5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural, a product of acid-catalyzed degradation of sugars during the heating and storage of foods that influences taste and physiological functions in the body.

Synonyms: NSC 40739

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Quality Control of 5-Hydroxymethyl-2-furancarboxylic acid Purity: 97% SDS Specification

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Porous dendritic BiSn electrocatalysts for hydrogenation of 5-hydroxymethylfurfural

Piao, Guangxia ; Yoon, Sun Hee ; Cha, Hyun Gil ; Han, Dong Suk ; Park, Hyunwoong ;

DOI: 10.1039/D2TA05969J J. Mater. Chem. A,2022,10,24006-24017.

Abstract: The electrocatalytic hydrogenation of 5-hydroxymethylfurfural (HMF) to 2,5-bis(hydroxymethyl)furan (BHMF) is an alternative to conventional heterogeneous catalysis with H2 at high temperatures and pressures. Although Ag is the most representative electrocatalyst, it works only under limited conditions. This study synthesizes highly porous dendritic Bi, Sn, and BiSn electrocatalysts using an in situ generated hydrogen bubble template. Density functional theory computations on the adsorption energy and elementary hydrogenation reaction steps of HMF predict the superiority of Bi to Sn and the intermediate behavior of BiSn between Bi and Sn. The dendritic BiSn catalyst generates a current density of ∼144 mA cm−2 at a faradaic efficiency (FE) of ∼100% for BHMF production at pH ∼ 7 (corresponding to the BHMF production rate of ∼2.7 mmol h−1 cm−2) in prolonged electrolysis. Considering the material cost (

Purchased from AmBeed: 13529-17-4 ; 823-82-5 ; 3238-40-2 ; 67-47-0 ; 6338-41-6 ; 1883-75-6

Product Details of 5-Hydroxymethyl-2-furancarboxylic acid

CAS No. :	6338-41-6
Formula :	C₆H₆O₄
M.W :	142.11
SMILES Code :	C1=C(OC(=C1)CO)C(=O)O
Synonyms :	NSC 40739
MDL No. :	MFCD03274472
InChI Key :	PCSKKIUURRTAEM-UHFFFAOYSA-N
Pubchem ID :	80642

Safety of 5-Hydroxymethyl-2-furancarboxylic acid

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 5-Hydroxymethyl-2-furancarboxylic acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 6338-41-6 ]

[ 6338-41-6 ] Synthesis Path-Downstream 1~41

1
[ 67-47-0 ]
[ 6338-41-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With nicotinamide adenine dinucleotide; sodium hydroxide; In aq. phosphate buffer; at 35℃; for 0.5h;pH 8.5;Enzymatic reaction;	ALD-003 (5mg), NOX-009 or NOX-001 (5mg) and NAD or NADP (2Omol% based upon the amount of ALD-003) was added to 0.5mL 0.25M KPi (pH 8.5). The pH was adjusted to pH 8.5 with 1M NaOH. 10mM DFF or HMF was added and the reaction was left in ashaking incubator at 35C. After a specified time the reaction was quenched with 1 M HCI, centrifuged and analysed by RP-HPLC. The results are found in Tables 5, 6, and 7A. Reaction Conditions: 0.SmL KPi 0.25M pH 8.5, 5mg CFE, 2Omol% cofactor, 5mg NOX,10mM Substrate, 35C, reaction time 30 minutes.
99%	With oxygen; sodium hydroxide; In water; at 20℃;	0.2g of 5-hydroxymethylfurfural,0.05g Ag-PVP/ZrO2 catalyst (Ag:PVP=1:0.5 (molar ratio), 2.5% load),0.126g NaOH, 50mL water was added to a 150mL three-necked flask,And oxygen is introduced, the oxygen flow rate is 60 mL/min, and the reaction is carried out at a temperature of 20 C.Real-time sampling,The product was determined by high performance liquid chromatography for the content of 5-hydroxymethylfurfural and 5-hydroxymethylnonanoic acid.When the reaction is 12h,The conversion rate of 5-hydroxymethylfurfural is 99%.Yield of 5-hydroxymethyl-furoic acid 99%The selectivity is 100%.
92%	With oxygen; sodium hydroxide; In water; at 80℃; under 3750.38 Torr; for 12h;Autoclave; Green chemistry;	Take 0.317 g of HMF, 2 g of NaOH (20%) and 3 ml of water into the autoclave. The reaction vessel was charged with 10 ml of polytetrafluoroethylene lined autoclave with 0.30 g Pt / NaY (Pt lwt% As the catalyst, the program temperature to 80 C, filled with 0.5MPa oxygen, the reaction 12 hours, the reaction process continue to add oxygen to ensure that the reaction at constant temperature and constant pressure. The reaction product was centrifuged and the supernatant was removed and analyzed using HPLC. The results showed that the conversion rate of HMF was 100% and the yield of HMFA was 92%. The reaction results are shown in Table 1.

