1530-89-8

Basic information

• Product Name: 4-MORPHOLINECARBONITRILE
• Synonyms: N-CYANOMORPHOLINE;N-CYANMORPHOLINE;MORPHOLINO-N-CARBONITRILE;4-MORPHOLINECARBONITRILE;morpholine-4-carbonitrile;4-MORPHOLINECARBONITRILE 97%;4-Morpholinecarbonitrile, 97+%;4-Cyanomorpholine
• CAS NO: 1530-89-8
• Molecular Formula: C₅H₈N₂O
• Molecular Weight: 112.13
• EINECS: 216-235-9
• Product Categories: Aromatic Morpholines;Building Blocks;Heterocyclic Building Blocks;Morpholines
• Mol File: 1530-89-8.mol

Chemical Properties

• Boiling Point: 71-73 °C0.6 mm Hg(lit.)
• Flash Point: 220 °F
• Appearance: clear colourless liquid
• Density: 1.109 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0175mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• PKA: -6.85±0.20(Predicted)
• CAS DataBase Reference: 4-MORPHOLINECARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-MORPHOLINECARBONITRILE(1530-89-8)
• EPA Substance Registry System: 4-MORPHOLINECARBONITRILE(1530-89-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1530-89-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Morpholinecarbonitrile is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its ability to form heterocyclic structures makes it a valuable component in the design and synthesis of novel drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 4-Morpholinecarbonitrile is used as a subject for studying its photoelectron spectra, specifically the He I and He II photoelectron spectra. This research helps in understanding the electronic structure and properties of the compound, which can be useful for further applications in various chemical processes.
Used in Synthesis of Substituted Heterocyclic Compounds:
4-Morpholinecarbonitrile is used as a key building block for the synthesis of substituted heterocyclic compounds. These compounds are important in various fields, including pharmaceuticals, agrochemicals, and materials science, due to their diverse chemical and biological properties. The versatility of 4-Morpholinecarbonitrile in forming heterocyclic structures makes it a valuable asset in the development of new and innovative compounds with potential applications in these industries.

InChI:InChI=1/C5H8N2O/c6-5-7-1-3-8-4-2-7/h1-4H2

Upstream product

• 110-91-8 morpholine 
• 7677-24-9 trimethylsilyl cyanide 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 696-57-1 N-allylmorpholine 
• 506-68-3 bromocyane 
• 35891-13-5 2,2,2-trichloro-1-morpholinoethanimine 
• 1271-28-9 nickelocene 
• 5625-98-9 morpholinoethyl amide 
• 151-50-8 potassium cyanide 
• 2158-02-3 morpholine-4-carboxylic acid amide 
• 542-90-5 ethyl isothiocyanate 
• 23328-69-0 4-chloromorpholine 

Downstream Products

• 298687-31-7 methyl 3-methyl-6-(morpholin-4-yl)-1-phenyl-4-(trifluoromethyl)-1H,4H-pyrazolo[4,3-e][1,3]oxazine-4-carboxylate 
• 371959-22-7 C₁₈H₁₆F₆N₄O₂ 
• 133237-33-9 5-(4-morpholinyl)-1H-1,2,3,4-tetrazole 
• 14294-10-1 morpholinothiourea 
• 2827-42-1 2,4-diamino-6-morpholino-1,3,5-triazine 
• 16781-67-2 2-morpholin-4-yl-2-thiazole-4(5H)-one 
• 2158-02-3 morpholine-4-carboxylic acid amide 
• 31075-58-8 4-(1H-benzo[d]imidazol-2-yl)morpholine 
• 49573-85-5 N-(4-bromophenyl)morpholine-4-carboximidamide 

Relevant articles and documents

Electrochemical strategies for: N -cyanation of secondary amines and α C -cyanation of tertiary amines under transition metal-free conditions

Transition metal-free electrochemical approaches for the N-cyanation of secondary amines and the α C-cyanation of tertiary amines have been well established, with products being obtained in moderate to good yields and with good functional group tolerance under ambient conditions. The synthetic application of the protocols has been highlighted through scale-up experiments in a galvanostatic mode. Preliminary mechanistic investigation has confirmed that TBAB played a critical role in N-cyanation transformation and has indicated that the transformation might proceed via a free radical process. This journal is

N-Cyanation of Primary and Secondary Amines with Cyanobenzio-doxolone (CBX) Reagent

An efficient electrophilic N-cyanation of amines with a stable and less-toxic cyanobenziodoxole reagent towards the synthesis of cyanamides is disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex molecules.

