1,4-Dichlorobenzene

Base Information

• Chemical Name: 1,4-Dichlorobenzene
• CAS No.: 106-46-7
• Molecular Formula: C6H4Cl2
• Molecular Weight: 147.004
• Hs Code.: 2903.61 Oral rat LD50: 500 mg/kg
• European Community (EC) Number: 203-400-5
• ICSC Number: 0037
• NSC Number: 36935
• UN Number: 3077
• UNII: D149TYB5MK
• DSSTox Substance ID: DTXSID1020431
• Nikkaji Number: J4.033I
• Wikipedia: 1,4-Dichlorobenzene
• Wikidata: Q161529
• NCI Thesaurus Code: C44297
• Metabolomics Workbench ID: 49669
• ChEMBL ID: CHEMBL190982
• Mol file: 106-46-7.mol

Synonyms:1,4-dichlorobenzene;4-dichlorobenzene;p-dichlorobenzene;para-dichlorobenzene;paradichlorobenzene

Chemical Property of 1,4-Dichlorobenzene

Chemical Property:

• Appearance/Colour: colourless or white crystal
• Vapor Pressure: 1.64mmHg at 25°C
• Melting Point: 52-54 °C(lit.)
• Refractive Index: 1.548
• Boiling Point: 174.1 °C at 760 mmHg
• Flash Point: 60.7 °C
• PSA: 0.00000
• Density: 1.297 g/cm³
• LogP: 2.99340
• Storage Temp.: 0-6°C
• Solubility.: 0.08g/l
• Water Solubility.: insoluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 145.9690055
• Heavy Atom Count: 8
• Complexity: 54.9
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dichlorobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,T,F
• Hazard Codes: Xn:Harmful;;
• Statements: R36:; R40:; R50/53:
• Safety Statements: S36/37:; S46:; S60:; S61:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fumigants
• Canonical SMILES: C1=CC(=CC=C1Cl)Cl
• Inhalation Risk: A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, respiratory tract and skin. The substance may cause effects on the blood. This may result in haemolytic anaemia. The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: The substance may have effects on the liver, central nervous system, blood and lungs. This may result in liver function impairment, neuropathy and anaemia. This substance is possibly carcinogenic to humans.
• Description: 1,4-Dichlorobenzene (also known as p-dichlorobenzene) is a chlorinated aromatic compound with a distinctive aromatic odor that is very strong at high concentrations. It is a white or colorless crystal at room temperature (Akron 2009, HSDB 2009). 1,4-Dichlorobenzene is practically insoluble in water; soluble in chloroform, carbon disulfide, benzene, and ether; and very soluble in ethanol and acetone. 1,4-Dichlorobenzene is noncorrosive, volatile, and combustible, and it is flammable when exposed to heat, flame, or oxidizers. When it is heated to decomposition, toxic gases and vapors (such as hydrochloric acid and carbon monoxide) are released (HSDB 2009). It is stable at room temperature under normal handling and storage in closed containers (Akron 2009).1,4-Dichlorobenzene is the primary ingredient in mothballs and deodorant cakes placed in toilet bowls, urinals, and animal holding facilities. People may also use it to control lice and mites in and around birdcages. 1,4-Dichlorobenzene is used as an insecticide on fruit and is used to control mold and mildew growth on tobacco seeds, leather, and certain fabrics. It is also approved for controlling wax moths in empty, stored beehives.
• Physical properties: Colorless to white crystals with a penetrating, sweet, mothball or almond-like odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 18 and 4.5 μg/L, respectively. Similarly, at 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 32 and 11 μg/L, respectively (Young et al., 1996). A detection odor threshold concentration of 73 μg/m3 (121 ppbv) was reported by Punter (1983).
• Uses: 1,4-Dichlorobenzene is used to make mothballs and solid deodorant blocks for garbage cans and restrooms. It is also used to control odors in places where animals are held. It has been used as an insecticide on fruit, and to control mold and mildew on tobacco seeds, leather and some fabrics. 1,4-Dichlorobenzene is sent into the air by plants that make or use it and a small amount is released to soil and water. This chemical can also be detected in indoor air where products containing 1,4-Dichlorobenzene are used.

