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
• Article Data: 52

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

Chemical Properties

WHITE TO LIGHT BEIGE CRYSTALS OR CRYSTAL. POWDER

Uses

2,2]-Paracyclophane is the raw material for the synthesis of parylene which is widely used in microelectronic integrated circuit.

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 
• 28667-63-2 2,11-dithia[3.3]paracyclophane 
• 7595-23-5 <3.2>(1,4)Cyclophan-2-on 
• 7215-86-3 2,11-diaza[3.3]paracyclophane 
• 623-24-5 1,4-bis(bromomethyl)benzene 
• 6337-67-3 4,4'-bis(bromomethyl)bibenzyl 
• 1073-67-2 4-vinylbenzyl chloride 
• 1908-61-8 4-bromo[2.2]paracyclophane 
• 196316-30-0 4,16-dibromo[2.2]paracyclophane 
• 62-53-3 aniline 
• 867376-59-8 p-bromomethylbenzyltrimethylsilane 
• 104-81-4 4-Methylbenzyl bromide 
• 16814-21-4 (4-methylbenzyl)trimethylammonium bromide 
• 85267-33-0 N-(4-methylbenzyl)triethylammonium bromide 

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 
• 135562-22-0 (-)-(R_P,S_S)-4-(p-toluenesulfinyl)<2.2>paracyclophane 
• 135562-22-0 (+)-(S_P,S_S)-4-(p-toluenesulfinyl)<2.2>paracyclophane 
• 157018-15-0 (S_p)-4-hydroxy-[2.2]paracyclophane 
• 10122-95-9 (S_p)-4-amino[2.2]paracyclophane 
• 124618-53-7 pseudo-m-dibenzoyl<2.2>paracyclophane 
• 107496-64-0 4-benzoyl<2.2>paracyclophane hydrazone 
• 95274-30-9 bis(α-hydroxybenzyl)<2.2>paracyclophane 
• 107496-62-8 [1-[13-(Hydrazono-phenyl-methyl)-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4⁽¹⁶⁾,5,7⁽¹⁵⁾,10⁽¹⁴⁾,11-hexaen-5-yl]-1-phenyl-meth-(Z)-ylidene]-hydrazine 
• 95274-32-1 pseudo-o-dibenzoyl<2.2>paracyclophane 

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.

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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 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.

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 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%.

A resolution method for 4-amino-12-bromo[2.2]paracyclophane

A resolution method for 4-amino-12-bromo[2.2]paracyclophane is provided. L-proline protected by t-butyloxycarbonyl and racemic 4-amino-12-bromo[2.2]paracyclophane are reacted to generate a mixture of intermediates having configurations of (Rp, S) and (Sp, S). By utilizing a physical property difference (polar difference) of the intermediates having configurations of (Rp, S) and (Sp, S), the intermediates are separated by utilizing column chromatography, then recrystallization is performed for purification, and acidolysis is performed to obtain optically pure Sp-4-amino-12-bromo[2.2]paracyclophane and Rp-4-amino-12-bromo[2.2]paracyclophane. A resolution agent used in the method is cheap and nontoxic, resolution operation steps are simple, and high yields and good optical purities can be achieved, so that the method is suitable for large-scale preparation of the optically pure 4-amino-12-bromo[2.2]paracyclophane.