Product Name

  • Name

    2,5-Dimethoxytetrahydrofuran

  • EINECS 211-797-1
  • CAS No. 696-59-3
  • Article Data12
  • CAS DataBase
  • Density 1.02 g/cm3
  • Solubility 350 g/L (20 °C) in water
  • Melting Point -45 °C
  • Formula C6H12O3
  • Boiling Point 145.7 °C at 760 mmHg
  • Molecular Weight 132.159
  • Flash Point 35 °C
  • Transport Information UN 1993 3/PG 3
  • Appearance Colorless to light yellow liquid
  • Safety 26-36-36/37/39-16
  • Risk Codes 10-36/37/38-36-20/21
  • Molecular Structure Molecular Structure of 696-59-3 (2,5-Dimethoxytetrahydrofuran)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 2,5-Bis(methyloxy)tetrahydrofuran;Dimethoxytetrahydrofuran;NSC 7911;Tetrahydro-2,5-dimethoxyfuran;
  • PSA 27.69000
  • LogP 0.74180

Synthetic route

methanol
67-56-1

methanol

(1E,3E)-1,4-Bis-trimethylsilanyloxy-buta-1,3-diene
79668-89-6

(1E,3E)-1,4-Bis-trimethylsilanyloxy-buta-1,3-diene

cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

Conditions
ConditionsYield
With hydrogenchloride at -70 - -65℃;56%
methanol
67-56-1

methanol

cyclohexa-1,3-diene
1165952-91-9

cyclohexa-1,3-diene

A

cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

B

succinaldehyde bis(dimethyl acetal)
6922-39-0

succinaldehyde bis(dimethyl acetal)

C

4,4-dimethoxybutanal
56681-97-1

4,4-dimethoxybutanal

Conditions
ConditionsYield
With 2,3-dimercapto-succinic acid; ozone 1) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

5-amino-4-cyano-1-methylpyrazole
5334-41-8

5-amino-4-cyano-1-methylpyrazole

4-cyano-1-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazole
146885-48-5

4-cyano-1-methyl-5-(1H-pyrrol-1-yl)-1H-pyrazole

Conditions
ConditionsYield
With acetic acid for 0.5h; Heating;100%
In acetic acid for 0.5h; Heating;95%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

1,4-Dibromo-1,4-dimethoxy-butane
86428-39-9

1,4-Dibromo-1,4-dimethoxy-butane

Conditions
ConditionsYield
100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

1,4-Diiodo-1,4-dimethoxy-butane
86428-40-2

1,4-Diiodo-1,4-dimethoxy-butane

Conditions
ConditionsYield
100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

thiophenol
108-98-5

thiophenol

1,1,4,4-tetrakis(phenylthio)butane
53480-95-8

1,1,4,4-tetrakis(phenylthio)butane

Conditions
ConditionsYield
With hydrogenchloride for 19.5h;100%
With hydrogenchloride at 25℃; for 7.5h; Yield given;
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

aniline
62-53-3

aniline

1-phenylpyrrole
635-90-5

1-phenylpyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

benzylamine
100-46-9

benzylamine

1-benzyl-1H-pyrrole
2051-97-0

1-benzyl-1H-pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-p-toluenesulfonylpyrrole
17639-64-4

N-p-toluenesulfonylpyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

1H–1–(5–chloro–2–nitrophenyl)pyrrole
311807-83-7

1H–1–(5–chloro–2–nitrophenyl)pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

1-amino-naphthalene
134-32-7

1-amino-naphthalene

N-naphthylpyrrole
92163-14-9

N-naphthylpyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

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-aminoisoindoline-1,3-dione

2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(N-pyrrolyl)isoindoline-1,3-dione

2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-(N-pyrrolyl)isoindoline-1,3-dione

Conditions
ConditionsYield
In acetic acid for 2h; Heating / reflux;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