Technology Process of 1,4-Dichlorobenzene

There total 204 articles about 1,4-Dichlorobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1,2,4,5-tetrachlorobenzene (95-94-3) → para-dichlorobenzene (106-46-7,84348-21-0) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With potassium hydroxide; hydrogen; palladium on activated charcoal; In water; at 50 ℃; for 0.92h; Yields of byproduct given;

DOI:10.1021/jo00071a041

Reference yield: 73.0%

1,2,4,5-tetrachlorobenzene (95-94-3) → para-dichlorobenzene (106-46-7,84348-21-0) + chlorobenzene (108-90-7) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1) + 1,2,4-Trichlorobenzene (120-82-1,63697-18-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With potassium hydroxide; hydrogen; palladium on activated charcoal; In water; at 50 ℃; for 0.5h; Product distribution; Aliquat 336 and other phase-transfer catalysts, different multiphase systems, different time and solvents;

DOI:10.1021/jo00071a041

Reference yield: 13.7%

1,2,4-Trichlorobenzene (120-82-1,63697-18-7) → para-dichlorobenzene (106-46-7,84348-21-0) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1)

Guidance literature:

With radical anion of p,p'-di-tert-butylbiphenyl; In tetrahydrofuran; at -60 ℃; Product distribution; Rate constant; Mechanism; Irradiation; radical anion of naphthalene, different temperatures;

DOI:10.1021/jo00011a037

upstream raw materials:

bromochlorobenzene

2,5 dichloroaniline

4-chlorophenyldiazonium salt

p-hydoroxybenzenesulfonic acid

Downstream raw materials:

4-(2,5-dichloro-phenyl)-butyric acid

4-chlorophenyl-methyl-dichlorosilane

Si,Si,Si',Si'-tetrachloro-Si,Si'-dimethyl-Si,Si'-p-phenylene-bis-silane

4-(2-chlorophenyl)-4-oxobutanoic acid

Refernces

• 1、 Freeman, Peter K.,Srinivasa, Ramanujan,Campbell, J.-A.,Deinzer, Max L.. "The Photochemistry of Polyhaloarenes. 5. Fragmentation Pathways in Polychlorobenzene Radical Anions". . p. 5531 - 5536. Retrieved 1986.
• 2、 Huizinga,Scholten,Wortel,van Bekkum. "Zeolite ZSM-5 and related materials as catalyst in benzene chlorination". . p. 3809 - 3812. Retrieved 1980.
• 3、 Nakamura, Tadashi,Shinoda, Kiyonori,Yasuda, Kensei. "Chlorination of Benzene with L-Zeolite Catalyst in the Presence of Oxygen and Various Solvents". . p. 1881 - 1882. Retrieved 1992.
• 4、 Kimura, Masaru,Okamoto, Hideki,Kura, Hisatoshi,Okazaki, Ayumi,Nagayasu, Eiji,et al.. "A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties". . p. 3908 - 3911. Retrieved 1988.
• 5、 Blank,Fischer. "". . p. 905,907,908,911. Retrieved 1971.
• 6、 Stiles Martin. "Nickel Complexes as Soluble Catalysts for Reductive Dehalogenation of Aromatic Halides". . p. 5381 - 5385. Retrieved 1994.
• 7、 Kut'in,Gubanova,Zorin,Zanozina,Markova,Suprunova,Bykova. "Thermolysis of hexachlorocyclohexane in a flow-through packed reactor". . p. 1518 - 1522. Retrieved 2004.
• 8、 Wibaut,van de Lande,Wallagh. "-". . p. 65,67, 68. Retrieved 1937.
• 9、 Kachevskii,Golubina,Lokteva,Lunin. "Palladium on ultradisperse diamond and activated carbon: The relation between structure and activity in hydrodechlorination". . p. 866 - 873. Retrieved 2007.
• 10、 Lishchiner, I. I.,Plakhotnik, V. A.,Kuzmicheva, A. N.,Mortikov, E. R.. "Catalytic isomerization of dihalobenzenes C6H3X2R in the presence of high-silica zeolites". . p. 1809 - 1811. Retrieved 1994.