99-58-1

Basic information

• Product Name: 3-BROMO-4-METHOXYBENZOIC ACID
• Synonyms: RARECHEM AL BO 0751;TIMTEC-BB SBB009955;3-BROMO-4-METHOXYBENZOIC ACID;3-BROMO-P-ANISIC ACID;AKOS BBB/210;AKOS 211-11;3-Bromo-4-methoxybenzoic acid, 98+%;3-BROMO-P-ANISIC ACID, 98+%
• CAS NO: 99-58-1
• Molecular Formula: C₈H₇BrO₃
• Molecular Weight: 231.04
• EINECS: 202-768-4
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Acids & Esters;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds
• Mol File: 99-58-1.mol

Chemical Properties

• Melting Point: 220-222 °C(lit.)
• Boiling Point: 326 °C at 760 mmHg
• Flash Point: 151 °C
• Appearance: white powder
• Density: 1.625 g/cm³
• Vapor Pressure: 9.02E-05mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), methanol (Slightly)
• PKA: 4.08±0.10(Predicted)
• BRN: 2087585
• CAS DataBase Reference: 3-BROMO-4-METHOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-METHOXYBENZOIC ACID(99-58-1)
• EPA Substance Registry System: 3-BROMO-4-METHOXYBENZOIC ACID(99-58-1)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 99-58-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-methoxybenzoic acid is used as a reagent for the preparation of benzamide compounds, which serve as ABL1, ABL2, and BCR-ABL1 inhibitors. These inhibitors are crucial in the treatment of cancer and central nervous system (CNS) disorders, as they target specific enzymes involved in the development and progression of these diseases.
In the synthesis of benzamide compounds, 3-bromo-4-methoxybenzoic acid acts as a starting material, which can be further modified and functionalized to create the desired active pharmaceutical ingredients (APIs). The benzamide class of compounds has been found to possess significant biological activity, making them valuable in the development of new therapeutic agents for various medical conditions.

InChI:InChI=1/C8H7BrO3/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4H,1H3,(H,10,11)/p-1

Upstream product

• 4374-35-0 α-bromoethyl 3-bromo-4-methoxyphenyl ketone 
• 21702-84-1 2,4-dibromoanisole 
• 200956-55-4 3-bromo-4-methoxybenzamide 
• 860584-79-8 2-bromo-4-(2-bromo-ethyl)-anisole 
• 100-09-4 4-methoxybenzoic acid 
• 60-29-7 diethyl ether 
• 925-90-6 ethylmagnesium bromide 
• 2476-35-9 5-bromo-2-methoxybenzoic acid 
• 35310-75-9 3-bromo-4-methoxyacetophenone 
• 35450-37-4 methyl 3-bromo-4-methoxybenzoate 
• 50870-43-4 2-bromo-4-(2-bromo-vinyl)-anisole 
• 50870-46-7 trans-3,β-Dibrom-4-methoxystyrol 
• 7726-95-6 bromine 
• 10507-69-4 4-methoxybenzohydroxamic acid 

Downstream Products

• 35450-37-4 methyl 3-bromo-4-methoxybenzoate 
• 460079-82-7 ethyl 3-bromo-4-methoxybenzoate 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 14348-41-5 3-bromo-4-hydroxy-benzoic acid 
• 36324-64-8 2-Bromo-4,6-dinitroanisole 
• 24507-33-3 3-bromo-4-methoxy-benzoic acid-(2-diethylamino-ethylamide) 
• 81324-61-0 3-bromo-4-methoxy-benzoic acid chloride 
• 100-09-4 4-methoxybenzoic acid 
• 206876-43-9 2-Cyano-4-methoxy-3-(4-methoxy-benzyl)-benzoic acid 
• 5197-28-4 2-bromo-4-nitroanisole 
• 954815-08-8 3-bromo-4-methoxy-5-nitro-benzoic acid 
• 876752-69-1 3-bromo-4-methoxybenzoic acid tert-butyl ester 
• 876752-70-4 3-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-4-methoxy-benzoic acid tert-butyl ester 

Relevant articles and documents

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

We developed a mild aromatic halogenation reaction using a combination of N-halosuccinimide and PhSSiMe3 or PhSSPh. Less reactive aromatic compounds, such as methyl 4-methoxybenzoate, were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the absence of PhSSiMe3 or PhSSPh. This method is also applicable to chlorination reactions using N-chlorosuccinimide and PhSSPh.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Intermolecular Aryl C?H Amination through Sequential Iron and Copper Catalysis

