100-73-2

Basic information

• Product Name: 2-Formyl-3,4-dihydro-2H-pyran
• Synonyms: Acrolein dimer(stabilized);2,3-Dihydro-1,4-pyran-2-karboxaldehyd;2,6-epoxy-5-hexena;2,6-epoxy-5-Hexenal;2-Formyl-3,4-dihydro-2H-pyran;2-Formyl-3,4-dihydro-2N-pyran;2H-Pyran-2-carboxaldehyde, 3,4-dihydro-;α-FROMY-3.4-DIHYDIO-2H-PYRAN
• CAS NO: 100-73-2
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• EINECS: 202-884-5
• Mol File: 100-73-2.mol

Chemical Properties

• Melting Point: -99.9°C
• Boiling Point: 146 °C(lit.)
• Flash Point: 54 °C
• Appearance: colorless or yellow liquid with a pungent disagreeable odor
• Density: 1.08 g/mL at 25 °C
• Vapor Pressure: 3.28mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• CAS DataBase Reference: 2-Formyl-3,4-dihydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Formyl-3,4-dihydro-2H-pyran(100-73-2)
• EPA Substance Registry System: 2-Formyl-3,4-dihydro-2H-pyran(100-73-2)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38-41
• Safety Statements: 16-26-33-36/37/39-45
• RIDADR: UN 2607
• RTECS: UP6825000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 100-73-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Processes:
2-Formyl-3,4-dihydro-2H-pyran is used as a reagent in various chemical processes. Its chemical properties make it a valuable intermediate for the synthesis of a wide range of compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Formyl-3,4-dihydro-2H-pyran is used as a key building block for the development of novel drug candidates. Its unique structure allows for the creation of diverse molecular entities with potential therapeutic applications.
Used in Plastics Industry:
2-Formyl-3,4-dihydro-2H-pyran is also utilized in the plastics industry for the production of various types of plastics. Its incorporation into the polymer matrix can enhance the properties of the final product, such as strength, flexibility, and durability.
Used in Agrochemicals:
In the agrochemical sector, 2-Formyl-3,4-dihydro-2H-pyran is employed as a starting material for the synthesis of new pesticides and other crop protection agents. Its versatility in chemical reactions enables the development of innovative products with improved efficacy and reduced environmental impact.
Used in Specialty Chemicals:
2-Formyl-3,4-dihydro-2H-pyran is also used in the production of specialty chemicals, such as fragrances, dyes, and additives. Its unique chemical properties allow for the creation of new compounds with specific characteristics, catering to the diverse needs of various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 3126, 1970 DOI: 10.1021/ja00713a034

Air & Water Reactions

Flammable. Soluble in water.

Reactivity Profile

Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. May polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Mildly toxic by ingestion. A skin and severe eye irritant. A flammable liquid when exposed to heat, flame, or powerful oxidizing agents. To fight fire, use alcohol foam and multipurpose dry chemical. When heated to decomposition it emits acrid smoke and fumes

InChI:InChI=1/C4H10O2/c1-2-6-4-3-5/h5H,2-4H2,1H3

Upstream product

• 107-02-8 acrolein 
• 3749-36-8 2-hydroxymethyl-3,4-dihydro-2H-pyran 
• 111-34-2 -butyl vinyl ether 
• 292638-85-8 acrylic acid methyl ester 
• 3540-36-1 (3,4-dihydro-2H-pyran-2-yl)methyl 3,4-dihydro-2H-pyran-2-carboxylate 
• 78-94-4 methyl vinyl ketone 
• 78-85-3 2-methylpropenal 
• 928-55-2 ethyl 1-propenyl ether 

Downstream Products

• 107922-39-4 benzoyloxy-(3,4-dihydro-2H-pyran-2-yl)-acetonitrile 
• 22975-99-1 opt.-inakt. Phenyl-<3,4-dihydro-2H-pyranyl-(2)>-methanol 
• 6302-36-9 3,4-dihydro-2H-pyran-2-carbaldehyde-methallylimine 
• 100-72-1 Tetrahydropyran-2-methanol 
• 3749-36-8 2-hydroxymethyl-3,4-dihydro-2H-pyran 
• 19611-45-1 tetrahydro-pyran-2-carbaldehyde 
• 34201-01-9 3,4-dihydro-2H-pyran-2-carboxylic acid 
• 110-94-1 1,5-pentanedioic acid 
• 83568-11-0 racem. ethyl 3,4-dihydro-2H-pyran-2-carboxylate 
• 106-69-4 hexane-1,2,6-triol 
• 141-31-1 2-hydroxyadipaldehyde 
• 3540-36-1 (3,4-dihydro-2H-pyran-2-yl)methyl 3,4-dihydro-2H-pyran-2-carboxylate 
• 54774-92-4 2-Morpholinomethyl-2,3-dihydro-4H-pyran 
• 91704-01-7 [1-(3,4-Dihydro-2H-pyran-2-yl)-meth-(E)-ylidene]-(1-phenyl-ethyl)-amine 

