80866-93-9

Basic information

• Product Name: 3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID
• Synonyms: 3,4-dihydro-2,2-dimethyl-4-oxo-2h-pyran-6-carboxylicaci;5,6-dihydro-6,6-dimethyl-4-oxo-4h-pyran-2-carboxylicaci;5,6-dihydro-6,6-dimethyl-4-oxo-4h-pyran-2-carboxylicacid;acidedimethyl-6,6dihydro-5,6pyrone-4carboxylique-2;4-Oxo-6,6-dimethyl-5,6-dihydro-4H-pyran-2-carboxylic acid;3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid,98%;3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC;3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID
• CAS NO: 80866-93-9
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.16
• EINECS: 279-596-1
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyrans
• Mol File: 80866-93-9.mol

Chemical Properties

• Melting Point: 170 °C (dec.)(lit.)
• Boiling Point: 219.79°C (rough estimate)
• Flash Point: 102.4ºC
• Appearance: /
• Density: 1.1456 (rough estimate)
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.4425 (estimate)
• CAS DataBase Reference: 3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID(80866-93-9)
• EPA Substance Registry System: 3,4-DIHYDRO-2,2-DIMETHYL-4-OXO-2H-PYRAN-6-CARBOXYLIC ACID(80866-93-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: UP6990000
• Hazardous Substances Data: 80866-93-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid is used as a photoprotective reagent during the photolysis of the Salmonella sialidase. This application is crucial for protecting sensitive biological molecules from the damaging effects of light exposure during experimental procedures.
Used in Consumer Goods Industry:
The butyl ester of 3,4-dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylic acid is commonly used as a mosquito repellent. This application takes advantage of the compound's ability to deter mosquitoes, providing a means of protection against insect-borne diseases and enhancing the overall comfort in outdoor settings.

InChI:InChI=1/C8H10O4/c1-8(2)4-5(9)3-6(12-8)7(10)11/h3H,4H2,1-2H3,(H,10,11)/p-1

Upstream product

• 108097-78-5 hydroxy-2 oxo-4 methyl-6 heptadiene-2,5 oate de methyle 
• 7647-01-0 hydrogenchloride 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 5464-36-8 ethyl 2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxylate 

Downstream Products

• 141921-96-2 2,2-Dimethyl-6-(2-phenyl-oxazolidine-3-carbonyl)-2,3-dihydro-pyran-4-one 
• 141921-83-7 6,6-Dimethyl-4-oxo-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl-isopropyl-amide 
• 141921-82-6 6,6-Dimethyl-4-oxo-5,6-dihydro-4H-pyran-2-carboxylic acid benzyl-methyl-amide 
• 141921-81-5 6,6-Dimethyl-4-oxo-5,6-dihydro-4H-pyran-2-carboxylic acid dibenzylamide 
• 1033586-60-5 6-[1-(4-bromo-2-chlorophenyl)-2-(2-chlorophenyl)-1H-imidazol-4-yl]-2,2-dimethyl-2,3-dihydropyran-4-one 
• 1033585-61-3 6-[1-(3-chloro-3'-methanesulfonylbiphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazol-4-yl]-2,2-dimethyl-2,3-dihydropyran-4-one 
• 1414928-20-3 N-[(2S)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]-2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxamide 
• 1414928-22-5 N-[(2R)-1-{4-[(2β,3α,5α,20R)-3,20-dihydroxypregnan-2-yl]piperazin-1-yl}-1-oxo-3-phenylpropan-2-yl]-2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-6-carboxamide 

Relevant articles and documents

Metal-Free Visible Light-Mediated Photocatalysis: Controlling Intramolecular [2 + 2] Photocycloaddition of Enones through Axial Chirality

Atropisomeric enone-imides and enone-amides featuring N-CAryl bond rotation were evaluated for intramolecular [2 + 2] photocycloaddition. Straight addition product was observed over cross-addition product with good control over reactivity. The atropselectivity was found to be dependent on the substituent on the aryl ring. Substitution-dependent atropselectivity was rationalized on the basis of a divergent mechanistic pathway.

Synthesis and pharmacologic evaluation of some dihydropyran carboxylic acids

The synthesis of three new dihydropyran carboxylic acids has been performed by uncommon procedures: cyanosilylation, cyclisation of oxime. Their chemical structure was confirmed by I.R. and N.M.R. data. In a pharmacological evaluation they were found to possess significant effects on the passive cutaneous anaphylaxis test and on the central nervous system; one of them showed an interesting antiallergic effect whilst another showed an interesting sedative effect.