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8.05894

Sigma-Aldrich

4-Methylmorpholine

for synthesis

Synonym(s):

4-Methylmorpholine, NMM, N-Methylmorpholine

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About This Item

Empirical Formula (Hill Notation):
C5H11NO
CAS Number:
109-02-4
Molecular Weight:
101.15
MDL number:
MFCD00006175
UNSPSC Code:
12352005
EC Index Number:
203-640-0
NACRES:
NA.22

vapor pressure

23.5 hPa ( 20 °C)

Quality Level

200

Assay

≥98% (GC)

form

liquid

autoignition temp.

165 °C (DIN 51794)

potency

1960 mg/kg LD50, oral (Rat)
1240 mg/kg LD50, skin (Rabbit)

expl. lim.

2.1 % (v/v)

pH

10.6 (20 °C, 50 g/L in H2O)

bp

112-114 °C/1013 hPa

mp

-66 °C

transition temp

flash point 12.5 °C (DIN 51755 Part 1)

density

0.92 g/cm3 at 20 °C

storage temp.

2-30°C

InChI

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

InChI key

SJRJJKPEHAURKC-UHFFFAOYSA-N

Application

4-Methylmorpholine can be used as:
  • A precursor to prepare N-methylmorpholine N-oxide and 1-butyl-1-methylmorpholinium bromide ([BMmo][Br]), a monocation ionic liquid.
  • A reactant to synthesize quaternary ammonium complexes applicable as complexing agents in redox flow batteries.
  • A basic catalyst in the synthesis of thiobenzamides via Willgerodt-Kindler′s reaction.
  • An activating agent to synthesize hyaluronic acid-based biopolymer for cosmetic, pharmaceutical, and nutraceutical applications.

Analysis Note

Assay (GC, area%): ≥ 98 %
Density (d 20 °C/ 4 °C): 0.917 - 0.918
Identity (IR): passes test

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Enantioselective arene epoxidation under mild conditions by Jacobsen catalyst: The role of protic solvent and co-catalyst in the activation of hydrogen peroxide
Rocha M, et al.
Applied Catalysis A: General, 460, 116-123 (2013)
Comparative study of acid and basic catalysis in microwave assistance of Willgerodt-Kindler reaction for thiobenzamides and derivatives synthesis
Agnimonhan FH, et al.
International journal of biological and chemical sciences, 8(1), 386-393 (2014)
Sabrina Sciabica et al.
Pharmaceutics, 13(10) (2021-10-24)
Hyaluronic acid (HA), an excellent biomaterial with unique bio properties, is currently one of the most interesting polymers for many biomedical and cosmetic applications. However, several of its potential benefits are limited as it is rapidly degraded by hyaluronidase enzymes.
Uxua Jiménez-Blasco et al.
International journal of molecular sciences, 22(17) (2021-09-11)
Redox flow batteries (RFB) are one of the most interesting technologies in the field of energy storage, since they allow the decoupling of power and capacity. Zinc-bromine flow batteries (ZBFB) are a type of hybrid RFB, as the capacity depends
Jiale Yang et al.
Journal of agricultural and food chemistry, 66(36), 9418-9425 (2018-08-23)
To elucidate the relationship between the structure of ionic liquid (IL) and its enrichment ability to trace pesticides from an environmental water sample, a series of imidazole-based ILs were synthesized to extract four fungicides (boscalid, cyprodinil, fluazinam, and pyrimethanil) through

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