527-69-5

Basic information

• Product Name: 2-Furoyl chloride
• Synonyms: 2-Furanoic acid chloride;2-Furanylcarbonyl chloride;Furan-2-carboxylic chloride;2-Furancarbonyl chloride 2-Furoic acid chloride;2-Furoic acid chloride;Furan-2-carboxylic acid chloride;2-Furoyl chloride, 98+% 100ML;Furoyl chlorid
• CAS NO: 527-69-5
• Molecular Formula: C₅H₃ClO₂
• Molecular Weight: 130.53
• EINECS: 208-422-9
• Product Categories: Pharmaceutical Intermediates
• Mol File: 527-69-5.mol

Chemical Properties

• Melting Point: −2 °C(lit.)
• Boiling Point: 173-174 °C(lit.)
• Flash Point: 185 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.324 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.44mmHg at 25°C
• Refractive Index: n20/D 1.531(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: soluble in Ether,Acetone
• Water Solubility: DECOMPOSES
• Sensitive: Moisture Sensitive
• Merck: 14,4310
• BRN: 110144
• CAS DataBase Reference: 2-Furoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furoyl chloride(527-69-5)
• EPA Substance Registry System: 2-Furoyl chloride(527-69-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: LT9925000
• F: 10-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 527-69-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Furoyl chloride is used as a key intermediate in the synthesis of novel dibenzothiepins, which exhibit antibiofilm activity. These compounds have potential applications in the development of new antibiotics to combat biofilm-related infections.
Used in Analytical Chemistry:
2-Furoyl chloride is used for the characterization of mixtures of polyethoxylated alcohols and their sulfates. It serves as a derivatizing agent to facilitate the analysis and identification of these compounds in complex mixtures.
Used in Organic Synthesis:
2-Furoyl chloride is used in the preparation of S-2-furoyl-O-alkyldithiocarbonic anhydrides, which are valuable intermediates in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.

Synthetic route

2-furanoic acid (88-14-2) → 2-furancarbonyl chloride (527-69-5)

Conditions	Yield
With thionyl chloride for 3h; Heating;	95%
With thionyl chloride In benzene for 18h; Heating;	86%
With thionyl chloride for 0.5h; Heating;	82%

2-amino-4,6-difluoro-benzothiazole (119256-40-5) → 2-furancarbonyl chloride (527-69-5) + furan-2-carboxylic acid (4,6-difluoro-benzothiazol-2-yl)-amide

Conditions	Yield
	A n/a B 81%

1-(2-furyl)-1-ethanone (1192-62-7) → 2-furancarbonyl chloride (527-69-5)

Conditions	Yield
Stage #1: 1-(2-furyl)-1-ethanone With pyridine; disulfur dichloride In chlorobenzene at 20℃; for 2h; Stage #2: With sulfuryl dichloride In chlorobenzene at 20 - 132℃; for 15.5h;	65%
Stage #1: 1-(2-furyl)-1-ethanone With pyridine; sulfur monochloride In chlorobenzene at 75℃; for 2.5h; Stage #2: In chlorobenzene at 137℃; for 19h;
With pyridine; disulfur dichloride at 70 - 138℃; for 21.5h;	44 %Spectr.

pyromucate ethylamine → 2-furancarbonyl chloride (527-69-5) + N,N'-diethyl-furan-2-carboxamidine

Conditions	Yield
With phosphorus pentachloride anschliessend Destillieren;

pyromucate ethylamine → 2-furancarbonyl chloride (527-69-5) + N.N'-diethyl-furfurenylamidine

Conditions	Yield
With phosphorus pentachloride Destillieren des Reaktionsprodukts;

2-furanoic acid (88-14-2) + thionyl chloride → 2-furancarbonyl chloride (527-69-5)

Conditions	Yield
In dichloromethane for 12h; Heating;

2-furanoic acid (88-14-2) + N-cyclohexyl-cyclohexanamine (101-83-7) → 2-furancarbonyl chloride (527-69-5)

Conditions	Yield
With thionyl chloride In dichloromethane

potassium furan-2-carboxylate (20842-02-8) → 2-furancarbonyl chloride (527-69-5)

Conditions	Yield
With oxalyl dichloride In dichloromethane for 3.5h; Cooling with ice; Reflux;

2-furanoic acid (88-14-2) + 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline (3416-93-1) → 2-furancarbonyl chloride (527-69-5)

Conditions	Yield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide

2-furancarbonyl chloride (527-69-5) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → N-<2-(3,4-dimethoxyphenyl)ethyl>furan-2-carboxamide

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 3h;	100%
With triethylamine In chloroform for 2h; Ambient temperature;	73%
neat (no solvent);

2-furancarbonyl chloride (527-69-5) + 3-methyl-piperazine-1-carboxylic acid tert-butyl ester (120737-59-9) → 4-(furan-2-ylcarbonyl)-3-methylpiperazine-1-carboxylic acid tert-butyl ester (146951-98-6)

Conditions	Yield
With triethylamine In chloroform for 48h; Ambient temperature;	100%

2-furancarbonyl chloride (527-69-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-furancarboxamide (95091-92-2)

Conditions	Yield
With pyridine; sodium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;	100%
With triethylamine In dichloromethane Ambient temperature;	92%
With potassium carbonate In 2-methyltetrahydrofuran; water at 0 - 20℃;	92%

2-furancarbonyl chloride (527-69-5) + phenethylamine (64-04-0) → N-phenethylfuran-2-carboxamide (153579-79-4)

Conditions	Yield
With pyridine In acetonitrile at 20℃; for 3h;	100%
In dichloromethane at 20 - 70℃; for 5h; Alkaline conditions;	44%

tetrahydrofuran (109-99-9) + 2-furancarbonyl chloride (527-69-5) → furan-2-carboxylic acid 4-iodo-butyl ester

Conditions	Yield
With bis(iodozinc)methane at 25℃; Substitution;	100%

(4aR,5R,6R,7R)-1-Benzyl-6-hydroxy-7-methoxy-3,4a,5-trimethyl-1,4,4a,5,6,7-hexahydro-benzo[f]indol-2-one (209332-44-5) + 2-furancarbonyl chloride (527-69-5) → (4AR,5R,6R,7R)-1-Benzyl-6-(2-furancarbonyloxy)-7-methoxy-4a,5,6,7-tetrahydro-3,4a,5-trimethylbenz[f]indol-2(4H)-one

Conditions	Yield
With pyridine at 20℃;	100%

7-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-3,4a,5-trimethyl-4a,5,6,7-tetrahydro-4H-naphtho[2,3-b]furan-2-one (194789-88-3) + 2-furancarbonyl chloride (527-69-5) → Furan-2-carboxylic acid (4aR,5R,6R,7S)-7-(tert-butyl-dimethyl-silanyloxy)-3,4a,5-trimethyl-2-oxo-2,4,4a,5,6,7-hexahydro-naphtho[2,3-b]furan-6-yl ester (902462-74-2)

Conditions	Yield
With dmap In dichloromethane at 20℃; for 3h;	100%

2-furancarbonyl chloride (527-69-5) + 2-amino-6-[2-(methoxymethoxy)phenyl]-5-methyl-4-(3-nitrophenyl)pyridine-3-carbonitrile (925923-78-0) → N-{3-cyano-6-[2-(methoxymethoxy)phenyl]-5-methyl-4-(3-nitrophenyl)pyridin-2-yl}furan-2-carboxamide (925923-79-1)

Conditions	Yield
With pyridine at 20℃; for 20h;	100%

2-furancarbonyl chloride (527-69-5) + (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one (1262676-25-4) → (3S,5S)-7-Oxa-8-cholesten-6-on-3-ol furan-2-carboxylate (1262677-21-3)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 3h;	100%

2-furancarbonyl chloride (527-69-5) + 3-methyl-3,4-dihydro-2(1H)-quinazolinone (24365-65-9) → 6-(furan-2-carbonyl)-3-methyl-3,4-dihydroquinazolin-2(1H)-one

Conditions	Yield
With aluminum (III) chloride In carbon disulfide at 50℃; for 24h; Friedel-Crafts Acylation; Reflux;	100%

2-furancarbonyl chloride (527-69-5) + 2-(4-isopropyl-5-methylhex-3-en-1-yl)-2-(pent-4-yn-1-yl)propane-1,3-diol (930116-67-9) → 2-(4-isopropyl-5-methylhex-3-en-1-yl)-2-(pent-4-yn-1-yl)propane-1,3-diyl bis(furan-2-carboxylate)

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 22h; Schlenk technique; Inert atmosphere;	100%

2-furancarbonyl chloride (527-69-5) + C21H26F2O5 → C26H28F2O7

Conditions	Yield
With diethylamine In butanone at 20 - 30℃; Reagent/catalyst; Solvent;	100%

thiophene (188290-36-0) + 2-furancarbonyl chloride (527-69-5) → (furan-2-yl)(thiophen-2-yl)methanone (20409-51-2)

Conditions	Yield
With ethylaluminum dichloride In dichloromethane at 0℃; for 2h; Inert atmosphere;	99%
With tin(IV) chloride; benzene Behandeln des Reaktionsgemisches mit Wasser;

2-furancarbonyl chloride (527-69-5) + phenol (108-95-2) → furan-2-carboxylic acid phenyl ester (2948-14-3)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Reflux;	99%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Schlenk technique; Inert atmosphere;	85%
With triethylamine In dichloromethane at 20℃; for 0.5h;	77%

2-furancarbonyl chloride (527-69-5) → 2-furoic anhydride (615-08-7)

Conditions	Yield
With water; triethylamine In acetone at 20℃; for 0.5h;	99%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at -10℃; for 3h;	60%
With zinc In N,N-dimethyl-formamide; pentane at 20℃; for 20h; Inert atmosphere; Schlenk technique;	36%

2-furancarbonyl chloride (527-69-5) + 1,2,3-Benzotriazole (95-14-7) → 2-furoyl-1H-1,2,3-benzotriazole (144223-33-6)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;	99%
With triethylamine In dichloromethane for 4h; Heating;	87%
With triethylamine In dichloromethane at 0 - 20℃;

2-furancarbonyl chloride (527-69-5) + (2S,5S)-2,5-bis(methoxymethyl)pyrrolidine (90290-05-4, 93621-94-4, 105016-60-2, 144993-81-7) → (2'S,5'S)-[2',5'-Bis(methoxymethyl)-2',3',4',5'-tetrahydro-1'H-pyrrol-1'-yl](2-furyl)methanone (328575-55-9)

Conditions	Yield
With sodium hydroxide In dichloromethane	99%
With sodium hydroxide In dichloromethane at 20℃; for 24h;	99%
With sodium hydroxide In dichloromethane at 20℃;	99%

2-furancarbonyl chloride (527-69-5) + phenylboronic acid (98-80-6) → (furan-2-yl)(phenyl)methanone (2689-59-0)

Conditions	Yield
With PEG200; sodium carbonate; palladium diacetate at 60℃; for 1h; Suzuki reaction;	99%
With sodium dodecyl-sulfate; potassium carbonate; palladium dichloride In water at 60℃; for 6h;	88%
With potassium carbonate In water; acetone at 50℃; for 0.17h; Catalytic behavior; Suzuki-Miyaura Coupling;	87%

2-furancarbonyl chloride (527-69-5) + beta-methyl aspartate hydrochloride + dichloromethane (75-09-2) → methyl 3-Carboxy-3-(2-furoylamino)propionate

Conditions	Yield
With triethylamine	99%

2-furancarbonyl chloride (527-69-5) + 9,11-epoxy-17α-hydroxy-16α-methyl-3-oxandrosta-1,4-diene-17β-carboxylic acid → 9,11-epoxy-17α-[(2-furanylcarbonyl)oxy]-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Conditions	Yield
Stage #1: 2-furancarbonyl chloride; 9,11-epoxy-17α-hydroxy-16α-methyl-3-oxandrosta-1,4-diene-17β-carboxylic acid With triethylamine In acetone at 25 - 30℃; for 4h; Stage #2: With diethylamine In acetone at 10 - 20℃; for 1h;	99%