A mild, efficient and regioselective method for para-amination of activated arenes has been developed through a combination of iron and copper catalysis. A diverse range of products were obtained from an operationally simple one-pot, two-step procedure involving bromination of the aryl substrate with the powerful Lewis acid iron(III) triflimide, followed by a copper(I)-catalysed N-arylation reaction. This two-step dehydrogenative process for the regioselective coupling of aromatic C?H bonds with non-activated amines was applicable to anisole-, phenol-, aniline- and acetanilide-type aryl compounds. Importantly, the arene substrates were used as the limiting reagent and required no protecting-group manipulations during the transformation.

Promising hydrogen peroxide stabilizers for large-scale application: unprecedented effect of aryl alkyl ketones

Aryl alkyl ketones with substituents in the aromatic ring taken in an amount from 0.005 to 0.5% efficiently stabilize hydrogen peroxide in an aqueous solution during storage at 22–25°C for 16–24 months.

A Metal-Free Approach to Carboxylic Acids by Oxidation of Alkyl, Aryl, or Heteroaryl Alkyl Ketones or Arylalkynes

The metal-free oxidation of dialkyl, alkyl aryl, or alkyl heteroaryl ketones or arylalkynes to the corresponding carboxylic acids is achieved using an oxidative mixture of Oxone and trifluoroacetic acid. This green method is a simple and mild protocol to obtain carboxylic derivatives in excellent yields.

DMSO/I2 mediated C-C bond cleavage of α-ketoaldehydes followed by C-O bond formation: A metal-free approach for one-pot esterification

A novel and efficient I2/DMSO mediated metal-free strategy is presented for the direct C-C bond cleavage of aryl-/heteroaryl- or aliphatic α-ketoaldehydes by C2-decarbonylation and C1-carbonyl oxidation to give the corresponding carboxylic acids followed by esterification in one pot, offering excellent yields in both the steps. Here, DMSO acts as the oxygen source/oxidant and this reaction works very well under both conventional heating and microwave irradiation. This is a very simple and convenient protocol.

Bromination of arenes using I2O5-KBr in water

An efficient and environmentally benign bromination of various aromatic compounds using aN aqueous I2O5-KBr system at room temperature has been developed in this work. A series of aromatic compounds such as acetophenones, benzaldehydes, benzoic acids, anilines, amides, and aminopyridine have been successfully brominated in excellent regioselectivities and good yields under the typical reaction conditions. The features of KBr as brominating reagent, water as solvent, and mild conditions make this system an attractive synthetic procedure. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

A mild oxidation of deactivated naphthalenes and anthracenes to corresponding para-quinones by N-bromosuccinimide

A new method to synthesize 1,4-naphthoquinone and 9,10-anthraquinone from naphthalene and anthracene functionalized with either -CHO or -COOH groups, using N-bromosuccinimide (NBS) in aqueous N,N-dimethylformamide at 75-80 °C, has been developed. Further, -CN and -CONH2 functionalized naphthalenes and anthracenes can also be transformed into respective para-quinones in a one pot reaction, after successive acid hydrolysis and subsequent reaction with NBS. We believe that the present finding may serve as a valuable alternative to the classical approaches for the synthesis of polycyclic quinones from polyaromatic carbaldehydes through Dakin oxidation followed by further oxidation of the resulting hydroquinone by heavy metal oxides.

Synthesis and biological activities of new halophenols

A series of new halophenols were synthesized, and their structures were established on the basis of 1H, 13C NMR and mass spectral data. All of the prepared compounds were screened for their in vitro protein tyrosine kinase (PTK) and vascular smooth muscle cell (VSMC) proliferation inhibitory activity. Twelve halophenols showed significant PTK inhibitory activity, most of them exhibited stronger activities than that of genistein, a positive reference compound. Several halophenols also displayed moderate VSMC proliferation inhibitory activity, compound 8c showed higher activity than that of tetrandrine, a positive reference compound. The preliminary structure-activity relationships of these compounds were investigated and discussed. The results provided a foundation for the action mechanism study and further structure optimization of the halophenols.