4-Bromomethyl-7-methoxycoumarin

Base Information

• Chemical Name: 4-Bromomethyl-7-methoxycoumarin
• CAS No.: 35231-44-8
• Molecular Formula: C11H9BrO3
• Molecular Weight: 269.095
• Hs Code.: 29322090
• European Community (EC) Number: 252-448-3
• UNII: 4K32PB5K8Q
• DSSTox Substance ID: DTXSID70188723
• Nikkaji Number: J207.993C
• Wikidata: Q72447332
• Metabolomics Workbench ID: 74023
• Mol file: 35231-44-8.mol

Synonyms:4-(bromomethyl)-7-methoxy-2-oxo-2H-benzopyran;4-bromomethyl-7-methoxycoumarin

Chemical Property of 4-Bromomethyl-7-methoxycoumarin

Chemical Property:

• Appearance/Colour: Light green-yellow crystals
• Vapor Pressure: 3.83E-06mmHg at 25°C
• Melting Point: 213-215 °C(lit.)
• Refractive Index: 1.594
• Boiling Point: 385.3 °C at 760 mmHg
• Flash Point: 186.8 °C
• PSA: 39.44000
• Density: 1.552 g/cm³
• LogP: 2.69650
• Storage Temp.: 2-8°C
• Solubility.: chloroform: soluble20mg/mL, clear, colorless to faintly yellow
• Water Solubility.: insoluble
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 267.97351
• Heavy Atom Count: 15
• Complexity: 288

Purity/Quality:

99% ^*data from raw suppliers

4-Bromomethyl-7-methoxycoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C(=CC(=O)O2)CBr
• Uses: 4-Bromomethyl-7-methoxycoumarin can be used as fluorescent label for fatty acids. For derivatization, TLC and HPLC separation, and fluorometric analysis of a wide range of naturally occurring acids, including bile and thromboxane B2. Used for derivatization, TLC and HPLC separation, and fluorometric analysis of a wide range of naturally occurring acids, including bile and thromboxane B2 4-Bromomethyl-7-methoxycoumarin has been used:as derivatization reagent in determination of 5-fluorouracil (5-FU) in human plasma by HPLC-tandem mass spectrometryas derivatization reagent in fluorescence detection of sodium monofluoroacetate (MFA-Na) in biological samples by HPLCin the synthesis of new caged derivatives of hydrolysis-resistant 8-bromoadenosine cyclic 3′,5′-monophosphate (8-Br-cAMP) and 8-bromoguanosine cyclic 3′,5′-monophosphate (8-Br-cGMP)in TLC and HPLC separation and fluorometric analysis of a wide range of naturally occurring acids, including bile and thromboxane B2

Technology Process of 4-Bromomethyl-7-methoxycoumarin

There total 5 articles about 4-Bromomethyl-7-methoxycoumarin 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: 73.0%

4-methyl-7-methoxy-2H-1-benzopyran-2-one (2555-28-4) → 4-(bromomethyl)-7-methoxycoumarin (35231-44-8)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 8h; Reflux;

DOI:10.1016/j.bmc.2010.03.069

Reference yield: 51.0%

O-methylresorcine (150-19-6) + 4-bromoethyl acetoacetate (13176-46-0) → 4-(bromomethyl)-7-methoxycoumarin (35231-44-8)

Guidance literature:

aluminium trichloride; In nitrobenzene; at 20 ℃; for 3h;

Reference yield:

recorcinol (108-46-3) → 4-(bromomethyl)-7-methoxycoumarin (35231-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid

2: acetone; potassium carbonate

With sulfuric acid; potassium carbonate; acetone;

upstream raw materials:

4-methyl-7-methoxy-2H-1-benzopyran-2-one

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

dimethyl sulfate

2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetic acid

Downstream raw materials:

7-Methoxy-4-p-tolyloxymethyl-chromen-2-one

4-(2-Chloro-phenoxymethyl)-7-methoxy-chromen-2-one

7-Methoxy-4-(5-methyl-benzofuran-2-yl)-chromen-2-one

7-Methoxy-4-(p-tolylamino-methyl)-chromen-2-one

Refernces

• 1、 Saxena, Alpana,Shastri, Lokesh,Sunagar, Vinay. "Green approach for the synthesis of 4-coumarin-4H-pyrans from 4-formylcoumarins and their antibacterial study". . p. 1570 - 1576. Retrieved 2017.
• 2、 Mane, Smita G.,Reddy, Dinesh S.,Katagi, Kariyappa S.,Kumar, Amit,Munnolli, Ravindra S.,Kadam, Nikhil S.,Akki, Mahesh C.,Nagarajaiah,Joshi, Shrinivas D.. "Design, synthesis, molecular docking, anti-proliferative and anti-TB studies of 2H-chromen-8-azaspiro[4.5]decane-7,9-dione conjugates". . . Retrieved 2020/11/13.
• 3、 Reddy, Dinesh S.,Kongot, Manasa,Singh, Vishal,Maurya, Neha,Patel, Rajan,Kumar Singhal, Nitin,Avecilla, Fernando,Kumar, Amit. "Coumarin tethered cyclic imides as efficacious glucose uptake agents and investigation of hit candidate to probe its binding mechanism with human serum albumin". . . Retrieved 2019/08/27.