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381055

Sigma-Aldrich

2-Methyl-1-pyrroline

95%

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Empirical Formula (Hill Notation):
C5H9N
CAS Number:
872-32-2
Molecular Weight:
83.13
EC Number:
212-822-9
MDL number:
MFCD00128806
PubChem Substance ID:
24863786
NACRES:
NA.22

Quality Level

100

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

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This Item
377112M79506423998
2-Methyl-1-pyrroline 95%

Sigma-Aldrich

381055

2-Methyl-1-pyrroline

3-Pyrroline 95%

Sigma-Aldrich

377112

3-Pyrroline

1-Methyl-3-pyrrolidinol 95%

Sigma-Aldrich

M79506

1-Methyl-3-pyrrolidinol

Methyl 1-pyrrolecarboxylate 98%

Sigma-Aldrich

423998

Methyl 1-pyrrolecarboxylate

refractive index

n20/D 1.444 (lit.)

refractive index

n20/D 1.46 (lit.)

refractive index

n20/D 1.464 (lit.)

refractive index

n20/D 1.489 (lit.)

bp

104-105 °C (lit.)

bp

90-91 °C/748 mmHg (lit.)

bp

50-52 °C/1 mmHg (lit.)

bp

180 °C/770 mmHg (lit.)

density

0.878 g/mL at 25 °C (lit.)

density

0.91 g/mL at 25 °C (lit.)

density

0.921 g/mL at 25 °C (lit.)

density

1.113 g/mL at 25 °C (lit.)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225 - H315 - H319 - H335

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

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USP

USP

1622317

Steviol Glycosides System Suitability

N-Methylpyrrolidine 97%

Sigma-Aldrich

M79204

N-Methylpyrrolidine

Asiaticoside analytical standard

Supelco

43191

Asiaticoside

Methylglyoxal solution ~40% in H2O

Sigma-Aldrich

M0252

Methylglyoxal solution

1-Methylpyrrolidine ≥98.0% (GC)

Sigma-Aldrich

69110

1-Methylpyrrolidine

2,4,6-Trimethylpyridine puriss. p.a., ≥99.0% (GC)

Sigma-Aldrich

27690

2,4,6-Trimethylpyridine

1-Vinyl-2-pyrrolidinone contains sodium hydroxide as inhibitor, ≥99%

Sigma-Aldrich

V3409

1-Vinyl-2-pyrrolidinone

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
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)
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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