Available from stock

2-Morpholinoethyl isocyanide

SKU: M0701

Category: Building Blocks, Intermediates, Reagents

Synonyms: 4-(2-Isocyanoethyl)morpholine, MEI; 78375-48-1
CAS-Number: C₇H₁₂N₂O
Molecular Formula: 140.18
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (GC)
Appearance: Colorless to very dark yellow liquid
Identity: 1H-NMR

Properties

Solvents: Soluble in chloroform.
Boiling Point: 72-73 °C/0.7 mmHg (lit.)
Refractive Index: n20/D 1.469
Density: 1.017 g/ml at 20 °C (lit.)

Shipping: BLUE ICE
Short Term Storage: -20°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H301 + H311 + H331 - H315 - H319 - H335
Precautionary statements: P261 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338
GHS Symbol: GHS06
Signal word: Danger
RIDADR: UN2810
Transportation: Packing Group III

Description: 2-Morpholinoethyl isocyanide is a buildig block and intermediate for organic synthesis. The principal synthetic application of 2-morpholinoethyl isocyanide is as a coupling reagent of amino acids to yield peptides. It is a potent coupling reagent for peptide synthesis giving higher yields and less racemization than DCCI. It also reacts with aldehydes or ketones to yield amides, with acids to yield imidazolinium salts, and has been used as a ligand in spectroscopic studies to examine shielding effects. 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. It can also be used as a ligand in bis-cyclometalated iridium complexes for the organic light emitting diodes (OLEDs).
Smiles: [C-]#[N+]CCN1CCOCC1
InChi Key: MFRZPLYKVDHOSN-UHFFFAOYSA-N
References: (1) A.M.L. Hoel & J. Nielsen, Tetrahedr. Lett. 40, 3941 (1999) , (2) K. Dedeian, et al., Inorg. Chem. 46, 1603 (2007) , (3) A.T. Khan, et al., Tetrahedr. Lett. 53, 2211 (2012) , (4) H. Osborn & J.F. Schneider, Encyclopedia of Reagents for Organic Synthesis (EROS) (2012) , (5) A. Sagirli, et al., Tetrahedr. 69, 69 (2013) , (6) A. Sehlinger, et al., Polym. Chem. 6, 3828 (2015) , (7) M. Hartweg, et al., Polym. Chem., 9, 482 (2018) , (8) H.W. Liang, et al., Angew. Chem. Int. Ed. Engl. 57, 5720 (2018) , (9) M.D. Ambule, et al., Chem. Commun. 55, 10872 (2019)

2-Morpholinoethyl isocyanide is a buildig block and intermediate for organic synthesis. The principal synthetic application of 2-morpholinoethyl isocyanide is as a coupling reagent of amino acids to yield peptides. It is a potent coupling reagent for peptide synthesis giving higher yields and less racemization than DCCI. It also reacts with aldehydes or ketones to yield amides, with acids to yield imidazolinium salts, and has been used as a ligand in spectroscopic studies to examine shielding effects. 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. It can also be used as a ligand in bis-cyclometalated iridium complexes for the organic light emitting diodes (OLEDs).

SKU: M0701 Category: Building Blocks, Intermediates, Reagents

Additional information

Additional information

Synonyms	4-(2-Isocyanoethyl)morpholine, MEI
Purity	≥98% (GC)
Appearance	Colorless to very dark yellow liquid
CAS-Number	78375-48-1
Molecular Formula	C7H12N2O
Molecular Weight	140.18
Identity	1H-NMR
Solvents	Soluble in chloroform.
Boiling Point	72-73 °C/0.7 mmHg (lit.)
Refractive Index	n20/D 1.469
Density	1.017 g/ml at 20 °C (lit.)
Smiles	[C-]#[N+]CCN1CCOCC1
InChi Key	MFRZPLYKVDHOSN-UHFFFAOYSA-N
Shipping	BLUE ICE
Short Term Storage	-20°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H301 + H311 + H331 – H315 – H319 – H335
Precautionary statements	P261 – P280 – P301 + P310 – P302 + P352 + P312 – P304 + P340 + P311 – P305 + P351 + P338
GHS Symbol	GHS06
Signal word	Danger
RIDADR	UN2810
Transportation	Packing Group III
References	(1) A.M.L. Hoel & J. Nielsen, Tetrahedr. Lett. 40, 3941 (1999), (2) K. Dedeian, et al., Inorg. Chem. 46, 1603 (2007), (3) A.T. Khan, et al., Tetrahedr. Lett. 53, 2211 (2012), (4) H. Osborn & J.F. Schneider, Encyclopedia of Reagents for Organic Synthesis (EROS) (2012), (5) A. Sagirli, et al., Tetrahedr. 69, 69 (2013), (6) A. Sehlinger, et al., Polym. Chem. 6, 3828 (2015), (7) M. Hartweg, et al., Polym. Chem., 9, 482 (2018), (8) H.W. Liang, et al., Angew. Chem. Int. Ed. Engl. 57, 5720 (2018), (9) M.D. Ambule, et al., Chem. Commun. 55, 10872 (2019)
Quantity	10 ml, 25 ml