150867-03-1

Basic information

• Product Name: 2-formyl-5-methylbenzoic acid
• CAS NO: 150867-03-1
• Molecular Weight: 164.161
• Mol File: 150867-03-1.mol

Chemical Properties

• CAS DataBase Reference: 2-formyl-5-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-formyl-5-methylbenzoic acid(150867-03-1)
• EPA Substance Registry System: 2-formyl-5-methylbenzoic acid(150867-03-1)

Safety Data

• Hazardous Substances Data: 150867-03-1(Hazardous Substances Data)

Upstream product

• 82431-20-7 4-methylbenzocyclobutene-1,2-dione 
• 13730-55-7 methyl 2,5-dimethylbenzoate 
• 848498-20-4 2-bromomethyl-5-methylbenzoic acid methyl ester 
• 72985-23-0 6-methylisobenzofuran-1(3H)-one 
• 72985-22-9 2-(hydroxymethyl)-5-methylbenzoic acid 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 68-12-2 N,N-dimethyl-formamide 

Relevant articles and documents

TiCl4-Mediated Preparation of Thiophthalide Derivatives via Formal Thio-Passerini Reactions

By the formal extension of the Passerini reaction to thiocarbonyl derivatives, the straightforward preparation of thiophthalides is disclosed. This method involves the intermediate formation of a sulfanyl-phthalide and a titanium tetrachloride mediated is

Indium-Catalyzed C?F Bond Transformation through Oxymetalation/β-Fluorine Elimination to Access Fluorinated Isocoumarins

Fluorinated heterocycles have attracted much attention in the pharmaceutical and agrochemical industries. Many strategies have already been developed to achieve the synthesis of fluorinated heterocycles. Formidable challenges remain, however, in the synthesis of fluorinated isocoumarin derivatives that are among the most alluring structural motifs. Herein, the indium-catalyzed C?F bond transformation of 2-(2,2-difluorovinyl) benzoates is reported, which are readily accessible compounds, to give a diverse array of fluorinated isocoumarins. The present reaction proceeds smoothly using inexpensive reagents: a catalytic amount of indium salt in the presence of zinc salt. A theoretical calculation of potential energy profiles showed that the reaction consists of oxymetalation with the elimination of alkyl halide and the β-fluorine elimination.

Synthesis of chiral isoindolinones via asymmetric propargylation/lactamization cascade

A Zn-mediated propargylation/lactamization cascade reaction with chiral 2-formylbenzoate derived N-tert-butanesulfinyl imines was realized, which provided a practical and efficient method for the synthesis of chiral isoindolinones. High diastereoselectivities (up to 97:3 dr) and good reaction yields were observed for most examined cases.

Structure-based design of potent human dihydroorotate dehydrogenase inhibitors as anticancer agents

It has been proven that inhibiting human dihydroorotate dehydrogenase (hDHODH) restricts the growth of rapidly proliferating cells, thus hDHODH can be developed as a promising target for the treatment of immunological disease and cancer. Here, a succession of substituted hydrazino-thiazole derivatives were designed, synthesized, and biologically evaluated through structure-based optimization, of which compound 22 was the most potent inhibitor of hDHODH with an IC50 value of 1.8 nM. Furthermore, 22 exhibited much better antiproliferative activity than brequinar, both in HCT-116 and BxPC-3 cancer cell lines. Flow cytometry analysis revealed that 22 induced S phase cell cycle arrest and promoted induction of apoptosis. All results established a proof that blocking the pyrimidine de novo synthesis pathway by inhibiting the rate-limiting enzyme hDHODH is an attractive therapy for cancer.

Enantioselective addition of arylboronic acids to methyl 2-formylbenzoates by using a ruthenium/Me-BIPAM catalyst for synthesis of chiral 3-aryl-isobenzofuranones

Ruthenium/Me-BIPAM-catalyzed asymmetric addition of arylboronic acids to methyl 2-formylbenzoates afforded chiral 3-aryl-isobenzofuranones. [RuCl2(p-cymene)]2/Me-BIPAM and RuCl2(PPh3)3/Me-BIPAM catalyst systems tolerate a variety of functional groups and give high yields with high enantioselectivities.

Highly enantioselective synthesis of 2,3-dihydro-1 H-imidazo[2,1-a isoindol-5(9b H)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization

Highly enantioselective catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization of N1-alkylethane-1,2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.

CARBOLINE CARBOXAMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS

Compounds having formula (I), and enantiomers, and diastereomers, stereoisomers, pharmaceutically-acceptable salts thereof, formula (I) are useful as kinase modulators, including Btk modulation.

Reactions of carbonyl compounds in basic solutions. Part 24. 1 The mechanism of the base-catalysed ring fission of substituted benzocyclobutene-1,2-diones

The rate coefficients for the base-catalysed ring fission of a series of substituted benzocyclobutenediones to give the corresponding 2-formylbenzoic acids have been determined in water at 25.0 and 60.0°C. The effects of 4-substituents and 4,5-di-substituents on the rates have been correlated using a modified Hammett equation to give a reaction constant, ρ, equal to ca. 3.6 at 25.0°C. The activation parameters have been calculated. The effect of solvent composition on the rates has been studied. The kinetic solvent isotope effect, product composition and enrichment in 18O-enriched water have also been studied. All the evidence indicates a mechanistic pathway which proceeds by rapid reversible addition of hydroxide anion to the dione, followed by intramolecular nucleophilic attack on the second carbonyl group and formation of a carbanionic intermediate.