696-59-3

Basic information

• Product Name: 2,5-Dimethoxytetrahydrofuran
• Synonyms: 2,5-Dimethoxytetrahydrofuran,c&t;2,5-dimethoxytetrahydrofuran,mixtureofcis-andtransisomers;cis,trans-2,5-Dimethoxytetrahydrofuran;dimethoxytetrahydrofuran(tetrahydro-2,5-demethoxy-furan);Protectol DMT;2,5-Dimethoxytetrahydrofuran,mixture of cis and trans isomers ,99％;2,5-Dimethoxytetrahy;2,5-DiMethoxytetrahydrofuran, Mixture of cis- and trans isoMers, 99% 100GR
• CAS NO: 696-59-3
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• EINECS: 211-797-1
• Product Categories: Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Oxygen cyclic compounds;Aromatic Hydrocarbons (substituted) & Derivatives;Furan&Benzofuran;Furans;Building Blocks;Heterocyclic Building Blocks;Pharmaceutical
• Mol File: 696-59-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: -45 °C
• Boiling Point: 145-147 °C(lit.)
• Flash Point: 95 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.023 g/mL at 20 °C(lit.)
• Vapor Pressure: 6.06mmHg at 25°C
• Refractive Index: n20/D 1.418
• Storage Temp.: Flammables area
• Solubility: 300g/l
• Explosive Limit: 2.0-12.3%(V)
• Water Solubility: 350 g/L (20 ºC)
• Sensitive: Air & Light Sensitive
• BRN: 104261
• CAS DataBase Reference: 2,5-Dimethoxytetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethoxytetrahydrofuran(696-59-3)
• EPA Substance Registry System: 2,5-Dimethoxytetrahydrofuran(696-59-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38-36-20/21
• Safety Statements: 26-36-36/37/39-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 696-59-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

2,5-Dimethoxytetrahydrofuran is a tetrahydrofuran derivative that finds application in proteomics research and in organic synthesis. It is also used as an intermediate for atropine sulfate, which is an anticholinergic drug. Further, it acts as a precursor of butanediol. In addition to this, it is used as a photographic hardener and as disinfectant in formulations.

InChI:InChI=1/C6H12O3/c1-7-5-3-4-6(8-2)9-5/h5-6H,3-4H2,1-2H3/t5-,6+

Synthetic route

methanol (67-56-1) + (1E,3E)-1,4-Bis-trimethylsilanyloxy-buta-1,3-diene (79668-89-6) → cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3)

Conditions	Yield
With hydrogenchloride at -70 - -65℃;	56%

methanol (67-56-1) + cyclohexa-1,3-diene (1165952-91-9) → cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + succinaldehyde bis(dimethyl acetal) (6922-39-0) + 4,4-dimethoxybutanal (56681-97-1)

Conditions	Yield
With 2,3-dimercapto-succinic acid; ozone 1) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 5-amino-4-cyano-1-methylpyrazole (5334-41-8) → 4-cyano-1-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazole (146885-48-5)

Conditions	Yield
With acetic acid for 0.5h; Heating;	100%
In acetic acid for 0.5h; Heating;	95%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + trimethylsilyl bromide (2857-97-8) → 1,4-Dibromo-1,4-dimethoxy-butane (86428-39-9)

Conditions	Yield
	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + trimethylsilyl iodide (16029-98-4) → 1,4-Diiodo-1,4-dimethoxy-butane (86428-40-2)

Conditions	Yield
	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + thiophenol (108-98-5) → 1,1,4,4-tetrakis(phenylthio)butane (53480-95-8)

Conditions	Yield
With hydrogenchloride for 19.5h;	100%
With hydrogenchloride at 25℃; for 7.5h; Yield given;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + aniline (62-53-3) → 1-phenylpyrrole (635-90-5)

Conditions	Yield
With bismuth (III) nitrate pentahydrate at 90℃; for 0.0833333h; Microwave irradiation; neat (no solvent);	100%
With bismuth (III) nitrate pentahydrate at 20℃; for 0.0833333h; Sonication; Neat (no solvent);	99%
With copper dichloride In water Reflux;	99%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + benzylamine (100-46-9) → 1-benzyl-1H-pyrrole (2051-97-0)

Conditions	Yield
In pyridine; acetic acid Heating;	100%
With phosphorus pentoxide In toluene at 110℃; for 0.166667h;	96%
With water at 140℃; for 0.333333h; Paal-Knorr pyrrole synthesis; Microwave irradiation;	92%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + toluene-4-sulfonamide (70-55-3) → N-p-toluenesulfonylpyrrole (17639-64-4)

