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59760

Sigma-Aldrich

1-Methylimidazolium hydrogen sulfate

95%

Synonym(s):

1-Methylimidazole hydrogen sulfate

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About This Item

Empirical Formula (Hill Notation):
C4H6N2 · H2SO4
CAS Number:
681281-87-8
Molecular Weight:
180.18
MDL number:
MFCD06798198
UNSPSC Code:
12352100
PubChem Substance ID:
57651695
NACRES:
NA.22

Quality Level

200

Assay

≥94.5% (HPLC)
95%

form

solid

impurities

≤1% water

anion traces

chloride (Cl-): ≤20 mg/kg

SMILES string

OS(O)(=O)=O.Cn1ccnc1

InChI

1S/C4H6N2.H2O4S/c1-6-3-2-5-4-6;1-5(2,3)4/h2-4H,1H3;(H2,1,2,3,4)

InChI key

TVEOIQKGZSIMNG-UHFFFAOYSA-N

Application

1-Methylimidazolium hydrogen sulfate is a Brønsted acidic ionic liquid that can be used:
  • As a component of a catalytic system along with chlorotrimethylsilane used in the preparation of 3,4-dihydropyrimidin-2(1H)-ones and hydroquinazoline-2,5-diones.
  • As a catalyst in the preparation of biologically important 2,5-dimethyl-N-substituted pyrroles.
  • As a reusable catalyst in the preparation of spiro[indoline-3′,2-quinazoline]2′,4(3H)-dione.
  • In the leaching of copper and zinc in brass dross using H2O2 as an oxidant.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

>536.0 °F - (External MSDS)

Flash Point(C)

> 280 °C - (External MSDS)

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC4400
BCBW6234
BCBS0762V
BCBM4097V
BCBD9302V

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1-Methylimidazolium hydrogen sulfate/chlorotrimethylsilane: an effective catalytic system for the synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones and hydroquinazoline-2, 5-diones
Kefayati H, et al.
Journal of Molecular Liquids, 172, 147-151 (2012)
Application of 1-methylimidazolium hydrogen sulfate ionic liquid to the oxidative leaching of copper and zinc in industrial brass dross
Energy Technology 2015, 209-215 (2015)
An environmental friendly approach for the synthesis of spiro [indoline-3′, 2-quinazoline] 2′, 4 (3H)-dione using 1-methylimidazolium hydrogen sulfate, as reusable catalyst
Kefayati H, et al.
J. Chin. Chem. Soc., 60(10), 1197-1201 (2013)
Daqing Li et al.
Ultrasonics sonochemistry, 20(5), 1144-1148 (2013-03-15)
Ionic liquid [HMIM]HSO4 was found to be an efficient catalyst for the synthesis of N-substituted pyrroles through the reaction of 2,5-hexanedione with amines under ultrasonic irradiation at room temperature. These reactions proceed with good yields under short reaction time. Furthermore

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