	With oxygen; sodium carbonate; In water; at 20 - 50℃; for 2h;	Catalytic Reaction Of HMF To FDCA For this reaction, Na2C03 was used as the base. 1 g of extracted HMF was first dissolved in 5 g of water. The Na2C03 was separately prepared by dissolving Na2C03 in water. The oxidation catalyst was then added follow by the HMF solution at ambient room temperature. With oxygen gas bubbling, the solution was first heated to 50C for 2 hours, and HMF was fully converted to HFCA. After that, the reaction was heat to 95C and kept for 7 hour. The pH of the aqueous solution was then adjusted to 1 and FDCA was precipitated from the solution. The precipitate was filtered and washed with ethanol.
2.74 g	With 4% Au/TiO2; oxygen; sodium hydroxide; In water; at 70℃; for 7h;pH 10;	10 g of HMF, 150 g of water, and 1 g of catalyst (4% Au/TiO2) were added into a round bottom bottle (250 mL) and then heated to 70 C. Air under atmosphere pressure was introduced into the liquid in the flask. The pH value of the above reaction was controlled to 10 by adding a sodium hydroxide aqueous solution into the flask. The reaction was continued for 7 hours to obtain a crude aqueous solution. The crude aqueous solution was extracted by 200 mL of ethyl acetate two times, and the aqueous phase of the extractions was collected by a separatory funnel. The collected aqueous phase was titrated by concentrated hydrochloric acid (HCl) until its pH value reached 3. The acidified aqueous phase was extracted by 200 mL of ethyl acetate two times, and the organic phase of the extractions was collected. The collected organic phase was vacuumed concentrated to obtain 2.74 g of solid, which was 5-hydroxymethyl-2-furoic acid (HMFCA). The above reaction is shown in Formula 8. The product of Formula 8 had NMR spectra as below: 1H NMR (400 MHz, d-DMSO): 13.08 (br, 1H), 7.14 (d, 1H, J=3.4 Hz), 6.45 (d, 1H, J=3.4 Hz), 5.59 (s, 1H), 4.44 (s, 2H); 13C NMR (100 M Hz, d-DMSO): 160.1, 159.8, 144.4, 119.0, 109.4, 56.2.
2.74g	With gold on titanium oxide; oxygen; sodium hydroxide; In water; at 70℃; under 760.051 Torr; for 7h;pH 10;	10 g of HMF,150 g of water,And 1 g of 4% Au / TiO2 catalyst250 mL of a round bottom flask,Heated to 70 C,And air was introduced under normal pressure.The pH of the reaction was then controlled to 10 with the addition of aqueous sodium hydroxide,After 7 hours of continuous reaction, an aqueous solution of the crude product was obtained.The crude aqueous solution was added to 200 mL of ethyl acetate for extraction twice,The water layer was taken in a separatory funnel.The aqueous layer was titrated with concentrated hydrochloric acid (HCl) until the pH was 3.After extraction twice with 200 mL of ethyl acetate, the organic layer was taken.The organic layer was concentrated under reduced pressure to give 2.74 g of a solid,5-hydroxymethyl-2-furoic acid (HMFCA).The above reaction is shown in Formula 8 below.
	With sodium hydroxide; In water; at 30℃; under 2250.23 Torr; for 5h;	The Au / MgO (Au0.5 wt%) catalyst, 1 mmol of 5-hydroxymethylfurfural, NaOH, 10 ml of water was charged to a stainless steel autoclave with a Teflon-lined internal metal, 5-hydroxymethylfurfural: NaOH = 0.015: 1: 4 (mol: mol: mol).Using automatic temperature control program temperature to the reaction temperature of 30 C, adding 0.3MPa oxygen, reaction 5 hours, the reaction process to maintain the same pressure.The reaction product was analyzed by HPLC.
95%Chromat.	With recombinant Escherichia coli cells expressing 3-succinoylsemialdehyde-pyridine dehydrogenase from Comamonastestosteroni SC1588; In aq. phosphate buffer; at 30℃; for 5h;pH 7;Enzymatic reaction;	General procedure: Typically, 4 mL of phosphate buffer (0.2 M, pH 7) containing 50mMFF and 50 mg (cell wet weight) per mL microbial cells was incubated at30 C and 160 r/min. Aliquots were withdrawn from the reaction mixturesat specified time intervals and diluted with the correspondingmobile phase prior to HPLC analysis. The conversion was defined as theratio of the consumed substrate amount to the initial substrate amount(in mol). The yield was defined as the ratio of the formed productamount to the theoretical value based on the initial substrate amount(in mol). The selectivity was defined as the ratio of the formed productamount to the total amount of all products (in mol). All the experimentswere conducted at least in duplicate, and the values were expressed asthe means ± standard deviations.

