Product Name

  • Name

    Furan

  • EINECS 203-727-3
  • CAS No. 110-00-9
  • Article Data303
  • CAS DataBase
  • Density 0.942 g/cm3
  • Solubility insoluble in water
  • Melting Point -85.6 °C
  • Formula C4H4O
  • Boiling Point 31.36 °C at 760 mmHg
  • Molecular Weight 68.0752
  • Flash Point -35 °C
  • Transport Information UN 2811 6.1/PG 2
  • Appearance clear colorless liquid
  • Safety 53-45-61
  • Risk Codes 45-12-19-20/22-38-48/22-52/53-68
  • Molecular Structure Molecular Structure of 110-00-9 (Furan)
  • Hazard Symbols ToxicT, HighlyF+
  • Synonyms Divinyleneoxide;Furfuran;Oxacyclopentadiene;Oxole;Tetrole;
  • PSA 13.14000
  • LogP 1.27960

Synthetic route

furfural
98-01-1

furfural

furan
110-00-9

furan

Conditions
ConditionsYield
With carbon dioxide; palladium/alumina at 145℃; under 45004.5 Torr; for 6.5h; Green chemistry;99%
With carbon dioxide; 5% Pd(II)/C(eggshell) at 250℃; under 112511 Torr; Supercritical conditions;98%
With palladium nanoparticles deposited on porous SBA-15 In cyclohexane at 150℃; for 24h; Molecular sieve;96%
2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>
82660-71-7

2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>

A

furan
110-00-9

furan

B

1-oxaspiro<4.4>non-3-en-2-one
5732-90-1

1-oxaspiro<4.4>non-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 130℃;A n/a
B 98%
[3-(1-Benzylamino-pentyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

[3-(1-Benzylamino-pentyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

A

furan
110-00-9

furan

B

(Z)-4-Benzylamino-oct-2-en-1-ol

(Z)-4-Benzylamino-oct-2-en-1-ol

Conditions
ConditionsYield
at 120℃; for 0.25h; Irradiation;A n/a
B 98%
{3-[1-(4-Methoxy-benzylamino)-pentyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl}-methanol

{3-[1-(4-Methoxy-benzylamino)-pentyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl}-methanol

A

furan
110-00-9

furan

B

(Z)-4-(4-Methoxy-benzylamino)-oct-2-en-1-ol

(Z)-4-(4-Methoxy-benzylamino)-oct-2-en-1-ol

Conditions
ConditionsYield
at 120℃; for 0.25h; Irradiation;A n/a
B 98%
[3-(1-Dibenzylamino-pentyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

[3-(1-Dibenzylamino-pentyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

A

furan
110-00-9

furan

B

(Z)-4-Dibenzylamino-oct-2-en-1-ol

(Z)-4-Dibenzylamino-oct-2-en-1-ol

Conditions
ConditionsYield
at 140℃; for 0.166667h; Irradiation;A n/a
B 98%
{3-[4-Benzyloxy-1-(4-methoxy-benzylamino)-butyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl}-methanol

{3-[4-Benzyloxy-1-(4-methoxy-benzylamino)-butyl]-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl}-methanol

A

furan
110-00-9

furan

B

(Z)-7-Benzyloxy-4-(4-methoxy-benzylamino)-hept-2-en-1-ol

(Z)-7-Benzyloxy-4-(4-methoxy-benzylamino)-hept-2-en-1-ol

Conditions
ConditionsYield
at 120℃; for 0.25h; Irradiation;A n/a
B 98%
[3-(4-Benzyloxy-1-dibenzylamino-butyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

[3-(4-Benzyloxy-1-dibenzylamino-butyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol

A

furan
110-00-9

furan

B

(Z)-7-Benzyloxy-4-dibenzylamino-hept-2-en-1-ol

(Z)-7-Benzyloxy-4-dibenzylamino-hept-2-en-1-ol

Conditions
ConditionsYield
at 140℃; for 0.166667h; Irradiation;A n/a
B 98%
2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>
82660-72-8

