4-Bromo-2H-chromen-2-one

Base Information

• Chemical Name: 4-Bromo-2H-chromen-2-one
• CAS No.: 938-40-9
• Molecular Formula: C9H5BrO2
• Molecular Weight: 225.041
• DSSTox Substance ID: DTXSID90366824
• Nikkaji Number: J260.186I
• Wikidata: Q82152250
• Mol file: 938-40-9.mol

Synonyms:4-Bromo-2H-chromen-2-one;938-40-9;2H-1-Benzopyran-2-one, 4-bromo-;4-Bromocoumarin;MFCD00463529;4-bromochromen-2-one;CBDivE_005811;SCHEMBL1535058;DTXSID90366824;4-Bromo-2H-1-benZopyran-2-one;AKOS015966930;SY026916;E70006

Chemical Property of 4-Bromo-2H-chromen-2-one

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 223.94729
• Heavy Atom Count: 12
• Complexity: 235

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC(=O)O2)Br

Technology Process of 4-Bromo-2H-chromen-2-one

There total 6 articles about 4-Bromo-2H-chromen-2-one 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: 96.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → 4-Bromo-2H-1-benzopyran-2-one (938-40-9)

Guidance literature:

4-hydroxy[1]benzopyran-2-one; With tetrabutylammomium bromide; In toluene; at 100 ℃; Inert atmosphere;

With phosphorus pentoxide; In toluene; for 3h; Inert atmosphere; Heating;

DOI:10.1055/s-0036-1588955

Reference yield:

3,4-dibromo-3,4-dihydrocoumarin (42974-18-5) → 4-Bromo-2H-1-benzopyran-2-one (938-40-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2008.03.085

Reference yield:

1-phenyl-2-hydroxyethanone (582-24-1) → 4-Bromo-2H-1-benzopyran-2-one (938-40-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / 3.5 h / 0 - 100 °C / Inert atmosphere

2: tetrabutylammomium bromide; phosphorus pentoxide / toluene / 3.25 h / 120 °C

With phosphorus pentoxide; tetrabutylammomium bromide; sodium hydride; In toluene;

DOI:10.1021/acs.jmedchem.6b00158

upstream raw materials:

4-hydroxy[1]benzopyran-2-one

3,4-dibromo-3,4-dihydrocoumarin

1-phenyl-2-hydroxyethanone

o-hydroxyacetophenone

Downstream raw materials:

4-(phenylamino)-2H-chromen-2-one

coumarin

4-(3-Methoxyphenyl)-2H-1-benzopyran-2-one

4-(p-tolyl)coumarin

Refernces

• 1、 Ga?par, Jan,Némethová, Zuzana,Janeková, Hana,Gáplovsky, Anton,Stankovi?ová, Henrieta. "Amino acid-sensitive reagents with coumarin moiety for latent prints examination". . p. 1787 - 1794. Retrieved 2018.
• 2、 Zhao, Lei,Zhang, Jian,Liu, Ting,Mou, Honglan,Wei, Chunle,Hu, Deyu,Song, Baoan. "Design, Synthesis, and Antiviral Activities of Coumarin Derivatives Containing Dithioacetal Structures". . p. 975 - 981. Retrieved 2020.
• 3、 -. "CHIRALITY SENSING WITH MOLECULAR CLICK CHEMISTRY PROBES". Paragraph 0247-0248. . Retrieved 2020/02/23.