References: [1]Patent: WO2016/202858,2016,A1 .Location in patent: Page/Page column 53.
[2]Patent: CN109912549,2019,A .Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020-0026.
[3]Green Chemistry,2015,vol. 17,p. 3718 - 3722.
[4]Patent: CN103626726,2016,B .Location in patent: Paragraph 0050-0052.
[5]Green Chemistry,2018,vol. 20,p. 3530 - 3541.
[6]Chemistry - A European Journal,2013,vol. 19,p. 14215 - 14223.
[7]Green Chemistry,2018,vol. 20,p. 5261 - 5265.
[8]Organic and Biomolecular Chemistry,2018,vol. 16,p. 8955 - 8964.
[9]Bulletin de la Societe Chimique de France,1987,p. 855 - 860.
[10]Polish Journal of Chemistry,1994,vol. 68,p. 693 - 698.
[11]Applied Catalysis A: General,2014,vol. 478,p. 107 - 116.
[12]ChemSusChem,2016,vol. 9,p. 1096 - 1100.
[13]Green Chemistry,2011,vol. 13,p. 824 - 827.
[14]Chemisches Zentralblatt,1910,vol. 81,p. 539.
[15]Recueil des Travaux Chimiques des Pays-Bas,1919,vol. 38,p. 42.
[16]Helvetica Chimica Acta,1926,vol. 9,p. 1068.
[17]Proceedings of the National Academy of Sciences of the United States of America,2010,vol. 107,p. 4919 - 4924.
[18]Catalysis Today,2011,vol. 160,p. 55 - 60.
[19]Green Chemistry,2012,vol. 14,p. 143 - 147.
[20]Catalysis Letters,2012,vol. 142,p. 1089 - 1097.
[21]Green Chemistry,2014,vol. 16,p. 2762 - 2770.
[22]Journal of Molecular Catalysis A: Chemical,2014,vol. 388-389,p. 123 - 132.
[23]Green Chemistry,2014,vol. 16,p. 3778 - 3786.
[24]ChemSusChem,2013,vol. 6,p. 609 - 612.
[25]Patent: WO2015/41601,2015,A1 .Location in patent: Page/Page column 31-32.
[26]Chemical Science,2015,vol. 6,p. 4940 - 4945.
[27]Patent: US9321744,2016,B1 .Location in patent: Page/Page column 5.
[28]Patent: TWI542583,2016,B .Location in patent: Paragraph 0015.
[29]Patent: CN103724303,2016,B .Location in patent: Paragraph 0018; 0019.
[30]Applied Catalysis A: General,2017,vol. 547,p. 230 - 236.
[31]ChemSusChem,2017,vol. 10,p. 3524 - 3528.
[32]Green Chemistry,2017,vol. 19,p. 4544 - 4551.
[33]Green Chemistry,2016,vol. 18,p. 5957 - 5961.
[34]Green Chemistry,2018,vol. 20,p. 3931 - 3943.
[35]Molecular catalysis,2019,vol. 469,p. 68 - 74.
[36]ACS Catalysis,2019,vol. 9,p. 8306 - 8315.
[37]ChemSusChem,2019.

2
[ 39131-44-7 ]
[ 6338-41-6 ]

References: [1]Journal of the Chemical Society,1899,vol. 75,p. 424.
Journal of the Chemical Society,1901,vol. 79,p. 363.

3
[ 13529-17-4 ]
[ 6338-41-6 ]
[ 3238-40-2 ]

References: [1]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 241,245.
[2]Collection of Czechoslovak Chemical Communications,1934,vol. 6,p. 241,245.

