1633-22-3

Basic information

• Product Name: [2.2]Paracyclophane
• Synonyms: TRICYCLO[8.2.2.24,7]HEXADECA-4,6,10,12,13,15-HEXAENE;TRICYCLO[8.2.2.2]HEXADECA-4,6,10,12,13,15-HEXAENE;[2.2]paracylophan;Cyclobis(benzene-1,4-dimethylene);Di-1,4-xylylene;Tricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene;4,4'-DIMETHYLENE-1,2-DIPHENYLETHANE;[2.2]PARACYCLOPHAN
• CAS NO: 1633-22-3
• Molecular Formula: C₁₆H₁₆
• Molecular Weight: 208.3
• EINECS: 216-644-2
• Product Categories: Cyclophanes;Functional Materials;Macrocycles for Host-Guest Chemistry;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;Arenes;Building Blocks;Chemical Synthesis;Organic Building Blocks;coating
• Mol File: 1633-22-3.mol

Chemical Properties

• Melting Point: 285-288 °C(lit.)
• Boiling Point: 282.51°C (rough estimate)
• Flash Point: 154 °C
• Appearance: white to light beige crystalline powder
• Density: 1.0102 (estimate)
• Vapor Pressure: 0.000587mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: INSOLUBLE
• BRN: 1910888
• CAS DataBase Reference: [2.2]Paracyclophane(CAS DataBase Reference)
• NIST Chemistry Reference: [2.2]Paracyclophane(1633-22-3)
• EPA Substance Registry System: [2.2]Paracyclophane(1633-22-3)

Safety Data

• Hazard Codes: Xi,C,F
• Statements: 11-34
• Safety Statements: 24/25-45-36/37/39-26-16
• WGK Germany: 3
• RTECS: YD2404000
• TSCA: Yes
• Hazardous Substances Data: 1633-22-3(Hazardous Substances Data)

Usage

Uses

Used in Microelectronic Industry:
[2.2]Paracyclophane is used as a raw material for the synthesis of parylene, which is widely utilized in the microelectronic integrated circuit industry. Parylene is valued for its excellent dielectric properties, chemical inertness, and ability to form conformal coatings on various substrates, making it an essential material for protecting and insulating electronic components.
Additionally, parylene is known for its biocompatibility, which has led to its use in medical applications such as implantable devices and drug delivery systems. However, since the provided materials do not specifically mention these applications, they are not included in the organized description.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 1043, 1981 DOI: 10.1021/jo00318a047

Flammability and Explosibility

Notclassified

Purification Methods

Purify it by recrystallisation from AcOH. 1H-NMR : 1.62 (Ar-H) and -1.71 (CH2) [Waugh & Fessenden J Am Chem Soc 79 846 1957, IR and UV: Cram et al. J Am Chem Soc 76 6132 1954, Cram & Steinberg J Am Chem Soc 73 5691 1951. It complexes with unsaturated compounds: Cram & Bauer J Am Chem Soc 81 5971 1959, Syntheses: Brink Synthesis 807 1975, Givens et al. J Org Chem 44 16087 1979, Kaplan et al. Tetrahedron Lett 3665 1976]. [Beilstein 5 IV 2223.]

InChI:InChI=1/C16H16/c1-2-14-4-3-13(1)9-10-15-5-7-16(8-6-15)12-11-14/h1-8H,9-12H2

Upstream product

• 106-42-3 para-xylene 
• 26050-79-3 2,3',5,6'-Tetrahydro<2.2>paracyclophane 
• 18001-37-1 p-<(trimethylsilyl)methyl>benzyl chloride 
• 122212-78-6 C₂₂H₁₈N₂ 
• 108-88-3 toluene 
• 7595-23-5 <3.2>(1,4)Cyclophan-2-on 
• 877774-21-5 2,5-dimethyl-p-xylylene 
• 502-86-3 p-xylylene 
• 85267-33-0 N-(4-methylbenzyl)triethylammonium bromide 
• 16814-21-4 (4-methylbenzyl)trimethylammonium bromide 
• 104-81-4 4-Methylbenzyl bromide 
• 116072-95-8 3,12-Diselena-tricyclo[12.2.2.2^6,9]icosa-1⁽¹⁷⁾,6⁽²⁰⁾,7,9⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene 
• 117632-87-8 3,10-Dinitroso-3,10-diaza-tricyclo[10.2.2.2^5,8]octadeca-1⁽¹⁵⁾,5⁽¹⁸⁾,6,8⁽¹⁷⁾,12⁽¹⁶⁾,13-hexaene 
• 78808-35-2 1,4-bis(phenylselenomethyl)benzene 

