74852-81-6

Basic information

• Product Name: 4-(2-METHYLIMIDAZOL-1-YL)PHENYLAMINE
• Synonyms: AKOS B029445;4-(2-METHYLIMIDAZOL-1-YL)PHENYLAMINE;4-(2-methyl-1h-imidazol-1-yl)aniline;4-(2-METHYL-1H-IMIDAZOL-1-YL)PHENYLAMINE;CHEMBRDG-BB 4010370;ASINEX-REAG BAS 08767582;4-(2-Methylimidazol-1-yl)phenylamine95%;4-(2-methylimidazolyl)-aniline
• CAS NO: 74852-81-6
• Molecular Formula: C₁₀H₁₁N₃
• Molecular Weight: 173.21
• Mol File: 74852-81-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 111.5 °C
• Boiling Point: 378.506 °C at 760 mmHg
• Flash Point: 182.714 °C
• Appearance: /
• Density: 1.171 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.49±0.10(Predicted)
• CAS DataBase Reference: 4-(2-METHYLIMIDAZOL-1-YL)PHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-METHYLIMIDAZOL-1-YL)PHENYLAMINE(74852-81-6)
• EPA Substance Registry System: 4-(2-METHYLIMIDAZOL-1-YL)PHENYLAMINE(74852-81-6)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 74852-81-6(Hazardous Substances Data)

Usage

General Description

4-(2-Methylimidazol-1-yl)phenylamine is a chemical compound that consists of a 2-methylimidazole group attached to a phenylamine molecule. It is commonly used in the synthesis of pharmaceutical drugs and agrochemicals. 4-(2-METHYLIMIDAZOL-1-YL)PHENYLAMINE has a wide range of applications, including its use as a building block in the production of various organic compounds and as a reagent in chemical reactions. Its chemical structure and properties make it suitable for use in the development of new medications and agricultural products. Additionally, it can be used in laboratory research and chemical testing. Overall, 4-(2-Methylimidazol-1-yl)phenylamine is a versatile and valuable chemical compound with numerous practical applications.

InChI:InChI=1/C10H11N3/c1-8-12-6-7-13(8)10-4-2-9(11)3-5-10/h2-7H,11H2,1H3

Upstream product

• 73225-15-7 1-(4-nitrophenyl)-2-methylimidazole 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 218299-77-5 1-(3'-aminobenzisoxazol-5'-yl)-3-trifluoromethyl-5-[(4'(2''-methylimidazol-1''-yl)phenyl)aminocarbonyl]pyrazole TFA salt 
• 1201902-17-1 [6-(2-methyl-1H-imidazol-1-yl)-2-(4-methoxyphenyl)]quinoline 
• 1312098-88-6 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazole 
• 1312099-59-4 1-(4-bromophenyl)-2-methyl-1H-imidazole 
• 1255700-54-9 2-(2-(1,3-dimethyl-1H-pyrazol-5-yl)-8-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile 
• 1226887-39-3 1-(4-(2-methyl-1H-imidazol-1-yl)phenyl)guanidine 
• 1201902-59-1 3-ethoxy-N-[4-(2-methyl-1H-imidazol-1-yl)phenyl]acrylamide 
• 1159710-67-4 2-iodo-4-(2-methyl-1H-imidazol-1-yl)aniline 
• 1142948-09-1 C₂₈H₂₄N₆O₂S₂ 
• 1138473-43-4 4-(benzo[b]thiophen-2-yl)-5-methyl-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)pyrimidin-2-amine 
• 218299-67-3 1-(3'-aminobenzisoxazol-5'-yl)-5-[[4-(2'-methylimidazol-1'-yl)phenyl]aminocarbonyl]tetrazole TFA salt 
• 218299-57-1 1-(3'-aminobenzisoxazol-5'-yl)-3-ethyl-5-[[4-(2'-methylimidazol-1'-yl)phenyl]aminocarbonyl]pyrazole TFA salt 

Relevant articles and documents

Mechanistic Studies on the Palladium-Catalyzed Direct C-5 Arylation of Imidazoles: The Fundamental Role of the Azole as a Ligand for Palladium

An in-depth mechanistic study on the palladium-catalyzed direct arylation of imidazoles at the C-5 position is presented. The interactions of triphenylphosphine (PPh3)-ligated aryl-Pd species with 1,2-dimethyl-1H-imidazole (dmim) have been studied in detail. In contrast with previous suggestions, phosphine-ligated organo-Pd species are not active and the reaction proceeds through imidazole-ligated organo-Pd intermediates. The kinetics of the oxidative addition of aryl halides with dmim-ligated Pd(0) species have been characterized in a Pd(dba)2/dmim model system. A thorough study of the equilibria involving novel [ArPd(dmim)2X] complexes (X=I, OAc) and the unexpected cationic [ArPd(dmim)3]+ is also reported. The ability of these species to effect the C-H arylation of dmim at room temperature in the presence of acetate is also demonstrated.

PYRROLOTHIAZOLES AS PI3-KINASE INHIBITORS

A series of 4,5-dihydro-6H-pyrrolo[3,4-d][1,3]thiazol-6-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly o

Discovery of 1-(3′-aminobenzisoxazol-5′-yl)-3-trifluoromethyl- N-[2-fluoro-4-[(2′-dimethylaminomethyl)imidazol-1-yl]phenyl] -1H-pyrazole-5-carboxyamide hydrochloride (razaxaban), a highly potent, selective, and orally bioavailable factor Xa inhibitor

Modification of a series of pyrazole factor Xa inhibitors to incorporate an aminobenzisoxazole as the P1 ligand resulted in compounds with improved selectivity for factor Xa relative to trypsin and plasma kallikrein. Further optimization of the P4 moiety led to compounds with enhanced permeability and reduced protein binding. The SAR and pharmacokinetic profile of this series of compounds is described herein. These efforts culminated in 1-(3′-aminobenzisoxazol-5′-yl)-3-trifluoromethyl-N-[2-fluoro-4- [(2′-dimethylaminomethyl)imidazol-1-yl]phenyl]-1H-pyrazole-5-carboxyamide (11d), a potent, selective, and orally bioavailable inhibitor of factor Xa. On the basis of its excellent in vitro potency and selectivity profile, high free fraction in human plasma, good oral bioavailability, and in vivo efficacy in antithrombotic models, the HCl salt of this compound was selected for clinical development as razaxaban (DPC 906, BMS-561389).