4
[ 6338-41-6 ]
[ 64-17-5 ]
[ 76448-73-2 ]

References: [1]Journal of the Chemical Society,1944,p. 667,670.
[2]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.

5
[ 6338-41-6 ]
5-hydroxymethyl-tetrahydro-furan-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of the Chemical Society,1945,p. 1,3.
[2]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.

6
[ 108153-38-4 ]
[ 6338-41-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1953,vol. 580,p. 169,187.

7
[ 50-99-7 ]
[ 6338-41-6 ]

References: [1]Journal of the Agricultural Chemical Society of Japan,1929,vol. 5,p. 11.
Chemisches Zentralblatt,1930,vol. 101,p. 1089.
[2]Journal of the Agricultural Chemical Society of Japan,1931,vol. 7,p. 62.
Chemisches Zentralblatt,1933,vol. 104,p. 1536.
[3]Patent: US2018/57897,2018,A1 .
[4]Patent: US2018/57897,2018,A1 .

8
[ 133-42-6 ]
[ 6338-41-6 ]
[ 20246-35-9 ]

References: [1]Chemische Berichte,1894,vol. 27,p. 1535.

9
[ 99187-01-6 ]
[ 6338-41-6 ]

References: [1]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 101,106.
Chem.Abstr.,1959,p. 18934.

10
[ 57-50-1 ]
[ 6338-41-6 ]

References: [1]Journal of the Agricultural Chemical Society of Japan,1931,vol. 7,p. 62.
Chemisches Zentralblatt,1933,vol. 104,p. 1536.
[2]Journal of the Agricultural Chemical Society of Japan,1929,vol. 5,p. 11.
Chemisches Zentralblatt,1930,vol. 101,p. 1089.

11
[ 67-56-1 ]
[ 6338-41-6 ]
[ 36802-01-4 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

12
[ 6338-41-6 ]
[ 13529-17-4 ]
[ 3238-40-2 ]

References: [1]Polish Journal of Chemistry,1994,vol. 68,p. 693 - 698.
[2]Polish Journal of Chemistry,1994,vol. 68,p. 693 - 698.
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 6515 - 6518.
Angew. Chem.,2014,vol. 126,p. 6633 - 6636,4.
[4]ChemCatChem,2016,vol. 8,p. 3636 - 3643.
[5]Green Chemistry,2019,vol. 21,p. 4090 - 4099.

13
[ 6338-41-6 ]
[ 3238-40-2 ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; sodium carbonate; In water; at 95℃; for 7h;	Catalytic Reaction Of HMF To FDCA For this reaction, Na2C03 was used as the base. 1 g of extracted HMF was first dissolved in 5 g of water. The Na2C03 was separately prepared by dissolving Na2C03 in water. The oxidation catalyst was then added follow by the HMF solution at ambient room temperature. With oxygen gas bubbling, the solution was first heated to 50C for 2 hours, and HMF was fully converted to HFCA. After that, the reaction was heat to 95C and kept for 7 hour. The pH of the aqueous solution was then adjusted to 1 and FDCA was precipitated from the solution. The precipitate was filtered and washed with ethanol.
	With Ru/Pt on active carbon; oxygen; In water; at 90℃; under 1034.32 Torr; for 20h;Alkaline conditions;	This examples shows the oxidation of the FDCA precursor (here FFCA) into FDCA. A series of reactions were prepared as shown in the following Table. All reactions contained 100 mM of commercial FFCA. The reactions were performed in screw capped vials under air (in all reactions with H2O2 and controls runs 11-13) or under oxygen at about 20 psi. All reactions were incubated for 20 h before samples were analyzed by TLC for product formation. All reactions conversions described in the Table above are based on TLC analysis. For example, >90% indicates the result of TLC analysis where FDCA was detected as the only product. ?About? 50% indicates that FFCA and FDCA spots with similar intensity were observed.
	With oxygen; cobalt(II) acetate; manganese(II) acetate; acetic acid; sodium bromide; at 180℃; under 42133 Torr; for 1h;	5-hydroxymethyl-2-furoic acid (2.5 g), acetic acid (30 ml), cobalt acetate (0.083 g), sodium bromide (0.07 1 g), and manganese acetate (0.084 g) are mixed in a batch reactor and placed under an excess of oxygen at 800 psig with vigorous mixing for 1 hour at 180 C. LC analysis of the total reaction mixture shows conversion of 5-hydroxym- ethyl-2-furoic acid to thrandicarboxylic acid.

