70-30-4

Basic information

• Product Name: 2,2'-Methylenebis(3,4,6-trichlorophenol)
• Synonyms: Germa-Medica;Hexachlorofen;2,2',3,3',5,5'-Hexachloro-6,6'-dihydroxydiphenylmethane;2,2'-Dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethane;2,2'-Dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane;2,2'-Methylenebis[3,4,6-trichlorophenol];Bis(2-hydroxy-3,5,6-trichlorophenyl)methane;Bis(3,5,6-trichloro-2-hydroxyphenyl)methane
• CAS NO: 70-30-4
• Molecular Formula: C₁₃H₆Cl₆O₂
• Molecular Weight: 406.90354
• EINECS: 200-733-8
• Mol File: 70-30-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 470.928 °C at 760 mmHg
• Flash Point: 238.609 °C
• Appearance: Off-white crystalline solid
• Density: 1.714 g/cm³
• CAS DataBase Reference: 2,2'-Methylenebis(3,4,6-trichlorophenol)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Methylenebis(3,4,6-trichlorophenol)(70-30-4)
• EPA Substance Registry System: 2,2'-Methylenebis(3,4,6-trichlorophenol)(70-30-4)

Safety Data

• Hazardous Substances Data: 70-30-4(Hazardous Substances Data)

Usage

General Description

2,2'-Methylenebis(3,4,6-trichlorophenol) is a synthetic chemical compound commonly known as hexachlorophene. It is a white crystalline powder that has antiseptic and disinfectant properties and is commonly used in healthcare settings. It is effective against a wide range of bacteria and fungi, making it valuable in controlling infections. However, it has been largely phased out of use in many countries due to potential toxic effects, particularly on the central nervous system and the potential for organ damage. Additionally, it has been linked to environmental hazards and contamination. As a result, its use has been restricted and closely regulated.

Synthetic route

formaldehyd (50-00-0) + 2,4,5-trichlorophenol (95-95-4) → hexachlorophene (70-30-4)

Conditions	Yield
With sulfuric acid at 0 - 5℃;
With sulfuric acid at 65 - 135℃;
With sulfuric acid
With sulfuric acid In methanol; water

formaldehyd (50-00-0) + sulfuric acid (7664-93-9) + 2,4,5-trichlorophenol (95-95-4) → hexachlorophene (70-30-4)

hexachlorophene (70-30-4) + methyl iodide (74-88-4) → bis(2,3,5-trichloro-6-methoxyphenyl)methane (4936-91-8)

Conditions	Yield
With potassium carbonate In acetone for 14h;	85%

hexachlorophene (70-30-4) + p-tolyl phosphorodichloridothionate (18961-95-0) → 1,2,4,8,10,11-Hexachloro-6-p-tolyloxy-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	66%

(2-chloroethyl)phosphonic dichloride (690-12-0) + hexachlorophene (70-30-4) → 6-(2'-chloroethyl)-1,2,4,8,10,11-hexachloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide

Conditions	Yield
With triethylamine In toluene at 0 - 55℃;	65%

hexachlorophene (70-30-4) + 2-methylpheylphosphorodichloridate (91674-47-4) → 1,2,4,8,10,11-Hexachloro-6-o-tolyloxy-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	64%

hexachlorophene (70-30-4) + dichlorothiophosphoric acid O-m-tolyl ester (165064-39-1) → 1,2,4,8,10,11-Hexachloro-6-m-tolyloxy-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	62%

hexachlorophene (70-30-4) + 4-chlorophenyl-carbamidophosphoric acid dichloride (4797-12-0) → N-chlorophenyl-N'-[1,2,4,8,10,11-hexachloro-6-oxido-12H-dibenzo[d,g]-1,3,2-dioxaphosphocin-6-yl]urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	62%

hexachlorophene (70-30-4) + O-phenylphosphorodichloridothioate (18961-96-1) → 1,2,4,8,10,11-Hexachloro-6-phenoxy-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	61%

hexachlorophene (70-30-4) + C8H8Cl3N2O2P (603964-78-9) → 1-(2-chloromethyl-phenyl)-3-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	61%

hexachlorophene (70-30-4) + 4-chlorophenyl dichlorothiophosphate (19081-37-9) → 6-(4'-chlorophenoxy)-1,2,4,8,10,11-hexachloro-12H-dibenzo<1,3,2>dioxaphosphocin-6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	60%

hexachlorophene (70-30-4) + N-4-methylphenylureidophosphoryl dichloride (101252-13-5) → 1-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-3-p-tolyl-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	60%

phosphorodichloridothioic acid O-ortho-chlorophenyl ester (68591-34-4) + hexachlorophene (70-30-4) → 1,2,4,8,10,11-Hexachloro-6-(2-chloro-phenoxy)-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	59%

hexachlorophene (70-30-4) + phenylcarbamidophosphoric acid dichloride (4797-10-8) → 1-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-3-phenyl-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	59%

hexachlorophene (70-30-4) + 4-bromophenyl carbamidophosphoric acid dichloride (86623-97-4) → 1-(4-bromo-phenyl)-3-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	59%

hexachlorophene (70-30-4) + C8H9Cl2OPS (165064-40-4) → 1,2,4,8,10,11-Hexachloro-6-(2,3-dimethyl-phenoxy)-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	57%

allylphosphonic dichloride (1498-47-1) + hexachlorophene (70-30-4) → 6-allyl-1,2,4,8,10,11-hexachloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide

Conditions	Yield
With triethylamine In toluene at 0 - 55℃;	56%

hexachlorophene (70-30-4) + [1]naphthylcarbamoyl-amidophosphoryl chloride (4797-20-0) → 1-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-3-naphthalen-1-yl-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	56%

hexachlorophene (70-30-4) + C8H9Cl2OPS (165064-41-5) → 1,2,4,8,10,11-Hexachloro-6-(2,4-dimethyl-phenoxy)-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
With triethylamine In toluene at 60℃; for 8h;	54%

hexachlorophene (70-30-4) + C9H11Cl2N2O4P (651731-57-6) → 1-(3,4-dimethoxy-phenyl)-3-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	53%

hexachlorophene (70-30-4) + 2,4-dimethylphenyl carbamidophosphoric acid dichloride (41018-19-3) → 1-(2,4-dimethyl-phenyl)-3-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	52%

hexachlorophene (70-30-4) + benzylphosphonic dichloride (1499-19-0) → 6-benzyl-1,2,4,8,10,11-hexachloro-12H-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxide

Conditions	Yield
With triethylamine In toluene at 0 - 55℃;	51%

hexachlorophene (70-30-4) + C7H13Cl2N2O2P (603964-77-8) → 1-cyclohexyl-3-(1,2,4,8,10,11-hexachloro-6-oxo-12H-5,7-dioxa-6λ5-phospha-dibenzo[a,d]cycloocten-6-yl)-urea

Conditions	Yield
With triethylamine In toluene at 45 - 50℃; for 5h;	51%

Lawessons reagent (19172-47-5) + hexachlorophene (70-30-4) → 1,2,4,8,10,11-hexachloro-6-(4-methoxy-phenyl)-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-sulfide

Conditions	Yield
In acetonitrile for 12h; Heating;	32%

hexachlorophene (70-30-4) + benzoyl chloride (98-88-4) → bis-(2-benzoyloxy-3,5,6-trichloro-phenyl)-methane (103049-12-3)

Conditions	Yield
With sodium hydroxide

undecanoyl chloride (17746-05-3) + hexachlorophene (70-30-4) → Hexachlorophen-diundecanoat (19809-92-8)

Conditions	Yield
With pyridine

undecylenic acid (112-37-8) + hexachlorophene (70-30-4) → Hexachlorophen-monoundecanoat (19809-93-9)

Conditions	Yield
With sulfuric acid In xylene Heating;

hexachlorophene (70-30-4) → Bis(2-hydroxyphenyl)methane (2467-02-9)

Conditions	Yield
With nickel

hexachlorophene (70-30-4) + 3-monochloro-1,2-propanediol (96-24-2) → 3,3',5,5',6,6'-Hexachlor-2,2'-bis-(2,3-dihydroxy-propoxy)-diphenylmethan

Conditions	Yield
With sodium ethanolate In ethanol Heating;

hexachlorophene (70-30-4) → 1,2,4,6,8,10,11-heptachloro-12H-dibenzo<1,3,2>dioxaphosphocin-6-sulfide (173547-17-6)

Conditions	Yield
With trichlorothiophosphine; triethylamine In toluene at 50 - 60℃; for 4h;

Upstream product

• 50-00-0 formaldehyd 
• 7664-93-9 sulfuric acid 
• 95-95-4 2,4,5-trichlorophenol 

Downstream Products

• 4936-91-8 bis(2,3,5-trichloro-6-methoxyphenyl)methane 
• 108042-06-4 ortho,ortho-bisphenol F bis(2,3-dihydroxypropyl) ether 
• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 19809-92-8 Hexachlorophen-diundecanoat 

Relevant articles and documents

Compositions

The problem of providing a storage stable anti-calculus toothpaste comprising a tripolyphosphate salt is remedied by incorporating more than 4% of the salt and having the pH from about 8 to about 10. A tripolyphosphate salt may also be combined with a noncationic anti-bacterial agent such as triclosan to provide a composition having anti-calculus and anti-plaque activity.

Dentifrice compositions

It is disclosed that a dentifrice which includes a surfactant and an anti-plaque agent comprising a substantially water-insoluble non-cationic antimicrobial agent or a zinc salt or a mixture thereof has enhanced activity when the dentifrice comprises at least 0.2% by weight of a lamellar liquid crystal surfactant phase having a lamellar spacing of less than 6.0 nm.

NEW PHENOLIC ETHERS. I. SYNTHESIS AND PHARMACOLOGY OF ALPHA-GLYCERYL

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