Morpholine

Morpholine[1]
numbered skeletal formula of the morpholine molecule
numbered skeletal formula of the morpholine molecule
perspective skeletal formula of the morpholine molecule
perspective skeletal formula of the morpholine molecule
ball-and-stick model of the morpholine molecule
ball-and-stick model of the morpholine molecule
space-filling model of the morpholine molecule
space-filling model of the morpholine molecule
Names
Preferred IUPAC name
Morpholine[2]
Other names
Diethylenimide oxide
1,4-Oxazinane
Tetrahydro-1,4-oxazine
Diethylene imidoxide
Diethylene oximide
Tetrahydro-p-oxazine
Identifiers
3D model (JSmol)
102549
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.469 Edit this at Wikidata
EC Number
  • 203-815-1
1803
KEGG
RTECS number
  • QD6475000
UNII
UN number 2054
  • InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2 checkY
    Key: YNAVUWVOSKDBBP-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
    Key: YNAVUWVOSKDBBP-UHFFFAOYAU
  • C1CNCCO1
Properties
C4H9NO
Molar mass 87.122 g·mol−1
Appearance Colorless liquid
Odor Weak ammonia-like or fish-like[3]
Density 1.007 g/cm3
Melting point −5 °C (23 °F; 268 K)
Boiling point 129 °C (264 °F; 402 K)
miscible
Vapor pressure 6 mmHg (20 °C)[3]
Acidity (pKa) 8.36[4] (of conjugate acid)
-55.0·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, Corrosive
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H226, H302, H312, H314, H332
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point 31 °C (88 °F; 304 K)
275 °C (527 °F; 548 K)
Explosive limits 1.4%–11.2%[3]
Lethal dose or concentration (LD, LC):
1220 mg/kg (mammal, oral)
525 mg/kg (mouse, oral)
1050 mg/kg (rat, oral)[5]
365 ppm (mouse, 2 hr)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 20 ppm (70 mg/m3) [skin][3]
REL (Recommended)
TWA 20 ppm (70 mg/m3) ST 30 ppm (105 mg/m3) [skin][3]
IDLH (Immediate danger)
1400 ppm[3]
Safety data sheet (SDS) hazard.com
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid generates the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor.[6] The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.[7]

  1. ^ National Institute for Occupational Safety and Health (2000). "Morpholine". International Chemical Safety Cards. Retrieved 5 November 2005.
  2. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0437". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines1". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  5. ^ a b "Morpholine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. ^ "CDC - NIOSH Pocket Guide to Chemical Hazards - Morpholine". www.cdc.gov. Retrieved 4 January 2022.
  7. ^ F. Silversmith, Ernest; Nickon, Alex (2013-10-22). Organic Chemistry : Modern Coined Terms and Their Origins. Elsevier Science. p. 313. ISBN 978-1483145235.