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377112

Sigma-Aldrich

3-Pyrroline

95%

Synonym(s):

2,5-Dihydropyrrole

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About This Item

Empirical Formula (Hill Notation):
C4H7N
CAS Number:
109-96-6
Molecular Weight:
69.11
Beilstein:
103173
EC Number:
203-723-1
MDL number:
MFCD00005213
UNSPSC Code:
12352100
PubChem Substance ID:
24863493
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.46 (lit.)

bp

90-91 °C/748 mmHg (lit.)

density

0.91 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

C1NCC=C1

InChI

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

InChI key

JVQIKJMSUIMUDI-UHFFFAOYSA-N

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General description

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.

Application

3-Pyrroline is suitable for use in a study to investigate the core-level binding energies of simple unsaturated organic molecules bonded to the Si(001) surface by X-ray photoelectron spectroscopy (XPS). It may be used in the synthesis of renin inhibitors and vasodilators.

accessory

Product No.
Description
Pricing

Signal Word

Danger

Hazard Statements

H225,H302 + H332,H314

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

-0.4 °F - closed cup

Flash Point(C)

-18 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

377112-1G:
377112-VAR:
377112-BULK:
377112-250MG:

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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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