23687-25-4

Basic information

• Product Name: 4-Isoquinolinamine
• Synonyms: isoquinolin-4-amine; Isoquinolin-4-amine
• CAS NO: 23687-25-4
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.1732
• EINECS: 245-823-8
• Product Categories: wq;Building Blocks;Isoquinoline;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Quinoline series;Amines;Quinolines, Isoquinolines & Quinoxalines;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 23687-25-4.mol

Chemical Properties

• Melting Point: 108.0 to 112.0 °C
• Boiling Point: 360 °C at 760 mmHg
• Flash Point: 198.9 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 2.29E-05mmHg at 25°C
• Refractive Index: 1.708
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 6.29±0.10(Predicted)
• CAS DataBase Reference: 4-Isoquinolinamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isoquinolinamine(23687-25-4)
• EPA Substance Registry System: 4-Isoquinolinamine(23687-25-4)

Safety Data

• Hazard Codes: Xi:
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 23687-25-4(Hazardous Substances Data)

Usage

Uses

4-Isoquinolylamine can be used for synthesis of Rho kinase inhibitors.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 783, 1942 DOI: 10.1021/ja01256a012

InChI:InChI=1/C9H8N2/c10-9-6-11-5-7-3-1-2-4-8(7)9/h1-6H,10H2

Upstream product

• 1532-97-4 4-bromoisoquinoline 
• 20377-03-1 4-azidoisoquinoline 
• 75-08-1 ethanethiol 
• 36073-93-5 4-nitro-isoquinoline 
• 881668-81-1 N-benzylisoquinolin-4-amine 
• 1421429-90-4 N-(diphenylmethylene)-isoquinolin-4-amine 
• 1532-91-8 4-chloroisoquinoline 

Downstream Products

• 136849-93-9 4-acetamidoisoquinoline 
• 681448-78-2 N-(isoquinolin-4-yl)benzamide 
• 857622-00-5 N-acetyl-sulfanilic acid-[4]isoquinolylamide 
• 130831-67-3 5,6,7,8-tetrahydro-[4]isoquinolylamine 
• 20377-03-1 4-azidoisoquinoline 
• 40073-37-8 4-amino-3-bromoisoquinoline 
• 14901-96-3 N-(1,2,3,4-tetrahydroisoquinolin-4-yl)benzamide 
• 681448-81-7 4-amino-1,2,3,4-tetrahydroisoquinoline 
• 342899-40-5 N-(3-chloro-4-isoquinolinyl)-2-cyclopropylamino-3-pyridinecarboxamide 
• 271784-15-7 4-N-benzylamino-3-bromoisoquinoline 
• 271784-11-3 3-bromo-4-tert-butyloxycarbonylaminoisoquinoline 
• 271784-23-7 1-phenylsulfonyl-1H-pyrrolo[3,2-c]isoquinoline 
• 81764-43-4 (5H-Benzo[e][1,3]diazepin-1-yl)-cyclohexyl-amine 
• 102877-49-6 5,6,7,8-tetrahydro-isoquinolin-4-ol 

Relevant articles and documents

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.

HETEROCYCLIC CARBOXYLIC ACID AMIDE LIGAND AND APPLICATIONS THEREOF IN COPPER CATALYZED COUPLING REACTION OF ARYL HALOGENO SUBSTITUTE

Provided are a heterocyclic carboxylic acid amide ligand and applications thereof in a copper catalyzed coupling reaction. Specifically, provided are uses of a compound represented by formula (I), definitions of radical groups being described in the specifications. The compound represented by formula (I) can be used as the ligand in the copper catalyzed coupling reaction of the aryl halogeno substitute, and is used or catalyzing the coupling reaction for forming the aryl halogeno substitute having C—N, C—O, C—S and other bonds.

6,6-Fused heterocyclic ureas as highly potent TRPV1 antagonists

A series of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N′-(6,6-fused heterocyclic) ureas have been investigated as hTRPV1 antagonists. Among them, compound 15 showed highly potent TRPV1 antagonism to capsaicin, with Ki(ant) = 0.2 nM, as well as antagonism to other activators, and it was efficacious in a pain model. A docking study of 15 with our hTRPV1 homology model indicates that there is crucial hydrogen bonding between the ring nitrogen and the receptor, contributing to its potency.

Nickel-catalyzed monoarylation of ammonia

Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.

Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia

A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.

Efficient asymmetric synthesis of Tryptophan Analogues having useful Photophysical properties

Two new fluorescent probes of protein structure and dynamics have been prepared by concise asymmetric syntheses using the Sch?llkopf chiral auxiliary. The site-specific incorporation of one probe into dihydrofolate reductase is reported. The utility of these tryptophan derivatives lies in their absorption and emission maxima which differ from those of tryptophan, as well as in their large Stokes shifts and high molar absorptivities.

SUBSTITUTED BICYCLIC AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted bicyclic aromatic carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

Substituted Bicyclic Aromatic Carboxamide and Urea Compounds as Vanilloid Receptor Ligands

Substituted bicyclic aromatic carboxamide and urea compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds, and a method of using these compounds in the treatment and/or inhibition of pain and further diseases and/or disorders mediated at least in part via the vanilloid receptor 1 (VR1/TRPV1).

PROCESS FOR THE SYNTHESIS OF ARYLAMINES FROM THE REACTION OF AN AROMATIC COMPOUND WITH AMMONIA OR A METAL AMIDE

A catalytic process for the synthesis of aromatic primary amines, reagent compositions for effecting the process, and transition metal complexes useful in the process, are provided.

PYRAZOLE COMPOUNDS USEFUL IN THE TREATMENT OF INFLAMMATION

There is provided compounds of formula (I), wherein R1, R2, Ra and Rb have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful in the treatment of diseases in which inhibition of the activity of a lipoxygenase (e.g. 15-lipoxygenase) is desired and/or required, and particularly in the treatment of inflammation.