10375-34-5

Basic information

• Product Name: 2,5-Furandicarbonyldichloride(9CI)
• Synonyms: 2,5-Furandicarbonyldichloride(9CI);2,5-Furandicarbonyl dichloride;Furan-2,5-dicarbonyl dichloride;furan-2,5-dicarbonyl chloride
• CAS NO: 10375-34-5
• Molecular Formula: C₆H₂Cl₂O₃
• Molecular Weight: 192.99
• Product Categories: ACIDHALIDE
• Mol File: 10375-34-5.mol

Chemical Properties

• Melting Point: 76.0 to 80.0 °C
• Boiling Point: 245°C(lit.)
• Appearance: /
• Density: 1.543±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,5-Furandicarbonyldichloride(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Furandicarbonyldichloride(9CI)(10375-34-5)
• EPA Substance Registry System: 2,5-Furandicarbonyldichloride(9CI)(10375-34-5)

Safety Data

• RIDADR: UN 3261 8/PG II
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 10375-34-5(Hazardous Substances Data)

Usage

Uses

2,5-Furandicarbonyl Dichloride is used as a modifier in wood.

Upstream product

• 3238-40-2 furan-2,5-dicarboxylic acid 
• 75-36-5 acetyl chloride 
• 13529-17-4 5-Formyl-2-furancarboxylic acid 
• 823-82-5 2,5-diformylfurane 
• 1623-88-7 5-chloromethylfurfural 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 63-42-3 D-(+)-lactose 
• 526-99-8 meso-galactaric acid 
• 13341-79-2 5-acetyl-2-furancarboxylic acid methyl ester 
• 83598-30-5 1,5-di(5-carboxyfuran-2-yl)-2,4-dioxapentan 
• 2144-38-9 methyl 5-(acetoxymethyl)furan-2-carboxylate 
• 2144-37-8 methyl 5-(chloromethyl)-2-furoate 
• 36802-01-4 Methyl ester of 5-hydroxymethylfuran 2-carboxylic acid 
• 6338-41-6 5-hydroxymethyl-furan-2-carboxylic acid 

Downstream Products

• 118044-39-6 furan-2,5-dicarboxylic acid bis-(8-benzoylamino-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 121255-71-8 furan-2,5-dicarboxylic acid bis-(4-anilino-9,10-dioxo-2-sulfo-9,10-dihydro-[1]anthrylamide) 
• 119246-74-1 furan-2,5-dicarboxylic acid bis-(9,10-dioxo-2-sulfo-4-o-toluidino-9,10-dihydro-[1]anthrylamide) 
• 118044-40-9 furan-2,5-dicarboxylic acid bis-(2-bromo-9,10-dioxo-4-o-toluidino-9,10-dihydro-[1]anthrylamide) 
• 103390-04-1 furan-2,5-dicarboxylic acid bis-(2-bromo-9,10-dioxo-4-p-phenetidino-9,10-dihydro-[1]anthrylamide) 
• 103566-93-4 furan-2,5-dicarboxylic acid bis-(4-anilino-2-bromo-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 118044-41-0 furan-2,5-dicarboxylic acid bis-(2-bromo-9,10-dioxo-4-p-toluidino-9,10-dihydro-[1]anthrylamide) 
• 103566-95-6 furan-2,5-dicarboxylic acid bis-(9,10-dioxo-4-phenylsulfanyl-9,10-dihydro-[1]anthrylamide) 
• 118113-09-0 furan-2,5-dicarboxylic acid bis-(4-p-anisidino-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 104741-83-5 furan-2,5-dicarboxylic acid bis-[4-(4-methylsulfanyl-anilino)-9,10-dioxo-9,10-dihydro-[1]anthrylamide] 
• 118044-53-4 furan-2,5-dicarboxylic acid bis-(2-bromo-9,10-dioxo-4-m-toluidino-9,10-dihydro-[1]anthrylamide) 
• 118113-11-4 furan-2,5-dicarboxylic acid bis-(4-o-anisidino-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 117500-02-4 furan-2,5-dicarboxylic acid bis-(9,10-dioxo-4-p-phenetidino-9,10-dihydro-[1]anthrylamide) 
• 117500-22-8 furan-2,5-dicarboxylic acid bis-(9,10-dioxo-4-o-phenetidino-9,10-dihydro-[1]anthrylamide) 

