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Merck

185922

Furan

≥99%

Synonym(s):

1,4-Epoxybuta-1,3-diene, Divinylene oxide, Oxacyclopentadiene, Oxole, Tetrole

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About This Item

Empirical Formula (Hill Notation):
C4H4O
CAS Number:
110-00-9
Molecular Weight:
68.07
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24851189
EC Number:
203-727-3
Beilstein/REAXYS Number:
103221
MDL number:
MFCD00003222
Assay:
≥99%
Form:
liquid

Key Documents

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InChI key

YLQBMQCUIZJEEH-UHFFFAOYSA-N

InChI

1S/C4H4O/c1-2-4-5-3-1/h1-4H

SMILES string

c1ccoc1

vapor density

2.35 (vs air)

vapor pressure

1672 mmHg ( 55 °C), 31.66 psi ( 55 °C), 493 mmHg ( 20 °C), 9.22 psi ( 20 °C)

assay

≥99%

form

liquid

contains

0.025 wt. % BHT as inhibitor

expl. lim.

14.3 %

Quality Level

100

bp

32 °C/758 mmHg (lit.)

solubility

alcohols: freely soluble, diethyl ether: freely soluble, water: insoluble

density

0.936 g/mL at 25 °C (lit.)

shipped in

wet ice

storage temp.

2-8°C

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General description

Furan is a five membered heterocyclic compound that is highly volatile, flammable and a potential carcinogen. It undergoes Diels-Alder reaction with 2-bromoacrolein catalyzed by oxazaborolidine to yield chiral 7-oxabicyclo[2.2.1]heptene derivatives. Cationic bis(4-tert-butyloxazoline)Cu(II) complex catalyzed enantioselective Diels-Alder reaction between acryloyl oxazolidinone and furan to afford ent-shikimic acid has been described. Lewis acid catalyzed Diels-Alder reaction between furan and some dienophiles affords substituted cyclohexenols and cyclohexadienols.

Application

Furan was used in the following processes:
  • Preparation of the starting material required for the synthesis of calix[6]pyrrole.
  • To investigate the kinetics and mechanism of reactions of chlorine atoms with volatile organic compounds.
  • Catalytic transformation of furan to aromatics and olefins.

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Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 1B - Flam. Liq. 1 - Muta. 2 - Skin Irrit. 2 - STOT RE 2

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-32.8 °F - closed cup

flash_point_c

-36 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4912
MKCW0259
BCCJ4966
MKCQ8662
MKCL3735

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Cationic bis (oxazoline) Cu (II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid.
Evans DA and Barnes DM.
Tetrahedron Letters, 38(1), 57-58 (1997)
Samah R Khalil et al.
Ecotoxicology and environmental safety, 192, 110256-110256 (2020-02-06)
The modulatory role of the Spirulina platensis (SP) against furan-induced (FU) hepatic and renal damage was assessed in this study. For achieving this, sixty rats were distributed into six groups: control group, SP-administered group (300 mg/kg b.wt orally for 28 days)
Chemistry of furan conversion into aromatics and olefins over HZSM-5: a model biomass conversion reaction.
Cheng YT and Huber GW.
ACS Catalysis, 1(6), 611-628 (2011)
From Large Furan-Based Calixarenes to Calixpyrroles and Calix
Cafeo et al.
Angewandte Chemie (International ed. in English), 39(8), 1496-1498 (2000-04-25)
Catalytic enantioselective Diels-Alder addition to furan provides a direct synthetic route to many chiral natural products.
Corey EJ and Loh T-P.
Tetrahedron Letters, 34(25), 3979-3982 (1993)
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Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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