6-Bromochromen-2-one

Base Information

• Chemical Name: 6-Bromochromen-2-one
• CAS No.: 19063-55-9
• Molecular Formula: C9H5 Br O2
• Molecular Weight: 225.041
• Hs Code.: 2932209090
• NSC Number: 146624
• DSSTox Substance ID: DTXSID20301844
• Nikkaji Number: J394.272D
• Wikidata: Q82046158
• ChEMBL ID: CHEMBL1650558
• Mol file: 19063-55-9.mol

Synonyms:6-bromochromen-2-one;19063-55-9;6-bromo-2H-chromen-2-one;6-bromocoumarin;2H-1-Benzopyran-2-one, 6-bromo-;MFCD01327473;2H-1-Benzopyran-2-one,6-bromo-;6-Bromcumarin;NSC146624;6-bromo-chromen-2-one;SCHEMBL875198;CHEMBL1650558;DTXSID20301844;AMY16407;AKOS015834771;AS-3079;CS-W005186;NSC 146624;NSC-146624;SY112628;10.14272/XXRJDOQENVGLJT-UHFFFAOYSA-N;doi:10.14272/XXRJDOQENVGLJT-UHFFFAOYSA-N;J-518428

Chemical Property of 6-Bromochromen-2-one

Chemical Property:

• Vapor Pressure: 4.77E-05mmHg at 25°C
• Melting Point: 164 °C
• Boiling Point: 349.2°Cat760mmHg
• Flash Point: 165°C
• PSA: 30.21000
• Density: 1.688g/cm³
• LogP: 2.55550
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 223.94729
• Heavy Atom Count: 12
• Complexity: 225

Purity/Quality:

98%min ^*data from raw suppliers

6-Bromochromen-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=O)O2)C=C1Br

Technology Process of 6-Bromochromen-2-one

There total 52 articles about 6-Bromochromen-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: 98.0%

ethyl (E)-3-(5-bromo-2-hydroxxyphenyl)propenoate (515877-70-0) → 6-bromo-2H-chromen-2-one (19063-55-9)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); In acetonitrile; at 20 ℃; for 24h; Sealed tube; Irradiation; Inert atmosphere;

Reference yield: 97.0%

2-O-acetyl-4-bromosalicylaldehyde (138116-09-3) → 6-bromo-2H-chromen-2-one (19063-55-9)

Guidance literature:

2-O-acetyl-4-bromosalicylaldehyde; With 18-crown-6 ether; bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate; potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 20 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In methanol; at 85 ℃; for 0.5h;

DOI:10.1016/j.bmc.2016.09.020

Reference yield: 86.0%

methyl chloroacetate (96-34-4) + 5-bromosalicyclaldehyde (1761-61-1) → 6-bromo-2H-chromen-2-one (19063-55-9) + (E)-methyl 5’-bromo-2’-hydroxycinnamate (39100-04-4)

Guidance literature:

With 1-(2-OPPh₂-propyl)-3-methylimidazolium hexafluorophosphate; sodium methylate; at 110 ℃; for 0.183333h; Ionic liquid; Microwave irradiation;

DOI:10.1080/00397910902898650

upstream raw materials:

acetic anhydride

5-bromosalicyclaldehyde

C₆H₄(CH₂CH₂C(O)O)

2-(5-Chloro-2-nitro-benzylidene)-malonic acid

Downstream raw materials:

3-(5-bromo-2-hydroxy-phenyl)-propionic acid

6-(4-hydroxyphenyl)-2H-chromen-2-one

6-phenyl-2H-chromen-2-one

6-(p-tolyl)-2H-chromen-2-one

Refernces

• 1、 Shockravi, Abbas,Valizadeh, Hassan,Heravi, Majid M.. "A one-pot and convenient synthesis of coumarins in solventless system". . p. 501 - 504. Retrieved 2003.
• 2、 Chandrasekhar, Sosale,Kumar, Honnaiah Vijay. "An expeditious coumarin synthesis via a "Pseudocycloaddition" between salicylaldehydes and ketene". . p. 232 - 235. Retrieved 2015.
• 3、 -. "Synthesis method of coumarin derivatives". Paragraph 0036-0038. . Retrieved 2020/09/23.
• 4、 Feng, Zhao,Wu, Yong,Wu, Zhaoxin,Yang, Xiaolong,Yu, Yue,Zhou, Guijiang. "Unsymmetric Heteroleptic Ir(III) Complexes with 2-Phenylquinoline and Coumarin-Based Ligand Isomers for Tuning Character of Triplet Excited States and Achieving High Electroluminescent Efficiencies". supporting information. p. 12362 - 12374. Retrieved 2020/09/15.