Tris(3,5-dimethylpyrazolyl)methane copper(I) complexes featuring one disubstituted cyanamide ligand

The complexes [Cu{HC(3,5-Me2pz)3}(NCNR2)][BF4] (1–8; R2 = Me2 1, Et2 2, C5H10 3, C4H8O 4, C4H8 5, C3H

Benzoxazinone derivatives and their use as antibacterial agents

The invention discloses benzoxazinone derivatives, a synthesis method and applications thereof. The derivatives can be used as an antibacterial agent for treating infectious diseases caused by bacteria, especially tuberculosis (TB) caused by mycobacterium. Specifically, the invention relates to compounds represented by the formula (I), pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the provided compounds; wherein the R1 to R4 are defined in the description. The invention aim to prepare novel compounds capable of inhibiting the mycobacterium activity, the compounds can be used as a potential novel drug for treating infectious diseases caused by bacteria, moreover, the compounds can be used to treat or prevent tuberculosis (TB) caused by mycobacterium, at the same time the problems related with drug resistance can be solved, and the drug metabolism property can be improved on the basis that the mycobacterium tuberculosis resistant activity is not influenced.

A allyl uncle amine compound by one-step synthesis method of cyano uncle amine compound (by machine translation)

The invention relates to a one-step synthesis of amine compound allyl unclecyano uncle amine compounds, which belongs to the technical field of organic synthetic method. The method specific synthetic process is as follows: in the airtight reaction environment, to the anhydrous organic solvent is added in the cyanogen bromide, under protection of inert gas, and then added dropwise to the solution in the allylic and high yield amine compound, to obtain allyl uncle amine compound concentration is 0.8 - 1 mol/L solution, at room temperature the reaction 16 - 24 hours later, after column chromatography separation and purification, to obtain a corresponding cyano uncle amine compound. The method to get rid of the expensive deallylation use of the catalyst, the synthesis step is less, raw materials are easy, cheap, mild reaction conditions, the operation is simple, easy to craft and industrialization. Yield 50% - 80% between. (by machine translation)

Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan-amides through an N-deallylation reaction and an N-cyanation reaction in one pot.

N-Cyanation of Secondary Amines Using Trichloroacetonitrile

A one-pot N-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide.

Iron(III) catalysed synthesis of unsymmetrical di and trisubstituted ureas - A variation of classical Ritter reaction

An application of the classical Ritter reaction for the synthesis of unsymmetrical di and trisubstituted ureas catalyzed by FeCl3 is described. The protocol is of significant interest in view of the easy availability of precursors, mild reaction conditions employed and interestingly its applicability for the alkylation of alcohols capable of forming stable carbocationic intermediates even to the sterically hindered moieties. The Royal Society of Chemistry 2012.

AMINOTHIAZOLE DERIVATIVE

A compound represented by formula (1) or a pharmaceutically acceptable salt thereof, which has a PI3 kinase 3 inhibitory effect and is useful as a prophylactic or therapeutic agent for articular rheumatism, Crohn''s disease, irritable colitis, Sjoegren''s syndrome, multiple sclerosis, systemic lupus erythematosus, asthma, atopic dermatitis, arteriosclerosis, organ transplant rejection, cancer, retinopathy, psoriasis, arthrosis deformans, age-related macular degeneration, type II diabetes, insulin resistance, obesity, non-alcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), hyperlipemia, etc.

Gas-phase pyrolysis in organic synthesis: A route for synthesis of cyanamides

(Chemical Equation Presented) Pyrolysis of 1,7-di-[(E)-1- morpholinomethylidene]- and 1,7-di-[(E)-1-piperidino-methylidene]-4,6,10,12- tetramethylamino-2,8-dioxo-1,7-diaza-3,5,9,11-cyclododecatetraene-3, 9-dicarbonitrile 6a,b afforded pyridone 10 in addition to cyanamides 11a,b. On the other hand, pyrolysis of 1-[E-(4-(E-3-cyano-4,6-dimethyl-2-oxopyridin-1(2H)- ylimino) methylpiperazin-1-yl] methylenamino-4,6-dimethyl-2-oxo-1,2- dihydropyridine-3-carbonitrile 8 gave 1-amino-4,6-dimethyl-2-oxo-1,2- dihydropyridine-3-carbonitrile 13 as well as piperazine. The mechanism of pyrolysis and the effect of stereochemistry of pyrolyzed substrates on the nature of the pyrolysates are discussed.