2',6'-exo-spirodioxatricyclo<5.2.1.02,6>dec-8'-en-3'-one>

A

furan
110-00-9

furan

B

1-oxa-spiro[4.5]dec-3-en-2-one
4435-19-2

1-oxa-spiro[4.5]dec-3-en-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 130℃; under 7 Torr;A n/a
B 97%
epoxybutene
930-22-3

epoxybutene

A

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

B

furan
110-00-9

furan

C

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

Conditions
ConditionsYield
tetra-n-heptylammonium iodide; tributyltin iodide In para-xylene at 109 - 117℃; for 0.75h;A 96.1%
B n/a
C n/a
2-methoxyfuran
25414-22-6

2-methoxyfuran

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

dichloroacetic acid (DCA)

dichloroacetic acid (DCA)

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
346440-54-8

(2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one

furan
110-00-9

furan

Conditions
ConditionsYield
In diethyl ether; chloroform95%
3-bromofurane
22037-28-1

3-bromofurane

A

furan
110-00-9

furan

B

furan-3-d
6142-87-6

furan-3-d

Conditions
ConditionsYield
With n-butyllithium; deuteromethanol In tetrahydrofuran; cyclohexane at -65℃;A 6%
B 93%
1-(2-furyl)ethanol
4208-64-4

1-(2-furyl)ethanol

furan
110-00-9

furan

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate; silver nitrate; sodium hydroxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Autoclave; Green chemistry;91%
C13H13NO4
95641-44-4

C13H13NO4

A

furan
110-00-9

furan

B

1,3,5-trimethyl-4H-furo<3,4-c>pyrrole-4,6(5H)-dione

1,3,5-trimethyl-4H-furo<3,4-c>pyrrole-4,6(5H)-dione

Conditions
ConditionsYield
at 500℃; under 0.01 Torr; Irradiation;A n/a
B 90%
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

furan
110-00-9

furan

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; copper diacetate; silver nitrate; sodium hydroxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Autoclave; Green chemistry;90%
(1R,2S,5R,6S,7S)-5-(2'-oxo-1'-propyl)-4,10-dioxatricyclo<5.2.1.O2,6>dec-8-ene
124031-50-1

(1R,2S,5R,6S,7S)-5-(2'-oxo-1'-propyl)-4,10-dioxatricyclo<5.2.1.O2,6>dec-8-ene

A

furan
110-00-9

furan

B

(R)-2-(2'-oxo-1'-propyl)-2,5-dihydrofuran
124031-52-3

(R)-2-(2'-oxo-1'-propyl)-2,5-dihydrofuran

Conditions
ConditionsYield
at 500℃; under 0.01 Torr; flash termolyses, contact time = 50 ms;A n/a
B 82%
2-Furan-2-yl-4-hydroxy-6-oxo-4-phenyl-cyclohexanecarboxylic acid ethyl ester
148066-39-1

2-Furan-2-yl-4-hydroxy-6-oxo-4-phenyl-cyclohexanecarboxylic acid ethyl ester

A

furan
110-00-9

furan

B

ethyl 3-hydroxy-[1,1'-biphenyl]-4-carboxylate
148066-43-7

ethyl 3-hydroxy-[1,1'-biphenyl]-4-carboxylate

Conditions
ConditionsYield
With perchloric acid In benzene for 10h; Heating;A n/a
B 82%
(1R,2S,5R,6S,7S)-5-cyanomethyl-4,10-dioxatricyclo<5.2.1.O2,6>dec-8-ene
124031-49-8

