43192-33-2

Basic information

• Product Name: 4-BROMO-2-METHOXYBENZALDEHYDE
• Synonyms: 2-Methoxy-4-broMobenzaldehyde;5-Bromo-2-formylanisole, 4-Bromo-o-anisaldehyde;4-BroMo-2-Methoxybenzaldehyde, 97%+
• CAS NO: 43192-33-2
• Molecular Formula: C₈H₇BrO₂
• Molecular Weight: 215.05
• Mol File: 43192-33-2.mol

Chemical Properties

• Melting Point: 67-71 °C
• Boiling Point: 288.106 °C at 760 mmHg
• Flash Point: 128.042 °C
• Appearance: /
• Density: 1.522 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: 4-BROMO-2-METHOXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-METHOXYBENZALDEHYDE(43192-33-2)
• EPA Substance Registry System: 4-BROMO-2-METHOXYBENZALDEHYDE(43192-33-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 24/25
• WGK Germany: 2
• Hazardous Substances Data: 43192-33-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-methoxybenzaldehyde is used as a building block for the synthesis of a nonacid degradable linker for solid-phase synthesis. This application is particularly relevant in the pharmaceutical industry, where it plays a crucial role in the development of new drugs and therapeutic agents. The nonacid degradable linker allows for the efficient and controlled release of synthesized compounds from the solid support, facilitating the synthesis of complex molecules with high purity and yield.
Used in Chemical Synthesis:
In the broader field of chemical synthesis, 4-Bromo-2-methoxybenzaldehyde serves as a valuable building block for the creation of various organic compounds. Its unique structural features, including the bromine atom and methoxy group, enable it to participate in a range of chemical reactions, such as cross-coupling, substitution, and condensation reactions. This versatility makes it a popular choice for the synthesis of a wide array of molecules, including pharmaceuticals, agrochemicals, and advanced materials.

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

Upstream product

• 2398-37-0 3-methoxyphenyl bromide 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 57848-46-1 4-bromo-2-fluorobenzaldehyde 
• 1666-28-0 4-bromosalicylic acid 
• 4885-02-3 Dichloromethyl methyl ether 
• 330793-38-9 4-bromo-2-methoxybenzonitrile 
• 139102-34-4 methyl 4-bromo-2-methoxybenzoate 
• 591-20-8 3-Bromophenol 
• 95970-08-4 1,4-dibromo-2-methoxybenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 22532-62-3 4-bromosalicylaldehyde 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1050477-31-0 BAY₉₄₈₈₆₂ 
• 1050477-43-4 2-cyanoethyl 4-(4-cyano-2-methoxyphenyl)-2,8-dimethyl-5-oxo-1,4,5,6-tetrahydro-l,6-naphthyridine-3-carboxylate 
• 1050477-44-5 2-cyanoethyl 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxylate 
• 1050477-45-6 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxylic acid 
• 21962-45-8 4-formyl-3-methoxy-benzonitrile 

Relevant articles and documents

PREPARATION OF A CHK1 INHIBITOR COMPOUND

The invention provides a novel synthetic route for the preparation of the Chk-1 inhibitor compound; also provided by the invention is a novel process for the preparation of the synthetic intermediate of formula (11); as well as novel process intermediates

Tricyclic Indazoles - A Novel Class of Selective Estrogen Receptor Degrader Antagonists

Herein, we report the identification and synthesis of a series of tricyclic indazoles as a novel class of selective estrogen receptor degrader antagonists. Replacement of a phenol, present in our previously reported tetrahydroisoquinoline scaffold, with an indazole group led to the removal of a reactive metabolite signal in an in vitro glutathione trapping assay. Further optimization, guided by X-ray crystal structures and NMR conformational work, varied the alkyl side chain and pendant aryl group and resulted in compounds with low turnover in human hepatocytes and enhanced chemical stability. Compound 9 was profiled as a representative of the series in terms of pharmacology and demonstrated the desired estrogen receptor α degrader-antagonist profile and demonstrated activity in a xenograft model of breast cancer.

METHOD FOR THE PREPARATION OF (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1-6-NAPHTHYRIDINE-3-CARBOXAMIDE AND RECOVERY OF (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1-6-NAPHTHYRIDINE-3-CARBOXAMIDE BY ELECTROCHEMICAL METHODS

The present invention relates to a novel process for preparing (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) and recovering (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) proceeding from (4R)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula ent-(I)

METHOD FOR THE PREPARATION OF (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1-6-NAPHTHYRIDINE-3-CARBOXAMIDE AND THE PURIFICATION THEREOF FOR USE AS AN ACTIVE PHARMACEUTICAL INGREDIENT

The present invention relates to a novel and improved process for preparing (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I)

METHOD FOR THE PREPARATION OF (4S)-4-(4-CYANO-2-METHOXYPHENYL)-5-ETHOXY-2,8-DIMETHYL-1,4-DIHYDRO-1-6-NAPHTHYRIDINE-3-CARBOX-AMIDE AND THE PURIFICATION THEREOF FOR USE AS AN ACTIVE PHARMACEUTICAL INGREDIENT

The present invention relates to a novel and improved process for preparing (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I) and also the preparation and use of the crystalline polymorph I of (4S)-4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide of the formula (I).

INDAZOLE DERIVATIVES THAT DOWN-REGULATE THE ESTROGEN RECEPTOR AND POSSESS ANTI-CANCER ACTIVITY

The specification relates to compounds of Formula (I) and pharmaceutically acceptable salts thereof. The specification also relates to processes and intermediates used for their preparation, pharmaceutical compositions containing them and their use in the treatment of cell proliferative disorders.

Iterative design of a biomimetic catalyst for amino acid thioester condensation

Herein, the design of a catalyst that combines lessons learned from peptide biosynthesis, enzymes, and organocatalysts is described. The catalyst features a urea scaffold for carbonyl recognition and elements of nucleophilic catalysis. In the presence of 10 mol % of the organocatalyst, the rate of peptide bond formation is accelerated by 10000-fold over the uncatalyzed reaction between Fmoc-amino acid thioesters and amino acid methyl esters.

5-HT2A/5-HT2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism

The toxic hallucinogen 25B-NBOMe is very rapidly degraded by human liver microsomes and has low oral bioavailability. Herein we report on the synthesis, microsomal stability, and 5-HT2A/5-HT2C receptor profile of novel analogues of 25B-NBOMe modified at the primary site of metabolism. Although microsomal stability could be increased while maintaining potent 5-HT2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.

Small molecule inhibitors of anthrax lethal factor toxin

This manuscript describes the preparation of new small molecule inhibitors of Bacillus anthracis lethal factor. Our starting point was the symmetrical, bis-quinolinyl compound 1 (NSC 12155). Optimization of one half of this molecule led to new LF inhibitors that were desymmetrized to afford more drug-like compounds.

A one-pot allylation-hydrostannation sequence with recycling of the intermediate tin waste

A one-pot allylation and hydrostannation of alkynals where the tin byproduct formed in the first step of the reaction is recycled and used in the second step of the sequence is presented. Specifically, a BF3· OEt2-promoted allylstannation of the aldehyde moiety in the alkynal is followed by the introduction of polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3, which convert the tin byproduct of the allylation into Bu3SnH, which then hydrostannates the alkyne in the molecule. 119Sn and 11B NMR data suggest an organotin fluoride species is formed during the allylation step and involved in the tin recycling step.