morpholine

• ChemBase ID: 77100
• Molecular Formular: C4H9NO
• Molecular Mass: 87.12036
• Monoisotopic Mass: 87.06841391
• SMILES: N1CCOCC1
• Canonical SMILES: C1CNCCO1
• InChI: InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
• InChIKey: YNAVUWVOSKDBBP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: morpholine
• IUPAC Traditional name: morpholine
• Synonyms: Morpholine; Morpholine, ACS; Diethyleneimide oxide; 1-Oxa-4-azacyclohexane; Morpholine; Diethylenimide Oxide; 1,4-oxazinane; Tetrahydro-1,4-oxazine; MORPHOLINE, REAGENT GRADE; 四氢-1,4-噁嗪; 吗啉; 吗啉, ACS

Database IDs

• CAS Number: 110-91-8
• EC Number: 203-815-1
• MDL Number: MFCD00005972
• Beilstein Number: 102549
• Merck Index: 146277
• PubChem SID: 24885993; 24855203; 24864597; 24848140; 162041974; 24889311
• PubChem CID: 8083
• CHEBI ID: 34856
• CHEMBL: 276518
• Chemspider ID: 13837537
• KEGG ID: C14452
• Unique Ingredient Identifier: 8B2ZCK305O
• Wikipedia Title: Morpholine

CALCULATED PROPERTIES

• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.218641
• LogD (pH = 7.4): -1.5465257
• Log P: -0.41137892
• Molar Refractivity: 23.7679 cm^3
• Polarizability: 9.589044 Å^3
• Polar Surface Area: 21.26 Å^2

PROPERTIES

Physical Property

• Solubility: miscible in water
• Apperance: APHA: ≤15; Colorless liquid; Liquid
• Melting Point: -5 °C; -5°C; -5°C; -7 to -5°C; -7--5 °C(lit.)
• Boiling Point: 126.0-130.0 °C; 128 - 130 °C; 128°C; 129 °C; 129 °C(lit.); 129°C; 129°C
• Flash Point: 31 °C; 31°C; 31°C (87.8°F); 32 °C (DIN 51755); 35°C(95°F); 87.8 °F
• Auto Ignition Point: 275 °C (DIN 51794); 275°C (527°F); 590 °F
• Density: 0.996; 0.996 g/mL at 25 °C(lit.); 1 g/cm^3 at 20 °C; 1 g/ml; 1.000 g/mL at 20 °C; 1.007; 1.007 g/cm^3
• Refractive Index: 1.454; 1.4540; n20/D 1.453-1.455; n20/D 1.454(lit.); n20/D 1.455
• Vapor Pressure: 10 hPa at 20 °C; 31 mmHg ( 38 °C); 7 mmHg ( 20 °C)
• Vapor Density: 3 (vs air); 3.00 (air = 1)
• pKa: 8.36 (of conjugate acid)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Corrosive/Flammable/Harmful/Hygroscopic/Air Sensitive/Store under Argon; Hygroscopic
• RTECS: QD6475000
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2054; UN2054
• German water hazard class: 2
• Hazard Class: 3; 8
• Packing Group: 1; I
• Australian Hazchem: 2W
• Risk Statements: 10-20/21/22-34; R:10-20/21/22-34; R10 R20/21/22 R34
• Safety Statements: 23-36-45; S:23-36-45; S1/2 S23 S36 S45
• EU Classification: CF1
• EU Hazard Identification Number: 8A
• Emergency Response Guidebook(ERG) Number: 132
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• Main Hazard: Flammable, Corrosive
• NFPA704:
  

  3

  3

  0
• Explode Limits: 10.8 %
• GHS Hazard statements: H226-H302-H312-H314-H332; H314-H226-H302-H312-H332
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2054 8/PG 1

Product Information

• Purity: ~99%; ≥98.0% (GC); ≥99%; ≥99.0%; ≥99.0% (GC); ≥99.5%; ≥99.5% (GC); 99%; 99.0% min
• Grade: ACS reagent; analytical standard; PESTANAL®, analytical standard; puriss. p.a.; purum; REAGENT; ReagentPlus®
• Impurities: ≤0.3% water
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤0.5 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• Purified By: redistillation
• Empirical Formula (Hill Notation): C4H9NO

DETAILS

MP Biomedicals - 02190234

Purity: ~99%
1 ml = approx. 1.00 g

MP Biomedicals - 05204583

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 394467

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 45592

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 252360

Packaging
1 L in glass bottle
5, 100, 500 mL in glass bottle

Sigma Aldrich - 134236

Packaging
100, 500 mL in glass bottle
2, 2.5 L in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Reagent for the cleavage of Fmoc protecting groups in peptide synthesis (see 9-Fluorenylmethyl chloroformate, A11683): J. Am. Chem. Soc., 92, 5748 (1970); J. Org. Chem., 37, 3404 (1972). See Appendix 6 for peptide reagents.
• In the Kindler modification of the Willgerodt reaction, aryl ketones are converted to ω-arylalkanoic acids by reaction with sulfur and an amine, usually morpholine: Org. Synth. Coll., 9, 99 (1998); reviews: Org. React., 3, 83 (1946); Synthesis, 358 (1975).
• Lithium morpholide adds to aromatic aldehydes at low temperature, a useful means for the protection of the aldehyde group in lithiations: Tetrahedron Lett., 25, 4213 (1981); J. Org. Chem., 48, 2356 (1983).
• Chlorination with hypochlorite gives N-chloromorpholine, a useful reagent in strongly acid media for the selective chlorination of activated aromatics: Org. Synth. Coll., 8, 167 (1993), and references therein.