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Sigma-Aldrich

2-Morpholinoethyl isocyanide

≥98.0% (GC)

Synonym(s):

4-(2-Isocyanoethyl)morpholine, MEI

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About This Item

Empirical Formula (Hill Notation):
C7H12N2O
CAS Number:
Molecular Weight:
140.18
Beilstein:
4666990
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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

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.
  • Variety of imidazo[1,2-a]pyridines and α-acylaminoamides by Ugi condensation reaction.
  • 2-Aminobenzoxazoles and 3-aminobenzoxazines having important therapeutic activities.

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

Other Notes

Potent coupling reagent for peptide synthesis giving higher yields and less racemization than DCCI; Reagent used in a Passerini-like reaction to alpha-hydroxy amides

Pictograms

Skull and crossbones

Signal Word

Danger

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 Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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New and Easily Accessible Nitrogen Acyclic Gold (I) Carbenes: Structure and Application in the Gold-Catalyzed Phenol Synthesis as well as the Hydration of Alkynes.
Hashmi ASK, et al.
Advanced Synthesis & Catalysis, 352(8), 1315-1337 (2010)
J.-L. Fauchere
Helvetica Chimica Acta, 68, 770-770 (1985)
Nature, 578(7793), 82-93 (2020-02-07)
Cancer is driven by genetic change, and the advent of massively parallel sequencing has enabled systematic documentation of this variation at the whole-genome scale1-3. Here we report the integrative analysis of 2,658 whole-cancer genomes and their matching normal tissues across 38
Yuho Hamaoka et al.
Biochemical and biophysical research communications, 499(4), 920-926 (2018-04-08)
EphA2, a member of the Eph family of receptor tyrosine kinases, has been reported to promote tumor malignancy through phosphorylation of serine 897 (S897). Here, we found that overexpression of wild-type EphA2 induced S897 phosphorylation through ERK activation without growth
D. Seebach et al.
Chemische Berichte, 121, 507-507 (1988)

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