[3.3]Paracyclophane

Base Information

• Chemical Name: [3.3]Paracyclophane
• CAS No.: 2913-24-8
• Molecular Formula: C₁₈H₂₀
• Molecular Weight: 236.357
• DSSTox Substance ID: DTXSID00183387
• Nikkaji Number: J55.652A
• Wikidata: Q83054166
• Mol file: 2913-24-8.mol

Synonyms:(2.2)paracyclophane;(3.3)paracyclophane

Chemical Property of [3.3]Paracyclophane

Chemical Property:

• Vapor Pressure: 6.11E-06mmHg at 25°C
• Melting Point: 104.5-105.5 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.6420 (estimate)
• Boiling Point: 390.1°Cat760mmHg
• Flash Point: 207.8°C
• PSA: 0.00000
• Density: 0.997g/cm³
• LogP: 4.35060
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 236.156500638
• Heavy Atom Count: 18
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=C(CCCC3=CC=C(C1)C=C3)C=C2

Technology Process of [3.3]Paracyclophane

There total 20 articles about [3.3]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: 71.0%

[32](1,4)cyclophane-2,11-dione (7568-20-9) → [3.3]paracyclophane (2913-24-8)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; In diethylene glycol; at 130 - 200 ℃; for 4.5h;

DOI:10.1002/1099-0690(200009)2000:18<3195::aid-ejoc3195>3.0.co;2-1

Reference yield:

dodecahydro-[3.3]paracyclophane (284-02-6) → [3.3]paracyclophane (2913-24-8)

Guidance literature:

With palladium on activated charcoal; at 320 ℃;

DOI:10.1021/ja01652a081

Reference yield:

[2.2]Paracyclophan (1633-22-3) → [3.3]paracyclophane (2913-24-8)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) Br₂, (irradiation), (ii) AgOAc, AcOH, (iii) H₂O

2: CHCl₃

3: N₂H₂, KOH

With potassium hydroxide; diazene; In chloroform;

DOI:10.1021/ja00967a010

upstream raw materials:

dodecahydro-[3.3]paracyclophane

2,13-Dithia<4,4>paracyclophan

2,13-Dithia<4.4>paracyclophan-S,S,S',S'-tetraoxid

Tricyclo[10.2.2.2^5,8]octadeca-1⁽¹⁵⁾,5⁽¹⁸⁾,6,8⁽¹⁷⁾,12⁽¹⁶⁾,13-hexaene-2,2,11,11-tetracarbonitrile

Downstream raw materials:

5-bromo<3.3>paracyclophane

5-Nitro<3,3>paracyclophan

5-Acetyl-<3.3>paracyclophan

5-Acetamido<3.3>paracyclophan

Refernces

• 1、 Cram,D.J.,Helgeson,R.C.. "-". . p. 3515 - 3521. Retrieved 1966.
• 2、 Abboud, Khalil A.,Castellano, Ronald K.,Fagnani, Danielle E.,Henderson, Will R.,Liu, Guancen,Zhu, Yu. "Self-Assembling [ n. n]Paracyclophanes: A Structure-Property Relationship Study". supporting information. . Retrieved 2020/01/09.
• 3、 Cram, Donald J.,Jaeger, Ralf,Deshayes, Kurt. "Hemicarcerands that encapsulate hydrocarbons with molecular weights greater than two hundred". . p. 10111 - 10116. Retrieved 2007/10/02.