; cesiumhydroxide monohydrate; 1,3-diphenylpropanedione In water; dimethyl sulfoxide at 130℃; for 36h; Inert atmosphere;
Stage #2: With hydrogenchloride In dichloromethane; water; dimethyl sulfoxide at 20℃; Inert atmosphere; chemoselective reaction;
95%
With copper(l) iodide; potassium hydroxide In water at 100℃; Inert atmosphere;94%
potassium (4-chlorophenyl)trifluoroborate

potassium (4-chlorophenyl)trifluoroborate

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0333333h;99%
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation;60%
2-(4-chlorophenoxy)ethanol
1892-43-9

2-(4-chlorophenoxy)ethanol

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;99%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

p-chlorophenyl 2-benzoxazolyl ether
50798-82-8

p-chlorophenyl 2-benzoxazolyl ether

A

4-chloro-phenol
106-48-9

4-chloro-phenol

B

1-(2-benzoxazolyl)-1H-benzotriazole
25124-80-5

1-(2-benzoxazolyl)-1H-benzotriazole

Conditions
ConditionsYield
With hydridotetakis(triphenylphosphine)rhodium(I); o-phenylenebis(diphenylphosphine) In chlorobenzene for 5h; Inert atmosphere; Reflux;A 95%
B 99%
4-chlorophenyl acetate
876-27-7

4-chlorophenyl acetate

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; benzene at 80℃; for 40h;98%
With sodium tetrahydroborate; cobalt(II) chloride In ethanol at 0 - 25℃; for 10h;97%
With sodium hydrogencarbonate In water at 20℃; for 4h;97%
1-allyloxy-4-chlorobenzene
13997-70-1

1-allyloxy-4-chlorobenzene

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0333333h;98%
With iodine at 20℃; Reagent/catalyst;96%
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol at 0℃;90%
4-chloro-N-[2,2-dichloro-1-(4-chlorophenoxy)-2-phenylethyl]benzenesulfonamide
1329689-03-3

4-chloro-N-[2,2-dichloro-1-(4-chlorophenoxy)-2-phenylethyl]benzenesulfonamide

A

4-chloro-phenol
106-48-9

4-chloro-phenol

B

4-chloro-N-(2,2-dichloro-1-hydroxy-2-phenylethyl)benzenesulfonamide
360564-14-3

4-chloro-N-(2,2-dichloro-1-hydroxy-2-phenylethyl)benzenesulfonamide

Conditions
ConditionsYield
With waterA n/a
B 98%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;98%
sulfur bis(trifluoromethyl)amide chloride
1768-32-7

sulfur bis(trifluoromethyl)amide chloride

phenol
108-95-2

phenol

A

sulfur bis{bis(trifluoromethyl)amide}
1913-85-5

sulfur bis{bis(trifluoromethyl)amide}

B

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
In diethyl ether at 20℃; for 24h;A 95%
B 97%
4-chlorophenyl tetrahydro-2H-pyran-2-yl ether
20443-90-7

4-chlorophenyl tetrahydro-2H-pyran-2-yl ether

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With methanol at 20℃; for 0.5h;97%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;96%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃;96%
phenol
108-95-2

phenol

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With N-chloro-succinimide; 2C5HN10(3-)*2Mn(2+)*Cu(2+)*5H2O In acetonitrile at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; regioselective reaction;95%
With chloro(dimethyl)sulfonium chloride In dichloromethane at -25℃; for 4h;84%
Stage #1: phenol In acetonitrile at 80℃; for 0.166667h;
Stage #2: With N-chloro-succinimide In acetonitrile at 80℃; for 8h; regioselective reaction;
77%
di(p-tolyl) sulfoxide
1774-35-2

di(p-tolyl) sulfoxide

A

di-(p-tolyl)sulfane
620-94-0

di-(p-tolyl)sulfane

B

2-monochlorophenol
95-57-8

2-monochlorophenol

C

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With hydrogenchloride; phenol In dichloromethane at 0 - 25℃;A 95%
B n/a
C n/a
Z-L-Phe p-chlorophenyl ester
3272-95-5

