18385-83-6

Basic information

• Product Name: 6-methyl-2H-chromene
• Synonyms: 2H-1-benzopyran, 6-methyl-; 6-Methyl-2H-chromene
• CAS NO: 18385-83-6
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.1858
• Mol File: 18385-83-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 238.117°C at 760 mmHg
• Flash Point: 91.107°C
• Density: 1.068g/cm³
• Vapor Pressure: 0.066mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: 6-methyl-2H-chromene(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methyl-2H-chromene(18385-83-6)
• EPA Substance Registry System: 6-methyl-2H-chromene(18385-83-6)

Safety Data

• Hazardous Substances Data: 18385-83-6(Hazardous Substances Data)

Upstream product

• 5651-90-1 1-methyl-4-(2-propynyloxy)benzene 
• 38445-23-7 6-methyl-chromen-4-one 
• 106-44-5 p-cresol 
• 92-48-8 6-methylcoumarin 
• 53299-56-2 4-methyl-1-(2-chloro-2-propenoxy)benzene 
• 108-24-7 acetic anhydride 
• 122323-28-8 3-Bromo-6-methyl-2H-chromene 
• 59036-42-9 4-methyl-1-(3-chloro-2-propenoxy)benzene 
• 51765-10-7 2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol 

Downstream Products

• 41786-37-2 2-(4-methoxyphenyl)-6-methyl-2H-chromene 

Relevant articles and documents

Synthesis of 2 h-chromenes via hydrazine-catalyzed ring-closing carbonyl-olefin metathesis

The catalytic ring-closing carbonyl-olefin metathesis (RCCOM) of O-Allyl salicylaldehydes to form 2H-chromenes is described. The method utilizes a [2.2.1]-bicyclic hydrazine catalyst and operates via a [3 + 2]/retro-[3 + 2] metathesis manifold. The nature of the allyl substitution pattern was found to be crucial, with sterically demanding groups such as adamantylidene or diethylidene offering optimal outcomes. A survey of substrate scope is shown along with a discussion of mechanism supported by DFT calculations. Steric pressure arising from syn-pentane minimization of the diethylidene moiety is proposed to facilitate cycloreversion.

Ph3PAuNTf2 as a superior catalyst for the selective synthesis of 2H-chromenes: Application to the concise synthesis of benzopyran natural products

Ph3PAuNTf2 (≈1 mol-%) catalyzes the selective cycloisomerization of substituted aryl propargyl ethers into 2H-chromenes in excellent yields. Benzofuran byproducts are formed only in the case of electron-deficient arenes, in up to 7% relative yield. The Ph 3PAuNTf2-catalyzed cyclization of aryl propargyl ethers was applied as a key step to the concise synthesis of the naturally occurring benzopyrans seselin, xanthyletin, precocenes I and II, 8-(3′,3′- dimethylallyl)wenteria chromene, and 2,2-dimethyl-8-prenylchromene-6-propenoic acid. Ph3PAuNTf2 is a general, highly efficient, and product-selective catalyst for the clean synthesis of 2H-chromenes from the cycloisomerization of aryl propargyl ethers.The Ph3PAuNTf 2-catalyzed cyclization was applied as a key step in the synthesis of several benzopyran-bearing naturally occurring substances. Copyright

The Au(I)-catalyzed intramolecular hydroarylation of terminal alkynes under mild conditions: Application to the synthesis of 2H-chromenes, coumarins, benzofurans, and dihydroquinolines

(Chemical Equation Presented) Operationally simple Au(I)-catalyzed intramolecular hydroarylation (IMHA) reactions of terminal alkynes that proceed in high yield and under very mild conditions are described. These processes involve low catalyst loadings, mild reaction temperatures, and short reaction times, require no cocatalysts or additives, and allow for the generation of a number of important heterocyclic motifs from readily accessible starting materials.