2,3,7,8-Tetrachlorodibenzo-P-dioxin

Base Information

• Chemical Name: 2,3,7,8-Tetrachlorodibenzo-P-dioxin
• CAS No.: 1746-01-6
• Deprecated CAS: 56795-67-6
• Molecular Formula: C12H4 Cl4 O2
• Molecular Weight: 321.975
• Hs Code.: 2930909062
• European Community (EC) Number: 217-122-7
• ICSC Number: 1467
• UN Number: 2811,3077
• UNII: DO80M48B6O
• DSSTox Substance ID: DTXSID2021315
• Nikkaji Number: J3.677C
• Wikipedia: 2,3,7,8-Tetrachlorodibenzodioxin
• Wikidata: Q52822
• NCI Thesaurus Code: C864
• Pharos Ligand ID: D21FCSN83JM9
• Metabolomics Workbench ID: 51589
• ChEMBL ID: CHEMBL30327
• Mol file: 1746-01-6.mol

Synonyms:2,3,7,8-Tetrachlorodibenzo-p-dioxin;Chlorinated Dibenzo p dioxins;Chlorinated Dibenzo-p-dioxins;Dibenzo(b,e)(1,4)dioxin, 2,3,7,8-tetrachloro-;Dibenzo-p-dioxins, Chlorinated;Dibenzo-p-dioxins, Polychlorinated;Dibenzodioxin, Polychlorinated;Dibenzodioxins, Polychlorinated;PCDD;Polychlorinated Dibenzo p dioxins;Polychlorinated Dibenzo-p-dioxins;polychlorinated dibenzodioxin;Polychlorinated Dibenzodioxins;Polychlorodibenzo 4 dioxin;Polychlorodibenzo p dioxin;polychlorodibenzo-4-dioxin;polychlorodibenzo-p-dioxin;TCDD;Tetrachlorodibenzo p dioxin;Tetrachlorodibenzo-p-dioxin;Tetrachlorodibenzodioxin

Chemical Property of 2,3,7,8-Tetrachlorodibenzo-P-dioxin

Chemical Property:

• Vapor Pressure: 8.26E-07mmHg at 25°C
• Melting Point: 295
• Refractive Index: 1.655
• Boiling Point: 500(dec)
• Flash Point: 164.2°C
• PSA: 18.46000
• Density: 1.643g/cm³
• LogP: 6.19820
• Storage Temp.: Refrigerator
• Water Solubility.: 0.0000000019 g/100 mL
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 321.893590
• Heavy Atom Count: 18
• Complexity: 259
• Transport DOT Label: Poison

Purity/Quality:

2,3,7,8-Tetrachloro-p-dioxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62-46

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Polyaromatics
• Canonical SMILES: C1=C2C(=CC(=C1Cl)Cl)OC3=CC(=C(C=C3O2)Cl)Cl
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cardiovascular system, gastrointestinal tract, liver, nervous system and endocrine system. The effects may be delayed.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. May cause chloracne. The substance may have effects on the bone marrow, endocrine system, immune system, liver and nervous system. This substance is carcinogenic to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
• Description: The term dioxins refers to chlorinated hydrocarbons containing a dibenzo-p-dioxin structure (two benzene rings conjoined at their para carbons by two oxygen molecules). The nomenclature for chlorinated dibenzodioxins (CDD) is based on the number and position of the chlorine molecules and include mono- (MCDD), di- (DCDD), tri- (TrCDD), tetra- (TCDD), penta- (PeCDD), hexa- (HxCDD), hepta- (HpCDD), and octachlorinated (OCDD) congeners. There are 75 congeners in total. The 2,3,7,8-tetrachlorodienzo-p-dioxin (2,3,7,8-TCDD) congener is the most familiar congener due in part to its toxicity in animal models, its widespread distribution and persistence in the environment, its bioaccumulation potential, and because most data pertain to this congener. Dioxins in pure form are colorless solids and are formed as combustion products. Dioxins may be formed during the combustion of organic material in the presence of halogens, especially chlorine (and bromine), during waste incineration and forest fires. They also occur as contaminants in herbicides. Dioxin was a contaminant of Agent Orange and possibly responsible for some of the adverse health effects associated with exposure to the defoliant. Dioxin was the poisoning agent in a high-profile political incident in 2004. Dioxin was ultimately identified as the cause of the disfiguring acne-like skin (chloracne) condition suffered by Ukrainian opposition leader Viktor Yushchenko a few months prior to the first presidential election. The suspicion was that the dioxin was placed into soup consumed by Mr Yushchenko. The acne-like skin condition is a recognized hallmark of dioxin poisoning in humans. The actual intake of dioxin in this incident is unknown.
• Uses: A toxic polychlorinated dibenzo-p-dioxin detected in domestic meat and poultry. With the exception of its use in research, it is ironic that there are no known uses for any of the dioxins. They are unintended byproducts of chemical manufacturing and combustion. There is no commercial manufacture of these compounds. The limited production of dioxins for use in research involves production by condensation of polychlorophenol or, for a specific dioxin, by chlorination of the parent dibenzo-p-dioxin.