References: [1]Green Chemistry,2017,vol. 19,p. 5548 - 5552.
[2]Bulletin de la Societe Chimique de France,1987,p. 855 - 860.
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 6515 - 6518.
Angew. Chem.,2014,vol. 126,p. 6633 - 6636,4.
[4]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.
[5]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.
[6]Green Chemistry,2012,vol. 14,p. 143 - 147.
[7]Angewandte Chemie - International Edition,2014,vol. 53,p. 6515 - 6518.
Angew. Chem.,2014,vol. 126,p. 6633 - 6636,4.
[8]Patent: WO2015/41601,2015,A1 .Location in patent: Page/Page column 31-32.
[9]Patent: US9321744,2016,B1 .
[10]Patent: US9321744,2016,B1 .
[11]Patent: US9321744,2016,B1 .
[12]Patent: US9321744,2016,B1 .
[13]Patent: US9321744,2016,B1 .
[14]Patent: TWI542583,2016,B .
[15]Patent: TWI542583,2016,B .
[16]Patent: TWI542583,2016,B .
[17]Patent: TWI542583,2016,B .
[18]Patent: TWI542583,2016,B .
[19]Patent: US2017/50944,2017,A1 .Location in patent: Paragraph 0083-0084.
[20]ChemSusChem,2017,vol. 10,p. 3524 - 3528.
[21]Green Chemistry,2017,vol. 19,p. 4660 - 4665.
[22]Catalysis science and technology,2018,vol. 8,p. 164 - 175.
[23]Patent: US2018/57897,2018,A1 .Location in patent: Paragraph 0060.
[24]Green Chemistry,2019,vol. 21,p. 4090 - 4099.
[25]ChemSusChem,2019.

14
[ 2280-44-6 ]
[ 657-27-2 ]
[ 88-14-2 ]
[ 6338-41-6 ]
5-(3,4,5,6-tetrahydropyrid-3-ylidenemethyl)-2-furanmethanol [ No CAS ]
1-deoxy-1-(N⁶-lysino)-D-fructose [ No CAS ]
(+/-)-2-formyl-5-(hydroxymethyl)pyrrole-1-norleucine [ No CAS ]
[ 34371-14-7 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1984,vol. 38,p. 689 - 694.

15
[ 2144-38-9 ]
[ 6338-41-6 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

16
[ 83598-30-5 ]
[ 6338-41-6 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

17
[ 67-47-0 ]
[ 823-82-5 ]
[ 13529-17-4 ]
[ 6338-41-6 ]

Yield	Reaction Conditions	Operation in experiment
9%; 60%; 7%	With iron(II) phthalocyanine; In aq. phosphate buffer; at 37 - 80℃; for 16.0833h;pH 7;	HMF (100 mM) was added to KPi buffer (500 mM pH 7.0). GOase M35 (103p1 of3.3mg/mL), PaoABC (ipI of 28.9mg/mL) and a metal complex (see Table 4) were added at 37 00 and the pH was continuously adjusted with NaHCO3 for a period of 16 hours. The reaction was heated to 80 00 for 5 minutes and left to cool. The solution containing denatured protein was centrifuged and the supernatant removed and analysed by RP20 HPLC.

References: [1]Patent: WO2016/202858,2016,A1 .Location in patent: Page/Page column 51; 52.
[2]Journal of Carbohydrate Chemistry,1997,vol. 16,p. 299 - 309.

18
[ 6338-41-6 ]
[ 13529-17-4 ]

References: [1]ACS Catalysis,2019,vol. 9,p. 8306 - 8315.
[2]Journal of Carbohydrate Chemistry,1997,vol. 16,p. 299 - 309.
[3]Chemical Science,2015,vol. 6,p. 4940 - 4945.
[4]Green Chemistry,2017,vol. 19,p. 4660 - 4665.
[5]Journal of the American Chemical Society,2017,vol. 139,p. 15584 - 15587.

