51690-26-7

Basic information

• Product Name: 6-Formaldehydecoumarin
• Synonyms: 2-oxochromene-6-carbaldehyde;6-Formaldehydecoumarin;COUMARIN-6-CARBOXALDEHYDE;2-Oxo-2H-chromene-6-carboxaldehyde, 2-Oxo-2H-1-benzopyran-6-carboxaldehyde;2-oxo-2H-chromene-6-carbaldehyde
• CAS NO: 51690-26-7
• Molecular Formula: C₁₀H₆O₃
• Molecular Weight: 174.15
• Mol File: 51690-26-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 192-194
• Boiling Point: 383.1 °C at 760 mmHg
• Flash Point: 176 °C
• Appearance: /
• Density: 1.352 g/cm³
• Vapor Pressure: 4.51E-06mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 6-Formaldehydecoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Formaldehydecoumarin(51690-26-7)
• EPA Substance Registry System: 6-Formaldehydecoumarin(51690-26-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 51690-26-7(Hazardous Substances Data)

Usage

General Description

6-Formaldehydecoumarin, also known as 4-hydroxy-3-[(2E)-3-oxobut-1-en-1-yl]-2H-chromen-2-one, is a chemical compound that is derived from coumarin. It is commonly used in the production of perfumes, soaps, and other personal care products due to its sweet, vanilla-like aroma. However, it is important to note that 6-Formaldehydecoumarin has been identified as a potential allergen and skin irritant in some individuals, and its use in cosmetics is regulated in many countries. Additionally, there is some evidence suggesting that 6-Formaldehydecoumarin may have cytotoxic and genotoxic effects, though more research is needed to fully understand its potential health impacts.

InChI:InChI=1/C10H6O3/c11-6-7-1-3-9-8(5-7)2-4-10(12)13-9/h1-6H

Upstream product

• 50465-95-7 6-Bromomethyl-coumarin 
• 123-08-0 4-hydroxy-benzaldehyde 
• 878-00-2 4-formylphenyl acetate 
• 292638-85-8 acrylic acid methyl ester 
• 67-66-3 chloroform 
• 91-64-5 coumarin 
• 92-48-8 6-methylcoumarin 
• 6093-68-1 6-hydroxycoumarin 

Downstream Products

• 106235-49-8 cis-6-(β-carboxy-2'-3'-dimethoxystyryl)coumarin 
• 106235-46-5 trans-6-(β-carboxy-2'-3'-dimethoxystyryl)coumarin 
• 106235-43-2 cis-6-(β-carboxy-2'-3'-dimethoxystyryl)coumarin 
• 7734-80-7 2-oxo-2H-benzopyran-6-carboxylic acid 
• 269082-09-9 3-(2-isobutoxy-5-(4-isobutoxybenzoyl)phenyl)propionic acid 
• 874204-75-8 methyl 3-[2-hydroxy-5-(4-isobutoxybenzoyl)phenyl]propionate 
• 874204-71-4 methyl 3-[2-isobutoxy-5-(4-isobutoxybenzoyl)phenyl]propionate 
• 106235-45-4 6-(2'-3'-dimethoxyphenethyl)coumarin 
• 106235-44-3 cis-6-(2'-3'-dimethoxystyryl)coumarin 

Relevant articles and documents

A 4,4 '-di-substituted diphenyl ketone compound and its preparation method

The invention provides a 4,4'-dibasic benzophenone compound which has a structure shown in the following formula I. The compound can well inhibit activities of an AP-1 protein and an NDM-1 protein and has the IC50 value of 52.93 plus and minus 11.86muM fo

Derivatization of coumarins at the benzenoid ring in aqueous medium

Some 6-disubstituted, 8-disubstituted, and/6,8-disubstituted compounds have been prepared from coumarin, 7-methylcoumarin, and 3,4-benzocoumarin. The Reimer-Tiemann reaction, Lederer-Manasse reaction, bromination using molecular bromine as well as 2,4,4,6-tetrabromocyclohex-2,5-dien-1-one, Elbs reaction, and diazocoupling have been carried under controlled conditions to obtain various derivatives. Further, several reactions of aldehyde derivatives of these coumarins have been carried on to prepare important functional compounds including some heterocycles. It is noteworthy that these aldehydes behave as phenolic aldehydes under alkaline conditions to undergo the Dakin reaction. The reactions are mostly carried in aqueous media involving a dianionic intermediate and hence fulfill one important criterion of green chemistry.

Reimer-tiemann reaction of coumarins

Improved yields of aldehydes from the Reimer-Tiemann reaction of coumarin and two of its derivatives, namely 7-methylcoumarin and 3,4-benzocoumarin, are obtained by carrying the reaction in a two-step procedure. Using crown ether as phase transfer catalyst, a further improvement in the yield of products is achieved. Additionally, coumarin and 7- methylcoumarin are shown to give dialdehydes under this condition. Dialdehydes are reported for the first time from the Reimer-Tiemann reaction. Copyright Taylor & Francis Group, LLC.