10366-05-9

Basic information

• Product Name: Dichloro[2,2]paracyclophane
• Synonyms: Dichlorotricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene, mixed isomers;PARYLENE C;5,12-Dichlorotricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene;DICHLORODI-PARA-XYLYLENE;Dimer, Parylene C;Dichlorotricyclo(8,2,2,2[4,7])hexadeca-4,6,10,12,13,15-hexaene EINCIS;1,4'-Ethylene-1',4-ethylenebis(2-chlorobenzene);5,11-Dichlorotricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexene
• CAS NO: 10366-05-9
• Molecular Formula: C₁₆H₁₄Cl₂
• Molecular Weight: 277.193
• EINECS: 233-807-3
• Mol File: 10366-05-9.mol

Chemical Properties

• Melting Point: 165-167°C
• Boiling Point: 389.967 °C at 760 mmHg
• Flash Point: 181.488 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 6.16E-06mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Dichloro[2,2]paracyclophane(CAS DataBase Reference)
• NIST Chemistry Reference: Dichloro[2,2]paracyclophane(10366-05-9)
• EPA Substance Registry System: Dichloro[2,2]paracyclophane(10366-05-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 10366-05-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Semiconductors:
Dichloro[2,2]paracyclophane is used as a key component in the development of organic semiconductors due to its unique electronic properties. Its molecular structure allows for efficient charge transport and improved performance in electronic devices.
Used in Organic Light-Emitting Diodes (OLEDs):
In the field of OLEDs, Dichloro[2,2]paracyclophane is utilized as an active layer material for its ability to emit light upon the application of an electric field. Its unique optical properties contribute to enhanced device performance and efficiency.
Used in Field-Effect Transistors:
Dichloro[2,2]paracyclophane is employed as a semiconductor material in field-effect transistors, where its electronic properties enable the modulation of electrical current flow. This application takes advantage of the compound's ability to control charge transport, leading to improved device performance.
Used in Photovoltaic Devices:
In the photovoltaic industry, Dichloro[2,2]paracyclophane is used as a component in solar cells, harnessing its light-absorbing and charge-separating capabilities to convert sunlight into electricity. Its unique properties contribute to increased power conversion efficiency and overall device performance.
Used in Materials Synthesis:
Dichloro[2,2]paracyclophane is used as a building block in the synthesis of novel materials and molecular architectures. Its rigid and planar structure allows for the creation of new materials with tailored properties for various applications in science and technology.
Overall, Dichloro[2,2]paracyclophane has garnered significant interest for its potential in various technological and scientific applications due to its unique molecular structure and properties. Its versatility in different fields, such as organic semiconductors, OLEDs, field-effect transistors, photovoltaic devices, and materials synthesis, highlights its importance in advancing modern technology.

InChI:InChI=1/C16H14Cl2/c17-15-9-11-1-5-13(15)8-4-12-2-6-14(7-3-11)16(18)10-12/h1-2,5-6,9-10H,3-4,7-8H2

Upstream product

• 1633-22-3 [2.2]Paracyclophan 
• 95-72-7 2-chloro-1,4-dimethyl-benzene 
• 943742-24-3 2-chloro-4-bromostyrene 
• 868860-20-2 1-(bromomethyl)-2-chloro-4-methylbenzene 

Downstream Products

• 344938-52-9 4,12-dimethyl<2.2>paracyclophane 

Relevant articles and documents

Preparation method of parylene

The invention discloses a preparation method of parylene. The method comprises the steps: carrying out a reaction on a compound 1A to obtain a compound 2A; and reacting the compound 2A with a compound2B to obtain a parylene crude product, and purifying the parylene crude product to obtain a parylene fine product. According to the method, the reagent with lower price is used as a starting raw material, the final product is obtained through two-step reaction, the reaction condition of each step is mild, the yield of the obtained parylene is high, and the cost can be greatly reduced.

Method for synthesizing tetrachloro-paracyclophane

The invention discloses a method for synthesizing tetrachloro-paracyclophane, and relates to the technical field of chemical synthesis. The method comprises the following steps: taking 3-chloromethyl benzyl chloride as a raw material to obtain dichloro-paracyclophane as a intermediate by using a Hofmann elimination method; carrying out chlorination on the intermediate by using chlorine to obtain a coarse product; and decolorizing, concentrating and drying the coarse product to obtain a finished product. The preparation method of the tetrachloro-paracyclophane is simple in process, reaction conditions are easy to control, the purity of the product is high, triethylamine and a solvent can be recycled in a reaction process, and the method is safe and environmentally friendly, and is low in production cost and easy to popularize.

A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane

We report a green and convenient protocol to prepare 4,7,12,15-tetrachloro[2.2]paracyclophane, the precursor of parylene D, from 2,5-dichloro-p-xylene. In the first bromination step, with H2O2-HBr as a bromide source, this procedure becomes organic-waste-free and organic-solvent-free and can appropriately replace the existing bromination methods. The Winberg elimination-dimerization step, using aqueous sodium hydroxide solution instead of silver oxide for anion exchange, results in a significant improvement in product yield. Furthermore, four substituted [2.2]paracyclophanes were also prepared in this convenient way.

An improved method for the regiospecific synthesis of polysubstituted [2.2]paracyclophanes

4,16-Disubstituted, 4,7,12,15-tetrasubstituted, 4,8,12,16-tetrasubstituted and 4,5,7,8,12,13,15,16-octasubstituted [2.2]paracyclophanes can be prepared in significantly improved yields and excellent regiospecificities via the Winberg 1,6-elimination-dimerization reaction from substituted (4-methylbenzyl) trimethylammonium hydroxides. Using 2-chloro-phenothiazine instead of phenothiazine as a polymerization inhibitor results in a doubling of product yields. Georg Thieme Verlag Stuttgart.