Conditions	Yield
With phosphorus pentoxide In toluene at 110℃; for 0.333333h;	100%
With scandium tris(trifluoromethanesulfonate) In 1,4-dioxane at 100℃; for 0.666667h; Clauson-Kaas condensation;	95%
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h;	90%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 5-chloro-2-nitroaniline (1635-61-6) → 1H–1–(5–chloro–2–nitrophenyl)pyrrole (311807-83-7)

Conditions	Yield
With 4-chlorpyridine hydrochloride In 1,4-dioxane Clauson-Kaas Synthesis; Reflux;	100%
In acetic acid for 1h; Heating;	95%
With acetic acid for 1.5h; Reflux;	92%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 1-amino-naphthalene (134-32-7) → N-naphthylpyrrole (92163-14-9)

Conditions	Yield
With bismuth (III) nitrate pentahydrate at 75℃; for 0.0833333h; Microwave irradiation; neat (no solvent);	100%
With bismuth (III) nitrate pentahydrate at 20℃; for 0.0833333h; Sonication; Neat (no solvent);	95%
With scandium tris(trifluoromethanesulfonate) In 1,4-dioxane at 100℃; for 0.5h; Clauson-Kaas condensation;	94%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-aminoisoindoline-1,3-dione (253168-83-1) → 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(N-pyrrolyl)isoindoline-1,3-dione

Conditions	Yield
In acetic acid for 2h; Heating / reflux;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 4-amino-1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole (850362-77-5) → 1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-4-(pyrrol-1-yl)-1H-indazole (850363-10-9)

Conditions	Yield
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran; 4-amino-1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole With acetic acid In methanol at 60℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In methanol; water	100%

2-(2,2-dibromo-1-(trifluoromethyl)vinyl)-phenylamine (863870-47-7) + cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) → 1-[2-(2,2-dibromo-1-trifluoromethyl-vinyl)-phenyl]-1H-pyrrole (1146543-24-9)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-(2,2-dibromo-vinyl)-naphthalen-2-ylamine (886853-74-3) → 1-[2-(2,2-dibromo-vinyl)-naphthalen-1-yl]-1H-pyrrole (1146543-29-4)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-(2,2-dibromo-1-deuteriovinyl)-phenylamine (1006059-97-7) → C12H8(2)HBr2N (1146543-46-5)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 5-benzyloxy-2-(2,2-dibromo-vinyl)-phenylamine (886853-78-7) → 1-[5-benzyloxy-2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole (1146543-27-2)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 5-chloro-2-(2,2-dibromo-vinyl)-phenylamine (1067249-68-6) → 1-[5-chloro-2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole (1146543-28-3)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + C14H12BrN (1006059-96-6) → 1-[2-(2-bromo-2-phenyl-vinyl)-phenyl]-1H-pyrrole (1146543-49-8)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-bromo-5-fluoroaniline (1003-99-2) → 1-(2-bromo-5-fluorophenyl)-1H-pyrrole (1254221-18-5)

Conditions	Yield
With water; acetic acid In 1,2-dichloro-ethane at 80℃; Paal-Knorr pyrrole synthesis; Inert atmosphere;	100%
With acetic acid for 1h; Reflux;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-bromo-4-methyl-6-nitroaniline (827-24-7) → 1-(2-bromo-4-methyl-6-nitrophenyl)-1H-pyrrole (1254221-22-1)

Conditions	Yield
With acetic acid for 2h; Paal-Knorr pyrrole synthesis; Inert atmosphere; Reflux;	100%
With acetic acid at 120℃; for 2h;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + methyl 4-amino-3,5-diiodo-2-methoxybenzoate → methyl 3,5-diiodo-2-methoxy-4-(1H-pyrrol-1-yl)benzoate

Conditions	Yield
With acetic acid at 20 - 80℃; for 4h;	100%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-iodo-5-methylaniline (13194-69-9) → 1-(2-iodo-4-methylphenyl)-1H-pyrrole (1323975-44-5)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; for 12h; Paal-Knorr Pyrrole Synthesis;	99.2%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + methyl 3-amino-4-iodobenzoate (412947-54-7) → methyl 3-iodo-4-(1H-pyrrol-1-yl)benzoate

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; for 12h; Paal-Knorr Pyrrole Synthesis;	99.2%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + o-azidoaniline (1005-07-8) → 1-(2-azidophenyl)-1H-pyrrole (125187-91-9)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; for 6h;	99%
In acetic acid at 80℃; for 0.75h;	80%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + p-toluidine (106-49-0) → 1-(4-methylphenyl)-1H-pyrrole (827-60-1)