(1R,2S,5R,6S,7S)-5-cyanomethyl-4,10-dioxatricyclo<5.2.1.O2,6>dec-8-ene

A

furan
110-00-9

furan

B

(R)-2-cyanomethyl-2,5-dihydrofuran
124031-51-2

(R)-2-cyanomethyl-2,5-dihydrofuran

Conditions
ConditionsYield
at 500℃; under 0.01 Torr; flash termolyses, contact time = 50 ms;A n/a
B 80%
diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate
24736-85-4

diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate

aniline
62-53-3

aniline

A

furan
110-00-9

furan

B

diethyl (Z)-2-(phenylamino)but-2-enedioate

diethyl (Z)-2-(phenylamino)but-2-enedioate

Conditions
ConditionsYield
In neat (no solvent) at 90℃; for 6h; Solvent; Temperature; Schlenk technique; Green chemistry;A n/a
B 77%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

furan
110-00-9

furan

C

2-methylfuran
534-22-5

2-methylfuran

D

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
With hydrogen In methanol at 119.84℃; under 7500.75 Torr; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave;A 6.2%
B 8.9%
C 7.7%
D 75.5%
With hydrogen In isopropyl alcohol at 180℃; under 15001.5 Torr; for 5h; Kinetics; Catalytic behavior; Time; Autoclave; Sealed tube;A 13%
B 22%
C 54%
D 8%
With hydrogen at 250℃; under 760.051 Torr;A 10.2%
B 13.5%
C 38.6%
D 19%
furfural
98-01-1

furfural

A

furan
110-00-9

furan

B

2-methylfuran
534-22-5

2-methylfuran

Conditions
ConditionsYield
With hydrogen at 210℃; Catalytic behavior; Temperature;A 24.5%
B 75.4%
With nickel supported catalyst In methanol; water at 260℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Inert atmosphere; Autoclave;A 58%
B 31%
With hydrogen; palladium on activated charcoal at 200℃; Product distribution; other catalysts, other temperatures, different ratios of H2, other selectivity;
Conditions
ConditionsYield
at 358℃; for 0.000833333h; Product distribution; Curie-point pyrolysis;A 15.3%
B 74%
C 2%
morpholine
110-91-8

morpholine

diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate
24736-85-4

diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate

A

furan
110-00-9

furan

B

diethyl (Z)-2-(morpholino)-2-butenedioate
116308-60-2

diethyl (Z)-2-(morpholino)-2-butenedioate

Conditions
ConditionsYield
In neat (no solvent) at 90℃; for 0.0166667h; Schlenk technique; Green chemistry;A n/a
B 73%
furfural
98-01-1

furfural

A

furan
110-00-9

furan

B

2-methylfuran
534-22-5

2-methylfuran

C

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
With hydrogen In methanol at 119.84℃; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave;A 13.4%
B 10.3%
C 70.7%
With hydrogen at 210℃;A 56.6%
B 11.5%
C 16.2%
With hydrogen In isopropyl alcohol at 240℃; under 18751.9 Torr; for 1h; Catalytic behavior; Temperature;A 39%
B 7.3%
C 25.9%
1,4-butenediol
6117-80-2

1,4-butenediol

furan
110-00-9

furan

Conditions
ConditionsYield
With oxygen; palladium diacetate; copper (I) acetate at 40℃; for 20h;70%
4-(3,6-Dihydro-[1,2]oxazin-2-yl)-benzoic acid methyl ester
82698-71-3

4-(3,6-Dihydro-[1,2]oxazin-2-yl)-benzoic acid methyl ester

A

furan
110-00-9

furan

B

1-(4-(methyl carboxylate) phenyl) pyrrole
23351-08-8

1-(4-(methyl carboxylate) phenyl) pyrrole

C

4-methoxycarbonyl aniline
619-45-4

4-methoxycarbonyl aniline

Conditions
ConditionsYield
In methanol Irradiation;A n/a
B 70%
C 24%
diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate
24736-85-4

diethyl 7-oxabicyclo[2.2.1]hepta-2(3),5(6)-diene-2,3-dicarboxylate

4-phenyl-1-piperazine
92-54-6

4-phenyl-1-piperazine

A

furan
110-00-9

furan

B

diethyl 2-(4-phenylpiperazin-1-yl)fumarate

diethyl 2-(4-phenylpiperazin-1-yl)fumarate

Conditions
ConditionsYield
In neat (no solvent) at 90℃; for 0.0166667h; Schlenk technique; Green chemistry;A n/a
B 70%
D-Mannose
530-26-7