Technology Process of 2,3,7,8-Tetrachlorodibenzo-P-dioxin

There total 46 articles about 2,3,7,8-Tetrachlorodibenzo-P-dioxin 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: 80.0%

4-chlorophenylacetic Acid (1878-66-6) + 2,4-dichlorophenol (120-83-2,40477-79-0) → 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine (1746-01-6,56795-67-6)

Guidance literature:

With potassium hydroxide; copper(I) chloride; In 5,5-dimethyl-1,3-cyclohexadiene; water;

Reference yield:

acetylene (74-86-2,25067-58-7) → 1,3,7,8-tetrachloro-dibenzo[1,4]dioxine (50585-46-1) + 1,3,6,8-tetrachloro-dibenzo[1,4]dioxine (33423-92-6) + 1,3,7,9-tetrachlorodioxine (62470-53-5) + 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine (1746-01-6,56795-67-6)

Guidance literature:

With oxygen; copper dichloride; at 300 ℃; for 0.000555556h; Further byproducts given; Formation of xenobiotics;

DOI:10.1016/S0045-6535(99)00272-6

Reference yield:

chlorobenzene (108-90-7) → 2,3,7,8-Tetrachloro-dibenzo[1,4]dioxine (1746-01-6,56795-67-6)

Guidance literature:

With oxygen; at 900 ℃; Formation of xenobiotics; combustion;

DOI:10.1016/S0045-6535(99)00231-3

upstream raw materials:

dioxin

potassium salt of 2,4,5-trichlorophenol

potassium salt of 2,4,6-trichlorophenol

2,4,5-trichlorophenol

Downstream raw materials:

dioxin

1,2,3,6,7,8-hexachlorodibenzodioxin

HpCDD 1234678

1,2,3,4,6,7,8,9-octachlorodibenzodioxin

Refernces

• 1、 Molina,Diaz-Ferrero,Coll,Marti,Broto-Puig,Comellas,Rodriguez-Larena. "Study of evolution of PCDD/F in sewage sludge-amended soils for land restoration purposes". . p. 1173 - 1178. Retrieved 2000.
• 2、 Wunderli, Samuel,Zennegg, Markus,Dolezal, Ivan Samuel,Gujer, Erika,Moser, Urs,Wolfensberger, Max,Hasler, Philip,Noger, Dominik,Studer, Christoph,Karlaganis, Georg. "Determination of polychlorinated dibenzo-p-dioxins and dibenzo-furans in solid residues from wood combustion by HRGC/HRMS". . p. 641 - 649. Retrieved 2000.
• 3、 Buekens,Stieglitz,Hell,Huang,Segers. "Dioxins from thermal and metallurgical processes: Recent studies for the iron and steel industry". . p. 729 - 735. Retrieved 2001.
• 4、 Pekarek,Grabic,Marklund,Puncochar,Ullrich. "Effects of oxygen on formation of PCB and PCDD/F on extracted fly ash in the presence of carbon and cupric salt". . p. 777 - 782. Retrieved 2001.
• 5、 Hatanaka, Takeshi,Kitajima, Akio,Takeuchi, Masao. "Role of copper chloride in the formation of polychlorinated dibenzo-p-dioxins and dibenzofurans during incineration". . p. 73 - 79. Retrieved 2004.
• 6、 Hart, John R.. "Emissions of polychlorinated dibenzo- p -dioxins and dibenzofurans from catalytic and thermal oxidizers burning dilute chlorinated vapors". . p. 1539 - 1547. Retrieved 2004.
• 7、 Buser, Hans Rudolf,Rappe, Christoffer. "Isomer-Specific Separation of 2378-Substituted Polychlorinated Dibenzo-p-dioxins by High-Resolution Gas Chromatography/Mass Spectrometry". . p. 442 - 448. Retrieved 1984.
• 8、 Cieplik, Mariusz K.,Carbonell, Jose Pastor,Munoz, Christina,Baker, Sarah,Krueger, Sophie,Liljelind, Per,Marklund, Stellan,Louw, Robert. "On dioxin formation in iron ore sintering". . p. 3323 - 3331. Retrieved 2003.
• 9、 Muto, Hajime,Saitoh, Koki,Funayama, Hitoshi. "PCDD/DF formations by the heterogeneous thermal reactions of phenols and their TiO2 photocatalytic degradation by batch-recycle system". . p. 129 - 136. Retrieved 2001.