133-53-9

Basic information

• Product Name: 2,4-Dichloro-3,5-dimethylphenol
• Synonyms: 2,4-Dichloro-3,5-xelenol (DCMX);DICHLORO-m-XYLENOL;DcmxC8H8Cl2O2,4-Dichloro-3,5-Xylenol;Dcmx(Parachloxylenol);Parachloxylenol(Dcmx);2,4DichloroMetaXylenol;Dcmx2,4-Dichloro-3,5-Xylenol;Phenol, 2,4-dichloro-3,5-dimethyl-
• CAS NO: 133-53-9
• Molecular Formula: C₈H₈Cl₂O
• Molecular Weight: 191.05
• EINECS: 205-109-9
• Product Categories: Antibacterial agent;Preservative
• Mol File: 133-53-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 91-96 °C
• Boiling Point: 273.74°C (rough estimate)
• Flash Point: 138°C
• Appearance: light beige powder
• Density: 1.2559 (rough estimate)
• Vapor Pressure: 0.00526mmHg at 25°C
• Refractive Index: 1.5605 (estimate)
• PKA: 8.30±0.28(Predicted)
• Merck: 14,3076
• BRN: 2209273
• CAS DataBase Reference: 2,4-Dichloro-3,5-dimethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-3,5-dimethylphenol(133-53-9)
• EPA Substance Registry System: 2,4-Dichloro-3,5-dimethylphenol(133-53-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: 2430
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 133-53-9(Hazardous Substances Data)

Usage

Chemical Properties

light beige powder

Uses

Different sources of media describe the Uses of 133-53-9 differently. You can refer to the following data:
1. Bacteriostat in soaps; mold inhibitor, preservative.
2. 2,4-Dichloro-3,5-dimethylphenol is used as a preservative in aqueous functional fluids and as a microbicide in disinfectants, but in comparison with PCMX (38) is of lesser importance because it has a more intense smell and is less soluble in water.

Preparation

2,4-Dichloro-3,5-dimethylphenol is obtained by reaction of 4-chloro-3,5-dimethylphenol with N-chloroacetamide in glacial acetic acid with concentrated HCl.

Solubility in organics

2,4-Dichloro-3,5-dimethylphenol is soluble in alkali solutions, and readily soluble in organic solvents.

Solubility in water

It has a solubility in water of 0.2 g/L at 20 °C.

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE WHITE TO OFF WHITE POWDER OR BLOCK MASS POWDER ODOUR PHENOLIC CHARACTERISTIC ODOUR CONTENT OF ACTIVE MATTER 98.0% min MELT RANGE 92-95 ° C BOILING POINT 269 ° C SOLUBILITY 20 ° C/WATER 0.2g/L DRY LOSS 0.10% max IRON 80 ppm max RESIDUE ON IGNITION 0.5% max WATER 0.5% max TOTAL HEAVY METAL 0.001% max SOLUBILITY CLEAR SOLUTION

TEST ITEMS

SPECIFICATION

APPEARANCE

WHITE TO OFF WHITE POWDER OR BLOCK MASS POWDER

ODOUR

PHENOLIC CHARACTERISTIC ODOUR

CONTENT OF ACTIVE MATTER

98.0% min

MELT RANGE

92-95 ° C

BOILING POINT

269 ° C

SOLUBILITY 20 ° C/WATER

0.2g/L

DRY LOSS

0.10% max

IRON

80 ppm max

RESIDUE ON IGNITION

0.5% max

WATER

0.5% max

TOTAL HEAVY METAL

0.001% max

SOLUBILITY

CLEAR SOLUTION

InChI:InChI=1/C8H8Cl2O/c1-4-3-6(11)8(10)5(2)7(4)9/h3,11H,1-2H3

Synthetic route

N-chloroacetamide (598-49-2) + 4-Chloro-3,5-dimethylphenol (88-04-0) → 2,4-dichloro-3,5-dimethylphenol (133-53-9)

Conditions	Yield
With hydrogenchloride; acetic acid

3,5-Dimethylphenol (108-68-9) → 2,4-dichloro-3,5-dimethylphenol (133-53-9)

Conditions	Yield
With sulfuryl dichloride; chloroform
With hydrogenchloride; manganese(II) sulfate; dihydrogen peroxide In water at 80℃;	86 %Chromat.