D-Mannose

A

furan
110-00-9

furan

B

furfural
98-01-1

furfural

C

Glycolaldehyde
141-46-8

Glycolaldehyde

D

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

Conditions
ConditionsYield
at 358℃; for 0.000833333h; Product distribution; Curie-point pyrolysis;A 2.2%
B 63.4%
C 18.4%
D 7.2%
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride
6118-51-0

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

Conditions
ConditionsYield
In neat (no solvent, solid phase) for 1h; Diels-Alder Cycloaddition; Milling;100%
In toluene at 110℃; for 24h; Diels-Alder Cycloaddition; Reflux; stereospecific reaction;100%
at 25℃; for 16h; Diels-Alder reaction;98%
furan
110-00-9

furan

tetrahydrofuran
109-99-9

tetrahydrofuran

Conditions
ConditionsYield
With 3% Pd/C; hydrogen In isopropyl alcohol at 219.84℃; under 25858.1 Torr; for 5h; Inert atmosphere;100%
With hydrogen; acetic acid In water at 39.84℃; for 2h; Inert atmosphere;98%
With ruthenium; hydrogen; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; under 22502.3 Torr; for 36h; Autoclave; chemoselective reaction;95%
furan
110-00-9

furan

maleic anhydride
108-31-6

maleic anhydride

7-oxanorborn-5-ene-2,3-dicarboxylic anhydride
5426-09-5

7-oxanorborn-5-ene-2,3-dicarboxylic anhydride

Conditions
ConditionsYield
In diethyl ether Diels-Alder reaction;100%
In diethyl ether at 20℃; for 6h; Diels-Alder Cycloaddition;98%
In toluene at 20℃; for 72h;97%
furan
110-00-9

furan

cyclobutanone
1191-95-3

cyclobutanone

1-(furan-2-yl)cyclobutan-1-ol
131041-44-6

1-(furan-2-yl)cyclobutan-1-ol

Conditions
ConditionsYield
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere;
Stage #2: cyclobutanone In tetrahydrofuran; hexanes at -78℃; for 1h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water
100%
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 4h; Inert atmosphere;
Stage #2: cyclobutanone In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
82%
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
Stage #2: cyclobutanone In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere;
71%
furan
110-00-9

furan

dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

2-((Z)-4-Oxo-but-2-enylidene)-malonic acid dimethyl ester
120508-09-0

2-((Z)-4-Oxo-but-2-enylidene)-malonic acid dimethyl ester

Conditions
ConditionsYield
With rhodium(II) acetate at 20℃; for 96h;100%
furan
110-00-9

furan

Se-methyl heptaneselenoate
67132-63-2

Se-methyl heptaneselenoate

1-furan-2-yl-heptan-1-one
5466-40-0

1-furan-2-yl-heptan-1-one

Conditions
ConditionsYield
With copper (I) trifluoromethane sulfonate benzene In benzene for 0.25h; Ambient temperature;100%
With <(CF3SO3Cu)2PhH>; calcium carbonate In benzene for 0.25h; Ambient temperature; Yield given;
furan
110-00-9

furan

ethyl bromopyruvate tert-butoxycarbonylhydrazone
136035-18-2

ethyl bromopyruvate tert-butoxycarbonylhydrazone

t-Butyl ethyl 1,4,4a,7a-tetrahydrofuro<3,2-c>pyridazine-1,3-dicarboxylate
136035-33-1

t-Butyl ethyl 1,4,4a,7a-tetrahydrofuro<3,2-c>pyridazine-1,3-dicarboxylate

Conditions
ConditionsYield
With sodium carbonate In dichloromethane for 16h; Ambient temperature;100%
furan
110-00-9

furan

acrylonitrile
107-13-1

acrylonitrile

5-cyano-7-oxabicyclo<2.2.1>hept-2-ene
53750-68-8

5-cyano-7-oxabicyclo<2.2.1>hept-2-ene

Conditions
ConditionsYield
With zinc(II) iodide at 40℃; for 48h;100%
With zinc(II) chloride at 20℃; for 16h;90%
Stage #1: acrylonitrile With zinc(II) chloride at 20℃; for 0.166667h;
Stage #2: furan at 20℃; for 14h;
83%
furan
110-00-9

