619-04-5

Basic information

• Product Name: 3,4-Dimethylbenzoic acid
• Synonyms: RARECHEM AL BO 0330;O-XYLENE-4-CARBOXYLIC ACID;1-Carboxy-3,4-dimethylbenzene;3,4-dimethyl-benzoicaci;3,4-DIMETHYLBENZOIC ACID;AKOS BBS-00007820;ASYM-O-XYLYLIC ACID;Benzoic acid, 3,4-dimethyl- (7CI,8CI,9CI)
• CAS NO: 619-04-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 210-576-7
• Product Categories: CARBOXYLICACID;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzenes;Acids & Esters
• Mol File: 619-04-5.mol

Chemical Properties

• Melting Point: 163-165 °C(lit.)
• Boiling Point: 271.51°C (estimate)
• Flash Point: 134.9 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.0937 (estimate)
• Vapor Pressure: 0.000728mmHg at 25°C
• Refractive Index: 1.5188 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 4.44±0.10(Predicted)
• Water Solubility: 129.2mg/L(temperature not stated)
• BRN: 907267
• CAS DataBase Reference: 3,4-Dimethylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dimethylbenzoic acid(619-04-5)
• EPA Substance Registry System: 3,4-Dimethylbenzoic acid(619-04-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• RTECS: DG8734020
• TSCA: Yes
• Hazardous Substances Data: 619-04-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethylbenzoic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific diseases or conditions.
Used in Chemical Synthesis:
In the chemical industry, 3,4-Dimethylbenzoic acid serves as a versatile building block for the synthesis of a wide range of organic compounds. Its reactivity and structural properties make it an ideal candidate for the production of various chemicals, including dyes, pigments, and additives.
Used in Flavor and Fragrance Industry:
3,4-Dimethylbenzoic acid is used as a component in the creation of various flavors and fragrances. Its unique chemical structure contributes to the development of distinct scents and tastes, making it a valuable asset in the formulation of perfumes, cosmetics, and other consumer products.
Used in Material Science:
3,4-Dimethylbenzoic acid can be utilized in the development of advanced materials, such as polymers and coatings, due to its chemical properties. Its incorporation into these materials can enhance their performance, durability, and other desirable characteristics.

Purification Methods

Crystallise it from EtOH or H2O (m 168-168.5o), and sublime it in vacuo. The phenyl ester has m 68o (from EtOH or pet ether) and b 155-157o/2mm. [Beilstein 9 II 353, 9 III 2441, 9 IV 1803.]

InChI:InChI=1/C9H10O2/c1-6-3-4-8(9(10)11)5-7(6)2/h3-5H,1-2H3,(H,10,11)

Upstream product

• 56-23-5 tetrachloromethane 
• 6578-78-5 1,1-bis(3,4-dimethylphenyl)ethylene 
• 79-37-8 oxalyl dichloride 
• 95-47-6 o-xylene 
• 463-72-9 carbamic chloride 
• 95-63-6 1,2,4-Trimethylbenzene 
• 934-80-5 1,2-dimethyl-4-ethylbenzene 
• 27831-13-6 3,4-dimethylstyrene 
• 3982-66-9 1,2-dimethyl-4-propyl-benzene 
• 51036-98-7 3-(3,4-dimethylbenzoyl)propionic acid 
• 873979-12-5 2,2,2-trichloro-1-(3,4-dimethyl-phenyl)-ethanone 
• 40207-05-4 3-(chloromethyl)-4-methylbenzoic acid 
• 871896-99-0 δ-oxy-δ-(3.4-dimethyl-phenyl)-α-amylene 
• 141-53-7 sodium formate 

Downstream Products

• 3637-01-2 3,4-dimethylacetophenone 
• 95-47-6 o-xylene 
• 5156-01-4 2-methylterephthalic acid 
• 681448-23-7 3,4-dimethyl-cyclohexanecarboxylic acid 
• 95-64-7 4-amino-o-xylene 
• 16155-55-8 2-(3,4-dimethylphenyl)benzo[d]oxazole 
• 89075-57-0 2-(3,4-Dimethyl-phenyl)-3H-imidazo[4,5-c]pyridine 
• 38404-42-1 methyl 3,4-dimethylbenzoate 
• 120743-86-4 3-methyl-4-<(trimethylsilyl)methyl>benzoic acid 
• 33499-44-4 ethyl 3,4-dimethylbenzoate 
• 82955-74-6 3,4-Dimethyl-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester; compound with methanesulfonic acid 
• 4315-14-4 4,5-Dimethyl-2-nitrobenzoesaeure 
• 4315-13-3 3,4-Dimethyl-2-nitrobenzoesaeure 
• 74319-96-3 3,4-Dimethyl-5-nitrobenzoesaeure 

