2-Formyl-3,4-dihydro-2H-pyran
[CAS# 100-73-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyran compound
• Name: 2-Formyl-3,4-dihydro-2H-pyran
• Synonyms: 3,4-Dihydro-2H-pyran-2-carbaldehyde
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• CAS Registry Number: 100-73-2
• EC Number: 202-884-5
• SMILES: C1CC(OC=C1)C=O

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H312-H315-H318-H332-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2607

Discovery and Applications

2-Formyl-3,4-dihydro-2H-pyran is a notable compound in organic chemistry due to its versatile applications. It is a member of the pyran family, characterized by its six-membered ring that includes both carbon and oxygen atoms. The compound is synthesized through the formylation of dihydropyran, a process that involves treating dihydropyran with formylating agents such as formic acid or formyl chloride. This reaction yields 2-formyl-3,4-dihydro-2H-pyran, which is then purified to obtain the final product.

The compound is significant in pharmaceutical chemistry as it serves as a crucial building block for synthesizing various bioactive molecules. Its formyl group facilitates further chemical modifications, making it a valuable intermediate in drug development. Researchers use it to design new pharmaceuticals with specific therapeutic properties, potentially leading to more effective treatments for a range of diseases.

In the field of organic synthesis, 2-formyl-3,4-dihydro-2H-pyran is utilized as a starting material for creating complex organic compounds. Its reactivity allows it to participate in numerous chemical reactions, including condensation and cyclization, which are essential for the synthesis of intricate molecules. This property is exploited to develop new materials and functionalized compounds with desired characteristics.

The compound also finds applications in the synthesis of natural products. The pyran ring structure is prevalent in many natural substances, and modifications to this structure can lead to the creation of novel compounds with potential biological activity. Incorporating 2-formyl-3,4-dihydro-2H-pyran into synthetic routes aids in the discovery of new natural products and contributes to the development of compounds with beneficial properties.

In material science, 2-formyl-3,4-dihydro-2H-pyran's unique chemical properties are leveraged to design new materials with specific functionalities. Its ability to form stable bonds and interact with other chemical species makes it suitable for developing polymers and other materials with enhanced performance in various applications.

Overall, 2-formyl-3,4-dihydro-2H-pyran is a valuable compound with significant implications in pharmaceutical chemistry, organic synthesis, natural product synthesis, and material science. Its versatile chemical properties enable the creation of new and useful substances across different fields.

References

1998. Cyanosilylation of α-butylthioacrolein. Russian Chemical Bulletin, 47(7).
DOI: 10.1007/bf02495570

2019. Synthesis and Some Chemical Transformations of Unsaturated Ketones of the Dihydropyran Series. Russian Journal of Organic Chemistry, 55(9).
DOI: 10.1134/s1070428019090069

2019. The reaction of 4-aminocoumarin with β-carbonyl-substituted 4Н-chromenes: synthesis of 5H-chromeno[4,3-b]pyridin-5-one derivatives. Chemistry of Heterocyclic Compounds, 55(3).
DOI: 10.1007/s10593-019-02451-3