5-(hydroxymethyl)-2-furancarboxyaldehyde

5-(hydroxymethyl)-2-furancarboxyaldehyde
Compound Structure:
Synonyms: 5-HYDROXYMETHYLFURFURAL;67-47-0;5-Hydroxymethyl-2-furaldehyde;5-(hydroxymethyl)furan-2-carbaldehyde;5-(Hydroxymethyl)furfural;Hydroxymethylfurfural;5-Oxymethylfurfurole;5-Hydroxymethylfuraldehyde
Compound ID: NMPC-435
PubChem ID:

237332

Molecular Formula: C6H6O3
Canonical SMILES: C1=C(OC(=C1)C=O)CO
InChIKey: NOEGNKMFWQHSLB-UHFFFAOYSA-N
About the compound:

5-Hydroxymethylfurfural (5-HMF) is often referred to as a dormant powerhouse within the realm of biomass-derived platform chemicals, owing to its wide-ranging potential applications. Its extraction primarily depends on sugars and biomass not designated for food. However, the techniques currently in place for its production are hindered by issues like inefficient selectivity and conversion rates that are less than ideal. There is ongoing research aimed at enhancing catalytic systems and methods for a more effective transformation of polysaccharides into 5-HMF[1]. Progress in directly generating 5-HMF from a variety of raw biomass sources, including both edible and inedible lignocellulosic biomasses as well as food waste, has been noteworthy. This review underscores the necessity of pinpointing processes and catalytic systems capable of navigating around obstacles that stand in the way of widespread commercial use. The utilization of both edible and inedible lignocellulosic biomass as raw materials for producing 5-HMF is highlighted as a sustainable option, aiding in the shift towards a chemical industry that is kinder to the environment[2]. Advances have also been achieved in converting 5-HMF into valuable end products, such as fuels, fuel additives, and various commercial chemicals. These conversion processes encompass a variety of chemical reactions, including hydrogenation, oxidation, aldol condensation, rehydration, amination, polymerization, etherification, and decarbonylation. This diverse array of chemical modifications underscores the adaptability of 5-HMF and its contribution towards minimizing reliance on fossil fuels and reducing CO2 emissions. The review further elaborates on different catalysts and their significance in these transformations, providing a glimpse into how 5-HMF can be leveraged for the production of bio-based chemicals and fuels[3].

References 

1. Li, J., Zhang, R., Li, X., Qiao, Y., Lu, X., & Xiong, J. "Catalytic Systems for 5-Hydroxymethylfurfural Preparation from Different Biomass Feedstocks: A Review." Catalysts, 2024, 14(1), 30. MDPI. https://doi.org/10.3390/catal14010030.

2. Menegazzo, F., Ghedini, E., & Signoretto, M. "5-Hydroxymethylfurfural (HMF) Production from Real Biomasses." Molecules, 2018, 23(9), 2201. MDPI. https://doi.org/10.3390/molecules23092201.

3. Jiang, Z., Zeng, Y., Hu, D., Guo, R., Yan, K., & Luque, R. "Chemical transformations of 5-hydroxymethylfurfural into highly added value products: present and future." Green Chemistry, 2023, 25, 871-892. Royal Society of Chemistry. https://pubs.rsc.org/en/content/articlelanding/2022/gc/d2gc03444a.

GHS Hazard Statements

H315 (67.1%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (68.39%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (91.61%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H412 (73.23%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

126.11 g/mol

XLogP3

-0.6

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

3

Rotatable Bond Count

2

Exact Mass

126.031694049 g/mol

Monoisotopic Mass

126.031694049 g/mol

Topological Polar Surface Area

50.4Ų

Heavy Atom Count

9

Formal Charge

0

Complexity

103

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid with an odor of chamomile flowers; mp = 31.5 deg C; [Merck Index] Beige or yellow hygroscopic solid; mp = 32-35 deg C; [Alfa Aesar MSDS]

Boiling Point

BP: 115 °C at 1 mm Hg

Meting Point

31.5 °C

Density

1.2062 g/cu cm at 25 °C

Solubility 

Freely soluble in methanol, ethanol, acetone, ethyl acetate, dimethylformamide. Soluble in ether, benzene, chloroform. Less soluble in carbon tetrachloride. Sparingly soluble in petroleum ether.

Vapor Pressure

0.00528 [mmHg]

Source: PubChem

Source Species: Musa sapientum
Musa acuminata
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