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane for 24h; Clauson-Kaas Synthesis; Reflux;	99%
In water at 150℃; for 0.5h; Paal-Knorr condensation; Microwave irradiation;	98%
With iron(III) chloride heptahydrate In water at 60℃; Paal-Knorr pyrrole synthesis;	95%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 4-methoxy-aniline (104-94-9) → 1-(p-methoxyphenyl)pyrrole (5145-71-1)

Conditions	Yield
In water at 150℃; for 0.5h; Paal-Knorr condensation; Microwave irradiation;	99%
With magnesium iodide etherate In acetonitrile at 80℃; for 2h; Clauson-Kaas pyrrole synthesis; chemoselective reaction;	98%
With acetic acid Reflux;	98%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 4,5-dichloro-2-nitroaniline (6641-64-1) → 1H–1–(4,5–dichloro–2–nitrophenyl)pyrrole (59194-30-8)

Conditions	Yield
With acetic acid for 4h; Reflux;	99%
In acetic acid for 0.133333h; Heating; Irradiation;	86%
With acetic acid at 120℃; for 2h; Inert atmosphere;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + methyl 3-amino-4-(3-thienyl)-1H-pyrrole-2-carboxylate (683212-56-8) → methyl 4'-(3-thienyl)-1'H-1,3'-bipyrrole-2'-carboxylate (757188-99-1)

Conditions	Yield
With 4-chlorpyridine hydrochloride In 1,4-dioxane at 100℃; Clauson-Kaas reaction;	99%
With 4-chlorpyridine hydrochloride In 1,4-dioxane at 100℃; for 1.5h; Clauson-Kaas and Zdenek reaction;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + methyl 3-amino-4-(p-chlorophenyl)-1H-pyrrole-2-carboxylate (683212-52-4) → methyl 4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carboxylate (757189-01-8)

Conditions	Yield
With 4-chlorpyridine hydrochloride In 1,4-dioxane at 100℃; Clauson-Kaas reaction;	99%
With 4-chlorpyridine hydrochloride In 1,4-dioxane at 100℃; for 1.5h; Clauson-Kaas and Zdenek reaction;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate (890656-26-5) → ethyl 4'-bromo-1'H-1,3'-bipyrrole-2'-carboxylate (918331-09-6)

Conditions	Yield
With 4-chlorpyridine hydrochloride In 1,4-dioxane at 100℃; Clauson-Kaas reaction;	99%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + benzenesulfonamide (98-10-2) → N-phenylsulfonylpyrrole (16851-82-4)

Conditions	Yield
In water at 150℃; for 0.5h; Paal-Knorr condensation; Microwave irradiation;	99%
With montmorillonite K-10 at 100℃; for 0.05h; microwave irradiation;	93%
With iron(III) chloride heptahydrate In water at 60℃; for 2h; Paal-Knorr pyrrole synthesis;	90%

Upstream product

• 332-77-4 2,5-dihydro-2,5-dimethoxyfuran 
• 5143-07-7 (2S,5S)-2,5-Dimethoxy-2,5-dihydro-furan 
• 67-56-1 methanol 
• 1165952-91-9 cyclohexa-1,3-diene 
• 79668-89-6 (1E,3E)-1,4-Bis-trimethylsilanyloxy-buta-1,3-diene 

Downstream Products

• 159014-83-2 1-(2-Methanesulfinylmethyl-phenyl)-1H-pyrrole 
• 159014-85-4 1-(2-Methanesulfinylmethyl-4-methyl-phenyl)-1H-pyrrole 
• 159698-27-8 ethyl 5-(1-pyrrolyl)-3,4-diphenylthieno<2,3-c>pyridazine-6-carboxylate 
• 159014-84-3 1-(2-Methanesulfinylmethyl-6-methyl-phenyl)-1H-pyrrole 
• 159014-87-6 1-(2-Methanesulfinylmethyl-4-methoxy-phenyl)-1H-pyrrole 
• 53623-78-2 (S)-4-methyl-2-(1-pyrrolyl)pentanoic acid 
• 116763-08-7 methyl (S)-3-phenyl-2-(1H-pyrrol-1-yl)propanoate 
• 116763-11-2 (S)-3-(4-hydroxyphenyl)-2-pyrrol-1-yl-propionic acid methyl ester 
• 19167-98-7 pyrrol-1-yl-acetic acid 
• 187792-61-6 4,5-Diphenyl-2-pyrrol-1-yl-furan-3-carbonitrile 
• 186390-73-8 1-(2,5-Dimethoxy-4-nitro-phenyl)-1H-pyrrole 
• 187870-25-3 3-(4-chlorophenyl)-4-pyrrol-1-ylbutyric acid 
• 56721-98-3 4,5-dimethoxy-2-pyrrolo-1-nitrobenzene 
• 186390-78-3 1-(2,3,5,6-Tetramethyl-4-nitro-phenyl)-1H-pyrrole 

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