69893

2-Morpholinoethyl isocyanide

≥98.0% (GC)

• Synonym(s): 4-(2-Isocyanoethyl)morpholine, MEI
• Empirical Formula (Hill Notation): C₇H₁₂N₂O
• CAS Number: 78375-48-1
• Molecular Weight: 140.18
• Beilstein/REAXYS Number: 4666990
• MDL number: MFCD00040506
• UNSPSC Code: 12352100
• PubChem Substance ID: 57652222
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: ≥98.0% (GC)
• form: liquid
• refractive index: n20/D 1.469
• bp: 72-73 °C/0.7 mmHg (lit.)
• density: 1.017 g/mL at 20 °C (lit.)
• functional group: amine; ether; isonitrile
• storage temp.: −20°C
• SMILES string: [C-]#[N+]CCN1CCOCC1
• InChI: 1S/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2
• InChI key: MFRZPLYKVDHOSN-UHFFFAOYSA-N

Description

Application

2-Morpholinoethyl isocyanide can be used for the synthesis of:

• Nitrogen acyclic carbene (NAC) complexes to be used as catalysts for the synthesis of phenol and hydration of alkynes.[1]
• Variety of imidazo[1,2-a]pyridines[2] and α-acylaminoamides by Ugi condensation reaction.[3]
• 2-Aminobenzoxazoles and 3-aminobenzoxazines having important therapeutic activities.[4]

It can also be used as a ligand in bis-cyclometalated iridium complexes for the organic light emitting diodes (OLEDs).[5]

Other Notes

Potent coupling reagent for peptide synthesis giving higher yields and less racemization than DCCI[6][7][8][9]; Reagent used in a Passerini-like reaction to alpha-hydroxy amides[10]

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301 + H311 + H331,H315,H319,H335
• pcodes: P261 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: 230.0 °F - closed cup
• flash_point_c: 110 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter