4-(2-isocyanoethyl)morpholine

• ChemBase ID: 152486
• Molecular Formular: C7H12N2O
• Molecular Mass: 140.18298
• Monoisotopic Mass: 140.09496301
• SMILES: [C-]#[N+]CCN1CCOCC1
• Canonical SMILES: [C-]#[N+]CCN1CCOCC1
• InChI: InChI=1S/C7H12N2O/c1-8-2-3-9-4-6-10-7-5-9/h2-7H2
• InChIKey: MFRZPLYKVDHOSN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-isocyanoethyl)morpholine
• IUPAC Traditional name: 4-(2-isocyanoethyl)morpholine
• Synonyms: MEI; 4-(2-Isocyanoethyl)morpholine; 2-Morpholinoethyl isocyanide; 4-(2-异氰基乙基)吗啉; 2-吗啉代乙基异腈

Database IDs

• CAS Number: 78375-48-1
• MDL Number: MFCD00040506
• Beilstein Number: 4666990
• PubChem SID: 162246631; 24885997
• PubChem CID: 2759434

CALCULATED PROPERTIES

• Acid pKa: 16.20714
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.1829836
• LogD (pH = 7.4): -2.1585977
• Log P: -2.1582649
• Molar Refractivity: 48.6052 cm^3
• Polarizability: 15.440081 Å^3
• Polar Surface Area: 16.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 72-73 °C/0.7 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.017 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.469

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (GC)
• Empirical Formula (Hill Notation): C7H12N2O

DETAILS

Sigma Aldrich - 69893

Other Notes
Potent coupling reagent for peptide synthesis giving higher yields and less racemization than DCCI1,2,3,4; Reagent used in a Passerini-like reaction to alpha-hydroxy amides5
Packaging
10, 50 mL in glass bottle