78375-48-1

Basic information

• Product Name: 2-Morpholinoethyl isocyanide
• Synonyms: MEI;4-(2-ISOCYANOETHYL)MORPHOLINE;2-MORPHOLINOETHYL ISOCYANIDE;1-N-(2-ISOCYANOETHYL)-MORPHOLINE;Morpholino ethyl isocyanide;Morpholine, 4-(2-isocyanoethyl)-;MEI 2-MORPHOLINOETHYL ISOCYANIDE;Morpholinyl-4-ethylisocyanid-2
• CAS NO: 78375-48-1
• Molecular Formula: C₇H₁₂N₂O
• Molecular Weight: 140.18
• Product Categories: Nitro / Nitriles
• Mol File: 78375-48-1.mol

Chemical Properties

• Boiling Point: 72-73 °C0.7 mm Hg(lit.)
• Flash Point: 110 ºC
• Appearance: /
• Density: 1.017 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.469
• Storage Temp.: −20°C
• BRN: 4666990
• CAS DataBase Reference: 2-Morpholinoethyl isocyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Morpholinoethyl isocyanide(78375-48-1)
• EPA Substance Registry System: 2-Morpholinoethyl isocyanide(78375-48-1)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 78375-48-1(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Synthesis:
2-Morpholinoethyl isocyanide is used as a precursor for the synthesis of nitrogen acyclic carbene (NAC) complexes, which serve as efficient catalysts in the synthesis of phenol and hydration of alkynes. These catalysts are valuable for accelerating chemical reactions and improving the yield of desired products.
Used in Pharmaceutical Chemistry:
In the pharmaceutical industry, 2-Morpholinoethyl isocyanide is utilized as a reactant in Ugi condensation reactions, leading to the formation of a variety of imidazo[1,2-a]pyridines and α-acylaminoamides. These compounds possess significant therapeutic potential and are being explored for their applications in drug development.
Used in the Synthesis of Bioactive Heterocycles:
2-Morpholinoethyl isocyanide is also employed in the synthesis of 2-aminobenzoxazoles and 3-aminobenzoxazines, which are heterocyclic compounds with important therapeutic activities. These compounds are of interest in medicinal chemistry due to their diverse biological properties and potential use in the treatment of various diseases.
Used in Organic Light Emitting Diodes (OLEDs):
In the field of materials science, 2-Morpholinoethyl isocyanide can be used as a ligand in bis-cyclometalated iridium complexes. These complexes are integral components in the development of organic light emitting diodes (OLEDs), which are widely used in display technologies and lighting applications due to their high efficiency, low power consumption, and versatility in color emission.

InChI:InChI=1/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2

Upstream product

• 78375-50-5 N-(2-morpholinoethyl)formamide 
• 87024-45-1 8-Oxa-2-aza-5-azonia-spiro[4.5]dec-1-ene; chloride 
• 87024-47-3 Toluene-4-sulfonate8-oxa-2-aza-5-azonia-spiro[4.5]dec-1-ene; 

Downstream Products

• 112681-23-9 2-hydroxy-N-(2-morpholinoethyl)-2-phenylacetamide 
• 87024-47-3 Toluene-4-sulfonate8-oxa-2-aza-5-azonia-spiro[4.5]dec-1-ene; 

Relevant articles and documents

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

Gem-diphosphonic acids, and pharmaceutical compositions containing them

Diphosphonic acids of formula (I), wherein R1 and R2 are hydrogen or C1 -C4 alkyl; (A) is hydrogen, halogen, hydroxy or C1 -C12 alkyl; (B) is a bond, a C1 -C8 alkylene chain, a cycloalkylalkylene chain, an alkylene chain substituted by cyclohexyl or cyclopentyl groups, or an aralkyl chain, an alkyl chain containing an heteroatom (O, S or N--CH3) or an ureido residue --(CH2)nl --NHCONH--(CH2)n --with n ranging from 1 to 5, R3 is hydrogen, C1 -C9 alkyl, C3 -C6 cycloalkyl, benzyl, phenyl or p-methoxybenzyl; (C) is C1 -C5 alkyl, phenyl or an aralkyl chain; R4 is hudrogen, C1 -C5 alkyl or an amino group optionally substituted by alkyl, phenyl, benzyl, p-methoxybenzyl, acyl, amminoacidic or peptide groups; R5 and R6 are 2-haloethyl or together form a 1-aziridinyl residue, are useful as antitumor agent.