120-32-1

Basic information

• Product Name: Clorofene
• Synonyms: 4-Chloro-2-(phenylmethyl)phenol;4-CHLORO-2-BENZYL PHENOL;5-CHLORO-2-HYDROXYDIPHENYLMETHANE;2-BENZYL-4-CHLOROPHENOL;2-BENZYL-4-CHLORPHENOL;2-BENZYL-P-CHLOROPHENOL;benzyl-p-chlorophenol;BENZYL(2-)-4-CHLOROPHENOL
• CAS NO: 120-32-1
• Molecular Formula: C₁₃H₁₁ClO
• Molecular Weight: 218.68
• EINECS: 204-385-8
• Product Categories: Phenoles and thiophenoles;Alphabetic;B;BA - BH
• Mol File: 120-32-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 46-49 °C(lit.)
• Boiling Point: 160-162 °C(lit.)
• Flash Point: >230 °F
• Appearance: white to light tan or pink flakes or white crystals
• Density: 1.188 g/mL at 25 °C(lit.)
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 0.12g/l
• PKA: 9.81±0.43(Predicted)
• Water Solubility: <0.1 g/100 mL at 16℃
• Merck: 14,2407
• BRN: 1959194
• CAS DataBase Reference: Clorofene(CAS DataBase Reference)
• NIST Chemistry Reference: Clorofene(120-32-1)
• EPA Substance Registry System: Clorofene(120-32-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-37/38-41-50/53-51/53-36/37/38
• Safety Statements: 26-39-60-61-37/39
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: GO7175000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 120-32-1(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 120-32-1 differently. You can refer to the following data:
1. In household, hospital and veterinary disinfectant preparations.
2. Used in soaps, anionic detergents, cosmetics and aerosol spray products. It is a useful biochemical for proteomics research.

General Description

White to light tan or pink flakes or white crystals. Insoluble in water. Slight phenolic odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Clorofene is incompatible with acids and oxidizing agents . Is sensitive to light. Stable at temperatures up to 77°F when protected from light, but storage at 140° F causes decomposition.

Hazard

Highly toxic, an irritant.

Fire Hazard

Clorofene is combustible.

Flammability and Explosibility

Notclassified

InChI:InChI=1/2C13H11ClO/c2*14-12-6-7-13(15)11(9-12)8-10-4-2-1-3-5-10/h2*1-7,9,15H,8H2

Synthetic route

4-chloro-phenol (106-48-9) + benzyl alcohol (100-51-6) → chlorophene (120-32-1)

Conditions	Yield
With sulfated zirconia at 140℃; for 1.5h;	88%
With aluminium trichloride; Petroleum ether at 20 - 35℃;

4-chloro-phenol (106-48-9) + benzyl N-phenyl-sulfamoylcarbamate (497949-70-9) → chlorophene (120-32-1) + 4-chlorophenyl benzyl ether (7700-27-8)

Conditions	Yield
at 120℃; for 5h; Friedel-Crafts alkylation;	A 19% B 25%

benzyl bromide (100-39-0) + 4-chloro-phenol (106-48-9) → chlorophene (120-32-1) + 2,6-dibenzyl-4-chlorophenol (40395-08-2)

Conditions	Yield
With zinc(II) chloride at 60℃; for 2h; Friedel-Crafts Alkylation; Inert atmosphere;	A 0.6% B 1.2%

o-Benzylphenol (28994-41-4) → chlorophene (120-32-1)

Conditions	Yield
With sulfuryl dichloride anschliessendes Erwaermen auf 100grad;

4-chlorophenyl benzyl ether (7700-27-8) → chlorophene (120-32-1) + 2,7-dichloro-9-phenyl-xanthene (101879-94-1) + 4-chloro-phenol (106-48-9) + toluene (108-88-3)

Conditions	Yield
at 260℃;

benzyl chloride (100-44-7) + sodium 4-chlorophenolate (1193-00-6) → chlorophene (120-32-1) + 4-chlorophenyl benzyl ether (7700-27-8)

Conditions	Yield
With toluene

sodium methylate (124-41-4) + benzyl chloride (100-44-7) + 4-chloro-phenol (106-48-9) → chlorophene (120-32-1) + 4-chlorophenyl benzyl ether (7700-27-8)

Conditions	Yield
With methanol Dampfbad;

benzyl chloride (100-44-7) + 4-chloro-phenol (106-48-9) + sodium 4-chlorophenolate (1193-00-6) → chlorophene (120-32-1) + 4-chlorophenyl benzyl ether (7700-27-8)

benzyl chloride (100-44-7) + 4-chloro-phenol (106-48-9) → chlorophene (120-32-1)

Conditions	Yield
With zinc(II) chloride at 60℃; zuletzt bei 90grad;
With aluminium trichloride; Petroleum ether at 20 - 35℃;
With iron(III) oxide

benzyl methyl ether (538-86-3) + 4-chloro-phenol (106-48-9) → chlorophene (120-32-1)

