24173-43-1

Basic information

• Product Name: Benzoic acid, 5-methyl-2-[(4-methylphenyl)amino]-
• CAS NO: 24173-43-1
• Molecular Formula: C15H15NO2
• Molecular Weight: 241.29
• Mol File: 24173-43-1.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 5-methyl-2-[(4-methylphenyl)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 5-methyl-2-[(4-methylphenyl)amino]-(24173-43-1)
• EPA Substance Registry System: Benzoic acid, 5-methyl-2-[(4-methylphenyl)amino]-(24173-43-1)

Safety Data

• Hazardous Substances Data: 24173-43-1(Hazardous Substances Data)

Upstream product

• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 106-38-7 para-bromotoluene 
• 6967-82-4 2-bromo-5-methylbenzoic acid 
• 106-49-0 p-toluidine 
• 52548-14-8 2-iodoyl-5-methylbenzoic acid 

Downstream Products

• 1240314-96-8 methyl 2-(N-(4-methylphenyl)amino)-5-methylbenzoate 
• 1621107-13-8 C₁₆H₁₉NO 
• 1621107-01-4 5-methyl-2-(methyl(p-tolyl)amino)benzaldehyde 
• 194479-75-9 9-Amino-2,7-dimethylacridine 

Relevant articles and documents

Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters

A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.

Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression

The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.

PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives

A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

Preparation and characterization of thermochemiluminescent acridine-containing 1,2-dioxetanes as promising ultrasensitive labels in bioanalysis

Thermochemiluminescence is the luminescence process in which a thermodynamically unstable molecule decomposes with light emission when heated above a threshold temperature. We recently reported the thermochemiluminescence properties of an acridine-containing 1,2-dioxetane, which emits at relatively low temperatures (i.e., below 100 C). Herein, we explored the effect of the introduction of methyl substituents in the acridine system. The methyl group did not determine an excessive destabilization of 1,2-dioxetane ring nor significantly affect the general physical properties of the molecule. Monosubstituted methyl derivatives and a series of derivatives bearing several combinations of two, three, and four methyl groups were prepared. The rate of formation of 1,2-dioxetane derivatives 1b-k strongly depended on the methyl substitution pattern. All members of this library of mono-, di-, tri-, and tetramethyl-substituted derivatives were characterized in terms of photophysical and thermochemiluminescence properties. The introduction of methyl groups into the acridine ring caused a marked decrease in the activation energy of the thermochemiluminescent reaction. Tri- and tetramethyl-substituted acridones had the highest fluorescence quantum yields, in the range 0.48-0.52, and the corresponding 1,2-dioxetanes 1h and 1j showed in thermochemiluminescence imaging experiments limit of detection values more than ten times lower with respect to the unsubstituted derivative.

Direct experimental evidence for the priority of flexible ligand skeleton in asymmetric friedel-crafts alkylation of indole with nitroalkenes

Direct experimental evidence for the priority of flexible ligand skeleton in asymmetric Friedel-Crafts alkylation was obtained through XRD analysis of flexible ligand/ZnCl2 complex, as well as synthesis of dihydroacridine-linked bis(oxazoline) ligands with planar rigid scaffold. A transition state model without NH φ interaction was proposed for the rigid ligands to interpret the inversion of absolute configuration.

Simultaneous production of p-tolualdehyde and hydrogen peroxide in photocatalytic oxygenation of p-xylene and reduction of oxygen with 9-mesityl-10-methylacridinium ion derivatives

Photooxygenation of p-xylene by oxygen occurs efficiently under photoirradiation of 9-mesityl-2,7,10-trimethylacridinium ion (Me 2Acr+-Mes) to yield p-tolualdehyde and hydrogen peroxide, which is initiated via photoinduced electron transfer of Me2Acr +-Mes to produce the electron-transfer state.

The Effects of Substituents Introduced into 9-Aminoacridine on Frameshift Mutagenicity and DNA Binding Affinity

Some derivatives of 9-aminoacridine (1) were synthesized, and their frameshift mutagenicity and DNA binding affinity were studied. The introduction of a methyl group into the acridine ring of 1 reduced the mutagenic activity and the intercalative DNA bind

Potential anticancer agents derived from acridine

The compounds of the subject invention can be represented as follows: STR1 wherein each of R1, R2, R3, R4, are the same or different and are hydrogen (H), or a lower alkyl group of from about 1-4 carbon atoms, o