4-amino-1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole
850362-77-5

4-amino-1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-1H-indazole

1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-4-(pyrrol-1-yl)-1H-indazole
850363-10-9

1-tert-butoxycarbonyl-5-[4-(1-tert-butoxycarbonylamino-1-methylethyl)phenyl]-4-(pyrrol-1-yl)-1H-indazole

Conditions
ConditionsYield
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

2-(2,2-dibromo-1-(trifluoromethyl)vinyl)-phenylamine

cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

1-[2-(2,2-dibromo-1-trifluoromethyl-vinyl)-phenyl]-1H-pyrrole
1146543-24-9

1-[2-(2,2-dibromo-1-trifluoromethyl-vinyl)-phenyl]-1H-pyrrole

Conditions
ConditionsYield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

2-(2,2-dibromo-vinyl)-naphthalen-2-ylamine
886853-74-3

2-(2,2-dibromo-vinyl)-naphthalen-2-ylamine

1-[2-(2,2-dibromo-vinyl)-naphthalen-1-yl]-1H-pyrrole
1146543-29-4

1-[2-(2,2-dibromo-vinyl)-naphthalen-1-yl]-1H-pyrrole

Conditions
ConditionsYield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

2-(2,2-dibromo-1-deuteriovinyl)-phenylamine
1006059-97-7

2-(2,2-dibromo-1-deuteriovinyl)-phenylamine

C12H8(2)HBr2N
1146543-46-5

C12H8(2)HBr2N

Conditions
ConditionsYield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

5-benzyloxy-2-(2,2-dibromo-vinyl)-phenylamine
886853-78-7

5-benzyloxy-2-(2,2-dibromo-vinyl)-phenylamine

1-[5-benzyloxy-2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole
1146543-27-2

1-[5-benzyloxy-2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole

Conditions
ConditionsYield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

5-chloro-2-(2,2-dibromo-vinyl)-phenylamine
1067249-68-6

5-chloro-2-(2,2-dibromo-vinyl)-phenylamine

1-[5-chloro-2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole
1146543-28-3

1-[5-chloro-2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole

Conditions
ConditionsYield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

C14H12BrN
1006059-96-6

C14H12BrN

1-[2-(2-bromo-2-phenyl-vinyl)-phenyl]-1H-pyrrole
1146543-49-8

1-[2-(2-bromo-2-phenyl-vinyl)-phenyl]-1H-pyrrole

Conditions
ConditionsYield
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Inert atmosphere;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

2-bromo-5-fluoroaniline
1003-99-2

2-bromo-5-fluoroaniline

1-(2-bromo-5-fluorophenyl)-1H-pyrrole
1254221-18-5

1-(2-bromo-5-fluorophenyl)-1H-pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

2-bromo-4-methyl-6-nitroaniline
827-24-7

2-bromo-4-methyl-6-nitroaniline

1-(2-bromo-4-methyl-6-nitrophenyl)-1H-pyrrole
1254221-22-1

1-(2-bromo-4-methyl-6-nitrophenyl)-1H-pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

methyl 4-amino-3,5-diiodo-2-methoxybenzoate

methyl 4-amino-3,5-diiodo-2-methoxybenzoate

methyl 3,5-diiodo-2-methoxy-4-(1H-pyrrol-1-yl)benzoate

methyl 3,5-diiodo-2-methoxy-4-(1H-pyrrol-1-yl)benzoate

Conditions
ConditionsYield
With acetic acid at 20 - 80℃; for 4h;100%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

