3-(4-Bromophenyl)cyclobutanone

Base Information

• Chemical Name: 3-(4-Bromophenyl)cyclobutanone
• CAS No.: 254892-91-6
• Molecular Formula: C10H9BrO
• Molecular Weight: 225.085
• Hs Code.: 2914700090
• European Community (EC) Number: 822-589-0
• DSSTox Substance ID: DTXSID40404624
• Wikidata: Q82208900
• Mol file: 254892-91-6.mol

Synonyms:3-(4-Bromophenyl)cyclobutanone;254892-91-6;3-(4-bromophenyl)cyclobutan-1-one;Cyclobutanone, 3-(4-bromophenyl)-;3-(4-bromo-phenyl)-cyclobutanone;MFCD04038979;3-(4-BROMOPHENYL)-CYCLOBUTANE-1-ONE;SCHEMBL5612;DTXSID40404624;FOQRHYVNXUDNKL-UHFFFAOYSA-N;AKOS004115284;PB24838;AS-32459;SY017720;CS-0053973;FT-0719235;EN300-43632;A853975;F8889-7086;Z385459408

Chemical Property of 3-(4-Bromophenyl)cyclobutanone

Chemical Property:

• PSA: 17.07000
• LogP: 2.89560
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 223.98368
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

99%min. ^*data from raw suppliers

Cyclobutanone,3-(4-bromophenyl)- 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CC1=O)C2=CC=C(C=C2)Br
• Uses: 3-(4-Bromophenyl)cyclobutanone is used in the preparations of selective T-type calcium channel blockers.

Technology Process of 3-(4-Bromophenyl)cyclobutanone

There total 6 articles about 3-(4-Bromophenyl)cyclobutanone 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: 86.2%

3-(4-bromophenyl)-2,2-dichlorocyclobutan-1-one (254892-87-0) → 3-(4-bromophenyl)cyclobutanone (254892-91-6)

Guidance literature:

With acetic acid; zinc; at 20 ℃; for 4h; Reflux;

Reference yield: 56.0%

1-bromo-4-ethenyl-benzene (2039-82-9) + N,N-dimethyl acetamide (127-19-5,116057-81-9) → 3-(4-bromophenyl)cyclobutanone (254892-91-6)

Guidance literature:

N,N-dimethyl acetamide; With trifluoromethylsulfonic anhydride; In 1,2-dichloro-ethane; at 5 ℃; for 0.5h;

1-bromo-4-ethenyl-benzene; With 2,4,6-trimethyl-pyridine; In 1,2-dichloro-ethane; for 18h; Reflux;

DOI:10.1021/acs.orglett.8b03121

Reference yield: 25.42%

1-bromo-4-ethenyl-benzene (2039-82-9) + 1,2-dichloro-ethane (107-06-2,52399-93-6) → 3-(4-bromophenyl)cyclobutanone (254892-91-6)

Guidance literature:

1,2-dichloro-ethane; With trifluoromethylsulfonic anhydride; In N,N-dimethyl acetamide; at -15 ℃; for 0.5h; Large scale;

1-bromo-4-ethenyl-benzene; With 2,4,6-trimethyl-pyridine; In N,N-dimethyl acetamide; 1,2-dichloro-ethane; at 90 ℃; for 16h; Large scale;

upstream raw materials:

3-(4-bromophenyl)-2,2-dichlorocyclobutan-1-one

1-bromo-4-ethenyl-benzene

N,N-dimethyl acetamide

Ketene

Downstream raw materials:

3-(4-bromophenyl)cyclobutanol

1-bromo-4-(3,3-difluorocyclobutyl)benzene

Refernces

• 1、 Gao, Ziwei,Gou, Jing,Hao, Zhe,Hou, Jing,Li, Chaoqun,Li, Gaoqiang,Xing, Qingzhao,Yu, Binxun. "Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2". . p. 9563 - 9586. Retrieved 2021/07/20.
• 2、 Zhao, Xia,Ji, Liangshuo,Gao, Yu,Sun, Tengteng,Qiao, Jiamin,Li, Ankun,Lu, Kui. "Visible-Light-Promoted Selenocyanation of Cyclobutanone Oxime Esters Using Potassium Selenocyanate". . p. 11399 - 11406. Retrieved 2021/09/02.