4-(Bromomethyl)-7-hydroxy-2H-chromen-2-one

Base Information

• Chemical Name: 4-(Bromomethyl)-7-hydroxy-2H-chromen-2-one
• CAS No.: 161798-25-0
• Molecular Formula: C10H7 Br O3
• Molecular Weight: 255.068
• NSC Number: 667229
• UNII: 9B6VKC9ZVK
• DSSTox Substance ID: DTXSID80167241
• Nikkaji Number: J2.389.860H
• Wikidata: Q83036568
• ChEMBL ID: CHEMBL1996493
• Mol file: 161798-25-0.mol

Synonyms:161798-25-0;4-(Bromomethyl)-7-hydroxy-2H-chromen-2-one;7-Hydroxy-4-(bromomethyl)coumarin;4-(bromomethyl)-7-hydroxychromen-2-one;4-bromomethyl-7-hydroxycoumarin;NSC667229;9B6VKC9ZVK;2H-1-Benzopyran-2-one, 4-(bromomethyl)-7-hydroxy-;NSC 667229;NSC-667229;4-(BROMOMETHYL)-7-HYDROXY-CHROMEN-2-ONE;UNII-9B6VKC9ZVK;SCHEMBL3868315;CHEMBL1996493;DTXSID80167241;XFNVWGFZARBVBT-UHFFFAOYSA-N;4-(Bromomethyl)-7-hydroxycoumarin;GEO-02733;MFCD01862969;AKOS017547939;NCI60_023403;4-(bromomethyl)-7-hydroxy-2h-1-benzopyran-2-one;A858015;W-200149

Chemical Property of 4-(Bromomethyl)-7-hydroxy-2H-chromen-2-one

Chemical Property:

• Vapor Pressure: 1.07E-07mmHg at 25°C
• Boiling Point: 421.3°Cat760mmHg
• Flash Point: 208.6°C
• PSA: 50.44000
• Density: 1.726g/cm³
• LogP: 2.39350
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 253.95786
• Heavy Atom Count: 14
• Complexity: 275

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)OC(=O)C=C2CBr
• Use Description: 4-(bromomethyl)-7-hydroxy-chromen-2-one, a chemical compound, has applications in various fields. In the field of medicinal chemistry, it can serve as a valuable intermediate for the synthesis of pharmaceutical compounds, potentially leading to the development of novel drug candidates with therapeutic properties. Its role is pivotal in creating molecules with specific pharmacological actions, potentially targeting various biological pathways or receptors. Additionally, in academic research and organic chemistry, this compound can be employed as a building block for the synthesis of complex organic molecules, aiding in the study of chemical reactions and the development of new chemical methodologies. Its versatility across these fields underscores its significance in drug discovery, chemical research, and the potential advancement of treatments for various medical conditions, ultimately contributing to healthcare and scientific knowledge.

Technology Process of 4-(Bromomethyl)-7-hydroxy-2H-chromen-2-one

There total 6 articles about 4-(Bromomethyl)-7-hydroxy-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: 90.0%

2-bromoethyl acetoacetate (88488-47-5) + recorcinol (108-46-3) → 4-(bromomethyl)-7-hydroxy-2H-chromen-2-one (161798-25-0)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 8h;

DOI:10.1039/c7cc03241b

Reference yield: 87.0%

4-(bromomethyl)-7-methoxycoumarin (35231-44-8) → 4-(bromomethyl)-7-hydroxy-2H-chromen-2-one (161798-25-0)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bioorg.2020.103997

Reference yield: 85.0%

4-bromoethyl acetoacetate (13176-46-0) + recorcinol (108-46-3) → 4-(bromomethyl)-7-hydroxy-2H-chromen-2-one (161798-25-0)

Guidance literature:

With sulfuric acid; at 20 ℃; for 12h;

DOI:10.1039/c6tb02944b

upstream raw materials:

4-bromoethyl acetoacetate

recorcinol

7-acetoxy-4-bromomethyl-2H-1-benzopyran-2-one

7-hydroxy-4-methyl-chromen-2-one

Downstream raw materials:

4-(bromomethyl)-7-methoxycoumarin

(Z)-5-(3-bromobenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione

(Z)-5-(4-methoxybenzylidene)-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione

(Z)-5-[4-(dimethylamino)benzylidene]-3-[(7-hydroxy-2-oxo-2H-chromen-4-yl)methyl]thiazolidine-2,4-dione

Refernces

• 1、 Karthik,Prashanth Kumar,Gangopadhyay, Moumita,Mandal, Mahitosh,Singh, N. D. Pradeep. "A targeted, image-guided and dually locked photoresponsive drug delivery system". . p. 728 - 732. Retrieved 2015.
• 2、 Furusho, Hitoshi,Oishi, Motoi,Kishi, Tetsuo,Yasumori, Atsuo,Nagasaki, Yukio. "Preparation and molecular recognition of SERS probe based on gold nanoparticles constructed from PEG-oligoamine copolymer possessing a coumarin group between PEG and oligoamine". . p. 52 - 53. Retrieved 2010.
• 3、 Shankar, E. P. Shyam,Bahulayan, Damodaran. "Chemistry, chemical biology and photophysics of certain new chromene-triazole-coumarin triads as fluorescent inhibitors of CDK2 and CDK4 induced cancers". . p. 13863 - 13872. Retrieved 2019.
• 4、 Agbo, Emmanuel N.,Choong, Yee Siew,Gildenhuys, Samantha,More, Garland K.,Mphahlele, Malose J.. "Synthesis of furocoumarin–stilbene hybrids as potential multifunctional drugs against multiple biochemical targets associated with Alzheimer's disease". . . Retrieved 2020.
• 5、 Song, Xufen,Tu, Yayi,Wang, Renjie,Pu, Shouzhi. "A lysosome-targetable fluorescent probe for simultaneous detection and discrimination of Cys/Hcy and GSH by dual channels". . . Retrieved 2020.
• 6、 Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Metre, Tukaram V.,Kariduraganavar, Mahadevappa Y.,Margankop, Sheetal B.,Joshi, Shrinivas D.,Kumbar, Vijay M.. "Microwave facilitated one-pot three component synthesis of coumarin-benzoxazole clubbed 1,2,3-triazoles: Antimicrobial evaluation, molecular docking and in silico ADME studies". . p. 3460 - 3472. Retrieved 2021/10/02.