Z-L-Phe p-chlorophenyl ester

H-Gly-NH2
598-41-4

H-Gly-NH2

A

Z-L-phenylalanylglycinamide
17187-05-2

Z-L-phenylalanylglycinamide

B

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With thiolsubtilisin In water; N,N-dimethyl-formamide Ambient temperature; pH 8.0 phosphate buffer containing PhB(OH)2 traces;A 95%
B n/a
With thiolsubtilisin In water; N,N-dimethyl-formamide Ambient temperature; further acyl donors and acyl acceptors; method for enzymic peptid segment coupling;A 95%
B n/a
4-chlorophenyl benzoate
2005-08-5

4-chlorophenyl benzoate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-Phenylbenzothiazole
883-93-2

2-Phenylbenzothiazole

B

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.75h; Hydrolysis; cyclization; debenzoylation;A n/a
B 95%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

acetonitrile complex of hypofluorous acid

acetonitrile complex of hypofluorous acid

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
In dichloromethane at 20℃;95%
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

oxygen
80937-33-3

oxygen

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry;95%
With methylene blue; N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20℃; for 7h; Schlenk technique; Irradiation;
(5‐chloro‐2‐hydroxyphenyl)boronic acid
89488-25-5

(5‐chloro‐2‐hydroxyphenyl)boronic acid

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
In dimethyl sulfoxide at 120℃; for 18h;95%
3-(4-chlorophenoxy)-1-propanol
18673-04-6

3-(4-chlorophenoxy)-1-propanol

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;95%
1-chloro-4-((2-methoxyethoxy)methoxy)benzene

1-chloro-4-((2-methoxyethoxy)methoxy)benzene

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;94%
With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h;94%
bis(4-chlorophenyl)sulfoxide
3085-42-5

bis(4-chlorophenyl)sulfoxide

A

bis(4-chlorophenyl)sulfide
5181-10-2

bis(4-chlorophenyl)sulfide

B

2-monochlorophenol
95-57-8

2-monochlorophenol

C

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
With hydrogenchloride; phenol In dichloromethane at 0 - 25℃;A 93%
B n/a
C n/a
acetic anhydride
108-24-7

acetic anhydride

4-chloro-phenol
106-48-9

4-chloro-phenol

4-chlorophenyl acetate
876-27-7

4-chlorophenyl acetate

Conditions
ConditionsYield
K5 In acetonitrile at 20℃; for 0.25h;100%
With magnesium(II) perchlorate at 80℃; for 0.25h;100%
With sodium hydroxide for 0.0125h; microwave irradiation;99%
4-chloro-phenol
106-48-9

4-chloro-phenol

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

4-(4-chlorophenoxy)nitrobenzene
1836-74-4

4-(4-chlorophenoxy)nitrobenzene

Conditions
ConditionsYield
With cesium fluoride/clinoptilolite In dimethyl sulfoxide at 110℃; for 0.15h; Ullmann Condensation;100%
With potassium fluoride supported on Clinoptilolite In dimethyl sulfoxide at 110 - 115℃; for 1.66667h;95%
With potassium carbonate In dimethyl sulfoxide at 70℃;92%
4-chloro-phenol
106-48-9

4-chloro-phenol

4-chloro-2,6-dinitrophenol
88-87-9

4-chloro-2,6-dinitrophenol

Conditions
ConditionsYield
With dinitrogen tetraoxide; ferric nitrate In ethyl acetate for 0.0833333h; Heating;100%
With chromium(III) nitrate; dinitrogen tetraoxide In ethyl acetate for 0.166667h; Nitration; reflux;98%
With Tetraethylene glycol; silica gel; dinitrogen tetraoxide In ethyl acetate for 0.833333h; Heating;98%
4-chloro-phenol
106-48-9