19
[ 6338-41-6 ]
[ 105850-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; In toluene; for 5h;Heating / reflux;	Dimethylformamide (1 ml) was added to a mixture of 5- hydroxymethylfurancarboxylic acid (100 mmol), thionyl chloride (150 mmol) and toluene (100 ml), and the resulting reaction mixture was refluxed for 5 hrs. After completion of the reaction, the reaction solution was distilled at atmospheric pressure to remove the solvent and excessive thionyl chloride, thus generating 5- chloromethylfurancarbonylchloride (IV) in a liquid state. To the obtained compound, anhydrous methanol (50 ml) was added at room temperature and then powdered potassium carbonate (200 mmol) was added, followed by mixing with stirring for 1 hr. After removing methanol using a vacuum evaporator, water (100 ml) and ethylacetate (100 ml) were. added to the residue to separate an organic layer. The organic layer was dried with magnesium sulfate and filtered. After removing the organic solvent from the filtrate using a vacuum evaporator, the residue was subjected to column chlromatography, thus giving 5- chloromethylfuran-2-carboxylic acid methylester with a yield of 70percent.
	With thionyl chloride; In benzene;Reflux; Inert atmosphere;	5-(hydroxymethyl)furan-2-carboxylic acid (1.15 g, 8.09 mmol) was diluted with Benzene (81 ml). Thionyl chloride (3.54 ml, 48.6 mmol) was added and then the reaction is heated to reflux. The reaction was stirred overnight. The reaction was concentrated and carried on directly to the next step. The dichloride was dissolved in dichloromethane (1 12 mL) and 4- methylthiazol-2-amine (1.302 g, 1 1.17 mmol) was added followed by DMAP (0.138 g, 1.117 mmol) and triethylamine (3.89 ml, 27.9 mmol). The reaction was stirred at room temperature until complete by LC-MS analysis. The reaction was concentrated and purified by silica gel chromatography to yield the furanyl chloride (1.61 g) in 56percent yield over two steps. The furanyl chloride (63.1 mg, 0.246 mmol) was dissolved in dimethylformamide (2.5 mL). Sodium iodide (3.68 mg, 0.025 mmol), potassium carbonate (51.0 mg, 0.369 mmol) and 3-chlorophenol (31.6 mg, 0.246 mmol) were added and the reaction was stirred at room temperature until complete by LC-MS analysis. The reaction was concentrated under vacuum and purified by silica gel chromatography to provide 5- ((3-chlorophenoxy)methyl)-N-(4-methylthiazol-2-yl)furan-2-carboxamide (56 mg) (Compound-62) in 65percent yield.
	With thionyl chloride; In N,N-dimethyl-formamide; toluene; for 5h;Heating / reflux;	Dimethylformamide (1 ml) was added to a mixture of 5-hydroxymethylfurancarboxylic acid (100 mmol), thionyl chloride (150 mmol) and toluene (100 ml), and the resulting reaction mixture was refluxed for 5 hrs. After completion of the reaction, the reaction solution was distilled at atmospheric pressure to remove the solvent and excessive thionyl chloride, thus generating 5-chloromethylfurancarbonylchloride (IV) in a liquid state. To the obtained compound, anhydrous methanol (50 ml) was added at room temperature and then powdered potassium carbonate (200 mmol) was added, followed by mixing with stirring for 1 hr. After removing methanol using a vacuum evaporator, water (100 ml) and ethylacetate (100 ml) were added to the residue to separate an organic layer. The organic layer was dried with magnesium sulfate and filtered. After removing the organic solvent from the filtrate using a vacuum evaporator, the residue was subjected to column chromatography, thus giving 5-chloromethylfuran-2-carboxylic acid methylester with a yield of 70percent.

References: [1]Russian Journal of General Chemistry,1999,vol. 69,p. 551 - 556.
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 4844 - 4853.
[3]Patent: WO2004/37804,2004,A1 .Location in patent: Page 12; 22.
[4]Patent: WO2013/32907,2013,A1 .Location in patent: Page/Page column 53.
[5]Patent: US2008/221205,2008,A1 .Location in patent: Page/Page column 6.

