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377112

Sigma-Aldrich

3-Pyrrolin

95%

Synonym(e):

2,5-Dihydropyrrol

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About This Item

Empirische Formel (Hill-System):
C4H7N
CAS-Nummer:
109-96-6
Molekulargewicht:
69.11
Beilstein:
103173
EG-Nummer:
203-723-1
MDL-Nummer:
MFCD00005213
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24863493
NACRES:
NA.22

Qualitätsniveau

100

Assay

95%

Form

liquid

Brechungsindex

n20/D 1.46 (lit.)

bp

90-91 °C/748 mmHg (lit.)

Dichte

0.91 g/mL at 25 °C (lit.)

Lagertemp.

−20°C

SMILES String

C1NCC=C1

InChI

1S/C4H7N/c1-2-4-5-3-1/h1-2,5H,3-4H2

InChIKey

JVQIKJMSUIMUDI-UHFFFAOYSA-N

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Allgemeine Beschreibung

3-Pyrroline is a heterocyclic building block. The excited state dynamics of 3-pyrroline by Hamiltonian model based on the vibronic coupling model has been investigated. Trifluoromethylated azomethine ylide is reported as precursor for the synthesis of 3-pyrroline building blocks. 3-Pyrrolines are reported as highly useful intermediates for the synthesis of functionalized pyrrolines, pyrrolidines and other natural products. Preparation of 3-pyrroline(2,5-dihydro-1H-pyrrole) from (Z)-1,4-dichloro-2-butene, via Delépine Reaction has been reported. It is formed as intermediate in the synthesis of N-(tert-butyloxycarbonyl)-3-pyrroline. Reaction of Me3Al and Me3Ga with 3-pyrroline is reported.
Various 3-pyrrolines (2,5-dihydropyrroles) have been synthesized by two-step reaction sequence of alkylation/alkylidene carbene CH-insertion reaction. Synthesis of 3-pyrroline has been reported by employing cis-1,4-dichloro-2-butene as starting reagent.

Anwendung

Used in the synthesis of renin inhibitors and vasodilators.

Zubehör

Produkt-Nr.
Beschreibung
Preisangaben

Z693847

Scienceware® Break-Safe™ ampule opener

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 2 - Skin Corr. 1A

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 2

Flammpunkt (°F)

-0.4 °F - closed cup

Flammpunkt (°C)

-18 °C - closed cup

Persönliche Schutzausrüstung

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Analysenzertifikate (COA)

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2,5-Dimethylpyrrol 98%

Sigma-Aldrich

D183601

2,5-Dimethylpyrrol

Pyrrolidin ≥99.0%

Sigma-Aldrich

83240

Pyrrolidin

Pyrrol reagent grade, 98%

Sigma-Aldrich

131709

Pyrrol

K Yoshino et al.
Journal of medicinal chemistry, 33(8), 2192-2196 (1990-08-01)
Structural modifications of the calcium antagonist fostedil (KB-944) and their coronary vasodilator activity are described. Amidophosphonates 4a-m, lactam amidophosphonates 7a-1, and diamide dilactam 10 were prepared, and their coronary vasodilator activity was assessed in dogs. Many compounds exhibited coronary vasodilator
Reactions of cis-2, 3-Dimethylaziridine, 3-Pyrroline and Pyrrolidine with Me3Al and Me3Ga: Adducts and Dimeric Amides.
Zhang Y, et al.
European Journal of Inorganic Chemistry, 4, Reactions of cis-Reactions of ci2 (2003)
Nobuyoshi Morita et al.
Organic letters, 6(22), 4121-4123 (2004-10-22)
[reaction: see text] The gold(III) chloride-catalyzed cycloisomerization of various alpha-aminoallenes gave the corresponding 3-pyrrolines in good to high chemical yields. An interesting dependence of the chirality transfer and reactivity on the N-protecting group was observed. The 3-pyrrolines are highly useful
M P Green et al.
Organic letters, 3(21), 3377-3379 (2001-10-12)
[reaction: see text]. The synthesis of a range of 3-pyrrolines has been achieved from primary amine starting materials using a two-step alkylation/alkylidene carbene CH-insertion reaction sequence. We have shown that insertion into a range of CH-bond types is possible, and
Practical one-pot and large-scale synthesis of N-(tert-butyloxycarbonyl)-3-pyrroline.
Rajesh T, et al.
Organic Process Research & Development, 13(3), 638-640 (2009)
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