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Merck

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:

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Product Name

2,5-Dimethylfuran, 99%

InChI key

GSNUFIFRDBKVIE-UHFFFAOYSA-N

InChI

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

SMILES string

Cc1ccc(C)o1

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.)

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1 of 4

This Item
D130605110582D42003
assay

99%

assay

99%

assay

99%

assay

99%

refractive index

n20/D 1.441 (lit.)

refractive index

-

refractive index

n20/D 1.392 (lit.)

refractive index

-

mp

−62 °C (lit.)

mp

46-48 °C (lit.)

mp

-

mp

82-84 °C (lit.)

density

0.903 g/mL at 25 °C (lit.)

density

-

density

0.694 g/mL at 25 °C (lit.)

density

2.374 g/mL at 25 °C (lit.)

form

liquid

form

crystals

form

-

form

solid

bp

92-94 °C (lit.)

bp

146 °C/10 mmHg (lit.)

bp

108 °C (lit.)

bp

-

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.[1]
  • 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.[2]
  • A precursor to prepare p-xylene via Diels-Alder cycloaddition and subsequent dehydration reaction.[3]

General description

2,5-Dimethylfuran is a heterocyclic furan used as a building block in organic synthesis. [4] [5]

pictograms

FlameExclamation mark

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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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)
One-Pot Generation of Functionalized Benzynes from Readily Available 2-Hydroxyphenylboronic Acids
Ikawa T, et al.
The Journal of Organic Chemistry, 85(5) (2020)
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)
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

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    1 answer
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      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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