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Sigma-Aldrich

4-Methylmorpholine N-oxide

97%

Synonym(s):

NMO

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About This Item

Empirical Formula (Hill Notation):
C5H11NO2
CAS Number:
7529-22-8
Molecular Weight:
117.15
Beilstein:
507437
EC Number:
231-391-8
MDL number:
MFCD00005947
UNSPSC Code:
12352005
PubChem Substance ID:
24853425
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

Assay

97%

reaction suitability

reagent type: oxidant

mp

180-184 °C (lit.)

functional group

ether

storage temp.

2-8°C

SMILES string

C[N+]1([O-])CCOCC1

InChI

1S/C5H11NO2/c1-6(7)2-4-8-5-3-6/h2-5H2,1H3

InChI key

LFTLOKWAGJYHHR-UHFFFAOYSA-N

General description

4-Methylmorpholine N-oxide is an organic compound used as a co-oxidant along with OsO4 and ruthenates in organic synthesis. In recent studies, it has been used as a catalyst in silylcyanation of aldehydes and ketones.[1] Lyocell, a regenerated cellulose fiber, can be prepared using 4-methylmorpholine N-oxide in an eco-friendly manner.[2]

Application

Non-metallic catalyst for the cyanosilylation of ketones.[3] Co-oxidant for Sharpless asymmetric dihydroxylation in ionic liquids.[4]

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H228,H361f

Hazard Classifications

Flam. Sol. 1 - Repr. 2

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW8857
MKCW5540
WXBF1167V
0000267564
0000267551

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Luís C Branco et al.
The Journal of organic chemistry, 69(13), 4381-4389 (2004-06-19)
The use of room-temperature ionic liquids (RTILs) in the Sharpless catalytic asymmetric dihydroxylation (AD) as a cosolvent or replacement of the tert-butanol was studied in detail by screening 11 different RTILs. The AD reaction is faster in 1-n-butyl-3-methylimidazolium hexafluorophosphate [C(4)mim][PF(6)]
Marzieh Shafiei et al.
Bioresource technology, 102(17), 7879-7886 (2011-06-21)
Given that N-methylmorpholine-N-oxide (NMMO) is a promising alternative for the pretreatment of lignocelluloses, a novel process for ethanol and biogas production from wood was developed. The solvent, NMMO, is concentrated by multistage evaporation, and the wood is pretreated with the
Synlett, 6, 1077-1079 (2004)
N?Methylmorpholine N?Oxide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2008)
The N-Methylmorpholine-N-Oxide (NMMO) Process of Producing Regenerated Fibers
Innovative Biofibers from Renewable Resources (2014)
View All Related Papers

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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