4-chloro-phenol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

4-chlorophenoxytrimethylsilane
17005-59-3

4-chlorophenoxytrimethylsilane

Conditions
ConditionsYield
With aluminum potassium sulfate dodecahydrate In acetonitrile at 20℃; for 0.333333h;100%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 20℃; for 0.25h;98%
With melamine-N2,N4,N6-trisulfonic acid at 20℃; for 0.166667h; neat (no solvent); chemoselective reaction;98%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-chloro-phenol
106-48-9

4-chloro-phenol

1-<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene
126644-72-2

1-<(tert-butyldimethylsilyl)oxy>-4-chlorobenzene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;100%
With dmap; triethylamine In [D3]acetonitrile at 25℃; for 0.2h;99%
With triethylamine at 20℃; for 0.166667h; Inert atmosphere;95%
dichloromethane
75-09-2

dichloromethane

4-chloro-phenol
106-48-9

4-chloro-phenol

bis(p-chlorophenoxy)methane
555-89-5

bis(p-chlorophenoxy)methane

Conditions
ConditionsYield
With potassium hydroxide; benzyltrimethylammonium chloride In water at 40℃; for 72h;100%
With potassium hydroxide; benzyltrimethylammonium chloride In dichloromethane at 40℃; for 72h;100%
Stage #1: 4-chloro-phenol With sodium hydride In 1-methyl-pyrrolidin-2-one
Stage #2: dichloromethane In 1-methyl-pyrrolidin-2-one at 40℃; for 9h;
98%
With 1-methyl-pyrrolidin-2-one; sodium hydride at 40℃; for 9h;98%
With sodium hydroxide; Amberlite IRA-400 (Cl-) 2.) reflux, 15 h; Yield given. Multistep reaction;
dabsyl chloride
56512-49-3

dabsyl chloride

4-chloro-phenol
106-48-9

4-chloro-phenol

4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 4-chloro-phenyl ester
146303-65-3

4-(4-Dimethylamino-phenylazo)-benzenesulfonic acid 4-chloro-phenyl ester

Conditions
ConditionsYield
With carbonate-bicarbonate In acetone; acetonitrile for 0.25h; Product distribution; other (mono-, di- and trihydric) phenols; effect of reaction time, pH, molar ratio, concentration;100%
With carbonate-bicarbonate buffer In acetone; acetonitrile 1.) 15 min, 2.) reflux;100%
With carbonate-bicarbonate buffer In acetone for 0.5h; Heating;
4-chloro-phenol
106-48-9

4-chloro-phenol

1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

(4-Chloro-phenoxy)-dimethyl-silane
30342-25-7

(4-Chloro-phenoxy)-dimethyl-silane

Conditions
ConditionsYield
100%
at 20 - 160℃; for 2h; Inert atmosphere;
4-chloro-phenol
106-48-9

4-chloro-phenol

phenol
108-95-2

phenol

Conditions
ConditionsYield
With hydrogen; sodium hydroxide In water under 760.051 Torr; for 0.833333h; Kinetics; Reagent/catalyst; Solvent; Green chemistry;100%
With hydrogen; sodium hydroxide In water at 20℃; for 2h; Kinetics; Catalytic behavior; Solvent; Reagent/catalyst;99.1%
With hydrogen; sodium hydroxide In water at 25℃; under 760.051 Torr; for 2h; Reagent/catalyst; Solvent;99.9%
3,5-dinitrobenzotrifluoride
401-99-0

3,5-dinitrobenzotrifluoride

4-chloro-phenol
106-48-9

4-chloro-phenol

1-(4-chlorophenoxy)-3-nitro-5-trifluoromethylbenzene

1-(4-chlorophenoxy)-3-nitro-5-trifluoromethylbenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 98℃; for 3h;100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h; Activation energy; Inert atmosphere;54%
With potassium carbonate In N,N-dimethyl-formamide
4-fluorobenzonitrile
1194-02-1