furan

(Phenyl) iodonium triflate
1026360-69-9

(Phenyl) iodonium triflate

1,4-epoxy-1,4-dihydronaphthalene
573-57-9

1,4-epoxy-1,4-dihydronaphthalene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane for 0.166667h; Ambient temperature;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 20℃; for 0.5h;64%
furan
110-00-9

furan

<4-Methyl-6-(trimethylsilyl)phenyl>(phenyl) iodonium triflate

<4-Methyl-6-(trimethylsilyl)phenyl>(phenyl) iodonium triflate

6-Methyl-1,4-dihydronaphthalene-1,4-endo-oxide

6-Methyl-1,4-dihydronaphthalene-1,4-endo-oxide

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane Ambient temperature;100%
furan
110-00-9

furan

<2-Methyl-6-(trimethylsilyl)phenyl>(phenyl) iodonium triflate

<2-Methyl-6-(trimethylsilyl)phenyl>(phenyl) iodonium triflate

5-Methyl-1,4-dihydronaphthalene-1,4-endo-oxide

5-Methyl-1,4-dihydronaphthalene-1,4-endo-oxide

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane Ambient temperature;100%
furan
110-00-9

furan

methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate
98081-82-4

methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate

(1R,3R,4S,5S)-3-(2,6-Dichloro-phenyl)-8-oxa-2-aza-tricyclo[3.2.1.02,4]oct-6-ene-4-carboxylic acid methyl ester

(1R,3R,4S,5S)-3-(2,6-Dichloro-phenyl)-8-oxa-2-aza-tricyclo[3.2.1.02,4]oct-6-ene-4-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 168h; Ambient temperature;100%
furan
110-00-9

furan

(phenyl)[2,4,5-tris(trimethylsilyl)phenyl]iodonium triflate
1026471-76-0

(phenyl)[2,4,5-tris(trimethylsilyl)phenyl]iodonium triflate

1,4-endoxy-1,4-dihydro-6,7-bis(trimethylsilyl)naphthalene
220300-23-2

1,4-endoxy-1,4-dihydro-6,7-bis(trimethylsilyl)naphthalene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.333333h;100%
With tetrabutyl ammonium fluoride; diisopropylamine In tetrahydrofuran; dichloromethane for 0.166667h; Ambient temperature; Yield given;
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;600 mg
furan
110-00-9

furan

(5-(methoxycarbonyl)-2-(trimethylsilyl)phenyl)(phenyl)iodonium trifluoromethanesulfonate

(5-(methoxycarbonyl)-2-(trimethylsilyl)phenyl)(phenyl)iodonium trifluoromethanesulfonate

11-oxa-tricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-4-carboxylic acid methyl ester
232264-73-2

11-oxa-tricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 0℃; for 0.5h;100%
furan
110-00-9

furan

methyl 2,4,6-tri(tert-butyl)phenylglyoxylate

methyl 2,4,6-tri(tert-butyl)phenylglyoxylate

6-methoxycarbonyl-endo-6-(2',4',6'-tri(tert-butyl)phenyl)-2,7-dioxabicyclo[3.2.0]hept-3-ene

6-methoxycarbonyl-endo-6-(2',4',6'-tri(tert-butyl)phenyl)-2,7-dioxabicyclo[3.2.0]hept-3-ene

Conditions
ConditionsYield
In benzene Cycloaddition; UV-irradiation;100%
furan
110-00-9

furan

5,5,5',5'-Tetramethyl-5H,5'H-[3,3']bipyrazolyl
86958-27-2

5,5,5',5'-Tetramethyl-5H,5'H-[3,3']bipyrazolyl

A

2,7-dimethyl-octa-2,6-dien-4-yne
68470-88-2

2,7-dimethyl-octa-2,6-dien-4-yne

B

(1S,5S,6S)-6-(4-Methyl-pent-3-en-1-ynyl)-2-oxa-bicyclo[3.1.0]hex-3-ene
86958-28-3, 87036-98-4

