4-Methylbenzaldehyde

4-Methylbenzaldehyde
Names
	Preferred IUPAC name 4-Methylbenzaldehyde
	Other names p-Tolualdehyde; p-Tolylaldehyde
Identifiers
CAS Number	104-87-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:28617 ;
ChEMBL	ChEMBL190927 ;
ChemSpider	13865424 ;
ECHA InfoCard	100.002.952
KEGG	C06758 ;
PubChem CID	7725;
UNII	GAX22QZ28Q ;
CompTox Dashboard (EPA)	DTXSID9041520 ;
	InChI InChI=1S/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3 Key: FXLOVSHXALFLKQ-UHFFFAOYSA-N ; InChI=1/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3 Key: FXLOVSHXALFLKQ-UHFFFAOYAK;
	SMILES CC1=CC=C(C=C1)C=O; O=Cc1ccc(C)cc1;
Properties
Chemical formula	C8H8O
Molar mass	120.14852
Appearance	colorless liquid
Density	1.019 g/mL (25 °C)
Melting point	−6.00 °C (21.20 °F; 267.15 K)
Boiling point	204 to 205 °C (399 to 401 °F; 477 to 478 K)
Refractive index (nD)	1.545 (20 °C)
Hazards
Safety data sheet (SDS)	[1]
Related compounds
Related compounds	Benzaldehyde
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

4-Methylbenzaldehyde is the aromatic aldehyde with the formula CH₃C₆H₄CHO. It is a colorless liquid. Commercially available, it may be prepared from the Friedel-Crafts formylation of toluene with carbon monoxide and hydrogen chloride under Gattermann-Koch conditions.^[1]

Intermediate in Organic Synthesis

4-Methylbenzaldehyde has a diverse range of applications and potential biological activities. This compound is widely utilized in organic synthesis due to the presence of its reactive aldehyde group, making it an essential building block for various chemicals. In the realm of chemical manufacturing, it is frequently employed in the synthesis of dyes, pharmaceuticals, and flavoring agents. Its reactive nature allows it to participate in a multitude of organic reactions, such as aldol condensations, Grignard reactions, and Schiff base formations. Because of this versatility, 4-methylbenzaldehyde is often used as a precursor in creating more complex aromatic structures, including benzimidazoles and other heterocyclic compounds, which are of significant interest in medicinal chemistry for their antiviral, antimalarial, and anticancer properties.^[2]

Antifungal properties

Recent studies have revealed that 4-methylbenzaldehyde also exhibits antifungal properties. It has been shown to be effective against pathogenic fungi like Aspergillus fumigatus and Aspergillus flavus, both of which are known to cause serious infections and agricultural issues. The antifungal action of 4-methylbenzaldehyde is attributed to its ability to interfere with the fungi's redox homeostasis by generating reactive oxygen species (ROS), which disrupt cellular processes and inhibit growth. This ability to target the antioxidation systems within fungal cells makes it a candidate for developing new antifungal agents, which are in high demand due to the increasing resistance of fungi to traditional treatments.^[3]

Uses in fragrance and flavor industries

4-methylbenzaldehyde is used in the fragrance and flavor industries due to its aromatic structure and cherry-like scent. The presence of a methyl group at the para position enhances its aromatic properties, making it suitable for creating synthetic flavors and fragrances. This compound is used to impart a sweet, almond-like aroma to products and is often incorporated into the creation of perfumes and food flavorings to add depth and complexity. Its unique scent profile allows it to modify the aroma of various natural and synthetic formulations, making it a valuable component in both food and cosmetic products.^[4]

References

^ Coleman, G. H.; Craig, David (1932). "p-Tolualdehyde". Org. Synth. 12: 80. doi:10.15227/orgsyn.012.0080; Coll. Vol., vol. 2, 1943, p. 583.
^ Keri, Rangappa S.; Adimule, Vinayak; Kendrekar, Pravin; Sasidhar, B. S. (2022-02-10). "The Nano-Based Catalyst for the Synthesis of Benzimidazoles". Topics in Catalysis. doi:10.1007/s11244-022-01562-0. ISSN 1572-9028.
^ Rai, Gaurav S.; Maru, Jayesh J. (2020-08-01). "Recent synthetic approaches to 1H- and 2H-indazoles (microreview)". Chemistry of Heterocyclic Compounds. 56 (8): 973–975. doi:10.1007/s10593-020-02761-x. ISSN 1573-8353.
^ Felix Sahayaraj, A.; Joy Prabu, H.; Maniraj, J.; Kannan, M.; Bharathi, M.; Diwahar, P.; Salamon, J. (2023-07-01). "Metal–Organic Frameworks (MOFs): The Next Generation of Materials for Catalysis, Gas Storage, and Separation". Journal of Inorganic and Organometallic Polymers and Materials. 33 (7): 1757–1781. doi:10.1007/s10904-023-02657-1. ISSN 1574-1451.

[1] Coleman, G. H.; Craig, David (1932). "p-Tolualdehyde". Org. Synth. 12: 80. doi:10.15227/orgsyn.012.0080; Coll. Vol., vol. 2, 1943, p. 583.

[2] Keri, Rangappa S.; Adimule, Vinayak; Kendrekar, Pravin; Sasidhar, B. S. (2022-02-10). "The Nano-Based Catalyst for the Synthesis of Benzimidazoles". Topics in Catalysis. doi:10.1007/s11244-022-01562-0. ISSN 1572-9028.

[3] Rai, Gaurav S.; Maru, Jayesh J. (2020-08-01). "Recent synthetic approaches to 1H- and 2H-indazoles (microreview)". Chemistry of Heterocyclic Compounds. 56 (8): 973–975. doi:10.1007/s10593-020-02761-x. ISSN 1573-8353.

[4] Felix Sahayaraj, A.; Joy Prabu, H.; Maniraj, J.; Kannan, M.; Bharathi, M.; Diwahar, P.; Salamon, J. (2023-07-01). "Metal–Organic Frameworks (MOFs): The Next Generation of Materials for Catalysis, Gas Storage, and Separation". Journal of Inorganic and Organometallic Polymers and Materials. 33 (7): 1757–1781. doi:10.1007/s10904-023-02657-1. ISSN 1574-1451.

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