4-fluorobenzonitrile

4-chloro-phenol
106-48-9

4-chloro-phenol

4-(4'-chlorophenoxy)benzonitrile
74448-92-3

4-(4'-chlorophenoxy)benzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide for 24h; Reflux;100%
With potassium carbonate In N,N-dimethyl-formamide Reflux;96%
With sodium carbonate In N,N-dimethyl-formamide for 24h; Reflux;95%
bisphenol AF bisoxalyl chloride adduct
335148-89-5

bisphenol AF bisoxalyl chloride adduct

4-chloro-phenol
106-48-9

4-chloro-phenol

bisphenol-AF bis(4-chlorophenyl oxalate)

bisphenol-AF bis(4-chlorophenyl oxalate)

Conditions
ConditionsYield
In dichloromethane at -20℃; Heating / reflux;100%
{Ni(Al(O-i-Pr)4)2}

{Ni(Al(O-i-Pr)4)2}

4-chloro-phenol
106-48-9

4-chloro-phenol

{Ni(Al(O-i-Pr)(p-ClC6H4O)3)2}

{Ni(Al(O-i-Pr)(p-ClC6H4O)3)2}

Conditions
ConditionsYield
In benzene byproducts: isopropanol; anhyd. conditions; Ni(Al(OC3H7)4)2 : p-chlorophenol = 1 : 6; refluxed (4 h); solvent removed (reduced pressure);100%
{Co(Al(O-i-Pr)4)2}

{Co(Al(O-i-Pr)4)2}

4-chloro-phenol
106-48-9

4-chloro-phenol

{Co(Al(O-i-Pr)2(p-ClC6H4O)2)2}

{Co(Al(O-i-Pr)2(p-ClC6H4O)2)2}

Conditions
ConditionsYield
In benzene byproducts: isopropanol; anhyd. conditions; Co(Al(OC3H7)4)2 : p-chlorophenol = 1 : 4; refluxed (2 h); solvent removed (reduced pressure); elem.anal.;100%
2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

4-chloro-phenol
106-48-9

4-chloro-phenol

4-(2-iodobenzyloxy)-1-chlorobenzene
1332326-20-1

4-(2-iodobenzyloxy)-1-chlorobenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃;100%
4-chloro-phenol
106-48-9

4-chloro-phenol

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

A

4-chlorophenyl benzoate
2005-08-5

4-chlorophenyl benzoate

B

potassium 2,4-dinitrophenolate
14314-69-3

potassium 2,4-dinitrophenolate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 5h;A 100%
B n/a
ethyl 3-(chloromethyl)-4-methoxybenzoate
858124-04-6

ethyl 3-(chloromethyl)-4-methoxybenzoate

4-chloro-phenol
106-48-9

4-chloro-phenol

ethyl 3-[(4-chlorophenoxy)methyl]-4-methoxybenzoate
1360060-15-6

ethyl 3-[(4-chlorophenoxy)methyl]-4-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 13h;100%
5-methyl-3,4-hexadien-1-ol
54795-27-6

5-methyl-3,4-hexadien-1-ol

4-chloro-phenol
106-48-9

4-chloro-phenol

1-chloro-4-(5-methylhexa-3,4-dienyloxy)benzene
1376520-79-4

1-chloro-4-(5-methylhexa-3,4-dienyloxy)benzene

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;100%
4-chloro-phenol
106-48-9

4-chloro-phenol

dimethylamino sulfonyl chloride
13360-57-1

dimethylamino sulfonyl chloride

4-chlorophenyl N,N-dimethylsulfamate
1135-05-3

4-chlorophenyl N,N-dimethylsulfamate

Conditions
ConditionsYield
Stage #1: 4-chloro-phenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 0.166667h;
Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 16h;
100%
Stage #1: 4-chloro-phenol With sodium hydride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃; for 10h;
Stage #2: dimethylamino sulfonyl chloride In 1,2-dimethoxyethane; mineral oil at 0 - 20℃;
83%
2-methylbenzoic acid 2-pyridinyl ester
73686-46-1

