92-48-8

Basic information

• Product Name: 6-Methylcoumarin
• Synonyms: 6-MC;6-Methyl-1,2-benzopyrone;6-methyl-2h-1-benzopyran-2-on;6-methyl-2H-1-Benzopyran-2-one;6-Methyl-2-oxo-2H-benzopyran;6-Methyl-2-oxochronene;6-Methyl-chromen-2-one;6-methyl-coumari
• CAS NO: 92-48-8
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 160.17
• EINECS: 202-158-8
• Product Categories: Pharmaceutical Raw Materials;Coumarins;Miscellaneous;Building Blocks;Heterocyclic Building Blocks;Alphabetical Listings;Flavors and Fragrances;M-N;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 92-48-8.mol
• Article Data: 30

Chemical Properties

• Melting Point: 73-76 °C(lit.)
• Boiling Point: 303 °C725 mm Hg(lit.)
• Flash Point: 303°C/725mm
• Appearance: white to almost white crystalline powder
• Density: 1.0924 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 4222
• CAS DataBase Reference: 6-Methylcoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methylcoumarin(92-48-8)
• EPA Substance Registry System: 6-Methylcoumarin(92-48-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45
• WGK Germany: 3
• RTECS: GN7792000
• TSCA: Yes
• Hazardous Substances Data: 92-48-8(Hazardous Substances Data)

Usage

Chemical Properties

6-methylcoumarin is a white to almost white crystalline powder with has a somewhat coconut-like odor. the odor is also characterized as having a delicate fig or date sweetness. it has an almost bitter taste above 50 ppm, turning sweet and vanilla-like at lower levels. soluble in benzene, hot ethanol and non-volatile oil, insoluble in hot water.

Occurrence

Has apparently not been reported to occur in nature

Uses

6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps. It mainly used to prepare flavors such as coconut, vanilla and caramel.

Preparation

6-methylcoumarin is synthesized from p-cresol and fumaric acid. Preheat 72% sulfuric acid to 80 °C, add a mixture of fumaric acid and p-cresol, keep the reaction at 160-170 °C for 3-4 hours, cool, pour into crushed ice to precipitate a precipitate, and filter. The filtrate was extracted with benzene, and after adding benzene, the obtained crude product was subjected to vacuum distillation to obtain 6-methylcoumarin. synthesis of 6-methylcoumarin: By heating 6-methyl coumarin-3-carboxylic acid to 300 to 340°C; by condensation of p-cresol-disulfonic acid with fumaric acid in the presence of H2SO4; by condensation of p-homosalicyclic aldehyde with malonic acid in the presence of aniline, followed by heating for the lactone; from salicylaldehyde with propionic acid anhydride and sodium propionate.

Definition

ChEBI: 6-methylcoumarin is a member of the class of coumarins that is coumarin in which the hydrogen at position 6 is replaced by a methyl group. It has a role as a fragrance and an allergen.

Aroma threshold values

Aroma characteristics at 1.0%: sweet vanilla cake, creamy, coconut, coumarin-like and powdery, with herbaceous hay and tonka-like nuances.

Taste threshold values

Taste characteristics at 5 ppm: coconut, sweet vanilla, dairy creamy, hay-like with anisic and coumarin nuances.

General Description

6-methylcoumarin appears as white crystals with a flavor of vanilla. Insoluble in water. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Ketones, such as 6-Methylcoumarin, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

6-Methylcoumarin is combustible.

Safety Profile

Poison by subcutaneous route. Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3

Upstream product

• 19063-55-9 6-bromo-2H-chromen-2-one 
• 74-88-4 methyl iodide 
• 106-44-5 p-cresol 
• 617-48-1 malic acid 
• 10242-13-4 6-methyl-2-oxo-2H-chromene-3-carboxylic acid 
• 51047-94-0 fumaric acid mono-p-tolyl ester 
• 108843-93-2 2,11-dimethyl-(6ar,6bt,12bt,12cc)-6a,6b,12b,12c-tetrahydro-cyclobuta[1,2-c;4,3-c'] dichromium ene-6,7-dione 
• 110-16-7 maleic acid 
• 98712-54-0 4-hydroxy-toluene-3,5-disulfonic acid 
• 110-17-8 (2E)-but-2-enedioic acid 
• 114106-33-1 3-(2-Hydroxy-5-methyl-phenyl)-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester 
• 115560-39-9 3-Hydroxy-3-(2-methoxymethoxy-5-methyl-phenyl)-N,N-dimethyl-propionamide 
• 7664-93-9 sulfuric acid 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 101110-20-7 6-methyl-4-phenylsulfanyl-chroman-2-one 
• 109089-21-6 6-methyl-4-p-tolylmercapto-chroman-2-one 
• 101596-93-4 4-benzylmercapto-6-methyl-chroman-2-one 
• 109092-90-2 6-methyl-4-o-tolylmercapto-chroman-2-one 
• 60257-28-5 2H-<1>benzopyran-2-thione 
• 92-47-7 3,4-dihydro-6-methyl-2H-1-benzopyran-2-one 
• 50396-43-5 2-hydroxy-5-methyl-cinnamic acid 
• 33538-75-9 3-(2-hydroxy-5-methylphenyl)propan-1-ol 
• 76510-25-3 3-(2-hydroxy-5-methyl-phenyl)-propionic acid 
• 51765-10-7 2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol 
• 86761-35-5 methyl (E)-3-(2′-methoxy-5′-methylphenyl)acrylate 
• 10242-09-8 5-methylbenzofuran-2-carboxylic acid 
• 682804-15-5 3-amino-3-(2-hydroxy-5-methyl-phenyl)-propionic acid 
• 91843-23-1 3-(2-hydroxy-5-methyl-phenyl)-propionic acid amide 

Relevant articles and documents

Dehydrogenative Carbon-Carbon Bond Formation Using Alkynyloxy Moieties as Hydrogen-Accepting Directing Groups

In the presence of a catalyst system consisting of Pd(OAc)2, PCy3, and Zn(OAc)2, the reaction of alkynyl aryl ethers with bicycloalkenes, α,ss-unsaturated esters, or heteroarenes results in the site-selective cleavage of two C-H bonds followed by the formation of C-C bonds. In all cases, the alkynyloxy group acts as a directing group for the activation of an ortho C-H bond and as a hydrogen acceptor, thus rendering the use of additives such as an oxidant or base unnecessary. Alkyne into alkene: A palladium catalyst enables dehydrogenative C-C bond-forming reactions between alkynyl aryl ethers and alkenes or heteroarenes. The presence of the alkynyloxy group is key for these transformations as it acts as a directing group for the site-selective cleavage of two C-H bonds as well as an acceptor for the released hydrogen.

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.

Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters

An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.

Synthesis method for coumarins compound

The invention discloses a synthesis method for a coumarins compound. The structural formula is shown in the specification, wherein R1 is selected from one or more of -H, -CH3, -OCH3, -F, -Cl, -Br, -OH, -NO2 and N(CH2CH3)2 and R2 is selected from one of -H, -CH3 or CH2CH3. According to the invention, a 2-hydroxy cinnamate compound is directly utilized as a raw material and the coumarins compound is synthesized in one step under the catalytic effect of visible light. Compared with the present synthesis method, the synthesis method for the coumarins compound disclosed by the invention has the characteristics of simple method, mild condition and high yield; the reaction is carried out under normal temperature; and the visible light is utilized as a reaction energy source and is green and pollution-free.