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283754

2(5H)-Furanone

Name: 2(5<I>H</I>)-Furanone
Brand: ALDRICH

98%

Synonym(s):

γ-Crotonolactone, 2-Buten-1,4-olide

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About This Item

Empirical Formula (Hill Notation):

C₄H₄O₂

CAS Number:

497-23-4

Molecular Weight:

84.07

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24857130

EC Number:

207-839-3

Beilstein/REAXYS Number:

383585

MDL number:

MFCD00005376

Assay:

98%

Form:

liquid

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Properties

Quality Segment

200

assay

98%

form

liquid

refractive index

n20/D 1.469 (lit.)

bp

86-87 °C/12 mmHg (lit.)

mp

4-5 °C (lit.)

density

1.185 g/mL at 25 °C (lit.)

functional group

ester

storage temp.

2-8°C

SMILES string

O=C1OCC=C1

InChI

1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

InChI key

VIHAEDVKXSOUAT-UHFFFAOYSA-N

Description

General description

Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains.

Application

2(5H)-Furanone (γ-Crotonolactone) has been used in:

synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid
synthesis of 5-substituted 2(5H) furanones (γ-butenolides) via direct aldol reaction with aromatic aldehydes catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts
Michael addition reactions for synthesis of lignans
three-component Michael-Aldol reactions with an aldehyde anda thiolate or carbanion

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

213.8 °F - closed cup

Flash Point (°C)

101 °C - closed cup

PPE (personal protective equipment)

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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