135484-83-2

Basic information

• Product Name: Methyl 2-amino-4-bromobenzoate
• Synonyms: METHYL 2-AMINO-4-BROMOBENZOATE;METHYL 4-BROMO-2-AMINOBENZOATE;2-AMINO-4-BROMOBENZOIC ACID METHYL ESTER;Methyl 4-bromoanthranilate;4-Bromo-2-Amino Benzoic Acid Methyl Ester;8031 4-BROMO-2-AMINO BENZOIC ACID METHYL ESTER;Benzoic acid, 2-aMino-4-broMo-, Methyl ester;5-Bromo-2-(methoxycarbonyl)aniline, Methyl 4-bromoanthranilate
• CAS NO: 135484-83-2
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.06
• Product Categories: Aromatic Esters;Esters;Phenyls & Phenyl-Het;Phenylacetic acid;Phenyls & Phenyl-Het
• Mol File: 135484-83-2.mol

Chemical Properties

• Melting Point: 77-79°C
• Boiling Point: 319.3 °C at 760 mmHg
• Flash Point: 146.9 °C
• Appearance: white to off white powder
• Density: 1.578 g/cm³
• Vapor Pressure: 0.000342mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C(protect from light)
• Solubility: soluble in Methanol
• PKA: 1.33±0.10(Predicted)
• CAS DataBase Reference: Methyl 2-amino-4-bromobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-amino-4-bromobenzoate(135484-83-2)
• EPA Substance Registry System: Methyl 2-amino-4-bromobenzoate(135484-83-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 135484-83-2(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

InChI:InChI=1/C8H8BrNO2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,10H2,1H3

Upstream product

• 67-56-1 methanol 
• 20776-50-5 2-amino-4-bromobenzoic acid 
• 158580-57-5 methyl 4-bromo-2-nitrobenzoate 
• 7439-89-6 iron 
• 82-73-5 3-bromophthalic anhydride 
• 6941-75-9 5-Bromoisoindoline-1,3-dione 
• 591-19-5 m-Bromoaniline 
• 6326-79-0 6-bromoisatin 
• 99277-71-1 4-bromo-2-nitrobenzoic acid 

Downstream Products

• 4445-43-6 3-amino-[1,1'-biphenyl]-4-carboxylic acid 
• 62473-92-1 6-bromosaccharin 
• 791098-19-6 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoic acid methyl ester 
• 612537-88-9 5-bromo-2-cyano-N-(5-isopropyl-4-methyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 851044-98-9 methyl 4-bromo-2-isopropoxycarbonylaminobenzoate 
• 438535-18-3 methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino) benzoate 
• 1356854-67-5 5-bromo-2-[(6-chloropyridine-3-carbonyl)amino]benzoic acid methyl ester 
• 1152237-24-5 C₁₆H₁₄BrNO₂ 
• 1103931-04-9 methyl 4-bromo-2-[({2-[4-(diphenylmethyl)piperazin-1-yl]-2-oxoethoxy}acetyl)amino]benzoate 
• 1312446-90-4 C₉H₆BrNO₃ 
• 158580-61-1 4-bromo-2-methanesulfonylaminobenzoic acid 
• 1358608-70-4 methyl 4-bromo-2-(nitroamino)benzoate 
• 1352244-32-6 4-bromo-2-(5-chloro-2-[4-(4-methylpiperazin-1-yl)-3-vinylphenylamino]pyrimidin-4-ylamino)benzoic acid methyl ester 
• 1352244-18-8 4-bromo-2-(2,5-dichloropyrimidin-4-ylamino)benzoic acid methyl ester 

Relevant articles and documents

TRICYCLIC PYRIDONES AND PYRIMIDONES

A compound of Formula (I) is provided: (I) where the variables are defined herein.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

A pharmaceutical composition comprising the compound of Formula Ia, Formula Ib, Formula Ic, or Formula Id, or a pharmaceutically acceptable salt thereof, is set forth. (Formula Ia), (Formula Ib), (Formula Ic), (Formula Id)

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.

INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION

Compounds of Formula (I), including pharmaceutically acceptable salts thereof, and compositions and methods for treating human immunodeficiency virus (HIV) infection are set forth:

The Suzuki–Miyaura Cross-Coupling as the Key Step in the Synthesis of 2-Aminobiphenyls and 2,2'-Diaminobiphenyls: Application in the Synthesis of Schiff Base Complexes of Zn

2-Nitrophenylboronic acids serve as interesting starting materials for the construction of biphenyl- and terphenyl-based amines if subjected to the Suzuki–Miyaura reaction. Unfortunately, these boronic acids suffer from low reactivity in Suzuki reactions, alongside their low stability in the presence of Pd. Herein, a general method for the construction of 2-nitro-substituted bi- and terphenyls is presented, with special emphasis on the synthesis of 2-amino-2'-nitrobi- and terphenyls. Comparisons are made with other boronic acids that have some of the aforementioned issues. Finally, the application of the obtained 2-amino-2'-nitrobi- and terphenyls as starting materials for the synthesis of bi- and terphenyl based di- and triamines is encountered for, with emphasis on the use of these amines as precursors for Schiff base ligands. In addition, the synthesis of some Zn complexes of these ligands is presented.

ACLY INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of ATP citrate lyase (ACLY), compositions thereof, and methods of using the same.

Method for preparing 7-halo-6-nitro-1,4-dihydroquinoline-4-one-3-carbonitrile

The invention discloses a method for preparing 7-halo-6-nitro-1,4-dihydroquinoline-4-one-3-carbonitrile. The method comprises the following steps of: S1, adopting 2-amino-4-halo benzoic acid as a starting material, and performing esterification on simple fatty alcohol under the action of a catalyst so as to produce 4-halo-2-aminobenzoate; S2, performing a reaction between 4-halo-2-aminobenzoate and 3-dimethylaminoacrylonitrile under the action of an acidic catalyst so as to produce 4-halo-2-((2-cyanovinyl)amino) benzoate; S3, performing cyclization on 4-halo-2-((2-cyanovinyl)amino) benzoate under the action of strong base so as to produce 7-halo-1,4-dihydroquinoline-4-one-3-carbonitrile; and S4, performing nitrification on 7-halo-1,4-dihydroquinoline-4-one-3-carbonitrile in the presence ofa mixture of strong acid and nitric acid to obtain 7-halo-6-nitro-1,4-dihydroquinoline-4-one-3-carbonitrile. According to the method for preparing 7-halo-6-nitro-1,4-dihydroquinoline-4-one-3-carbonitrile, the process route is novel, the novel intermediates are obtained, and the total yield is more than 35%; the method has the advantages of a novel process route, mild reaction conditions and the like.

Identification of potent and selective small molecule inhibitors of the cation channel TRPM4

Background and Purpose: TRPM4 is a calcium-activated non-selective cation channel expressed in many tissues and implicated in several diseases, and has not yet been validated as a therapeutic target due to the lack of potent and selective inhibitors. We sought to discover a novel series of small-molecule inhibitors by combining in silico methods and cell-based screening assay, with sub-micromolar potency and improved selectivity from previously reported TRPM4 inhibitors. Experimental Approach: Here, we developed a high throughput screening compatible assay to record TRPM4-mediated Na+ influx in cells using a Na+-sensitive dye and used this assay to screen a small set of compounds selected by ligand-based virtual screening using previously known weakly active and non-selective TRPM4 inhibitors as seed molecules. Conventional electrophysiological methods were used to validate the potency and selectivity of the hit compounds in HEK293 cells overexpressing TRPM4 and in endogenously expressing prostate cancer cell line LNCaP. Chemical chaperone property of compound 5 was studied using Western blots and electrophysiology experiments. Key Results: A series of halogenated anthranilic amides were identified with TRPM4 inhibitory properties with sub-micromolar potency and adequate selectivity. We also showed for the first time that a naturally occurring variant of TRPM4, which displays loss-of-expression and function, is rescued by the most promising compound 5 identified in this study. Conclusions and Implications: The discovery of compound 5, a potent and selective inhibitor of TRPM4 with an additional chemical chaperone feature, revealed new opportunities for studying the role of TRPM4 in human diseases and developing clinical drug candidates.

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

A kind of novel 4,5-substituted-7-carboxylic acid methyl ester indole dione derivatives and their use in anti-tumor drug

The invention relates to a kind of novel 4,5-substituted-7-methyl formate indoledione derivatives and an application thereof in anti-tumor drugs. The derivatives are 4-floro-5-bromo-7-methyl formate indoledione, 4-floro-5-nitro-7-methyl formate indoledione, 4-chloro-5-bromo-7-methyl formate indoledione, 4,5-dibromo-7-methyl formate indoledione and the like. In the invention, the kind of 4,5-substituted-7-methyl formate indoledione derivatives are synthesized and tested for the in-vitro tumor cell inhibition activity, and the result indicates that the kind of derivatives realize certain inhibition effects (IC5010muM) on the human leukemia cell (K562), human colon cancer cell (HT-29) and human liver cancer cell (HepG2) and have broad prospects in the development and application of anti-tumor drugs.