7697-26-9

Basic information

• Product Name: 3-Bromo-4-methylbenzoic acid
• Synonyms: 3-BROMO-4-METHYLBENZOIC ACID;AKOS BBB/219;3-Bromo-p-toluic acid;3-BROMO-4-METHYLBENZOIC ACID, TECH., 85%;3-Bromo-4-methylbenzoic acid, 98+%;3-Bromo-4-methylbenzoic acid 90%;4-methyl-3-bromobenzoic acid;-Bromo-4-methylbenzoic acid
• CAS NO: 7697-26-9
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.04
• EINECS: 231-712-1
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Bromine Compounds;Acids & Esters;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 7697-26-9.mol

Chemical Properties

• Melting Point: 200-202 °C(lit.)
• Boiling Point: 329.8 °C at 760 mmHg
• Flash Point: 153.3 °C
• Appearance: White to light yellow crystal powder
• Density: 1.599 g/cm³
• Vapor Pressure: 6.97E-05mmHg at 25°C
• Storage Temp.: Room temperature.
• PKA: 3.98±0.10(Predicted)
• Water Solubility: Soluble in methanol. Insoluble in water.
• BRN: 1936510
• CAS DataBase Reference: 3-Bromo-4-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-4-methylbenzoic acid(7697-26-9)
• EPA Substance Registry System: 3-Bromo-4-methylbenzoic acid(7697-26-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-37/38-36
• Safety Statements: 26-37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 7697-26-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Bromo-4-methylbenzoic acid is used as a key intermediate in the synthesis of biphenyl amides and 2-benzazepine-4-acetic acid derivatives. These compounds have potential applications as pharmaceutical agents, with the former being used in the development of non-steroidal anti-inflammatory drugs and the latter as a potent, nonpeptide GPIIb/IIIa antagonist.
Used in Organic Chemistry:
As a versatile organic building block, 3-Bromo-4-methylbenzoic acid is used in the synthesis of various organic compounds, such as O-spiro C-aryl glucosides. These glucosides have potential applications in the development of new pharmaceuticals and agrochemicals.
Used in Catalysis:
3-Bromo-4-methylbenzoic acid is used as a catalytic agent in various chemical reactions, such as esterification, transesterification, and other organic transformations. Its presence can enhance the reaction rate and selectivity, making it a valuable component in the development of new catalytic processes.
Used in Petrochemical Industry:
3-Bromo-4-methylbenzoic acid is also used as a petrochemical additive, where it can improve the performance and properties of various petrochemical products. Its addition can lead to enhanced stability, reactivity, or other desirable characteristics in the final product.

InChI:InChI=1/C8H7BrO2/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4H,1H3,(H,10,11)/p-1

Upstream product

• 17070-97-2 2-bromo-4-ethyl-1-methyl-benzene 
• 42872-74-2 3-bromo-4-methyl-benzonitrile 
• 501356-96-3 2-bromo-1-methyl-4-propyl-benzene 
• 99-94-5 p-Toluic acid 
• 17746-74-6 4-Methyl-4-tribrommethyl-cyclohexadien-(2,5)-on-oxim 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 553-94-6 4-bromo-m-xylene 
• 2458-12-0 3-amino-p-toluic acid 
• 76-05-1 trifluoroacetic acid 
• 7726-95-6 bromine 
• 56-23-5 tetrachloromethane 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 108-88-3 toluene 

Downstream Products

• 586-30-1 3-hydroxy-4-methylbenzoic acid 
• 586-35-6 2-bromo-1,4-benzenedicarboxylic acid 
• 66417-30-9 2-bromo-1-methyl-4-(trifluoromethyl)benzene 
• 68120-35-4 (3-bromo-4-methyl-phenyl)-methanol 
• 101362-98-5 4-methyl-3-phenylthiobenzoic acid 
• 882-33-7 diphenyldisulfane 
• 160952-57-8 3-bromo-4-methylbenzoic acid tert-butyl ester 
• 21900-33-4 3-bromo-4-methylbenzoyl chloride 
• 3347-99-7 4-methyl isophthalic acid 
• 99-94-5 p-Toluic acid 
• 104901-43-1 methyl 3-bromo-4-methylbenzoate 
• 866721-92-8 3-bromo-4-(bromomethyl)benzoic acid 
• 147962-81-0 ethyl 3-bromo-4-methylbenzoate 

Relevant articles and documents

Industrialized synthetic method for halogen benzoic acid derivative

The invention discloses an industrialized synthetic method for a halogen benzoic acid derivative. The formula (I) of the halogen benzoic acid derivative is shown in the description, wherein a plurality of Rs are alkyls of C1-C20, and a plurality of Xs are halogens; the industrialized synthetic method comprises the following steps that alkyl substituted benzoic acid and water are added into a reaction container, halogen simple substances are added, a heating reaction is performed, the reaction is complete, and post processing is performed to obtain the target product halogen benzoic acid derivative. According to the industrialized synthetic method for the halogen benzoic acid derivative, no solvent needs to be recycled, little consumption is consumed, little waste gas, water and industrialresidues are caused, and by-product haloid acid can be directly sold or used for producing other products; accordingly, the industrialized synthetic method for the halogen benzoic acid derivative is safe, environmentally friendly and low in cost, and therefore the wide industrial application prospect is achieved.

Benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines as novel Na+/H+ exchanger inhibitors, synthesis and protection against ischemic-reperfusion injury

A novel series of benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines were designed and synthesized as Na+/H+exchanger inhibitors. Most of them were found to inhibit NHE1-mediated platelet swelling in a concentration-dependent manner, and to have significant cardioprotective effect against myocardial ischemic-reperfusion injury, among which compounds 10a and 34 were more potent than cariporide in both in vivo and in vitro tests.

Bromodecarbonylation and bromodecarboxylation of electron-rich benzaldehydes and benzoic acids with oxone and sodium bromide

Benzaldehydes and benzoic acids bearing ortho- and paraelectron donating substituents having unshared electron-pair have undergone bromodecarbonylation or bromodecarboxylation on treatment with sodium bromide in the presence of Oxone in aqueous methanol.

SYNTHESIS AND POLYMERIZATION OF 2,5-DISUBSTITUTED PHENYLACETYLENES CONTAINING TRIFLUOROMETHYL GROUPS

Four phenylacetylenes (2-R2-5-R5-C6H3CCH : 1a R2=R5=CF3; 1b R2=CF3, R5=CH3; 1c R2=CH3, R5=CF3; 1d R2=R5=CH3) were synthesized via lithio compounds or Grignard reagent.Bromo(methyl)benzotrifluorides, the precursors for the lithio compounds, were prepared by the fluorination of the corresponding benzoic acids with sulfur tetrafluoride.Polymerization using transition metal catalysts provided polyacetylenes in high yields for all the monomers, while the yields of γ-ray induced polymerization depended on the monomers.The molecular weights of polyacetylenes have a positive correlation with the yields for all the polymerizations.The substituent effects on the molecular weights and tehrmal stabilities of polymers obtained were discussed.

CATALYTIC AND STOICHIOMETRIC BROMINATION OF AROMATIC COMPOUNDS IN AQUEOUS TRIFLUOROACETIC ACID IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS

The mono- and polybromination of benzene, halogenobenzenes, toluene, p-xylene, anisole, biphenyl, benzotrifluoride, benzoic acid, p-nitro- and p-carboxytoluene, p-methoxybenzonitrile, tetralin, and naphtalene were studied in trifluoroacetic acid and its aqueous solutions in systems containing stoichiometric amounts of bromine or alkali-metal bromide and stoichiometric or catalytic (in the presence of oxygen or air) amounts of nitrogen-containing oxidizing agent (nitrogen(IV) oxide, alkali-metal nitrate or nitrite).It is suggested that the brominating agent under the investigated conditions is nitryl bromide NO2Br.Under the conditions of catalytic bromination anthracene is oxidized to anthraquinone with a preparative yield.

CARBOXYLATION OF ARENES

A two-step procedure for the carboxylation of aromatic rings is described, involving the intermediate preparation of 1-aryl-2,2,2-trichloroethanols (1), which form the corresponding benzoic acids by treatment with NaOH/H2O2.

Preparation of dibenzo[b,f]thiepin compounds

The preparation of dibenzo[b,f]thiepin compounds by a process comprising the direct carboxylation of an ortho-toluyl-aryl sulfide to introduce a phenylacetic acid side chain is disclosed.

OXIDATION BY THE SALTS OF METALS. IV. OXIDATIVE HALOGENATION OF TOLUENE AND PARA-SUBSTITUTED TOLUENES WITH ELECTRON-WITHDRAWING GROUPS PROMOTED BY CERIUM(IV) SALTS IN AQEOUS SOLUTIONS OF TRIFLUOROACETIC ACID

The oxidation of toluene and para-substituted toluenes with electron-withdrawing groups (para-toluic acid, methyl para-toluate, and para-nitrotoluene) by ammonium cerium(IV) nitrate and ammonium cerium(IV) sulfate was investigated in aqueous solutions of trifluoroacetic acid in the presence of alkali-metal chlorides and bromides.The rate and selectivity of oxidative halogenation in the side chain and/or aromatic ring under the investigated conditions depends strongly both on the nature of the substrate and the halide ion and on the reaction conditions and the ligand environment of the cerium(IV) atom.The oxidation of nitrotoluene takes place only in the presence of the bromide-containing systems and leads to the production of 4-nitrobenzyl bromide.For the other substrates halogenation in the aromatic ring can be realized with yields close to quantitative with ammonium cerium(IV) nitrate as oxidizing agent in concentrated aqueous solutions of trifluoroacetic acid (10 vol.percent of water).It was shown that the halogenating agents in this case are mainly the products from oxidation of the halide ions by the nitronium ions formed in the strongly acidic medium from the nitrate ions contained in the ammonium cerium(IV) nitrate.Bromination of the substituted toluenes in the presence of ammonium cerium(IV) sulfate and in the ammonium cerium(IV) nitrate-alkali-metal bromide systems with more than 10 vol.percent of water takes mainly in the side chain and can be used as a method for the production of 4-substituted benzyl halides with preparative yields.The effect of the composition of the solvent and the ratio of the oxidizing agent and alkali-metal halide on the rate and selectivity of oxidative bromination was studied.Possible reaction mechanisms are discussed.

Regioselective Diels-Alder Reactions. A Synthesis of the Left-Hand Portion of CC-1065

Diene 2b reacted regioselectively with dienophiles.Adduct 6 was converted into the left-hand portion of CC-1065 in 10percent overall yield.