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

Uses

Used in Proteomics Research:
2,5-Dimethoxytetrahydrofuran is used as a research compound for proteomics, the large-scale study of proteins, their structures, and functions. Its role in this field aids in understanding complex biological systems and their interactions.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 2,5-Dimethoxytetrahydrofuran contributes to the creation of various complex organic molecules, which can be utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used as an Intermediate for Atropine Sulfate:
2,5-Dimethoxytetrahydrofuran is used as an intermediate in the production of atropine sulfate, an anticholinergic drug that is primarily used to treat certain conditions affected by an overactive nervous system, such as organophosphate poisoning and bradycardia.
Used as a Precursor of Butanediol:
2,5-Dimethoxytetrahydrofuran also serves as a precursor to butanediol, an organic compound that is used in the manufacturing of various products, including solvents, plasticizers, and fibers.
Used in the Photographic Industry:
2,5-Dimethoxytetrahydrofuran is used as a photographic hardener, enhancing the durability and stability of photographic films and plates.
Used as a Disinfectant in Formulations:
In the field of sanitation and hygiene, 2,5-Dimethoxytetrahydrofuran is utilized as a disinfectant in various formulations, playing a crucial role in maintaining cleanliness and preventing the spread of diseases.

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

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

Downstream Products

• 699-22-9 1-pentyl-1H-pyrrole 
• 589-33-3 N-butylpyrrole 
• 2437-42-5 1-o-tolyl-1H-pyrrole 
• 135985-78-3 1,4-di(1H-pyrrol-1-yl)benzene 
• 635-90-5 1-phenylpyrrole 
• 77381-28-3 2,3-Bis-[1-furan-2-yl-meth-(E)-ylidene]-succinaldehyde 
• 50966-74-0 2-(1H-pyrrol-1-yl)pyridine 
• 88442-97-1 methyl 4-chloro-2-(1H-pyrrol-1-yl)benzoate 
• 70291-26-8 2-chloro-3-(1H-pyrrol-1-yl)pyridine 
• 63647-03-0 (pyrrolyl-1)-2 thiophene carbonitrile-3 
• 111998-67-5 (2S,5S)-1-(2-Hydroxy-1-methyl-2-phenyl-ethyl)-pyrrolidine-2,5-dicarbonitrile 
• 83140-93-6 methyl 3-(1H-pyrrol-1-yl)benzoate 
• 133662-26-7 5-methyl-2-(1H-pyrrol-1-yl)benzoic acid 
• 5096-76-4 3-chloro-6-(1H-pyrrol-1-yl)pyridazine 

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