Downstream Products

• 18869-29-9 (E)-4,4'-dimethylstilbene 
• 538-39-6 1,2-di-p-tolylethane 
• 38274-86-1 1-bromo[2.2]paracyclophane 
• 283-68-1 Perhydro<2.2>paracyclophane 
• 90817-44-0 1,2,2',3,4,5,5',6-Octahydro<2.2>paracyclophane 
• 10029-00-2 4-acetyl[2.2]paracyclophane 
• 71776-83-5 4,4'-bis-acetoxymethyl-bibenzyl 
• 71776-84-6 Propionic acid 4-[2-(4-propionyloxymethyl-phenyl)-ethyl]-benzyl ester 
• 109764-64-9 1,10-Dibrom<2.2>paracyclophan-1-en 
• 109764-63-8 1,9-Dibrom<2.2>paracyclophan-1-en 
• 109764-91-2 5',5''-Diphenyldibenzo<2.2>paracyclophan-1,9-dien-4',4''-dicarbaldehyd 
• 109764-90-1 4'',5'-Diphenyldibenzo<2.2>paracyclophan-1,9-dien-4',5''-dicarbaldehyd 
• 109764-87-6 2,5',5'',10-Tetrahydro-5',5''-diphenyldibenzo<2.2>paracyclophan-1,9-dien-4',4''-dicarbaldehyd 
• 109764-86-5 2,4'',5',9-Tetrahydro-4'',5'-diphenyldibenzo<2.2>paracyclophan-1,9-dien-4',5''-dicarbaldehyd 

Related news

Linear and nonlinear properties of novel materials based on DNA containing [2.2]paracyclophane moiety07/24/2019

In this study, the synthesis and the characterization of new deoxyribonucleic acid (DNA) based compounds containing [2.2]paracyclophane moiety are reported. The DNA molecule was functionalized with hexadecyltrimethylammonium chloride (CTMA), [2.2]paracyclophane-4-methoxy-5-formyl [A] and [2.2]pa...detailed

Relevant articles and documents

Organic nanocrystals of [2.2]paracyclophanes achieved via sonochemistry: Enhanced and red-shifted emission involving edge-to-face chromophores

We have prepared organic nanocrystals of [2.2]paracyclophane (pCp) and tetrakis(4-pyridylcyclobutyl)[2.2]paracyclophane (tpcp) via sonochemistry. Both nanocrystals exhibit an enhanced fluorescence compared to dilute solution, while the tpcp nanocrystals also demonstrate a red-shifted fluorescence.

SYNTHESIS OF CYCLOPHANES BY PHOTODESELENATIVE RINGCONTRACTION

Several cyclophanes were prepared by photodeselenation of diselenacyclophanes with hexamethylphosphorous triamide in excellent yields, compared with the other chalcogen-atom extrusion methods.

Laser flash photolysis of [3,n]paracyclophan-2-ones. Direct observation and chemical behavior of 4,4′-(1,n-alkanediyl)bisbenzyl biradicals

The 4,4′-(1,n-alkanediyl)bisbenzyl biradicals (2b-d) have been generated from the Norrish type-I reaction of [3,n]paracyclophan-2-ones (1b-d) giving the paracyclophanes 3b-d as the only reaction products. The behavior of biradicals 2b-d has been studied in detail and compared with the previously reported biradical 2a. The lifetimes increase as the chain length decreases and are affected by the solvent viscosity, thus showing the effect of the length of the chain on the conformations of the biradicals. Quenching with persistent radicals such as TEMPO resulted in length-dependent rate constants. Finally, the study of the magnetic field effects on the biradical lifetimes suggest that ISC control determines biradical lifetimes for long-chain systems.

A NEW SYNTHETIC METHOD OF CYCLOPHANES

Diazacyclophanes were converted to the correspondingcyclophanes via their N-nitroso derivatives by reductive extrusion of nitrogens.This reaction is simple, clean and mild, and may be an alternative synthetic way of cyclophanes.

A new synthetic method of [2.2]cyclopbanes from [3.3]cyclophane-2,11- diones via photodecarbonylation

Photoirradiation of [3,3]cyclophane-2,11-diones with a high-pressure Hg lamp in benzene provides the corresponding [2,2]cyclophanes in high yields along with [3,2]-cyclophane-2-ones.

A NEW AND FACILE ROUTE FROM A THIAPHANE TO A CYCLOPHANE VIA IRON PENTACARBONYL

2,11-Dithiaparacyclophane is converted into -paracyclophane in 62percent yield by treatment with Fe(CO)5 in refluxing toluene.

The 4,4′-(1,2-ethanediyl)bisbenzyl biradical: Its generation, detection, and (photo)chemical behavior in solution

The 4,4′-(1,2-ethanediyl)bisbenzyl biradical (2) is clearly and efficiently generated by photolysis of [3.2]paracyclophane-2-one (8) in cyclohexane solution. This intermediate is also formed via two-photon processes from [2.2]paracyclophane (3) and 1,2-bi

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.

The synthesis of a [2.2]paracyclophane-derived secondary phosphine oxide and a study of its reactivity

A planar chiral secondary phosphine oxide based on [2.2]paracyclophane was synthesized and its chemistry investigated; it was shown to be a competent pre-ligand in palladium(0)-mediated reactions, and displayed promising activity in gold(I)-catalysed cyclisations. The secondary phosphine oxide could be transformed into a collection of P-stereogenic tertiary phosphine oxides. These are rare examples of the planar chirality of [2.2]paracyclophane being combined with a P-stereogenic centre. Unfortunately, epimerisation of the phosphorus stereocentre during reduction limits the use of this chemistry.

The synthesis of planar chiral pseudo-gem aminophosphine pre-ligands based on [2.2]paracyclophane

The synthesis of three planar chiral pseudo-gem disubstituted [2.2]paracyclophane-derived P,N-pre-ligands is reported along with preliminary results of their activity in the amination of aryl bromides and chlorides. The pseudo-gem aminophosphines were capable of mediating the coupling reaction at a loading of 1 mol%.