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407313

Sigma-Aldrich

Methyl trans-3-pentenoate

90%

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About This Item

Linear Formula:
CH3CH=CHCH2CO2CH3
CAS Number:
20515-19-9
Molecular Weight:
114.14
MDL number:
MFCD00191576
UNSPSC Code:
12352100
PubChem Substance ID:
24865443

Assay

90%

form

liquid

refractive index

n20/D 1.421 (lit.)

bp

55-56 °C/20 mmHg (lit.)

density

0.93 g/mL at 25 °C (lit.)

SMILES string

[H]\C(C)=C(\[H])CC(=O)OC

InChI

1S/C6H10O2/c1-3-4-5-6(7)8-2/h3-4H,5H2,1-2H3/b4-3+

InChI key

KJALUUCEMMPKAC-ONEGZZNKSA-N

General description

Methyl trans-3-pentenoate is an ester. Ring-closing metathesis (RCM) of methyl trans-3-pentenoate using silica- and monolith supported Grubbs-Herrmann-type catalysts has been reported. The 1,3-dipolar cycloaddition of with C-ethoxycarbonyl nitrone to form isoxazolidines has been studied.

Application

Methyl trans-3-pentenoate may be used for the total synthesis of phytochemicals (-)-grandinolide and (-)-sapranthin.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

75.2 °F - closed cup

Flash Point(C)

24 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBC7248V
02402DJ
06912ED
07004CD
16328EU

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C-Alkoxycarbonyl nitrones: building blocks for the synthesis of butenolides, lactams and modified nucleosides.
Romeo G, et al.
Mini-Reviews in Organic Chemistry, 2(1), 59-77 (2005)
Total Syntheses of (-)-Grandinolide and (-)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyl trans-3-Pentenoate: Elucidation of the Stereostructure of (-)-Sapranthin.
Harcken C, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 4(11), 2342-2352 (1998)
Monolith-and Silica-Supported Carboxylate-Based Grubbs-Herrmann-Type Metathesis Catalysts.
Krause JO, et al.
Advanced Synthesis & Catalysis, 345(8), 996-1004 (2003)

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