1,2,4,5-(2.2.2.2)-Cyclophane

Base Information

• Chemical Name: 1,2,4,5-(2.2.2.2)-Cyclophane
• CAS No.: 54100-59-3
• Molecular Formula: C20H20
• Molecular Weight: 260.379
• Hs Code.: 2902909090
• DSSTox Substance ID: DTXSID60202447
• Nikkaji Number: J12.445A
• Wikidata: Q83075713
• Mol file: 54100-59-3.mol

Synonyms:54100-59-3;1,2,4,5-(2.2.2.2)-Cyclophane;1,2,4,5-[2.2.2.2]Cyclophane;[2.2.2.2](1,2,4,5)Cyclophane;DTXSID60202447

Chemical Property of 1,2,4,5-(2.2.2.2)-Cyclophane

Chemical Property:

• Boiling Point: 367.6°Cat760mmHg
• Flash Point: 190.4°C
• PSA: 0.00000
• Density: 1.161g/cm³
• LogP: 3.76760
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 260.156500638
• Heavy Atom Count: 20
• Complexity: 268

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC3=C4CCC5=C(CC3)C=C1C(=C5)CCC2=C4

Technology Process of 1,2,4,5-(2.2.2.2)-Cyclophane

There total 11 articles about 1,2,4,5-(2.2.2.2)-Cyclophane 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: 64.0%

1,2,4,5-tetrabromomethylbenzene (15442-91-8) → <24><1,2,3,4>cyclophane (54100-59-3)

Guidance literature:

With bis(triphenylphosphine)ethylenenickel⁽⁰⁾; In benzene; Ambient temperature;

DOI:10.1016/S0040-4039(01)81707-X

Reference yield: 7.2%

tricyclo[6.2.0.03,6]deca-1,3(6),7-triene (1610-51-1) → <24><1,2,3,4>cyclophane (54100-59-3) + 14,20-dimethyl<25>(1,2,4,5)(1,3,4)(1,3,4)cyclophane (94978-47-9) + deltaphane (94978-50-4)

Guidance literature:

In hexane; at 425 ℃; under 760 Torr; Product distribution;

DOI:10.1021/ja00293a030

Reference yield:

3,10-Dithia-tricyclo[10.2.2.25,8]octadeca-1(15),5(18),6,8(17),12(16),13-hexaene-6,17-dicarboxylic acid dimethyl ester (54143-26-9) → <24><1,2,3,4>cyclophane (54100-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1: P(OMe)3 / Irradiation

2: AlCl₃

4: LiAlH₄

5: TsOH*H₂O, AcOH / Heating

6: (i) TsNHNH₂, TsOH, (ii) NaOMe, (UV-irradiation)

With lithium aluminium tetrahydride; aluminium trichloride; toluene-4-sulfonic acid; acetic acid; phosphorous acid trimethyl ester;

DOI:10.1021/ja00502a032

upstream raw materials:

tricyclo[6.2.0.0^3,6]deca-1,3⁽⁶⁾,7-triene

1,2,4,5,7,8,10,11-Octahydrobiscyclobuta<4,5>benzo<1,2-a:1',2'-e>cycloocten

1,2,4,5-tetrabromomethylbenzene

12,14-Dimethyl-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4⁽¹⁶⁾,5,7⁽¹⁵⁾,10⁽¹⁴⁾,11-hexaene-5,15-dicarbaldehyde

Refernces

• 1、 Uhling, E.,Hipler, B.. "EINE EINFACHE SYNTHESE VON /2n/CYCLOPHANEN". . p. 5871 - 5874. Retrieved 2007/10/02.