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721778

Sigma-Aldrich

N,N-Dimethylformamide dimethyl sulfate adduct

95%

Synonym(s):

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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBK0515V
MKBC9033

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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)

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