Product Name

  • Name

    (2-Butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl)methanone

  • EINECS 1806241-263-5
  • CAS No. 141645-16-1
  • Article Data20
  • CAS DataBase
  • Density 1.302 g/cm3
  • Solubility 220μg/L at 20℃
  • Melting Point
  • Formula C19H17NO5
  • Boiling Point 559.472 °C at 760 mmHg
  • Molecular Weight 339.348
  • Flash Point 292.158 °C
  • Transport Information
  • Appearance Pale yellow solid
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 141645-16-1 ((2-Butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl)methanone)
  • Hazard Symbols
  • Synonyms (2-butyl-5-nitro-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone
  • PSA 96.26000
  • LogP 5.14340

Synthetic route

(2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone
141627-42-1

(2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Stage #1: (2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone With aluminum (III) chloride In chlorobenzene at 85℃; for 4h;
Stage #2: With water In chlorobenzene at 35 - 60℃;		92%
Stage #1: (2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone With aluminum (III) chloride In chlorobenzene at 75℃; for 2h;
Stage #2: With water In chlorobenzene at 5 - 65℃; for 0.5h;		92%
In aluminium chloride; ice-water; 1,1-dichloroethane90.1%
4-hydroxybenzoyl chloride
28141-24-4

4-hydroxybenzoyl chloride

2-(n-butyl)-5-nitrobenzofuran
133238-87-6

2-(n-butyl)-5-nitrobenzofuran

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at 0 - 20℃; for 2.5h; Friedel-Crafts Acylation;88%
1-(4-hydroxy-phenyl)-heptane-1,3-dione 3-[O-(4-nitro-phenyl)-oxime]
1253293-38-7

1-(4-hydroxy-phenyl)-heptane-1,3-dione 3-[O-(4-nitro-phenyl)-oxime]

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With formic acid; trifluoroacetic acid at 45℃; for 5h; Product distribution / selectivity; Inert atmosphere;87%
With formic acid; trifluoroacetic acid at 45℃; for 5h; Product distribution / selectivity; Inert atmosphere;87%
With formic acid; trifluoroacetic acid at 45℃; for 5h; Product distribution / selectivity; Inert atmosphere;87%
With acetic acid at 115℃; for 3h; Product distribution / selectivity; Industry scale;78%
4-hydroxy-benzoic acid
99-96-7

4-hydroxy-benzoic acid

2-(n-butyl)-5-nitrobenzofuran
133238-87-6

2-(n-butyl)-5-nitrobenzofuran

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; iron(III) chloride In chlorobenzene at 20 - 40℃; for 3.45 - 5h;
Stage #2: With ethanol In chlorobenzene at 0 - 30℃; for 0.45 - 0.5h; Product distribution / selectivity;		81.6%
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With dimethylsilicon dichloride; iron(II) chloride In chlorobenzene at 23 - 50℃; for 5h;
Stage #2: With ethanol In chlorobenzene at 20℃; Product distribution / selectivity;		76%
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With tetrachlorosilane; iron(III) chloride In chlorobenzene at 23 - 50℃; for 5h;
Stage #2: With ethanol In chlorobenzene at 20℃; Product distribution / selectivity;		75%
Stage #1: 4-hydroxy-benzoic acid; 2-(n-butyl)-5-nitrobenzofuran With Methyltrichlorosilane; bismuth(lll) trifluoromethanesulfonate In chlorobenzene at 23 - 60℃; for 15h;
Stage #2: With ethanol In chlorobenzene at 20℃; Product distribution / selectivity;		10%
With trichlorophosphate; zinc(II) chloride at 23 - 60℃; for 15h; Product distribution / selectivity;1%
1-(4-hydroxy-phenyl)-heptane-1,3-dione
1137261-89-2

1-(4-hydroxy-phenyl)-heptane-1,3-dione

p-nitrophenoxyamine
33543-55-4

p-nitrophenoxyamine

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With acetic acid at 70 - 100℃; for 25h; Product distribution / selectivity;80%
In acetic acid at 70 - 100℃; for 25h; Product distribution / selectivity;80%
With acetic acid at 70 - 100℃; for 17h; Product distribution / selectivity;80%
With hydrogen bromide; acetic acid at 20℃; for 1h;
1-(4-hydroxyphenyl)heptane-1,3-dione-3-[O-(4-nitrophenyl)oxime]
1137261-95-0

1-(4-hydroxyphenyl)heptane-1,3-dione-3-[O-(4-nitrophenyl)oxime]

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With acetic acid at 115℃; for 3h; Product distribution / selectivity;78%
4-acetoxyiodobenzene
33527-94-5