Relevant articles and documents

Small-scale screening of novel biobased monomers: the curious case of 1,3-cyclopentanediol

In this work, we report on the small scale polycondensation and consecutive analysis of novel polyesters based on the potentially renewable 1,3-cyclopentanediol (CPdiol). To avoid evaporation of monomers during thin-film polymerization reactions, trimer pre-polyesters have been synthesized from the corresponding acid-chlorides with diol monomers. Polymerization of these trimers was explored by thermogravimetric analysis to identify potential side reactions, and to assess the ideal polymerization temperature. In general we observe that trans-1,3-cyclopentanediol exhibits good thermal stability up to 200 °C, whereas thermal dehydration of the alcohol end-groups occurs upon further heating. In contrast, for cis-1,3-cyclopentanediol, the ester bonds of the cyclopentane end-groups become labile, thereby generating carboxylic acid end-groups, and 3-cyclopentenol already at 180 °C. The thermal dehydration reactions yield double bond end-groups, which in turn facilitate cross-linking through cross-coupling and Diels-Alder reactions, leading to an increase in molecular weight. Despite the limited thermal stability of CPdiol, here we demonstrate that polymerization of CPdiol can successfully be achieved in thin-film polycondensation conditions at 180 °C, yielding molecular weights well above 10 kg mol?1.

Solvent-dependent selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under neat conditions

An eco-friendly and economical route for the oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) with atmospheric dioxygen as the sole oxidant under acid-, base-, metal-, and external initiator-free conditions in minimal solvent was reported. In the present reaction, the 1,2-diethoxyethylane has a dual role: reaction medium and free-radical initiator. The FDCA easily crystallizes during the reaction and was simple purified via recrystallization to provide the pure FDCA.

Novel diamidino-substituted derivatives of phenyl benzothiazolyl and dibenzothiazolyl furans and thiophenes: Synthesis, antiproliferative and DNA binding properties

A series of new diamidino-, diisopropylamidino-, and diimidazolinyl- substituted derivatives of phenyl benzothiazolyl and dibenzothiazolyl furans and thiophenes were successfully prepared and evaluated for their antiproliferative activity on tumor cell lines in vitro, DNA binding propensity, and sequence selectivity as well as cellular distribution. A strong antiproliferative effect of the tested compounds was observed on all tested cell lines in a concentration-dependent response pattern. In general, imidazolinyl-substituted derivatives and/or the thiophene core were in correlation with increased antiproliferative activity. Two compounds (2b and 3b) were chosen for biological studies due to their differential antiproliferative properties. The DNA binding properties of this new series of compounds were assessed and evidenced their efficient minor groove binding properties with preferential interaction at AT-rich sites. Both compounds also present nuclear subcellular localization, suggesting that their cellular mode of action implies localization in the DNA compartment and direct inhibition of DNA replication and induction of apoptosis.

Pyridine/pyridinium symmetrical bisamides as functional materials: Aggregation, selective sensing and drug release

Pyrrole and furan-based pyridine/pyridinium bisamides 1-4 have been designed and synthesized with a view to establishing new supramolecular gelators. The neutral gelators 1 and 2 were explored for cation binding. While the furan analogue 1 forms gel in the presence of Ag+ and Cu2+ ions in DMSO:H2O (1:1, v/v), the pyrrole conjugate 2 exhibits metallogel formation selectively with Ag+ ions and corroborates the role of the heteroatom in the spacer that modulates the self assembly behavior of the gelators. As an application, the 1-Cu gel selectively distinguishes thiol-based amino acids from a series of other amino acids as well as effectively discriminates d-glucose from its C2-epimer d-mannose by exhibiting gel to sol transformation. Additionally, encapsulation and subsequent release of the chemopreventive drug curcumin has been studied using the 1-Cu gel. Placement of a cholesterol unit onto the structures 1 and 2 resulted in charged structures 3 and 4 of which compound 4 produced an unambiguous visual readout of F- and AcO- ions by showing gel to sol transition.

