25641-99-0

Basic information

• Product Name: 1,2-BIS(DICHLOROMETHYL)BENZENE
• Synonyms: 1,2-BIS(DICHLOROMETHYL)BENZENE;ALPHA,ALPHA,ALPHA',ALPHA'-TETRACHLORO-2-XYLENE;ALPHA,ALPHA,ALPHA',ALPHA'-TETRACHLORO-O-XYLENE;O-XYLYLENE TETRACHLORIDE;1,2-bis(dichloromethyl)-benzen;Benzene, 1,2-bis(dichloromethyl)-;Tetrachloroxylene;alpha,a,a,a-Tetrachloro-o-xylene
• CAS NO: 25641-99-0
• Molecular Formula: C₈H₆Cl₄
• Molecular Weight: 243.95
• EINECS: 247-159-4
• Product Categories: Industrial/Fine Chemicals
• Mol File: 25641-99-0.mol

Chemical Properties

• Melting Point: 85°C
• Boiling Point: 274 °C
• Flash Point: 134.25 °C
• Appearance: /
• Density: 1.6545 (estimate)
• Refractive Index: 1.5149 (estimate)
• CAS DataBase Reference: 1,2-BIS(DICHLOROMETHYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BIS(DICHLOROMETHYL)BENZENE(25641-99-0)
• EPA Substance Registry System: 1,2-BIS(DICHLOROMETHYL)BENZENE(25641-99-0)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37/38-36/37
• Safety Statements: 26-36/37/39-45-28-27
• RIDADR: 1759
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 25641-99-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,2-bis(dichloromethyl)benzene is used as a chemical intermediate for the production of dyes, pigments, and pharmaceuticals. Its unique structure allows for versatile reactions that facilitate the creation of a wide range of compounds.
Used in Solvent Applications:
1,2-bis(dichloromethyl)benzene is also utilized as a solvent in various industrial processes. Its solubility properties make it suitable for dissolving certain substances that are otherwise difficult to process.
Used in Organic Synthesis:
1,2-bis(dichloromethyl)benzene is employed in the synthesis of various organic compounds, where its reactivity and functional groups contribute to the formation of desired end products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1,2-bis(dichloromethyl)benzene is used as a precursor in the synthesis of specific drugs, highlighting its importance in medicinal chemistry.

Synthetic route

o-phthalic dicarboxaldehyde (643-79-8) → α,α,α',α'-tetrachloro-o-xylene (25641-99-0)

Conditions	Yield
With tungsten(VI) chloride In dichloromethane for 5h; Heating;	90%

o-xylene (95-47-6) → α,α,α',α'-tetrachloro-o-xylene (25641-99-0)

Conditions	Yield
With chlorine at 140℃; spaeter bei 160-170grad;
With phosphorus pentachloride at 170 - 200℃;

o-xylene (95-47-6) → α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + α,α,α'-trichloro-o-xylene (30293-58-4)

Conditions	Yield
at 140 - 160℃; Einleiten von Chlor;
at 142 - 160℃; Einleiten von Chlor;

o-xylene (95-47-6) + chlorine (7782-50-5) → α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + α,α,α'-trichloro-o-xylene (30293-58-4)

Conditions	Yield
at 140 - 160℃;

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) → o-dichloromethyltrichloromethylbenzene (2741-57-3)

Conditions	Yield
With chlorine In tetrachloromethane for 24h; Heating; Irradiation;	12.5%

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + triphenylphosphine (603-35-0) → 1,2-bis((diphenylphosphino)methyl)benzene (62144-65-4)

Conditions	Yield
With ammonia; sodium; ammonium chloride 1) 30 min., 2) 2 h; Yield given. Multistep reaction;

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + aqueous hydrazine solution → PHTHALAZINE (253-52-1)

Conditions	Yield
at 150℃;

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + water (7732-18-5) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
at 200 - 210℃;

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + water (7732-18-5) → o-phthalic dicarboxaldehyde (643-79-8)

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) + ammonia (7664-41-7) + nitrobenzene (98-95-3) + CuCl2 → copper (II)-phthalocyanin

α,α,α',α'-tetrachloro-o-xylene (25641-99-0) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With sodium hydroxide; water; acetic acid at 160℃; under 2850.29 - 2925.29 Torr; for 1h; Product distribution / selectivity;

Upstream product

• 95-47-6 o-xylene 
• 7782-50-5 chlorine 
• 643-79-8 o-phthalic dicarboxaldehyde 

Downstream Products

• 87-41-2 2-benzofuran-1(3H)-one 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 253-52-1 PHTHALAZINE 
• 2741-57-3 o-dichloromethyltrichloromethylbenzene 
• 62144-65-4 1,2-bis((diphenylphosphino)methyl)benzene 

Relevant articles and documents

New applications of tungsten hexachloride (WCl6) in organic synthesis. Halo-de-hydroxylation and dihalo-de-oxo-bisubstitution reactions

Tungsten hexachloride (WCl6) has been used for the halo-de-hydroxylation and dihalo-de-oxo-bisubstitution reactions of benzylic alcohols, benzaldehydes, acyloins, and epoxides to their chlorides, gem-dichlorides, vic-trichlorides, and vic-dichlorides respectively.

Process for the preparation of o-phthalaldehydes

A process for the preparation of o-phthalaldehydes is disclosed comprising the steps of (1) halogenating an o-xylene and (2) hydrolysis of the resulting tetrahalogeno-o-xylene.