Conditions	Yield
With zinc(II) chloride at 100℃; Ausschluss von Feuchtigkeit;

dibenzyl ether (103-50-4) + 4-chloro-phenol (106-48-9) → chlorophene (120-32-1)

Conditions	Yield
With zinc(II) chloride at 100℃; Ausschluss von Feuchtigkeit;

carbonic acid bis-(4-chloro-2-chloromethyl-phenyl ester) + benzene (71-43-2) → chlorophene (120-32-1)

Conditions	Yield
With aluminium trichloride Hydrolyse des Reaktionsprodukts;

(5-chloro-2-hydroxyphenyl)phenylmethanone (85-19-8) → chlorophene (120-32-1)

Conditions	Yield
(i) ClCO2Et, Et3N, (ii) NaBH4; Multistep reaction;

aluminium trichloride (7446-70-0) + benzyl chloride (100-44-7) + 4-chloro-phenol (106-48-9) + petroleum ether → chlorophene (120-32-1)

aluminium trichloride (7446-70-0) + carbonic acid bis-(4-chloro-2-chloromethyl-phenyl ester) + benzene (71-43-2) → chlorophene (120-32-1)

Conditions	Yield
at 20℃; zuletzt Behandeln bei Siedetemperatur;

benzyl alcohol (100-51-6) + BocNH-C(=NBoc)-SCH2-terminated resin → chlorophene (120-32-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.5 h / -10 °C 1.2: 78 percent / tetrahydrofuran / 2 h 2.1: 19 percent / 5 h / 120 °C View Scheme

carbonic acid bis-(4-chloro-2-methyl-phenyl ester) (39489-74-2) → chlorophene (120-32-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine / 170 °C 2: AlCl3 / Hydrolyse des Reaktionsprodukts View Scheme

benzyl bromide (100-39-0) + 4-chloro-phenol (106-48-9) → C20H17ClO (1050575-40-0) + chlorophene (120-32-1)

Conditions	Yield
at 120℃; for 0.583333h; microwave irradiation;	A 11 % Chromat. B 43 % Chromat.

benzyl bromide (100-39-0) + 4-chloro-phenol (106-48-9) → C20H17ClO (1050575-40-0) + chlorophene (120-32-1) + 4-chlorophenyl benzyl ether (7700-27-8) + benzyl 2-benzyl-4-chlorophenyl ether

Conditions	Yield
With potassium carbonate at 120℃; for 0.583333h; microwave irradiation;	A 3 % Chromat. B 14 % Chromat. C 73 % Chromat. D 10 % Chromat.

chlorophene (120-32-1) → C13H10ClNO3 (92044-51-4)

Conditions	Yield
With hydrogenchloride; potassium nitrate; sodium nitrite In diethyl ether; water for 2h;	100%

chlorophene (120-32-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → (2-benzyl-4-chloro-phenoxy)-trimethyl-silane

Conditions	Yield
With tetrabutylammonium phthalimide-N-oxyl In ethyl acetate for 0.416667h; Reflux;	95%

formaldehyd (50-00-0) + chlorophene (120-32-1) + bis[(2-pyridyl)methyl]amine (1539-42-0) → 2-benzyl-6-((bis(pyridin-2-ylmethyl)amino)methyl)-4-chlorophenol

Conditions	Yield
In methanol for 14h; Mannich Aminomethylation; Reflux;	82%

chlorophene (120-32-1) + 4-bromobenzenecarbonitrile (623-00-7) → 4-(2-benzyl-4-chlorophenoxy)benzonitrile

Conditions	Yield
With 2-Picolinic acid; copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere;	75%

chlorophene (120-32-1) + 1,3-dibromo-propane (109-64-8) → 2-benzyl-1-(3-bromo-propoxy)-4-chloro-benzene (787576-03-8)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20 - 80℃; for 1h;	72%

chlorophene (120-32-1) → 2-benzyl-4-chlorophenylsulfamate

Conditions	Yield
With formic acid; isocyanate de chlorosulfonyle In 1-methyl-pyrrolidin-2-one at 20℃; for 3h;	70%

chlorophene (120-32-1) + 2-bromoethanol (540-51-2) → 2-benzyl-1-(2-bromoethoxy)-4-chlorobenzene (68032-82-6)

Conditions	Yield
Stage #1: chlorophene With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.166667h; Mitsunobu reaction; Stage #2: 2-bromoethanol In tetrahydrofuran at 20℃; for 24h; Mitsunobu reaction;	67%
Stage #1: chlorophene With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 2-bromoethanol In tetrahydrofuran at 20℃; for 24h;	67%

(E)-1,3-diphenyl-2-propen-1-ol (62668-02-4) + chlorophene (120-32-1) → (E)-2-benzyl-4-chloro-6-(1,3-diphenylallyl)phenol

Conditions	Yield
With perrhenic acid anhydride In acetonitrile at 80℃; for 7h; Friedel-Crafts Alkylation;	62%

chlorophene (120-32-1) + 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (137886-82-9) → 4'-chloro-2'-benzylphenyl 2,3,4,6-tetra-O-acetyl-5-thio-β-D-glucopyranoside