(1S,5S,6S)-6-(4-Methyl-pent-3-en-1-ynyl)-2-oxa-bicyclo[3.1.0]hex-3-ene

C

N2

N2

Conditions
ConditionsYield
In various solvent(s) at 12℃; Irradiation; pyrex, Philips HPK 125;A 100%
B 68%
C n/a
furan
110-00-9

furan

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

2-[α-(4-tolyl)-α-hydroxymethyl]furan
224962-61-2

2-[α-(4-tolyl)-α-hydroxymethyl]furan

Conditions
ConditionsYield
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane for 1h; Reflux; Inert atmosphere;
Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane at 20℃; for 0.166667h;
100%
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 0.5h; Metallation; lithiation; Heating;
Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; hexane at 20℃; for 0.5h; Substitution;
84%
Stage #1: furan With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0℃; for 1h;
Stage #2: 4-methyl-benzaldehyde In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.25h;
56%
furan
110-00-9

furan

Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate

Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate

1,4-dihydronaphthalene-1,4-epoxide
573-57-9

1,4-dihydronaphthalene-1,4-epoxide

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination;100%
furan
110-00-9

furan

[2-methyl-6-(trimethylsilyl)phenyl](phenyl)iodonium triflate

[2-methyl-6-(trimethylsilyl)phenyl](phenyl)iodonium triflate

3-methyl-11-oxatricyclo[6.2.1.02,7]undeca-2(7)3,5,9-tetraene
19061-32-6

3-methyl-11-oxatricyclo[6.2.1.02,7]undeca-2(7)3,5,9-tetraene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination;100%
furan
110-00-9

furan

[4-methyl-2-(trimethylsilyl)phenyl](phenyl)iodonium triflate

[4-methyl-2-(trimethylsilyl)phenyl](phenyl)iodonium triflate

1,4-dihydro-1,4-epoxy-6-methylnaphthalene
19061-31-5

1,4-dihydro-1,4-epoxy-6-methylnaphthalene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; dichloromethane at 20℃; for 0.5h; cycloaddition; elimination;100%
furan
110-00-9

furan

2-azidoacrylic acid benzyl ester
328119-67-1

2-azidoacrylic acid benzyl ester

benzyl 8-oxa-2-azatricyclo[3.2.1.02,4]oct-6-ene-4-carboxylate

benzyl 8-oxa-2-azatricyclo[3.2.1.02,4]oct-6-ene-4-carboxylate

Conditions
ConditionsYield
Stage #1: 2-azidoacrylic acid benzyl ester In toluene at 110℃;
Stage #2: furan In toluene at 20℃; for 168h; Diels-Alder reaction; Further stages.;
100%
furan
110-00-9

furan

(1S,4R)-bicyclo[2.2.1]heptan-2-one
497-38-1, 2630-41-3

(1S,4R)-bicyclo[2.2.1]heptan-2-one

(1S,2R,4R)-2-endo-hydroxy-2-exo-(2'-furyl)bicyclo-[2.2.1]heptane

(1S,2R,4R)-2-endo-hydroxy-2-exo-(2'-furyl)bicyclo-[2.2.1]heptane

Conditions
ConditionsYield
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h;
Stage #2: (1S,4R)-bicyclo[2.2.1]heptan-2-one In tetrahydrofuran; hexane at 20℃; for 6h;
100%
With n-butyllithium In tetrahydrofuran at 20℃; for 18h;100%
furan
110-00-9

furan

maleiimide
541-59-3

maleiimide

3,6-epoxy-1,2,3,6-tetrahydrophthalimide
6253-28-7, 19878-26-3, 42074-03-3

3,6-epoxy-1,2,3,6-tetrahydrophthalimide

Conditions
ConditionsYield
In diethyl ether Diels-Alder reaction;100%
In diethyl ether at 100℃; for 8h; Autoclave;99%
In diethyl ether at 100℃; Inert atmosphere; Sealed tube;99%
furan
110-00-9

furan

3-maleimidepropionic acid
7423-55-4

3-maleimidepropionic acid

3-((3aR,4S,7R,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-epoxyisoindol-2-yl)propanoic acid