2-furancarbonyl chloride (527-69-5) + 7-amino-2-trifluoromethylbenzimidazole dihydrochloride → C13H8F3N3O2 (727663-80-1)

Conditions	Yield
Stage #1: 2-furancarbonyl chloride; 7-amino-2-trifluoromethylbenzimidazole dihydrochloride With pyridine In benzene at 20℃; Stage #2: With methanol; triethylamine for 1h; Heating; Further stages.;	99%

2-furancarbonyl chloride (527-69-5) + 9,11-epoxy-17α-hydroxy-16α-methyl-3-oxandrosta-1,4-diene-17β-carboxylic acid (159264-49-0) + diethylamine (109-89-7) → 9,11-epoxy-17α-[(2-furanylcarbonyl)oxy]16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (948565-89-7)

Conditions	Yield
Stage #1: 2-furancarbonyl chloride; 9,11-epoxy-17α-hydroxy-16α-methyl-3-oxandrosta-1,4-diene-17β-carboxylic acid With triethylamine In acetone at 10 - 30℃; for 4h; Stage #2: diethylamine In acetone at 10 - 20℃; for 1h;	99%

2-furancarbonyl chloride (527-69-5) + (S)-α,α-diphenyl-2-pyrrolidine-2-methanol → furan-2-yl-[(S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]-methanone (1152061-10-3)

Conditions	Yield
Stage #1: (S)-α,α-diphenyl-2-pyrrolidine-2-methanol With caesium carbonate In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2-furancarbonyl chloride In acetonitrile for 4h; Inert atmosphere;	99%

2-furancarbonyl chloride (527-69-5) + 3-amino-N-<(benzyloxy)carbonyl>-D-alanine methyl ester hydrochloride → (R)-2-benzyloxycarbonylamino-3-[(furan-2-carbonyl)amino]propionic acid methyl ester (1182348-97-5)

Conditions	Yield
With pyridine In dichloromethane at -10℃; for 6h;	99%

2-furancarbonyl chloride (527-69-5) + 2-amino-5-iodo-benzamide (32658-67-6) → N-(2-carbamoyl-4-iodophenyl)furan-2-carboxamide (1158963-83-7)

Conditions	Yield
With triethylamine In tetrahydrofuran for 2h;	99%

2-furancarbonyl chloride (527-69-5) + C20H31N3O2 → C25H33N3O4

Conditions	Yield
With triethylamine In dichloromethane	99%

2-furancarbonyl chloride (527-69-5) + 6,6,6-Trifluoro-1-phenyl-4-hexyn-3-ol (94792-93-5) → 6,6,6-trifluoro-1-phenylhex-4-yn-3-yl 2-furoate (1388859-81-1)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	99%

2-furancarbonyl chloride (527-69-5) + 1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one (16619-68-4) → 2-(3-phenylprop-2-ynoyl)phenyl furan-2-carboxylate (1415385-02-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	99%

2-furancarbonyl chloride (527-69-5) + 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2) → GW694301X

Conditions	Yield
Stage #1: 2-furancarbonyl chloride; 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid With triethylamine In acetone at 0 - 5℃; for 3h; Stage #2: With diethylamine In acetone at 40 - 45℃; for 2.5h;	99%

2-furancarbonyl chloride (527-69-5) + 1α,2α,8β,9α,15-pentacetoxy-4β,6β-dihydroxy-3β,13-[4′-(3-carboxybutyl)]nicotinic acid-dicarbolactone-β-dihydroagarofuran → 1α,2α,8β,9α,15-pentacetoxy-6β-(2-furoyloxy)-4β-hydroxy-3β,13-[4′-(3-carboxybutyl)]nicotinic acid-dicarbolactone-β-dihydroagarofuran

Conditions	Yield
With dmap; triethylamine In toluene for 24h; Reflux;	99%

Upstream product

• 88-14-2 2-furanoic acid 
• 119256-40-5 2-amino-4,6-difluoro-benzothiazole 
• 101-83-7 N-cyclohexyl-cyclohexanamine 
• 20842-02-8 potassium furan-2-carboxylate 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 13156-75-7 N,N-dimethyl-2-furfurylcarboxamide 

