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About This Item
Empirical Formula (Hill Notation):
C5H9N
CAS Number:
Molecular Weight:
83.13
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
95%
refractive index
n20/D 1.444 (lit.)
bp
104-105 °C (lit.)
density
0.878 g/mL at 25 °C (lit.)
SMILES string
CC1=NCCC1
InChI
1S/C5H9N/c1-5-3-2-4-6-5/h2-4H2,1H3
InChI key
CTSZPNIMMLSKDV-UHFFFAOYSA-N
General description
2-Methyl-1-pyrroline, a monocyclic imine, is a pyrroline derivative. It is a five-membered heterocyclic compound having various biological and pharmacological applications. It is formed during the Rh(I) complexes (containing N,N-donor ligands and N,P-donor ligand) immobilized on glassy carbon electrode surfaces catalyzed intramolecular hydroamination of 4-pentyn-1-amine. It reacts with with 2-oxopropanal to afford acetyl-1-pyrroline (AP).
Application
2-Methyl-1-pyrroline (2-MPN) may be used in the enantioselective enzymatic synthesis of (R)- and (S)-2-methylpyrroline in the presence of whole-cells catalysts isolated from Strptomyces sp. strains GF3587 and GF3546 respectively.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
51.8 °F - closed cup
Flash Point(C)
11 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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María Rodríguez-Mata et al.
Chembiochem : a European journal of chemical biology, 14(11), 1372-1379 (2013-07-03)
NADPH-dependent oxidoreductase Q1EQE0 from Streptomyces kanamyceticus catalyzes the asymmetric reduction of the prochiral monocyclic imine 2-methyl-1-pyrroline to the chiral amine (R)-2-methylpyrrolidine with >99% ee, and is thus of interest as a potential biocatalyst for the production of optically active amines.
2-Oxopropanal, hydroxy-2-propanone, and 1-pyrroline important intermediates in the generation of the roast-smelling food flavor compounds 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine.
Hofmann T and Schieberle P.
Journal of Agricultural and Food Chemistry, 46(6), 2270-2277 (1998)
M Bertoldi et al.
The Biochemical journal, 342 Pt 3, 509-512 (1999-09-08)
Ornithine decarboxylase (ODC) from Lactobacillus 30a catalyses the cleavage of alpha-methylornithine into ammonia and 2-methyl-1-pyrroline; glutamate decarboxylase (GAD) from Escherichia coli catalyses the cleavage of alpha-methylglutamate into ammonia and laevulinic acid. In our analyses, 2-methyl-1-pyrroline and laevulinic acid were identified
Andrey A Tregubov et al.
Journal of the American Chemical Society, 135(44), 16429-16437 (2013-10-04)
A series of N,N-donor ligands (bis(pyrazol-1-yl)methane (bpm), bis(N-methylimidazol-2-yl)methane (bim), 1-(phenylmethyl)-4-(1H-pyrazol-1-yl methyl)-1H-1,2,3-triazole (PyT)), and one N,P-donor ligand precursor (1-(3,5-dimethylpyrazol-1-yl)(2-bromoethane) (dmPyBr)) were synthesized and functionalized with aniline. Diazotization of the aniline into an aryl diazonium, using nitrous acid in aqueous conditions, was
Koichi Mitsukura et al.
Bioscience, biotechnology, and biochemistry, 75(9), 1778-1782 (2011-09-08)
The (R)-imine reductase (RIR) of Streptomyces sp. GF3587 was purified and characterized. It was found to be a NADPH-dependent enzyme, and was found to be a homodimer consisting of 32 kDa subunits. Enzymatic reduction of 10 mM 2-methyl-1-pyrroline (2-MPN) resulted
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