2-methylbenzoic acid 2-pyridinyl ester

4-chloro-phenol
106-48-9

4-chloro-phenol

2-methyl-benzoic acid-(4-chloro-phenyl ester)
500285-59-6

2-methyl-benzoic acid-(4-chloro-phenyl ester)

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 60℃; for 48h; Green chemistry;100%
2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

4-chloro-phenol
106-48-9

4-chloro-phenol

C9H5Cl2N3O

C9H5Cl2N3O

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 15h;100%
2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

4-chloro-phenol
106-48-9

4-chloro-phenol

2-chloro-3-(4-chlorophenoxy)pyrazine

2-chloro-3-(4-chlorophenoxy)pyrazine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 15h;100%
3-chloro-4-fluoronitrobenzene
350-30-1

3-chloro-4-fluoronitrobenzene

4-chloro-phenol
106-48-9

4-chloro-phenol

4-(4'-chlorophenoxy)-3-chloronitrobenzene
22544-07-6

4-(4'-chlorophenoxy)-3-chloronitrobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;100%
With caesium carbonate In dimethyl sulfoxide for 4h;
C16H11I

C16H11I

4-chloro-phenol
106-48-9

4-chloro-phenol

C22H15ClO

C22H15ClO

Conditions
ConditionsYield
Stage #1: 4-chloro-phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h;
Stage #2: C16H11I In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h;
100%
fluoroformyl chloride
353-49-1

fluoroformyl chloride

4-chloro-phenol
106-48-9

4-chloro-phenol

4-chlorophenyl fluoroformate
1644-73-1

4-chlorophenyl fluoroformate

Conditions
ConditionsYield
With triethylamine In toluene at 60℃;99.8%

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106-48-9Relevant articles and documents

Photodegradation of Azole Fungicide Triadimefon

Nag, Subir K.,Dureja, Prem

, p. 294 - 298 (1997)

To examine the photostability of the fungicide triadimefon [1-(4-chlorophenoxy)-3,3-dimethyl-1H-(1,2,4-triazol-1-yl)butan-2-one] in the field, model experiments with organic solvents were performed. Photolysis in methanol, hexane, and acetone resulted in considerable formation of 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one, 1-[(4-chlorophenoxy)methyl]-1H-1,2,4-triazole, 1H-(1,2,4-triazol-1-yl)-3,3-dimethylbutan-2-one, and 1-phenoxy-3,3-dimethyl-1H-(1,2,4-triazol-1-yl)butan-2-one. The rate of photodegradation in different solvents followed first-order rate kinetics with a significant correlation coefficient.

Regioselective chlorination of phenols in the presence of tetrahydrothiopyran derivatives

Smith, Keith,Williams, Des,El-Hiti, Gamal A.

, p. 529 - 538 (2019)

Four six-membered cyclic sulfides, namely tetrahydrothiopyran, 3-methyltetrahydrothiopyran, 4-methyltetrahydrothiopyran and 4,4-dimethyltetrahyrdrothiopyran have been used as moderators in chlorination reactions of various phenols with sulfuryl chloride in the presence of aluminum or ferric chloride. On chlorination of phenol, ortho-cresol and meta-cresol the para/ortho chlorination ratios and yields of the para-chloro isomers are higher than when no cyclic sulfide is used for all of the cyclic sulfides, but chlorination of meta-xylenol is less consistent, with some cyclic sulfides producing higher p/o ratios and others producing lower ratios than reactions having no sulfide present.