3-((3aR,4S,7R,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-epoxyisoindol-2-yl)propanoic acid

Conditions
ConditionsYield
In chloroform at 38℃; for 120h;100%
In chloroform at 35℃; for 336000h; Diels-Alder reaction;74%
Stage #1: furan; 3-maleimidepropionic acid In chloroform Darkness; Heating;
Stage #2: In methanol; ethyl acetate at 45℃; for 0.25h;
65%
furan
110-00-9

furan

C6H16N2*2C9H18N(1-)*C4H9Na*Mg(2+)

C6H16N2*2C9H18N(1-)*C4H9Na*Mg(2+)

C6H16N2*C4H3NaO*(C4H3O)2Mg

C6H16N2*C4H3NaO*(C4H3O)2Mg

Conditions
ConditionsYield
In hexane at 20℃; for 1h;100%
furan
110-00-9

furan

8-Bromo-1-octene
2695-48-9

8-Bromo-1-octene

2-(oct-7-enyl)furan

2-(oct-7-enyl)furan

Conditions
ConditionsYield
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 5h;
Stage #2: 8-Bromo-1-octene In tetrahydrofuran; hexane at -78 - 20℃;
100%
Stage #1: furan With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 4h;
Stage #2: 8-Bromo-1-octene In tetrahydrofuran; hexane at 20℃; Further stages.;
furan
110-00-9

furan

[Rh(H)(Ph)(η5-pentamethylcyclopentadienyl)(PMe3)]
81971-46-2

[Rh(H)(Ph)(η5-pentamethylcyclopentadienyl)(PMe3)]

(C5Me5)Rh(PMe3)(2-furanyl)H
161301-05-9

(C5Me5)Rh(PMe3)(2-furanyl)H

Conditions
ConditionsYield
In hexane N2-atmosphere; stirring (60°C, 23 h); evapn. (vac.);100%
furan
110-00-9

furan

[Ru(1,5-cyclooctadiene)(1,3,5-cyclooctatriene)]

[Ru(1,5-cyclooctadiene)(1,3,5-cyclooctatriene)]

triethylphosphine
554-70-1

triethylphosphine

[Ru(1-5-η5-C8H11)(2-furyl)(PEt3)2]
656260-97-8

[Ru(1-5-η5-C8H11)(2-furyl)(PEt3)2]

Conditions
ConditionsYield
In hexane (N2); standard Schlenk technique; hexane and PEt3 were added via syringeto mixt. of Ru complex and ligand; mixt. was stirred at room temp. for 20 h; volatiles evapd. with oil diffusion pump; crystd. from hexane at -30°C; recrystd. (pentane);100%
furan
110-00-9

furan

10-(trimethylsilyl)phenanthren-9-yl trifluoromethanesulfonate
252054-91-4

10-(trimethylsilyl)phenanthren-9-yl trifluoromethanesulfonate

1,4-dihydro-1,4-epoxytriphenylene

1,4-dihydro-1,4-epoxytriphenylene

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 40℃; for 16h; Inert atmosphere;100%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;81%
furan
110-00-9

furan

6-bromo-2,5,8-trimethoxy-4-methylquinoline
1136845-05-0

6-bromo-2,5,8-trimethoxy-4-methylquinoline

5-aza-8-methyl-6,9,10-Dimethoxy-1,4-dihydro-1,4-epoxyanthracene
1136845-02-7

5-aza-8-methyl-6,9,10-Dimethoxy-1,4-dihydro-1,4-epoxyanthracene

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -75℃; for 3h;100%

Furan Chemical Properties

Molecular Structure:

