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Sigma-Aldrich

2,5-Dimethylfuran

99%

Synonym(s):

2-Methyl-5-methylfuran

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About This Item

Empirical Formula (Hill Notation):
C6H8O
CAS Number:
Molecular Weight:
96.13
Beilstein:
106449
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.31 (vs air)

Assay

99%

form

liquid

refractive index

n20/D 1.441 (lit.)

bp

92-94 °C (lit.)

mp

−62 °C (lit.)

density

0.903 g/mL at 25 °C (lit.)

SMILES string

Cc1ccc(C)o1

InChI

1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3

InChI key

GSNUFIFRDBKVIE-UHFFFAOYSA-N

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General description

2,5-Dimethylfuran is a heterocyclic furan used as a building block in organic synthesis.

Application

2,5-Dimethylfuran can be used as:
  • A reactant to prepare exo-maleimide-dimethylfuran cyclo adduct, which is used in the synthesis of oligonucleotide conjugates.
  • An arynophile to synthesize 1,4-dimethyl-1,4-dihydro-1,4-epoxynaphthalene (fused benzene) by reacting with a mixture of neopentyl glycol and 2-hydroxyphenylboronic acid in the presence of a strong base.
  • A precursor to prepare p-xylene via Diels-Alder cycloaddition and subsequent dehydration reaction.

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

33.8 °F

Flash Point(C)

1 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Production of renewable p-xylene from 2, 5-dimethylfuran via Diels-Alder cycloaddition and dehydrative aromatization reactions over silica- alumina aerogel catalysts
Wijaya YP, et al.
Catalysis Communications, 70, 12-16 (2015)
Sara M Aschmann et al.
The journal of physical chemistry. A, 118(2), 457-466 (2014-01-02)
Products of the gas-phase reactions of OH radicals with furan, furan-d4, 2- and 3-methylfuran, and 2,3- and 2,5-dimethylfuran have been investigated in the presence of NO using direct air sampling atmospheric pressure ionization tandem mass spectrometry (API-MS and API-MS/MS), and
5-hydroxymethylfurfural hydrodeoxygenation to 2, 5-dimethylfuran in continuous-flow system over Ni on nitrogen-doped carbon
Francesco B et al.
Sustainable Chemistry and Pharmacy, 1, 9-9 (2020)
Baptiste Sirjean et al.
The journal of physical chemistry. A, 117(7), 1371-1392 (2013-01-19)
A detailed kinetic model describing the oxidation of 2,5-dimethylfuran (DMF), a potential second-generation biofuel, is proposed. The kinetic model is based upon quantum chemical calculations for the initial DMF consumption reactions and important reactions of intermediates. The model is validated
One-flow syntheses of diverse heterocyclic furan chemicals directly from fructose via tandem transformation platform
Guan-Young J et al.
NPG Asia materials, 7, e173-e173 (2015)

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