Benzene-, pyrrole-, and furan-containing diametrically strapped calix[4]pyrroles - An experimental and theoretical study of hydrogen-bonding effects in chloride anion recognition

(Figure Presented). Weak but important: The chloride anion binding properties of diametrically strapped calixpyrroles bearing benzene (see structure), pyrrole, and furan moieties in the strap have been studied in the solid state, in solution, and through theoretical analyses. The results obtained provide support for the notion that C-H...Cl- hydrogen bonds are significant and contribute substantially to the Cl- binding energetics.

A luminescent 2D zinc(II) metal–organic framework for selective sensing of Fe(III) ions and adsorption of organic dyes

A 2D porous multifunctional Zn(II) metal–organic framework (MOF) [ZnL(H2O)3]·3H2O·DMF (BIPT-1·3H2O·DMF) has been successfully synthesized by using bis-(3-carboxy-phenyl)furan-2,5-dicarboxamide (H2L) a

Production of 5-(chloromethyl)furan-2-carbonyl chloride and furan-2,5-dicarbonyl chloride from biomass-derived 5-(chloromethyl)furfural (CMF)

Acid chloride derivatives of 5-(chloromethyl)furan-2-carboxylic acid and furan-2,5-dicarboxylic acid (FDCA) can be produced in high yield by treatment of the precursor aldehydes 5-(chloromethyl) furfural (CMF) and 2,5-diformylfuran (DFF) with tert-butyl hypochlorite, which is inexpensively prepared from commercial bleach and tert-butanol. 5-(Chloromethyl)furan-2-carbonyl chloride (CMFCC) and furan-2,5-dicarbonyl chloride (FDCC) are highly useful intermediates for the production of furoate ester biofuels and polymers of FDCA.

Renewable-based poly((ether)ester)s from 2,5-furandicarboxylic acid

Polymers based on the renewable monomer 2,5-furandicarboxylic acid (FDCA) have witnessing an incessant growth in recent years, essentially motivated by their unique features and the current concerns about sustainability and environmental issues. However, to date, research has been mainly focused on FDCA-polyesters synthesis, while synthetic routes to afford poly((ether)ester)s remained unexplored until the present study, despite their inherent value. Herein, fully renewable-based poly((ether)ester)s from 2,5-furandicarboxylic acid, poly(ethylene glycol) (PEG) and isosorbide were straightforward synthesised by polycondensation reactions. Interestingly, these materials showed better or comparable thermal properties (e.g. glass transition temperature) than their fossil based counterparts, which can be simply tuned by changing the chain length of PEG segments and also by incorporating (or not) rigid isosorbide moieties. The ensuing products were characterised in detail by means of ATR FTIR, 1H NMR, TGA and DSC.

Synthesis of fluorine-containing esters of 2,5-furandicarboxylic acid

Fluorinated esters of 2,5-furandicarboxylic acid have been synthesized starting from 2,5-furan dicarboxylic acid dichloride and fluorine-containing diols. The reaction control was performed by means of 1H, 19F NMR, and IR-spectroscopy. Thermal stability, as well as glass transition temperature, and intrinsic viscosity parameters of the obtained oligomers have been determined.

2,5-Diamide-Substituted Five-Membered Heterocycles: Challenging Molecular Synthons

We describe synthetic routes for preparing previously unknown 2,5-diamide-substituted five-membered heterocycles based on the thiophene, pyrrole, and furan ring systems by exploiting Curtius-like rearrangement reactions. Conformation analysis of the 2,5-diamidothiophene derivatives identified a "closed" conformation, in which the two carbonyl O atoms are in close contact with the thiophene S atom.