Gas-phase oxychlorination of benzene

Born, Jan G. P.,Wart, Hans W. A. van der,Mulder, Peter,Louw, Robert

, p. 262 - 270 (1993)

Homogeneous gas-phase oxychlorination of benzene has been examined in a flow system between 722 and 1174 K.Experiments were performed at atmospheric pressure with nitrogen as an inert carrier gas, containing about equal molar amounts of oxygen, HCl and benzene.Apart from chlorobenzene, substantial amounts of o- and p-chlorophenol are produced.Using benzonitrile rather than benzene, the three isomers of ClC6H4CN are formed in about equal amounts.These findings suggest as homolytic mechanism with aryl radicals as key indermediates.Thermokinetic analysis points to formation of chloro phenols via reaction of phenoxyl (formed from phenyl and oxygen) with HOCl.Chlorination, C6H6 -> C6H5Cl, is explained by reaction between phenyl radicals and HOCl.With increasing temperature (and therefore, oxygen consumption), slow combustion is replaced by pyrolysis as the major reaction channel.As a result, above ca. 1000 K, the production of chlorobenzene diminishes, ultimately being governed by the equilibrium: C6H6 + HCl C6H5Cl + H2.

Regiospecific Chlorination of Aromatic Substrates using Donor-Acceptor and Hydrogen Bonding Interactions

Guy, Alain,Lemaire, Marc,Guette, Jean-Paul

, p. 8 - 9 (1980)

The chlorination of aromatic substances has been achieved with good regioselectivity using 2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one and 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dien-1-one as chlorinating agents.

HIGH ORTHO-SELECTIVITY IN THE CHLORINATION OF PHENOLS WITH N-CHLORODIALKYLAMINES IN THE PRESENCE OF SILICA.

Smith, Keith,Butters, Michael,Nay, Barry

, p. 1319 - 1322 (1988)

Phenols are readily chlorinated by N-chlorodialkylamines in the presence of silica.Furthermore, this approach allows greater selectivity for mono:di and ortho: para chlorination than is possible with many other approaches.

Kinetics and mechanism of the reaction of α-phenoxypropanoic acids with sodium salt of N-chlorobenzene-sulphonamide: EDTA catalysis

Meenakshisundaram, Subbiah,Selvaraju

, p. 27 - 33 (2002)

EDTA smoothly catalyses the oxidation cum chlorination of some 17 α-phenoxypropanoic acids with sodium salt of N-chlorobenzenesulphonamide in acidic solution. A ternary intermediate can be envisaged for describing the enhanced reactivity. Imperfections are observed in the linear Hammett relationship in the case of-NO2 substituents, irrespective of the position. The susceptibility constant, p(≈ + 1) indicates the development of an electron-rich transition state.

Surface decorated coral-like magnetic BiFeO3 with Au nanoparticles for effective sunlight photodegradation of 2,4-D and E. coli inactivation

Lam, Sze-Mun,Jaffari, Zeeshan Haider,Sin, Jin-Chung,Zeng, Honghu,Lin, Hua,Li, Haixiang,Mohamed, Abdul Rahman,Ng, Ding-Quan

, (2021)

In this report, gold nanoparticle-decorated on the coral-like magnetic BiFeO3 (Au-BiFeO3) composite has been successfully fabricated by facile two-steps hydrothermal technique. Incorporation of Au nanoparticles on the BiFeO3/su

Hydroxylation of Benzene with Dinitrogen Monoxide over H-ZSM-5 Zeolite

Suzuki, Eiichi,Nakashiro, Katsumi,Ono, Yoshio

, p. 953 - 956 (1988)

Phenol was obtained from benzene and dinitrogen monoxide over H-ZSM-5-zeolite at 603 K, a phenol yield on a benzene basis being 8.1percent at partial pressures of benzene and dinitrogen monoxide of 6.9 kPa and 51 kpa, respectively.Neither CO nor CO2 was detected in the product.

