Product

2(5H)-Furanone

CAS No.：497-23-4

Other grades of this product :

2(5H)-Furanone Basic information

Product Name:	2(5H)-Furanone
Synonyms:	.alpha.,.beta.-Crotonolactone;γ-Crotonolactone, 2-Buten-1,4-olide;2,5-Dihydrofuranone;5-Oxo-2,5-dihydrofuran-3-yl ester;a,b-Crotonolactone;Crotonic acid, 4-hydroxy-;2,5-Dihydrofuran-2-one;2(5H)-Furanone,γ-Crotonolactone, 2-Buten-1,4-olide
CAS:	497-23-4
MF:	C4H4O2
MW:	84.07
EINECS:	207-839-3
Product Categories:	Antibiotic;Heterocycles;Building Blocks;C4 to C7;Chemical Synthesis;Furans;Heterocyclic Building Blocks
Mol File:	497-23-4.mol

2(5H)-Furanone Chemical Properties

Melting point	4-5 °C (lit.)
Boiling point	86-87 °C/12 mmHg (lit.)
density	1.185 g/mL at 25 °C (lit.)
refractive index	n20/D 1.469(lit.)
FEMA	4138 \| 4-HYDROXY-2-BUTENOIC ACID GAMMA-LACTONE
Fp	214 °F
storage temp.	2-8°C
solubility	Chloroform, Ethyl Acetate (Slightly)
form	Liquid
color	Clear colorless to pale yellow or amber
Water Solubility	Immiscible with water.
JECFA Number	2000
BRN	383585
Stability:	Moisture Sensitive
InChIKey	VIHAEDVKXSOUAT-UHFFFAOYSA-N
CAS DataBase Reference	497-23-4(CAS DataBase Reference)
NIST Chemistry Reference	2(5H)-Furanone(497-23-4)
EPA Substance Registry System	2(5H)-Furanone (497-23-4)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26
WGK Germany	3
RTECS	LU3453000
F	8-10
Hazard Note	Irritant
HS Code	29322980
Hazardous Substances Data	497-23-4(Hazardous Substances Data)

MSDS Information

Provider	Language
Furan-2(5H)-one	English
SigmaAldrich	English
ALFA	English

2(5H)-Furanone Usage And Synthesis

Chemical Properties	2(5H)-Furanone is light brown liquid
Chemical Properties	Colorless to pale brown-yellow clear liquid
Occurrence	Reported found in coffee
Uses	2(5H)-Furanone is employed in the preparation of 5-substituted 2(5H) furanones (gamma-butenolides) catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts through direct aldol reaction with aromatic aldehydes. Further, it is used in the synthesis of lignans by Michael addition reactions. In addition to this, it is used in three-component Michael-Aldol reactions with an aldehyde and thiolate or carbanion.
Uses	2(5H)-Furanone is a heterocyclic organic compound that is used widely in the synthetic preparation of pharmaceutical goods.
Uses	2(5H)-Furanone is a versatile reagent used in Michael addition reactions1 for synthesis of lignans.2 Also employed in three-component Michael-Aldol reactions with an aldehyde anda thiolate3 or carbanion.4
Definition	2(5H)-Furanone is a mycotoxin that contains an α,β-unsaturated lactone moiety.
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.
Hazard	Extremely toxic.
Purification Methods	Fractionally distil the lactone under reduced pressure. IR: (CCl4) 1784 and 1742 cm-1, UV no max above 205nm ( 1160 cm-1 M-1) and 1HR: (CCl3) : 2.15 (pair of triplets 1H), 3.85 (pair of triplets 1H) and 5.03 (triplet 2H). [Price & Judge Org Synth Coll Vol V 255 1973, Smith & Jones Can J Chem 37 2007, 2092 1959, Beilstein 17/9 V 112.]

2(5H)-Furanone Preparation Products And Raw materials

Preparation Products

5-hydroxy-3-Methyl-2(5H)-furanone-->SUCCINALDEHYDIC ACID-->4-HYDROXY-BUT-2-ENOIC ACID-->3-Butenoic acid, 4-hydroxy-, gamma-lactone-->2-(TRIMETHYLSILYLOXY)FURAN-->5-HYDROXY-2[5H]-FURANONE-->Furan

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