2-iodo-5-methylaniline
13194-69-9

2-iodo-5-methylaniline

1-(2-iodo-4-methylphenyl)-1H-pyrrole
1323975-44-5

1-(2-iodo-4-methylphenyl)-1H-pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

methyl 3-amino-4-iodobenzoate
412947-54-7

methyl 3-amino-4-iodobenzoate

methyl 3-iodo-4-(1H-pyrrol-1-yl)benzoate

methyl 3-iodo-4-(1H-pyrrol-1-yl)benzoate

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

o-azidoaniline
1005-07-8

o-azidoaniline

1-(2-azidophenyl)-1H-pyrrole
125187-91-9

1-(2-azidophenyl)-1H-pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

p-toluidine
106-49-0

p-toluidine

1-(4-methylphenyl)-1H-pyrrole
827-60-1

1-(4-methylphenyl)-1H-pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

4-methoxy-aniline
104-94-9

4-methoxy-aniline

1-(p-methoxyphenyl)pyrrole
5145-71-1

1-(p-methoxyphenyl)pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

4,5-dichloro-2-nitroaniline
6641-64-1

4,5-dichloro-2-nitroaniline

1H–1–(4,5–dichloro–2–nitrophenyl)pyrrole
59194-30-8

1H–1–(4,5–dichloro–2–nitrophenyl)pyrrole

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

methyl 3-amino-4-(3-thienyl)-1H-pyrrole-2-carboxylate
683212-56-8

methyl 3-amino-4-(3-thienyl)-1H-pyrrole-2-carboxylate

methyl 4'-(3-thienyl)-1'H-1,3'-bipyrrole-2'-carboxylate
757188-99-1

methyl 4'-(3-thienyl)-1'H-1,3'-bipyrrole-2'-carboxylate

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

methyl 3-amino-4-(p-chlorophenyl)-1H-pyrrole-2-carboxylate
683212-52-4

methyl 3-amino-4-(p-chlorophenyl)-1H-pyrrole-2-carboxylate

methyl 4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carboxylate
757189-01-8

methyl 4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carboxylate

Conditions
ConditionsYield
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

cis,trans-2,5-dimethoxytetrahydrofuran

ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate
890656-26-5

ethyl 3-amino-4-bromo-1H-pyrrole-2-carboxylate

ethyl 4'-bromo-1'H-1,3'-bipyrrole-2'-carboxylate
918331-09-6

ethyl 4'-bromo-1'H-1,3'-bipyrrole-2'-carboxylate

Conditions
ConditionsYield
With 4-chlorpyridine hydrochloride In 1,4-dioxane at 100℃; Clauson-Kaas reaction;99%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

benzenesulfonamide
98-10-2

benzenesulfonamide

N-phenylsulfonylpyrrole
16851-82-4

N-phenylsulfonylpyrrole

Conditions
ConditionsYield
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%

2,5-DIMETHOXYTETRAHYDROFURAN Chemical Properties

MF: C6H12O3
MW: 132.16
EINECS: 211-797-1
mp:  -45 °C 
bp:  145-147 °C(lit.)
density:  1.023 g/mL at 20 °C(lit.)
refractive index:  n20/D 1.418
Fp:  95 °F
storage temp:  Flammables area
Water Solubility:  350 g/L (20 oC)
BRN:  104261

2,5-DIMETHOXYTETRAHYDROFURAN Toxicity Data With Reference

1、RTECS#: CAS# 696-59-3: None listed 
2、LD50/LC50: RTECS: Not available. Other: Inhalation, rat: LC50 > 6.2mg/l/4H Oral, rat: LD50 = 2040 mg/kg Skin, rabbit: LD50 > 400 mg/kg 
3、Carcinogenicity: 2,5-Dimethoxytetrahydrofuran, mixture of cis- and trans isomers - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. 
4、Other: The toxicological properties have not been fully investigated.

2,5-DIMETHOXYTETRAHYDROFURAN Safety Profile

Hazard Codes:  Xi,Xn
Risk 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
HazardClass:  3
PackingGroup:  III
HS Code:  29321900 .

2,5-DIMETHOXYTETRAHYDROFURAN Specification

Handling and Storage of 2,5-DIMETHOXYTETRAHYDROFURAN
1、Handling: Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Take precautionary measures against static discharges. Use only in a chemical fume hood. 
2、Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Flammables-area. 
 

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