Yield	Reaction Conditions	Operation in experiment
23.4%	With formaldehyd; In water; at 90℃; for 12h;	General procedure: Amberlyst - 15 Dry (manufactured by Organo Corporation) (2006) which is a solid acid catalyst and an aqueous formalin solution (manufactured by Wako Pure Chemical Industries, concentration: about 37 mass percent, methanol added 5 to 10 mass percent) (524) And mixed to obtain a mixture.Next, the obtained mixture was stirred at a reaction temperature (here, 90 ° C.) for 1 minute and then 2-furaldehyde (manufactured by Acronix) (1 mmol) was added. The resulting mixture was heated at reaction temperature 90 ° C. for 12 hours. After completion of heating, the product was analyzed by liquid chromatography to identify 5-hydroxymethyl-2-furaldehyde, yield (percent) {(molar amount of produced 5-hydroxymethyl-2-furaldehyde / Molar amount of 2-furaldehyde) × 100} was determined. The selectivity (percent) {(molar amount of formed 5-hydroxymethyl-2-furaldehyde) / molar ratio of molar distribution of 5-hydroxymethyl-2-furaldehyde to molar amount of consumed 2-furaldehyde / Molar amount of consumed 2-furaldehyde) × 100}. The selectivity is roughly synonymous with the morphology of 5-hydroxymethyl-2-furaldehyde in the product. The results are shown in Table 1. Amberlyst - 15 Dry has a group represented by the formula (5) in which n is 1.

22
5-acetoxymethyl-furfurol [ No CAS ]
[ 6338-41-6 ]

References: [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1929,vol. 180,p. 242.
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1929,vol. 180,p. 242.
[3]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1929,vol. 180,p. 242.

23
5-acetoxymethyl-pyromucic acid [ No CAS ]
[ 6338-41-6 ]

References: [1]Chemische Berichte,1903,vol. 36,p. 2589.

24
5-bromomethyl-pyromucic acid [ No CAS ]
[ 6338-41-6 ]

References: [1]American Chemical Journal,1893,vol. 15,p. 184.

25
5-oxymethyl-pyromucohydroxamic acid [ No CAS ]
[ 6338-41-6 ]

References: [1]Gazzetta Chimica Italiana,1912,vol. 42 II,p. 588.

26
[ 2144-37-8 ]
[ 6338-41-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.
[2]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

27
[ 1883-75-6 ]
[ 823-82-5 ]
[ 67-47-0 ]
[ 6338-41-6 ]
[ 3238-40-2 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 229 - 231.

28
[ 6338-41-6 ]
[ 354112-67-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.

29
[ 6338-41-6 ]
5-{4-[(4-fluoro-phenyl)-phenyl-methylene]-piperidin-1-ylmethyl}-tetrahydro-furan-2-carboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.

30
[ 6338-41-6 ]
[ 354112-68-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.

31
[ 6338-41-6 ]
5-{4-[(4-fluoro-phenyl)-phenyl-methylene]-piperidin-1-ylmethyl}-tetrahydro-furan-2-carboxylic acid amide; hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1313 - 1316.

32
[ 6338-41-6 ]
[ 105850-78-0 ]

References: [1]Russian Journal of General Chemistry,1999,vol. 69,p. 551 - 556.

33
[ 6338-41-6 ]
N,N-diethyl-5-(diethoxyphosphorylmethyl)-2-furancarboxamide [ No CAS ]

References: [1]Russian Journal of General Chemistry,1999,vol. 69,p. 551 - 556.

34
[ 6338-41-6 ]
5-chloromethyl-furan-2-carboxylic acid (2-{2-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-ethyldisulfanyl}-ethyl)-methyl-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4844 - 4853.

35
[ 6338-41-6 ]
5-chloromethyl-furan-2-carboxylic acid {6-[(4-amino-6,7-dimethoxy-quinazolin-2-yl)-methyl-amino]-hexyl}-methyl-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4844 - 4853.

36
[ 611-13-2 ]
[ 6338-41-6 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

37
[ 6338-41-6 ]
[ 2144-37-8 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

38
[ 6338-41-6 ]
[ 2144-38-9 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

39
[ 6338-41-6 ]
[ 30990-14-8 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

40
[ 6338-41-6 ]
[ 83598-30-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

41
[ 6338-41-6 ]
[ 36802-00-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 825 - 829.

Historical Records

Technical Information

• Appel Reaction • Arndt-Eistert Homologation • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Hunsdiecker-Borodin Reaction • Hydride Reductions • Jones Oxidation • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Preparation of Alcohols • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Alcohols • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Ritter Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Swern Oxidation • Ugi Reaction

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 6338-41-6

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CAS No.: 6338-41-6

Product Citations

Alternative Products

Product Details of 5-Hydroxymethyl-2-furancarboxylic acid

Safety of 5-Hydroxymethyl-2-furancarboxylic acid

Application In Synthesis of 5-Hydroxymethyl-2-furancarboxylic acid

[ 6338-41-6 ] Synthesis Path-Downstream 1~41

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