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

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

Uses

Used in Fragrance Industry:
6-Formaldehydecoumarin is used as a fragrance ingredient for its sweet, vanilla-like scent. It is incorporated into perfumes, soaps, and other personal care products to provide a pleasant and long-lasting aroma.
Used in Flavor Industry:
In addition to its use in fragrances, 6-Formaldehydecoumarin is also utilized as a flavoring agent. Its unique aroma profile makes it suitable for enhancing the taste of various food and beverage products, particularly those with a vanilla or sweet flavor profile.
Used in Pharmaceutical Industry:
6-Formaldehydecoumarin has potential applications in the pharmaceutical industry as well. Its chemical structure allows it to interact with biological systems, making it a candidate for the development of new drugs or as a component in existing formulations.
Used in Cosmetic Industry:
In the cosmetic industry, 6-Formaldehydecoumarin is used as an active ingredient in various skin care and hair care products. Its aromatic properties, along with potential skin conditioning and hair conditioning effects, make it a valuable addition to these formulations.
Used in Research and Development:
6-Formaldehydecoumarin is also used in research and development settings. Its unique chemical properties and potential applications in various industries make it an interesting subject for scientific studies and the development of new technologies.

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

Upstream product

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

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 
• 106235-44-3 cis-6-(2'-3'-dimethoxystyryl)coumarin 
• 106235-45-4 6-(2'-3'-dimethoxyphenethyl)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 

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

Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation

An efficient annulation strategy involving the reaction of phenolic acetates with acrylates in the presence of [Rh2(OAc)4] as catalyst and formic acid as reducing agent, leading to the high yield synthesis of coumarin derivatives, has been developed. The addition of NaOAc as a base increased the yield of the products. The reaction is quite successful for both electron-rich as well as electron-deficient phenolic acetates, affording coumarins with excellent regioselectivity, and proceeds via C-H bond activation proven by deuterium incorporation studies.

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.

Palladium-catalyzed synthesis of benzofurans and coumarins from phenols and olefins

Triple C-H functionalization: Palladium-catalyzed synthesis of benzofurans and coumarins by reacting phenols and unactivated olefins is described. The reaction comprises sequential C-H functionalization and shows diverse functional group compatibility. Preliminary mechanistic studies shed light into the possible mechanisms. Copyright

IBX-mediated one-pot synthesis of benzimidazoles from primary alcohols and arylmethyl bromides

A variety of primary alcohols are shown to be converted to the corresponding benzimidazoles in one pot by employing IBX and o-phenylenediamine in DMSO at room temperature. o-Iodobenzoic acid is the end product of IBX, which is employed in 1.0 equiv. Arylmethyl bromides are also shown to be converted likewise to benzimidazoles in moderate yields in one pot, albeit at slightly elevated temperatures.

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.

NOVEL CURCUMIN DERIVATIVE

The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R2 represents a 1H-indol-6-yl group or the like.