11,11-difluorobicyclo[4.4.1]undeca-1,3,5,7,9-pentaene

Base Information

• Chemical Name: 11,11-difluorobicyclo[4.4.1]undeca-1,3,5,7,9-pentaene
• CAS No.: 19026-91-6
• Molecular Formula: C₁₁H₈F₂
• Molecular Weight: 178.181
• Mol file: 19026-91-6.mol

Synonyms:1,6-(Difluoromethano)[10]annulene;11,11-Difluoro-1,6-methano[10]annulene

Chemical Property of 11,11-difluorobicyclo[4.4.1]undeca-1,3,5,7,9-pentaene

Chemical Property:

• Vapor Pressure: 0.00277mmHg at 25°C
• Boiling Point: 295°Cat760mmHg
• Flash Point: 110°C
• Density: 1.18g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 11,11-difluorobicyclo[4.4.1]undeca-1,3,5,7,9-pentaene

There total 2 articles about 11,11-difluorobicyclo[4.4.1]undeca-1,3,5,7,9-pentaene 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: 59.0%

2-bromo-11,11-difluorobicyclo<4.4.1>undeca-1,3,5,7,9-pentaene (58081-08-6) + potassium phtalimide (1074-82-4) → 11,11-difluoro-1,6-methano<10>annulene (19026-91-6) + 11,11-difluoro-2-phthalimido-1,6-methano<10>annulen (134956-31-3)

Guidance literature:

With copper(l) iodide; In N,N-dimethyl acetamide; for 24h; Heating;

DOI:10.1007/BF00809362

Reference yield:

4a,8a-Difluormethano-1,4,4a,5,8,8a-hexahydro-naphthalin → 11,11-difluoro-1,6-methano<10>annulene (19026-91-6)

Guidance literature:

Multistep reaction; (i) (bromination), (ii) KOH, MeOH;

Reference yield:

2-butynedinitrile (1071-98-3) + 11,11-difluoro-1,6-methano<10>annulene (19026-91-6) → 13,13-Difluor-tetracyclo<6.2.2.12,7.02,7>trideca-3,5,9,11-tetraen-9,10-dicarbonitril (20027-13-8)

Guidance literature:

upstream raw materials:

2-bromo-11,11-difluorobicyclo<4.4.1>undeca-1,3,5,7,9-pentaene

potassium phtalimide

Downstream raw materials:

13,13-Difluor-tetracyclo<6.2.2.1^2,7.0^2,7>trideca-3,5,9,11-tetraen-9,10-dicarbonitril

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