3,5-Dimethylphenol (108-68-9) → 4-Chloro-3,5-dimethylphenol (88-04-0) + 2,4-dichloro-3,5-dimethylphenol (133-53-9)

Conditions	Yield
With N-chlorotriethylammonium chloride In trifluoroacetic acid Ambient temperature; Yield given. Yields of byproduct given;

chloroform (67-66-3) + 3,5-Dimethylphenol (108-68-9) + sulfuryl chloride (2 mol) → 2,4-dichloro-3,5-dimethylphenol (133-53-9)

3,5-Dimethylphenol (108-68-9) → 4-Chloro-3,5-dimethylphenol (88-04-0) + 2,4-dichloro-3,5-dimethylphenol (133-53-9) + o-chloro-m-xylenol (5538-41-0)

Conditions	Yield
With iron(III) chloride; sulfuryl dichloride; 1,3-bis(methylthio)propane In dichloromethane at 20℃; for 4h; Reagent/catalyst; regioselective reaction;	A 75 %Chromat. B 9 %Chromat. C 10 %Chromat.

2,4-dichloro-3,5-dimethylphenol (133-53-9) + methyl iodide (74-88-4) → 2,4-dichloro-3,5-dimethylanisole (23400-00-2)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃;	95%

2,4-dichloro-3,5-dimethylphenol (133-53-9) → 2,4,6-trichloro-3,5-dimethyl-phenol (6972-47-0)

Conditions	Yield
With chlorine

2,4-dichloro-3,5-dimethylphenol (133-53-9) → 2-bromo-4,6-dichloro-3,5-dimethyl-phenol (874519-00-3)

Conditions	Yield
With bromine; acetic acid

2,4-dichloro-3,5-dimethylphenol (133-53-9) → 2,4-dichloro-6-iodo-3,5-dimethyl-phenol

Conditions	Yield
With Iodine monochloride; acetic acid

2,4-dichloro-3,5-dimethylphenol (133-53-9) + 4-Methylbenzyl chloride (104-82-5) → (2,4-dichloro-3,5-dimethyl-phenyl)-(4-methyl-benzyl)-ether

Upstream product

• 108-68-9 3,5-Dimethylphenol 
• 67-66-3 chloroform 
• 598-49-2 N-chloroacetamide 
• 88-04-0 4-Chloro-3,5-dimethylphenol 

Downstream Products

• 6972-47-0 2,4,6-trichloro-3,5-dimethyl-phenol 
• 874519-00-3 2-bromo-4,6-dichloro-3,5-dimethylphenol 
• 97357-26-1 (1,3,5-Tri-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-(2,4-dichlor-3,5-dimethyl-phenyl)-ether 
• 38730-52-8 2-Aminomethyl-4,6-dichloro-3,5-dimethyl-phenol; hydrochloride 

Relevant articles and documents

Regioselective synthesis of important chlorophenols in the presence of methylthioalkanes with remote SMe, OMe or OH substituents

Various methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes have been used as regioselectivity modifiers in the chlorination reactions of various phenols at room temperature. The process involves the use of a slight excess of sulfuryl chloride in the presence of aluminum or ferric chloride as an activator. Methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes having 2 and 3 methylene groups as a spacer were found to be good for the para-selective chlorination of o-cresol and phenol. On the other hand, methylthio alcohols, methoxy(methylthio)alkanes and bis(methylthio)alkanes having 6 and 9 methylene groups were found to be good for the selective para-chlorination of m-xylenol and m-cresol. Calculations using density functional theory on bis(methylthio)alkanes have suggested two different types of stable chlorinated intermediates depending on the number of methylene units as a spacer.

Method of disinfecting premises from coccidial oocysts using generated ammonia

A method of disinfecting premises from coccidial oocysts in which surface to be disinfected is thoroughly wetted with a first aqueous solution of ammonium salt containing approximately 0.5 to 1.5 molar of ammonium together with non-ionic surfactant and indicator having a color change in the region of pH 8 to pH 10 and the wetted surface is then covered with sufficient of a second aqueous solution of alkali metal hydroxide containing approximately 0.75 to 2.3 molar of hydroxide toether with phenolic bactericide to cause the indicator to change color on the treated surface. A preparation for use in such a method comprises a first package containing ammonium salt together with non-ionic surfactant and indicator and second package containing alkali metal hydroxide and phenolic bactericide, the molar amount of hydroxide in the second package being greater than the molar amount of ammonium in the first package.