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407704

Sigma-Aldrich

4-Methylmorpholine

purified by redistillation, ≥99.5%

Synonym(s):

NMM

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About This Item

Empirical Formula (Hill Notation):
C5H11NO
CAS Number:
109-02-4
Molecular Weight:
101.15
Beilstein:
102719
EC Number:
203-640-0
MDL number:
MFCD00006175
UNSPSC Code:
12352100
PubChem Substance ID:
24865480
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

200

vapor pressure

18 mmHg ( 20 °C)

Assay

≥99.5%

form

liquid

purified by

glass distillation
redistillation

refractive index

n20/D 1.435 (lit.)

pH

10.6 (20 °C, 50 g/L)

bp

115-116 °C/750 mmHg (lit.)

mp

−66 °C (lit.)

density

0.92 g/mL at 25 °C (lit.)

functional group

ether

SMILES string

CN1CCOCC1

InChI

1S/C5H11NO/c1-6-2-4-7-5-3-6/h2-5H2,1H3

InChI key

SJRJJKPEHAURKC-UHFFFAOYSA-N

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General description

4-Methylmorpholine is an economical cation useful for the preparation of morpholinium cation-based ionic liquids. The experimental FT-IR and FT-Raman spectra of 4-methylmorpholine has been recorded over the range 4000-400cm-1 and 3500-100cm-1 respectively. It undergoes fluorination with cobalt(III) fluoride to afford highly fluorinated morpholines, which were characterized by mass and NMR spectroscopy.

Application

4-Methylmorpholine may be used in the preparation of N-ethyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide.

Signal Word

Danger

Hazard Statements

H225,H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

53.6 °F - closed cup - DIN 51755 Part 1

Flash Point(C)

12 °C - closed cup - DIN 51755 Part 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN8658
SHBM4325
SHBK4884
SHBJ8302
SHBJ2457

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The fluorination of 4-methylmorpholine over cobalt (III) fluoride: The isolation and characterisation of some novel polyfluoro-4-methylmorpholines by mass spectrometry and nmr spectroscopy; the mechanism of the title reaction.
Rendell RW and Wright B.
Tetrahedron, 34(2), 197-203 (1978)
Ki-Sub Kim et al.
Chemical communications (Cambridge, England), (7)(7), 828-829 (2004-03-27)
Ionic liquids based on N-alkyl-N-methylmorpholinium salts have been synthesized and the physical and electrochemical characteristics of this family of ionic liquids have been investigated for use as electrolytes.
L Belin et al.
British journal of industrial medicine, 40(3), 251-257 (1983-08-01)
Investigations of respiratory symptoms among workers in a factory producing polyurethane foam included measurement of air pollution with amines and isocyanates and a simultaneous health investigation of the exposed workers. An increased bronchial reactivity to inhaled methacholine was found in
V Balachandran et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 97, 1101-1110 (2012-08-30)
The experimental FT-IR (4000-400 cm(-1)) and FT-Raman (3500-100 cm(-1)) spectra of 4-Methylmorpholine were recorded. The observed bands were interpreted with the aid of normal coordinate analysis and force field calculations based on density functional theory (DFT) using B3LYP functional theory
K Sitarek
Teratogenesis, carcinogenesis, and mutagenesis, 19(6), 369-376 (1999-12-10)
N-methylmorpholine, which is used as a catalyst in polyurethane foams producing, in solvents, stabilizing agents, and corrosion inhibitors, was administered to female rats by gavage at 100, 200, 600, and 900 mg/kg during organogenesis. It did not exhibit selective toxicity
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