Skip to Content
Merck
All Photos(2)

Documents

375403

Sigma-Aldrich

2-Methyl-2-imidazoline

95%

Synonym(s):

2-Methylimidazoline, 4,5-Dihydro-2-methyl-1H-imidazole, Lysidine, Methylglyoxalidine

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C4H8N2
CAS Number:
534-26-9
Molecular Weight:
84.12
EC Number:
208-596-6
MDL number:
MFCD00051490
UNSPSC Code:
12352100
PubChem Substance ID:
24863385
NACRES:
NA.22

Assay

95%

form

solid

mp

87 °C (dec.) (lit.)

SMILES string

[H]N1CCN=C1C

InChI

1S/C4H8N2/c1-4-5-2-3-6-4/h2-3H2,1H3,(H,5,6)

InChI key

VWSLLSXLURJCDF-UHFFFAOYSA-N

General description

2-Methyl-2-imidazoline is monomethyl derivative of imidazoline. The self-association of 2-methyl-2-imidazoline was studied in aqueous solution, at different pH values, by ultraviolet spectroscopy.
Kinetics of the reaction of 2-methyl-2-imidazoline with sulfate and hydrogen phosphate radicals has been investigated by flash-photolysis. Rate constant for the reaction was reported to be 108-109M-1s-1.

Application

2-Methyl-2-imidazoline may be used in the synthesis of series of N,N,N′-trisubstituted ethylenediamine derivatives. It may be used in the preparation of 1-alkyl-2-methyl-2-imidazolines, via alkylation with organic halides in the presence of phase transfer catalysis and absence of solvent.
Reactant for:
Synthesis of cyclic-amine-based dithiocarbamate chain transfer agents for RAFT polymerization
Dehydration reactions
Synthesis of push-pull alkenes
Producing organic reductants for transfer hydrogenation
Synthesis of orally available factor Xa inhibitors

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

Self-association of imidazole and its methyl derivatives in aqueous solution. A study by ultraviolet spectroscopy.
Peral F and Gallego E.
Journal of Molecular Structure, 415(1), 187-196 (1997)
Oxidation of ophthalmic drugs photopromoted by inorganic radicals.
Criado S, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 244, 32-37 (2012)
N-alkylation of 2-methyl-2-imidazolines by phase transfer catalysis without solvent.
Chen X, et al.
Synthetic Communications, 29(17), 3025-3030 (1999)
A Convenient Synthesis of N, N, N'-Trisubstituted Ethylenediamine Derivatives From 2-Methyl-2-imidazoline.
Xia C, et al.
Synthetic Communications, 30(18), 3307-3315 (2000)
Organoleptic Characteristics of Flavor Materials
Mosciano, G.
Perfumer & Flavorist, 28, 105-105 (2003)

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