Molecular Formula: C4H4O
Molecular Weight: 68.074
IUPAC Name: Furan
Synonyms of Furan (CAS NO.110-00-9): 1,4-Epoxy-1,3-butadiene ; 5-17-01-00291 (Beilstein Handbook Reference) ; AI3-24244 ; Axole ; BRN 0103221 ; CCRIS 3159 ; Divinylene oxide ; EINECS 203-727-3 ; Furfuran ; HSDB 89 ; NCI-C56202 ; Oxacyclopentadiene ; Oxole ; RCRA waste number U124 ; Tetrole ; Furan [UN2389] [Flammable liquid] ; UN2389
CAS NO: 110-00-9
Classification Code: Mutation data ; Reproductive Effect ; Tumor data
Melting point: -85.6 °C 
Index of Refraction: 1.427
Molar Refractivity: 18.55 cm3
Molar Volume: 72.2 cm3
Surface Tension: 24.8 dyne/cm
Density: 0.942 g/cm3
Enthalpy of Vaporization: 27.1 kJ/mol
Boiling Point: 31.4 °C at 760 mmHg
Vapour Pressure: 605 mmHg at 25°C
Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system  similar to benzene. Because of the aromaticity, the molecule is flat and lacks discrete double bonds. The other lone pair of electrons of the oxygen atom extends in the plane of the flat ring system. The sp2 hybridization is to allow one of the lone pairs of oxygen to reside in a p orbital and thus allow it to interact within the pi-system.

Furan History

  In 1780 by Carl Wilhelm Scheele, the first Furan (CAS NO.110-00-9) derivative to be described was 2-furoic acid. Another important derivative, furfural, was reported by Johann Wolfgang Döbereiner in 1831 and characterised nine years later by John Stenhouse. Furan itself was first prepared by Heinrich Limpricht in 1870, although he called it tetraphenol.

Furan Uses

  Furan (CAS NO.110-00-9) is mainly used to produce large quantities of hot-box process core Binder.

Furan Production

Furan can be obtained from FURFURAL by oxidation and decarboxylation of the resulting furan-2-carboxylic acid, the FURFURAL being derived by destructive distillation of corn cobs in the presence of SULFURIC ACID.
the Feist-Benary synthesis is the organic synthesis of classic furan.   
and there is a simple synthesis methods for furans is the reaction of 1,4-diketones with PHOSPHORUS PENTOXIDE  in the Paal-Knorr Synthesis. It is interesting that the Thiophene formation reaction of 1,4-diketones with Lawesson's reagent also forms furans as side products.

Furan Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 140mg/kg (140mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: HEMORRHAGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926.
dog LDLo oral 234mg/kg (234mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: HEMORRHAGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926.
mouse LC50 inhalation 120mg/m3/1H (120mg/m3) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979.
mouse LD50 intraperitoneal 7mg/kg (7mg/kg)   American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979.
rabbit LDLo oral 234mg/kg (234mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: HEMORRHAGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 26, Pg. 281, 1926.
rat LC50 inhalation 3398ppm/1H (3398ppm) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Hazelton Laboratories, Reports. Vol. HLA468-102, Pg. 1987,
rat LD50 intraperitoneal 5200ug/kg (5.2mg/kg)   American Industrial Hygiene Association Journal. Vol. 40, Pg. 310, 1979.

Furan Safety Profile

Hazard Codes of Furan (CAS NO.110-00-9): ToxicT,HighlyF+
Risk Statements: 45-12-19-20/22-38-48/22-52/53-68 
R45: May cause cancer. 
R12: Extremely flammable. 
R19: May form explosive peroxides. 
R20/22: Harmful by inhalation and if swallowed. 
R38: Irritating to skin. 
R48/22: Harmful: danger of serious damage to health by prolonged exposure if swallowed. 
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R68: Possible risk of irreversible effects.
Safety Statements: 53-45-61 
S53: Avoid exposure - obtain special instructions before use. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: OB3870000
F: 8-9-23
HazardClass: 3
PackingGroup: I

Furan Specification

Behavior of Furan (CAS NO.110-00-9) is quite dissimilar to that of the more typical heterocyclic ethers such as tetrahydrofuran due to its aromaticity, .It is considerably more reactive than benzene in electrophilic substitution reactions, due to the electron-donating effects of the oxygen heteroatom. Examination of the resonance contributors shows the increased electron density of the ring, leading to increased rates of electrophilic substitution.

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