4-acetoxyiodobenzene

carbon monoxide
201230-82-2

carbon monoxide

2-(hex-1-yn-1-yl)-4-nitrophenyl acetate
1636167-45-7

2-(hex-1-yn-1-yl)-4-nitrophenyl acetate

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 55℃; for 24h; Sealed tube;76%
...Expand
2-(2-pentanoyloxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone
1256921-45-5

2-(2-pentanoyloxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Stage #1: 2-(2-pentanoyloxy-5-nitrophenyl)-1-(4-methoxyphenyl)-ethanone With tributyl-amine In xylene for 8h; Molecular sieve; Reflux;
Stage #2: With hydrogenchloride; tributyl-amine at 200℃; for 4h;
Stage #3: With water In tert-butyl methyl ether at 20℃;		65%
1-(4-benzyloxyphenyl)-heptane-1,3-dione
1137261-88-1

1-(4-benzyloxyphenyl)-heptane-1,3-dione

p-nitrophenoxyamine
33543-55-4

p-nitrophenoxyamine

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃; for 6h; Product distribution / selectivity;59%
(2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone
141627-42-1

(2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone

2-n-butyl-5-nitro-3-(2'-methoxy)-acetophenonebenzofuran
856758-04-8

2-n-butyl-5-nitro-3-(2'-methoxy)-acetophenonebenzofuran

A

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

B

2-(n-butyl)-3-(2-hydroxybenzoyl)-5-nitrobenzofuran
856758-05-9

2-(n-butyl)-3-(2-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Stage #1: (2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone; 2-n-butyl-5-nitro-3-(2'-methoxy)-acetophenonebenzofuran; aluminum (III) chloride In chlorobenzene at 60℃; for 7h;
Stage #2: With water In chlorobenzene at 60℃;
...Expand
1-[4-(1-ethoxy-ethoxy)-phenyl]-ethanone

1-[4-(1-ethoxy-ethoxy)-phenyl]-ethanone

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium tert-butylate / Isobutyronitrile / 2 h / 0 - 95 °C
2: water / hydrogenchloride / Isobutyronitrile / 0.25 h / 0 °C
3: dichloromethane / 16 h / 20 °C
4: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / 1,4-dioxane; mineral oil / 3 h / 70 °C / Inert atmosphere
1.2: 0.5 h / 60 °C
2.1: dichloromethane / 16 h / 20 °C
3.1: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere
View Scheme
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid / tetrahydrofuran / 1.75 h / 0 °C
2: potassium tert-butylate / Isobutyronitrile / 2 h / 0 - 95 °C
3: water / hydrogenchloride / Isobutyronitrile / 0.25 h / 0 °C
4: dichloromethane / 16 h / 20 °C
5: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sulfuric acid / tetrahydrofuran / 1.75 h / 0 °C
2.1: sodium hydride / 1,4-dioxane; mineral oil / 3 h / 70 °C / Inert atmosphere
2.2: 0.5 h / 60 °C
3.1: dichloromethane / 16 h / 20 °C
4.1: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere
View Scheme
C17H24O4

C17H24O4

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water / hydrogenchloride / Isobutyronitrile / 0.25 h / 0 °C
2: dichloromethane / 16 h / 20 °C
3: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere
View Scheme
1-(4-hydroxy-phenyl)-heptane-1,3-dione
1137261-89-2

1-(4-hydroxy-phenyl)-heptane-1,3-dione

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 16 h / 20 °C
2: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere
View Scheme
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 4 h / 25 °C
2.1: aluminum (III) chloride / chlorobenzene / 4 h / 85 °C
2.2: 35 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / chlorobenzene / 2 h / 25 °C / Reflux
2.1: aluminum (III) chloride / chlorobenzene / 2 h / 75 °C
2.2: 0.5 h / 5 - 65 °C
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane
2: aluminum (III) chloride / chlorobenzene
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 22 h / 25 - 30 °C / Large scale
2.1: aluminum (III) chloride / 40 h / Reflux; Large scale
2.2: 15 °C / Large scale
View Scheme
2-(n-butyl)-5-nitrobenzofuran
133238-87-6

2-(n-butyl)-5-nitrobenzofuran

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 4 h / 25 °C
2.1: aluminum (III) chloride / chlorobenzene / 4 h / 85 °C
2.2: 35 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / chlorobenzene / 2 h / 25 °C / Reflux
2.1: aluminum (III) chloride / chlorobenzene / 2 h / 75 °C
2.2: 0.5 h / 5 - 65 °C
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane
2: aluminum (III) chloride / chlorobenzene
View Scheme
Multi-step reaction with 2 steps
1.1: aluminum (III) chloride / dichloromethane / 22 h / 25 - 30 °C / Large scale
2.1: aluminum (III) chloride / 40 h / Reflux; Large scale
2.2: 15 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere
2: aluminum (III) chloride / chlorobenzene / 2 h / 80 °C / Inert atmosphere
View Scheme
4-nitro-phenol
100-02-7

