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MilliporeSigma

377112

3-Pyrroline

95%

Synonym(s):

2,5-Dihydropyrrole

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$61.30

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About This Item

Empirical Formula (Hill Notation):
C4H7N
CAS Number:
109-96-6
Molecular Weight:
69.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24863493
EC Number:
203-723-1
Beilstein/REAXYS Number:
103173
MDL number:
MFCD00005213
Assay:
95%
Form:
liquid

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InChI key

JVQIKJMSUIMUDI-UHFFFAOYSA-N

InChI

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

SMILES string

C1NCC=C1

assay

95%

form

liquid

Quality Level

100

bp

90-91 °C/748 mmHg (lit.)

density

0.91 g/mL at 25 °C (lit.)

storage temp.

−20°C

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1 of 4

This Item
381055422169416762
3-Pyrroline 95%

Sigma-Aldrich

377112

3-Pyrroline

2-Methyl-1-pyrroline 95%

Sigma-Aldrich

381055

2-Methyl-1-pyrroline

2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile 98%

Sigma-Aldrich

422169

2,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

5-Bromo-2,4-dichloropyrimidine 97%

Sigma-Aldrich

416762

5-Bromo-2,4-dichloropyrimidine

assay

95%

assay

95%

assay

98%

assay

97%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

refractive index

n20/D 1.46 (lit.)

refractive index

n20/D 1.444 (lit.)

refractive index

-

refractive index

n20/D 1.603 (lit.)

form

liquid

form

-

form

solid

form

solid

density

0.91 g/mL at 25 °C (lit.)

density

0.878 g/mL at 25 °C (lit.)

density

-

density

1.781 g/mL at 25 °C (lit.)

storage temp.

−20°C

storage temp.

-

storage temp.

-

storage temp.

-

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.[1] Trifluoromethylated azomethine ylide is reported as precursor for the synthesis of 3-pyrroline building blocks.[2] 3-Pyrrolines are reported as highly useful intermediates for the synthesis of functionalized pyrrolines, pyrrolidines and other natural products.[3] Preparation of 3-pyrroline(2,5-dihydro-1H-pyrrole) from (Z)-1,4-dichloro-2-butene, via Delépine Reaction has been reported.[4] It is formed as intermediate in the synthesis of N-(tert-butyloxycarbonyl)-3-pyrroline.[5] Reaction of Me3Al and Me3Ga with 3-pyrroline is reported.[6]
Various 3-pyrrolines (2,5-dihydropyrroles) have been synthesized by two-step reaction sequence of alkylation/alkylidene carbene CH-insertion reaction.[7] Synthesis of 3-pyrroline has been reported by employing cis-1,4-dichloro-2-butene as starting reagent.[8]

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).[9] It may be used in the synthesis of renin inhibitors[10] and vasodilators.[11]

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

-0.4 °F - closed cup

flash_point_c

-18 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT4878
MKCP6752
MKBR1536V
MKBQ8754V
MKBQ7459V

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An X-ray photoelectron spectroscopy study of the bonding of unsaturated organic molecules to the Si (001) surface.
Liu H and HamersRJ.
Surface Science, 416(3), 354-362 (1998)
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
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
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)
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
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