204078-32-0

Basic information

• Product Name: 2-MORPHOLINOBENZONITRILE
• Synonyms: 2-MORPHOLINOBENZONITRILE;2-(MORPHOLIN-4-YL)BENZONITRILE;4-(2-Cyanophenyl)morpholine
• CAS NO: 204078-32-0
• Molecular Formula: C₁₁H₁₂N₂O
• Molecular Weight: 188.22578
• Mol File: 204078-32-0.mol

Chemical Properties

• Boiling Point: 357.4°C at 760 mmHg
• Flash Point: 169.9°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 2.74E-05mmHg at 25°C
• Refractive Index: 1.583
• PKA: 3.13±0.40(Predicted)
• CAS DataBase Reference: 2-MORPHOLINOBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MORPHOLINOBENZONITRILE(204078-32-0)
• EPA Substance Registry System: 2-MORPHOLINOBENZONITRILE(204078-32-0)

Safety Data

• Statements: 20/22
• Safety Statements: 36/37
• Hazardous Substances Data: 204078-32-0(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

InChI:InChI=1/C11H12N2O/c12-9-10-3-1-2-4-11(10)13-5-7-14-8-6-13/h1-4H,5-8H2

Upstream product

• 110-91-8 morpholine 
• 394-47-8 2-fluorobenzonitrile 
• 873-32-5 2-Chlorobenzonitrile 
• 2042-37-7 o-cyanobromobenzene 
• 87698-82-6 4-(2-bromophenyl)morpholine 

Downstream Products

• 204078-48-8 1-[2-(morpholin-4-yl)phenyl]methanamine 
• 67829-50-9 2-morpholinobenzamide 

Relevant articles and documents

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.

Cu(0)@Al2O3/SiO2 NPs: An efficient reusable catalyst for the cross coupling reactions of aryl chlorides with amines and anilines

The C-N cross coupling reaction of aryl chlorides with various alkyl/aryl amines catalyzed by copper nanoparticles impregnated on alumina/silica support (Cu(0)@Al2O3/SiO2) was investigated. The prepared catalyst was characterized for its intrinsic physico-chemical and textural properties using XRD, XPS, HR-TEM, BET surface area, SEM-EDAX, H2-TPR and ICP-AES techniques. The catalyst exhibits excellent reactivity and efficacy in the cross-coupling of a wide range of alkyl/aryl amines including challenging anilines with aryl chlorides. The catalyst offers significant advantages such as brevity, milder reaction conditions, excellent yields and high functional group tolerance for C-N cross coupling when compared with the other reported methods. Moreover, this atom-economical methodology does not require an additional ligand or co-catalyst/activator. The Cu(0)@Al2O3/SiO2 catalyst was efficiently applied to a gram scale synthesis of 7-chloro-4-(4-(2-nitrophenyl)piperazin-1-yl)quinolone (2k). The robustness of the catalyst was examined by reusing it for five consecutive runs.

SNAr reaction in aqueous medium in the presence of mixed organic and inorganic bases

N-Arylation of amines with fluorobenzonitriles in aqueous medium is described. A mixture of N,N-diisopropylethyl amine and Na2CO3 (1:1) is found to achieve maximum conversion by refluxing for 3 hours in water. The product can be easily isolated by solvent extraction.

Accelerating Effect of Triazolyl and Related Heteroaryl Substituents on SNAr Reactions: Evidence of Hydrogen-Bond Stabilized Transition States

The remarkable accelerating effect of 1,2,3-triazolyl substituents on SNAr reactions has been investigated through systematic experiments and density functional theory calculations. The lone pair electrons of an ortho-triazolo substituent play

Insertion of arynes into N-halo bonds: A direct approach to O -haloaminoarenes

A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a nitrogen-halide bond (N-X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized aminoarene derivatives.

Efficient construction of C=N double bonds via acceptorless dehydrogenative coupling

The efficient construction of C=N double bonds has been achieved by the Ir-catalyzed intramolecular acceptorless dehydrogenative cross-coupling of tertiary amines and amides. An iridium/2-hydroxypyridine complex was identified as the highly efficient catalyst. A number of quinazolinone derivatives was prepared in excellent yields. An iridium-mediated C-H activation mechanism is proposed. This finding provides an unprecedented strategy for the direct imidation of sp3 C-H bonds.

Air-stable and highly efficient indenyl-derived phosphine ligand: Application to Buchwald-Hartwig amination reactions

2-Mesitylindenyl phosphine ligand (1) and [(2-mesitylindenyl)dicyclohexyl- phosphine]PdCl2 (2) have been synthesized and fully characterized by NMR and elemental analysis, as well as by X-ray crystallography for 2. A Highly active catalyst system derived from a palladium precatalyst and bulky 2-mesitylindenyl phosphine ligand (1) for the Buchwald-Hartwig amination reaction of aryl halides with primary and secondary amines has been developed. This method allows for the preparation of a wide variety of amines in moderate to excellent yields and displays a high level of activity for the coupling of aryl chlorides as well as hindered aryl bromides.

Synthesis and in vitro activity of N-benzyl-1-(2,3-dichlorophenyl)-1H- tetrazol-5-amine P2X7 antagonists

Synthesis and biological evaluation of a novel class of substituted N-benzyl-1-(2,3-dichlorophenyl)-1H-tetrazol-5-amine derivatives resulted in the identification of potent P2X7 antagonists. These compounds were assayed for activity at both the

PARACYCLOPHANE-BASED LIGANDS, THEIR PREPARATION AND USE IN CATALYSIS

A substituted paracyclophane is described of formula (I) wherein X1 and X2 are linking groups comprising between 2 to 4 carbon atoms, Y1 and Y2 are selected from the group consisting of hydrogen, halide, oxygen, nitrogen, alkyl, cycloalkyl, aryl or heteroaryl and Z is a substituted or unsubstituted alkyl group, aryl group or heteroaryl group. Preferably X1 and X2 are -(C2H4)- and Z is a substituted aryl group. The substituted paracyclophane provides transition metal catalysts that are useful in C-C and C-N bond formation and asymmetric hydrogenation reactions.

Paracyclophane-based monophosphine ligand for palladium-catalyzed cross-coupling reactions of aryl chlorides

A new [2.2]paracyclophane-based electron-rich and sterically bulky monophosphine ligand has been synthesized by an efficient and straightforward method. When combined with palladium, this ligand shows excellent performance in the Buchwald-Hartwig amination and Suzuki-Miyaura coupling reactions of various aryl chlorides. In both types of reactions, ortho-substituted, deactivated aryl chlorides are shown to be viable substrates. However, the Suzuki-Miyaura coupling appears to be easier, with palladium loading at 0.1 mol% being feasible. The Royal Society of Chemistry 2009.