Relevant articles and documents

Microwave Induced Synthesis of 3,4-Dihydro-2H-pyran-2-carboxaldehyde: A Versatile Linker for Solid Phase Combinatorial Library

Procedures for the dimerization of acrolein to form 3,4-dihydro-2H-pyran-2-carboxaldehyde by microwave induced synthesis have been developed. Significant rate-enhancement and yield increase were observed. 3,4-Dihydro-2H-pyran-2-carboxaldehyde was obtained in 91% yield under microwave irradiation for 5 minutes instead of 39% yield by reacting at 190 °C for 40 min or at 160 °C for 4 hr.

Substituents influences on the rate of α-alkylacroleins dimerization

Kinetics of α-alkylacroleins dimerization was studied. It was established that both electronic and steric factors affect the process rate, with the prevalence of the latter factors.

Synthesis of 15N-labelled 3,5-dimethylpyridine

15N-labelled pyridines are liquid- and solid-state nuclear magnetic resonance (NMR) probes for chemical and biological environments because their 15N chemical shifts are sensitive to hydrogen-bond and protonation states. By variation of the type and number of substituents, different target pyridines can be synthesized exhibiting different pKa values and molecular volumes. Various synthetic routes have been described in the literature, starting from different precursors or modification of other 15N-labelled pyridines. In this work, we have explored the synthesis of 15N 15N-labelled pyridines using a two-step process via the synthesis of alkoxy-3,4-dihydro-2H-pyran as precursor exhibiting already the desired pyridine substitution pattern. As an example, we have synthesized 3,5-dimethylpyridine-15N (lutidine-15N) as demonstrated by 15N-NMR spectroscopy. That synthesis starts from methacrolein, propenyl ether, and 15N-labelled NH4Cl as nitrogen source.

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.

CCR2 MODULATORS

Compounds are provided that are modulators of the CCR2 receptor. The compounds have the general formula (I) and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activtation of CCR2 receptors.

Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs

A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.

Towards a library of chromene cannabinoids: A combinatorial approach on solid supports

A novel solid-phase synthesis towards classical cannabinoids is presented. Starting from immobilized salicylaldehydes the desired THC-analogous tricycles are obtained in four atom-economic steps including cleavage. The reagents of the employed reactions (domino oxa-Michael-aldol, Wittig, and Diels-Alder) can be varied easily, providing the basis for a combinatorial approach. Overall yields range from 20-60%. Georg Thieme Verlag Stuttgart New York.

Recrossing and dynamic matching effects on selectivity in a diels-alder reaction

Up and down the hill: The products from the hetero-Diels-Alder reaction of acrolein with methyl vinyl ketone arise from a single transition state (see scheme) and trajectory studies accurately predict the selectivity. In an extension of the dynamic matchi

Enantioconvergent synthesis by sequential asymmetric Horner-Wadsworth-Emmons and palladium-catalyzed allylic substitution reactions

A new method for enantioconvergent synthesis has been developed. The strategy relies on the combination of an asymmetric Horner-Wadsworth-Emmons (HWE) reaction and a palladium-catalyzed allylic substitution. Different α-oxygen-substituted, racemic aldehydes were initially transformed by asymmetric HWE reactions into mixtures of two major α,β-unsaturated esters, possessing opposite configurations at their allylic stereocenters as well as opposite alkene geometry. Subsequently, these isomeric mixtures of alkenes could be subjected to palladium-catalyzed allylic substitution reactions with carbon, nitrogen, and oxygen nucleophiles. In this latter step, the respective (E) and (Z) alkene substrate isomers were observed to react with opposite stereospecificity: the (E) alkene reacted with retention and the (Z) alkene with inversion of stereochemistry with respect to both the allylic stereocenter and the alkene geometry. Thus, a single γ-substituted ester was obtained as the overall product, in high isomeric purity. The method was applied to a synthesis of a subunit of the iejimalides, a group of cytotoxic macrolides.

Facile syntheses of 7,7-dimethyl-6,8-dioxabicyclo [3.2.1]octane, a constituent of the Japanese hop oil, and frontalin via hetero Diels-Alder reaction using dilution method

A constituent of the Japanese hop oil, Humulus lupulus, and frontalin has been prepared as racemates in short and the most convenient pathway via hetero Diels-Alder reaction using dilution method.