Nanoscale Fe0particles for pentachlorophenol removal from aqueous solution: Temperature effect and particles transformation

Cheng, Rong,Zheng, Xiang,Liu, Peng,Wang, Jian-Long

, p. 6941 - 6949 (2014)

Pentachlorophenol (PCP), as an important contaminant which was toxic and intractable, has received extensive attention. In this paper, the temperature effect during the transformation of PCP using nanoscale Fe0particles was studied, and the transformation processes of PCP and iron particles was explained. The results revealed that the removal processes of PCP followed pseudo first-order kinetics. The scale of dechlorination to the transformation of PCP increased with the increase of temperature, though the transformation rate decreased after reacting for 2 h under the experimental condition. However, the initial apparent transformation rate constants were calculated to be 0.312-0.536 h-1at the temperature of 20-50°C, which showed an increase of transformation rate along with the increase of temperature. And the surface-area-normalized rate constants were calculated to be 9.50 × 10-3- 1.63 × 10-2L·h-1· m-2. The experimental activation energy was calculated to be 15.0 kJ · mol-1from these rate constants using Arrhenius equation. A phenomenon observed at 50°C indicated that more than one chlorine atom was removed from PCP and suggested β-elimination might be the major pathway for transformation. Sorption experiments showed that the sorption process on the surface of particles could be ignored in the kinetics and thermodynamics models. The changes of morphologies of nanoparticles before and after reaction indicated the transformation process of iron particles, and could be used to explain the changes of activity of nanoparticles. Magnetite (Fe3O4) and/or maghemite (Fe2O3) and lepidocrocite (γ-FeOOH) were corrosion products of iron. And along with the increase of temperature, the increased intensity of XRD peaks revealed the related a better crystallizing. Copyright

Atmospheric chemistry of the phenoxy radical, C6H5O(?): UV spectrum and kinetics of its reaction with NO, NO2, and O2

Platz,Nielsen,Wallington,Ball,Hurley,Straccia,Schneider,Sehested

, p. 7964 - 7974 (1998)

Pulse radiolysis and FT-IR smog chamber experiments were used to investigate the atmospheric fate of C6H5O(?) radicals. Pulse radiolysis experiments gave σ(C6H5O(?))235 nm = (3.82 ± 0.48) × 10-17 cm2 molecule-1, k(C6H5O(?) + NO) = (1.88 ± 0.16) × 10-12, and k(C6H5O(?) + NO2) = (2.08 ± 0.15) × 10-12 cm3 molecule-1 s-1 at 296 K in 1000 mbar of SF6 diluent. No discernible reaction of C6H5O(?) radicals with O2 was observed in smog chamber experiments, and we derive an upper limit of k(C6H5O(?) + O2) -21 cm3 molecule-1 s-1 at 296 K. These results imply that the atmospheric fate of phenoxy radicals in urban air masses is reaction with NOx. Density functional calculations and gas chromatography-mass spectrometry are used to identify 4-phenoxyphenol as the major product of the self-reaction of C6H5O(?) radicals. As part of this study, relative rate techniques were used to measure rate constants for reaction of Cl atoms with phenol [k(Cl + C6H5OH) = (1.93 ± 0.36) × 10-10], several chlorophenols [k(Cl + 2-chlorophenol) = (7.32 ± 1.30) × 10-12, k(Cl + 3-chlorophenol) = (1.56 ± 0.21) × 10-10, and k(Cl + 4-chlorophenol) = (2.37 ± 0.30) × 10-10], and benzoquinone [k(Cl + benzoquinone) = (1.94 ± 0.35) × 10-10], all in units of cm3 molecule-1 s-1. A reaction between molecular chlorine and C6H5OH to produce 2- and 4-chlorophenol in yields of (28 ± 3)% and (75 ± 4)% was observed. This reaction is probably heterogeneous in nature, and an upper limit of k(Cl2 + C6H5OH) ≤ 1.9 × 10-20 cm3 molecule-1 s-1 was established for the homogeneous component. These results are discussed with respect to the previous literature data and to the atmospheric chemistry of aromatic compounds.

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