Skip to Content
MilliporeSigma
All Photos(1)

Documents

721778

Sigma-Aldrich

N,N-Dimethylformamide dimethyl sulfate adduct

95%

Synonym(s):

DMF-Dimethyl sulfate, Methoxymethylene-N,N-dimethyliminium methyl sulfate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C5H13NO5S
CAS Number:
89712-45-8
Molecular Weight:
199.23
MDL number:
MFCD16621484
UNSPSC Code:
12352108
PubChem Substance ID:
329763872
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.459

density

1.349 g/mL at 25 °C

SMILES string

CN(C)C=O.COS(=O)(=O)OC

InChI

1S/C3H7NO.C2H6O4S/c1-4(2)3-5;1-5-7(3,4)6-2/h3H,1-2H3;1-2H3

InChI key

UJKUJXVZLUTEAZ-UHFFFAOYSA-N

Application

DMF-Dimethyl sulfate adduct can be used as a reagent to synthesize:
  • 2-azetidinones by a reaction between Schiff bases and substituted acetic acids.
  • Dimethylamino methylene derivatives, which can be employed in the preparation of fluoroquinolines and 3-amino-4-cyano pyrazole.
  • Cis β-sultams by [2 + 2] annulation of aldimines with sulfonic acids.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Carc. 1B - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

190.0 °F - closed cup

flash_point_c

87.8 °C - closed cup

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

New reagents from ?N, N-Dimethyl amino methoxy methylenium methyl sulphate?-Synthesis of 3-Amino-4-cyano pyrazole
Arava VR, et al.
Der Pharma Chemica, 50(14), 178-186 (2010)
[2+ 2] Annulation of Aldimines with Sulfonic Acids: A Novel One-Pot cis-Selective Route to ?-Sultams
R Ankita, et al.
European Journal of Organic Chemistry, 2011(23), 4302-4306 (2011)
DMF-dimethyl sulfate as a new reagent for the synthesis of β-lactams.
Jarrahpour A and Zarei M.
Tetrahedron Letters, 50(14), 1568-1570 (2009)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service