Downstream Products

• 55984-17-3 2-chloroacetylfuran 
• 15109-94-1 1-(2-furyl)-2-bromoethanone 
• 20409-51-2 (furan-2-yl)(thiophen-2-yl)methanone 
• 67227-32-1 furan-2-carboxylic acid-[3-(2-methyl-piperidino)-propylester]; hydrochloride 
• 36880-64-5 3-(2'-furoyl)aminopyridine 
• 615-11-2 furfuryl 2-furoate 
• 97035-47-7 furan-2-carboxylic acid-(3,4-dimethyl-phenyl ester) 
• 112535-67-8 furan-2-carbothioic acid S-pentachlorophenyl ester 
• 13365-64-5 (4-bromophenyl)(furan-2-yl)methanone 
• 101431-58-7 [2]furyl-(4-pentyloxy-phenyl)-ketone 
• 16386-50-8 5-(furan-2-carbonyloxy)-benzo[1,3]dioxole 
• 17357-60-7 p-tolyl furan-2-carboxylate 
• 69241-43-6 2-(3,4-Dimethoxybenzoyl)furan 
• 101585-00-6 furan-2-carboxylic acid-(1-phenyl-2-pyrrolidino-ethyl ester); hydrochloride 

Relevant articles and documents

One-step Conversion of Amides and Esters to Acid Chlorides with PCl3

A general and efficient iodine-promoted chlorination of amides and esters with phosphorus trichloride is described. For the first time. Various inactivated amides including secondary and tertiary amides were directly converted to the corresponding acid chlorides in one-step. The substrate scope of methyl esters including aromatic and aliphatic esters was also explored under this system. This method is simple, scalable and wide in scope, which provides an approach to preparation of these acid chlorides.

METHOD FOR PREPARATION OF CARBOXYLIC ACID CHLORIDES FROM METHYL KETONES WITH TWO REAGENTS

The invention discloses a method for the preparation of carboxylic acid chlorides starting from methyl ketones with a sulfur chloride and a chlorinating reagent.

METHOD FOR PREPARATION OF CARBOXYLIC ACID CHLORIDES FROM METHYL KETONES

The invention discloses a method for the preparation of carboxylic acid chlorides starting from methyl ketones with a sulfur chloride.

One-Step Conversion of Methyl Ketones to Acyl Chlorides

Treatment of aromatic and heteroaromatic methyl ketones with sulfur monochloride and catalytic amounts of pyridine in refluxing chlorobenzene leads to the formation of acyl chlorides. Both electron-rich and electron-poor aryl methyl ketones can be used as starting materials. The resulting C1-byproduct depends on the precise reaction conditions chosen.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.

Synthesis of heteroaromatic tropeines and heterogeneous binding to glycine receptors

Heteroaromatic carboxylic esters of (nor)tropine were synthesized. Tropine esters displaced [3H]strychnine binding to glycine receptors of rat spinal cord with low Hill slopes. Two-site displacement resulted in nanomolar IC50,1 and m

Biaromatic compound activators of PPARy-type receptors

The invention relates to novel biaromatic compounds which correspond to the general formula (I) below: and also to the method for preparing them and their use in pharmaceutical compositions intended for use in human or veterinary medicine (in dermatology, and also in the field of cardiovascular diseases, immune diseases and/or diseases associated with lipid metabolism), or alternatively in cosmetic compositions.

Benzothiazole derivatives with activity as adenosine receptor ligands

The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.

Synthesis of furan derivatives condensed with carbohydrates

Eight new furan derivatives have been prepared and characterized. These compounds were obtained by condensation of aminosugar and aminocyclitol intermediates with furan derivatives.

11a-hydroxy steroid diester

The present invention relates to 21-(3-carboxy-1-oxopropoxy) -17α-hydroxy-11α-(3,3-dimethyl-1-oxobutoxy)pregna-1,4-diene-3,20 dione and pharmaceutically acceptable salts thereof which are useful steroid prodrugs.