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In toluene at 0 - 20℃; for 12h;	56%

chlorophene (120-32-1) + methyl 2-(4-(hydroxymethyl)-3,5-dimethylphenoxy)acetate → methyl 2-(4-(3-benzyl-4-hydroxybenzyl)-3,5-dimethylphenoxy)acetate

Conditions	Yield
With Dimethyl oxalate; manganese; 4,5-Diazafluoren-9-one; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In N,N-dimethyl-formamide at 80℃; for 35h; Glovebox; Inert atmosphere;	54%
With Dimethyl oxalate; 1,1'-bis-(diphenylphosphino)ferrocene; manganese; 4,5-Diazafluoren-9-one; [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In N,N-dimethyl-formamide at 80℃; for 35h; Inert atmosphere; Sealed tube; chemoselective reaction;	54%

formaldehyd (50-00-0) + chlorophene (120-32-1) → 6,6'-dibenzyl-4,4'-dichloro-2,2'-methanediyl-di-phenol

hexane-1,6-disulfonyl chloride (57630-57-6) + chlorophene (120-32-1) → hexane-1,6-disulfonic acid bis-(2-benzyl-4-chloro-phenyl ester) (104440-68-8)

Conditions	Yield
With sodium hydroxide

Upstream product

• 100-44-7 benzyl chloride 
• 1193-00-6 sodium 4-chlorophenolate 
• 124-41-4 sodium methylate 
• 106-48-9 4-chloro-phenol 
• 538-86-3 benzyl methyl ether 
• 103-50-4 dibenzyl ether 
• 100-51-6 benzyl alcohol 
• 85-19-8 (5-chloro-2-hydroxyphenyl)phenylmethanone 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 100-39-0 benzyl bromide 
• 7700-27-8 4-chlorophenyl benzyl ether 
• 39489-74-2 carbonic acid bis-(4-chloro-2-methyl-phenyl ester) 
• 497949-70-9 benzyl N-phenyl-sulfamoylcarbamate 

Downstream Products

• 104440-68-8 hexane-1,6-disulfonic acid bis-(2-benzyl-4-chloro-phenyl ester) 
• 343229-39-0 2-Benzyl-1-(4-bromo-butoxy)-4-chloro-benzene 
• 19809-68-8 3-(2-Benzyl-4-chlorphenoxy)-2-hydroxypropylchlorid 
• 19578-81-5 2-benzyl-4,6-dichloro-phenol 
• 40395-13-9 2-benzyl-4-chloro-1-methoxybenzene 
• 92044-51-4 C₁₃H₁₀ClNO₃ 
• 148-18-5 sodium N,N-diethyldithiocarbamate 
• 28994-41-4 o-Benzylphenol 
• 5333-61-9 2-benzylcyclohexan-1-ol 
• 68032-82-6 2-benzyl-1-(2-bromoethoxy)-4-chlorobenzene 
• 1351862-39-9 1-(2-(2-benzyl-4-chlorophenoxy)ethyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 1351862-32-2 1-(2-(2-benzyl-4-chlorophenoxy)ethyl)pyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Identification, library synthesis and anti-vibriosis activity of 2-benzyl-4-chlorophenol from cultures of the marine bacterium Shewanella halifaxensis

Summer Gut Syndrome (SGS) is caused by various Vibrio bacterial species and can have negative effects on aquaculture farms worldwide. In New Zealand, SGS is caused by Vibrio harveyii infecting King Salmon (Oncorhynchus tshawytscha). To find leads for the prevention of SGS, we screened the inhibitory effects of 16 strains of Shewanella upon V. harveyii growth in competitive solid phase cultures. The detailed investigation of Shewanella halifaxensis IRL548 revealed 2-benzyl-4-chlorophenol (1), a known, commercially available antibacterial agent, as the major bioactive component. Synthesis of a small library of congeners to confirm the natural product identity and to provide a structure-activity relationship for the observed activity was also completed. Compound 1 exhibits moderate activity against two pathogenic microorganisms.

Zirconia-modified superacid UDCaT-5: An efficient and versatile catalyst for alkylation reactions under solvent-free conditions

UDCaT-5, a modified version of zirconia, efficiently catalyzes alkylation of phenols with alcohols under environmentally safe, heterogeneous reaction conditions with high selectivity and in excellent yields. The high content present in UDCaT-5 with preservation of tetragonal phase of zirconia was responsible for the superactivity. Several phenolic compounds carrying either electron-sulfer releasing or electron-withdrawing substituents in the ortho, meta, and para positions afforded high yields of the products. Copyright Taylor & Francis Group, LLC.

Agent for protecting sawn timber

The present invention relates to an agent or concentrate for protecting sawn timber against wood-discolouring fungi, containing a fungicide on phenol basis and a fungicide on organo-iodine basis, optionally fungicides and insecticides, dissolved in an organochemical solvent or solvent mixture or in a mixture of water and organochemical solvent or solvent mixture and at least one emulsifier.