Relevant articles and documents

Diels-Alder reactions with 1,1-diethoxybut-3-yn-2-one and some 1,1-diethoxy-5-hydroxyalk-3-yn-2-ones and their acetates

The title compounds were reacted with a few conjugated dienes at room temperature and above. The alcohols were unreactive, but the other ynones reacted at a reasonable rate. Conceivably, the expected cyclohexa-1,4-diene adducts were formed, but they were unstable and aromatized to the corresponding benzene derivatives, which were isolated in low to excellent yield.

Palladium-catalyzed carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane

In this communication, we describe a new method for the carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane. With Pd(PPh3)4 as the catalyst and toluene as the solvent at 60 °C under 10 bar CO for 16 h, the desired acylstannanes were obtained in good to excellent yields. In order to facilitate isolation and analysis, the obtained acylstannanes were transformed into the corresponding benzoic acids by simply stirring under air for 5 h.

Visible-Light-Mediated Hydroxycarbonylation of Diazonium Salts

A visible light-promoted catalytic photoredox hydroxycarbonylation was achieved on aryl diazonium salts whether preformed or generated in situ from the corresponding anilines. This strategy allows a straightforward access to a variety of carboxylic acids under mild conditions. (Figure presented.).

Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes

Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.

A method of preparing 1,2,4,5-benzenetetracarboxylic acid or trimellitic acid from pinacol

The invention relates to a method of preparing 1,2,4,5-benzenetetracarboxylic acid or trimellitic acid from pinacol. The method includes a first step of selectively dehydrating the pinacol in an acid/ionic liquid catalytic system to generate 2,-3-dimethyl-1,3-butadiene; a second step of subjecting the 2,-3-dimethyl-1,3-butadiene and maleate or acrylate to a D-A cycloaddition/dehydrogenation tandemreaction to generate an aromatic ring product; and a third step of subjecting the aromatic ring product to hydrolysis and oxidation to prepare the 1,2,4,5-benzenetetracarboxylic acid or the trimellitic acid. The catalytic system adopted in the method is green, and can be recycled. The raw material is a biomass-based platform chemical, and is cheap and easily available. All reaction processes aresimple. The pinacol dehydration reaction, the dehydrogenation reaction of a D-A product and an oxidation reaction are high in activity and selectivity. The novel method for preparing the 1,2,4,5-benzenetetracarboxylic acid and the trimellitic acid which are fine chemicals from the pinacol that is a lignocelluloses based platform chemical is provided by the invention.

SO2F2-Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide

A one-pot Pd-catalyzed carbonylation of phenols into their corresponding aryl carboxylic acids and esters through the insertion of carbon monoxide has been developed. This procedure offers a direct synthesis of aryl carboxylic acids and esters from inexpensive and abundant starting materials (phenols, SO2F2 and CO) under mild conditions. This method tolerates a broad range of functional groups and is also applicable for the modification of complicated natural products.

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.

Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis

We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.

Sustainable production of pyromellitic acid with pinacol and diethyl maleate

Herein, we report an unprecedented and sustainable route to synthesize pyromellitic acid (PMA), a monomer of polyimide, with pinacol and diethyl maleate which can be derived from lignocellulose. Analogously, a sustainable route to trimellitic acid (TMA) was also developed using pinacol and acrylate as the feedstocks.

Metal-free oxidative cleavage of the C-C bond in α-hydroxy-β-oxophosphonates

The potential of TBHP to promote oxidative hydroxylation of α-hydroxy-β-oxophosphonates (HOPs) through C(CO)-C bond cleavage is described. This cleavage, as depicted in the mechanism is expected through an isomer of HOP that reacts with TBHP to generate acids.