2159-42-4

Basic information

• Product Name: 2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID
• Synonyms: 3',4'-DIMETHYLBENZOPHENONE-2-CARBOXYLIC ACID;2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID;AKOS BBS-00000727;2-[(3,4-dimethylphenyl)-oxomethyl]benzoic acid
• CAS NO: 2159-42-4
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Mol File: 2159-42-4.mol

Chemical Properties

• Melting Point: 168 °C
• Boiling Point: 468.6 °C at 760 mmHg
• Flash Point: 251.3 °C
• Appearance: /
• Density: 1.195 g/cm³
• Vapor Pressure: 1.39E-09mmHg at 25°C
• Refractive Index: 1.598
• Solubility: soluble in Methanol
• PKA: 3.43±0.36(Predicted)
• CAS DataBase Reference: 2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID(2159-42-4)
• EPA Substance Registry System: 2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID(2159-42-4)

Safety Data

• Hazardous Substances Data: 2159-42-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID is used as a reagent in organic synthesis for the preparation of benzotriazole derivatives. These derivatives are valued for their potential applications as corrosion inhibitors, UV stabilizers, and pharmaceutical intermediates, highlighting the compound's versatility in chemical manufacturing.
Used in the Chemical Industry:
In the chemical industry, 2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID is utilized in the manufacturing of dyes, pigments, and plastics. Its inclusion in these products is attributed to its ability to enhance color, stability, and other performance characteristics.
Used in the Cosmetics Industry:
2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID is studied for its potential use as a sunscreen agent. 2-(3,4-DIMETHYLBENZOYL)BENZOIC ACID's UV-absorbing properties make it a candidate for inclusion in cosmetic products designed to protect the skin from harmful ultraviolet radiation.

InChI:InChI=1/C16H14O3/c1-10-7-8-12(9-11(10)2)15(17)13-5-3-4-6-14(13)16(18)19/h3-9H,1-2H3,(H,18,19)

Upstream product

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Downstream Products

• 2571-39-3 (3,4-dimethylphenyl)(phenyl)methanone 
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• 93517-74-9 4-(3,4-dimethyl-phenyl)-2H-phthalazin-1-one 
• 858842-77-0 2-(3,4-dimethylbenzyl)benzoic acid 
• 5466-99-9 4-(2-carboxybenzoyl)phthalic acid 
• 1855-20-5 4-(3,4-dimethyl-phenyl)-benzo[d][1,2]oxazin-1-one 
• 143390-65-2 9b-(3,4-dimethyl-phenyl)-2,3-dihydro-9bH-[1,3]thiazolo[2,3-a]isoindol-5-one 
• 65-85-0 benzoic acid 
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• 329922-55-6 4-(3,4-dimethylphenyl)-2-(2-nitro-5-chlorophenyl)-1,2-dihydrophthalazin-1(2H)-one 
• 14189-53-8 3,4-dimethylbenzhydrol 
• 1055981-48-0 (S)-2-(3',4'-dimethylbenzoyl)-N-(α-phenylethyl)benzamide 
• 613-06-9 2,3-dimethylanthracene 

Relevant articles and documents

Mechanochemical Friedel-crafts acylations

Friedel-Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

Synthesis and anti-inflammatory evaluation of some condensed [4-(3,4-dimethylphenyl)-1(2H)-oxo-phthalazin-2-yl]acetic acid hydrazide

Some new 1,3,4-triazolo-, 1,3,4-oxadiazolo-, 1,3,4-thiadiazol-, and pyrazolo-3,4-dimethylphenyl-1(2H)-oxo-phthalazine derivatives were synthesized and identified by IR, 1H NMR, MS and elemental analysis. Most of the newly synthesized products were tested for their anti-inflammatory activities. Among them, compounds 11, 17b, 20, 21 and 22 are active compare to the activity of indomethacin.

An alternative route to syntheses of aryl keto acids in a chloroaluminate ionic liquid

The Lewis acidic 1-butyl-3-methylimidazolium chloroaluminate ionic liquid [bmim]Cl.AlCl3, N=0.67, is employed as a catalyst as well as the solvent for the quick and efficient syntheses of aryl keto acids by Friedel-Crafts acylation and aroylation of aromatic hydrocarbons using cyclic acid anhydrides.

Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen

Fluorescein is one of the best available fluorophores for biological applications, but the factors that control its fluorescence properties are not fully established. Thus, we initiated a study aimed at providing a strategy for rational design of functional fluorescence probes bearing fluorescein structure. We have synthesized various kinds of fluorescein derivatives and examined the relationship between their fluorescence properties and the highest occupied molecular orbital (HOMO) levels of their benzoic acid moieties obtained by semiempirical PM3 calculations. It was concluded that the fluorescence properties of fluorescein derivatives are controlled by a photoinduced electron transfer (PET) process from the benzoic acid moiety to the xanthene ring and that the threshold of fluorescence OFF/ON switching lies around -8.9 eV for the HOMO level of the benzoic acid moiety. This information provides the basis for a practical strategy for rational design of functional fluorescence probes to detect certain biomolecules. We used this approach to design and synthesize 9-[2-(3carboxy-9,10-dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one (DMAX) as a singlet oxygen probe and confirmed that it is the most sensitive probe currently known for 1O2. This novel fluorescence probe has a 9,10-dimethylanthracene moiety as an extremely fast chemical trap of 1O2. As was expected from PM3 calculations, DMAX scarcely fluoresces, while DMAX endoperoxide (DMAX-EP) is strongly fluorescent. Further, DMAX reacts with 1O2 more rapidly, and its sensitivity is 53-fold higher than that of 9-[2-(3-carboxy-9,10-diphenyl)anthryl]-6-hydroxy-3H-xanthen-3-ones (DPAXs), which are a series of fluorescence probes for singlet oxygen that we recently developed. DMAX should be useful as a fluorescence probe for detecting 1O2 in a variety of biological systems.

INVESTIGATION OF THE COMPOSITION OF PETROLEUM ANTHRACENE HYDROCARBONS

The optimum conditions of adduct formation with maleic anhydride for the isolation of ca. 100percent anthracene hydrocarbons from a mixture with phenanthrenes and other compounds are set out.Gas-liquid chromatography has been used to study the individual composition of anthracene and C1-C3 anthracenes isolated by the method proposed from concentrates of triaromatic hydrocarbons of crude oils from the Okha, Katangli (Sakhalin) and Dorokhovsk (Urals-Volga) fields.With the aid of the individual compounds synthesized, for the first time 2-ethylanthracene and 1,3- and 2,3-dimethylanthracene have been identified in crude oils, and the retention indices have also been calculated for certain C2- and C3-substituted anthracene hydrocarbons for chromatographic phase SE-54.