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Sigma-Aldrich

4-Methylmorpholine

purum, ≥98.0% (GC)

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Synonym(s):
N-Methylmorpholine, NMM
Empirical Formula (Hill Notation):
C5H11NO
CAS Number:
Molecular Weight:
101.15
Beilstein/REAXYS Number:
102719
EC Number:
MDL number:
PubChem Substance ID:

vapor density

>1 (vs air)

Quality Level

vapor pressure

18 mmHg ( 20 °C)

grade

purum

assay

≥98.0% (GC)

refractive index

n20/D 1.435 (lit.)
n20/D 1.435

bp

115-116 °C/750 mmHg (lit.)

mp

−66 °C (lit.)

density

0.918 g/mL at 20 °C
0.92 g/mL at 25 °C (lit.)

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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Application

4-Methylmorpholine(NMM) has been used for amidation of hyaluronic acid to synthesize its derivative with potential applications in hydrogel synthesis and gold coatings.
NMM can be used as a reactant for the synthesis of:
  • 1-Butyl-1-methylmorpholinium bromide ([BMmo][Br]), a monocation ionic liquid.
  • Quaternary ammonium complexes that can be used as complexing agents in redox flow batteries (RFBs).

It can also be used as an activating reagent:
  • For the synthesis of peptide-drug conjugate for targeted drug delivery.
  • To synthesize acrylate star polymers with application as magnetic resonance imaging (MRI) agents.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

53.6 °F - DIN 51755 Part 1

flash_point_c

12 °C - DIN 51755 Part 1

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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High relaxivity MRI imaging reagents from bimodal star polymers.
Adkins CT, et al.
Polym. Chem., 3(2), 390-398 (2012)
Complexing Additives to Reduce the Immiscible Phase Formed in the Hybrid ZnBr2 Flow Battery.
Bryans D, et al.
Journal of the Electrochemical Society, 164(13), A3342-A3348 (2017)
A Peptide-Guided System with Programmable Subcellular Translocation for Targeted Therapy and Bypassing Multidrug Resistance.
Zhu Y, et al.
Analytical Chemistry, 164(13), A3342-A3348 (2018)
Investigating triazine-based modification of hyaluronan using statistical designs.
Liang J, et al.
Carbohydrate Polymers, 132, 472-480 (2015)
Relationship between the Structure of Ionic Liquid and Its Enrichment Ability To Trace Fungicides from an Environmental Water Sample.
Yang J, et al.
Journal of Agricultural and Food Chemistry, 66(36), 9418-9425 (2018)

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