177717
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-914-3
Beilstein/REAXYS Number:
106449
MDL number:
Assay:
99%
Form:
liquid
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
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.
signalword
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
3 - Flammable liquids
wgk
WGK 3
flash_point_f
33.8 °F
flash_point_c
1 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Yuriy Román-Leshkov et al.
Nature, 447(7147), 982-985 (2007-06-22)
Diminishing fossil fuel reserves and growing concerns about global warming indicate that sustainable sources of energy are needed in the near future. For fuels to be useful in the transportation sector, they must have specific physical properties that allow for
Baptiste Sirjean et al.
Physical chemistry chemical physics : PCCP, 15(2), 596-611 (2012-11-28)
The unimolecular decomposition of 2,5-dimethylfuran (DMF), a promising next-generation biofuel, was studied at the CBS-QB3 level of theory. As most of its decomposition routes remain unknown, a large number of pathways were explored: initial C-H bond fission, biradical ring opening
Albert Sánchez et al.
Organic letters, 13(16), 4364-4367 (2011-07-28)
The reaction of maleimide-containing compounds with 2,5-dimethylfuran gives a mixture of exo and endo isomers from which the exo cycloadduct can be easily isolated taking advantage of its stability in concentrated aqueous ammonia. Bifunctional compounds incorporating a dimethylfuran-protected maleimide (exo