[2.2]Paracyclophane

Base Information

• Chemical Name: [2.2]Paracyclophane
• CAS No.: 1633-22-3
• Molecular Formula: C16H16
• Molecular Weight: 208.303
• Hs Code.: 29029080
• European Community (EC) Number: 216-644-2
• NSC Number: 91575
• UNII: 0I9PQB142O
• DSSTox Substance ID: DTXSID9061835
• Nikkaji Number: J12.885F
• Wikidata: Q72499536
• ChEMBL ID: CHEMBL3278516
• Mol file: 1633-22-3.mol

Synonyms:1,4-Carbophane;Cyclobis(benzene-1,4-dimethylene);Di-1,4-xylylene;Di-p-xylylene;NSC 91575;[2.2](1,4)Cyclophane;[2.2]-p-Cyclophane;2.2 -paracyclophane;[2.2]Paracyclophane;

Chemical Property of [2.2]Paracyclophane

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Vapor Pressure: 0.000587mmHg at 25°C
• Melting Point: 285-288 °C
• Refractive Index: 1.585
• Boiling Point: 320.7 °C at 760mmHg
• Flash Point: 154 °C
• PSA: 0.00000
• Density: 1.033 g/cm³
• LogP: 3.57040
• Storage Temp.: Store below +30°C.
• Water Solubility.: INSOLUBLE
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 208.125200510
• Heavy Atom Count: 16
• Complexity: 156

Purity/Quality:

99.0% ^*data from raw suppliers

[2.2]Paracyclophane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C,F
• Hazard Codes: Xi,C,F
• Statements: 11-34
• Safety Statements: 24/25-45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1CC2=CC=C(CCC3=CC=C1C=C3)C=C2
• Uses: 2,2]-Paracyclophane is the raw material for the synthesis of parylene which is widely used in microelectronic integrated circuit.

Technology Process of [2.2]Paracyclophane

There total 67 articles about [2.2]Paracyclophane 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: 97.0%

C14H26NSi(1+)*Br(1-) → [2.2]Paracyclophan (1633-22-3)

Guidance literature:

With sodium hydroxide; In water; at 60 ℃; for 0.0333333h;

Reference yield: 97.0%

[32](1,4)cyclophane-2,11-dione (7568-20-9) → [2.2]Paracyclophan (1633-22-3)

Guidance literature:

In benzene; for 4h; Ambient temperature; Irradiation;

DOI:10.1016/S0040-4039(98)00716-3

Reference yield: 95.0%

(Sp)-4-p-toluenesulfinyl[2.2]paracyclophane → [2.2]Paracyclophan (1633-22-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; N,N-dimethyl-formamide; pentane; at -78 ℃;

DOI:10.1055/s-0030-1258286

upstream raw materials:

para-xylene

4,4'-bis(bromomethyl)bibenzyl

(4-methylbenzyl)-trimethylammonium chloride

1,4-bis(bromomethyl)benzene

Downstream raw materials:

4-acetyl[2.2]paracyclophane

Propionic acid 4-[2-(4-propionyloxymethyl-phenyl)-ethyl]-benzyl ester

1-p-Tolyl-2-<4-(2-hydroxy-ethyl)-phenyl>-ethan

1-p-Tolyl-2-<4-methoxy-methyl-phenyl>-ethan

Refernces

• 1、 Brown,Farthing. "-". . p. 915. Retrieved 1949.
• 2、 Font-Sanchis, Enrique,Miranda, Miguel A.,Perez-Prieto, Julia,Scaiano. "Laser flash photolysis of [3,n]paracyclophan-2-ones. Direct observation and chemical behavior of 4,4′-(1,n-alkanediyl)bisbenzyl biradicals". . p. 6131 - 6135. Retrieved 2002.
• 3、 Burger,A. et al.. "-". . p. 1721 - 1728. Retrieved 1964.
• 4、 Bruhin,J.,Jenny,W.. "". . p. 1215 - 1218. Retrieved 1973.
• 5、 Isaji, Hajime,Sako, Katsuya,Takemura, Hiroyuki,Tatemitsu, Hitoshi,Shinmyozu, Teruo. "A new synthetic method of [2.2]cyclopbanes from [3.3]cyclophane-2,11- diones via photodecarbonylation". . p. 4303 - 4304. Retrieved 1998.
• 6、 Miranda,Font-Sanchis,Perez-Prieto,Scaiano. "The 4,4′-(1,2-ethanediyl)bisbenzyl biradical: Its generation, detection, and (photo)chemical behavior in solution". . p. 2717 - 2721. Retrieved 2001.
• 7、 Mungalpara, Maulik N.,Wang, Jingjing,Coles, Martyn P.,Plieger, Paul G.,Rowlands, Gareth J.. "The synthesis of a [2.2]paracyclophane-derived secondary phosphine oxide and a study of its reactivity". . p. 5519 - 5527. Retrieved 2018/05/26.
• 8、 -. "Method for using microchannel reactor to prepare paracyclophane monomeric compound". . . Retrieved 2017/08/23.