4-nitro-phenol

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: triethylamine / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere
2: aluminum (III) chloride / nitrobenzene / 5 h / 140 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C
4: bromine / dichloromethane / 1 h / 25 - 30 °C
5: aluminum (III) chloride / dichloromethane / 15 - 20 °C
6: triethylamine / dichloromethane / 2 h / 25 - 30 °C
7: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
8: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
9: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
10: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / water / 38 h / 40 - 55 °C / Large scale
2: 1,2-dichloro-ethane / 65 - 75 °C / Large scale
3: sodium hydrogencarbonate / 1,2-dichloro-ethane / 55 - 60 °C / Large scale
4: aluminum (III) chloride / 1,2-dichloro-ethane / 35 - 40 °C / Large scale
5: aluminum (III) chloride / chlorobenzene / 65 - 70 °C / Large scale
View Scheme
2-butyl-5-nitrobenzofuran-3(2H)-one

2-butyl-5-nitrobenzofuran-3(2H)-one

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
2: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
3: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
4: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
2-butyl-5-nitro-2,3-dihydrobenzofuran-3-ol

2-butyl-5-nitro-2,3-dihydrobenzofuran-3-ol

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
2: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
3: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
p-nitrophenyl hexanoate
956-75-2

p-nitrophenyl hexanoate

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: aluminum (III) chloride / nitrobenzene / 5 h / 140 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C
3: bromine / dichloromethane / 1 h / 25 - 30 °C
4: aluminum (III) chloride / dichloromethane / 15 - 20 °C
5: triethylamine / dichloromethane / 2 h / 25 - 30 °C
6: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
7: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
8: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
9: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
1-(2-hydroxy-5-nitrophenyl)hexan-1-one
1393093-65-6

1-(2-hydroxy-5-nitrophenyl)hexan-1-one

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C
2: bromine / dichloromethane / 1 h / 25 - 30 °C
3: aluminum (III) chloride / dichloromethane / 15 - 20 °C
4: triethylamine / dichloromethane / 2 h / 25 - 30 °C
5: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
6: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
7: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
8: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
1-(2-methoxy-5-nitrophenyl)hexan-1-one
1393093-66-7

1-(2-methoxy-5-nitrophenyl)hexan-1-one

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: bromine / dichloromethane / 1 h / 25 - 30 °C
2: aluminum (III) chloride / dichloromethane / 15 - 20 °C
3: triethylamine / dichloromethane / 2 h / 25 - 30 °C
4: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
5: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
6: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
7: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
2-bromo-1-(2-methoxy-5-nitrophenyl)hexan-1-one
1393093-67-8

2-bromo-1-(2-methoxy-5-nitrophenyl)hexan-1-one

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: aluminum (III) chloride / dichloromethane / 15 - 20 °C
2: triethylamine / dichloromethane / 2 h / 25 - 30 °C
3: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
4: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
5: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
6: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
2-bromo-1-(2-hydroxy-5-nitrophenyl)hexan-1-one
1393093-68-9

2-bromo-1-(2-hydroxy-5-nitrophenyl)hexan-1-one

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane / 2 h / 25 - 30 °C
2: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
3: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
4: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
5: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
Hexanoyl chloride
142-61-0

Hexanoyl chloride

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: triethylamine / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere
2: aluminum (III) chloride / nitrobenzene / 5 h / 140 °C
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 2 h / 25 - 30 °C
4: bromine / dichloromethane / 1 h / 25 - 30 °C
5: aluminum (III) chloride / dichloromethane / 15 - 20 °C
6: triethylamine / dichloromethane / 2 h / 25 - 30 °C
7: sodium tetrahydroborate / methanol / 0.5 h / 0 - 5 °C
8: hydrogenchloride / methanol; water / 5 h / 90 - 95 °C
9: aluminum (III) chloride / dichloromethane / 5.08 h / 0 - 30 °C
10: aluminum (III) chloride / chlorobenzene / 5.17 h / 20 - 80 °C
View Scheme
2-iodo-4-nitrophenyl acetate
504421-91-4

2-iodo-4-nitrophenyl acetate

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / tetrahydrofuran / 5.5 h / 20 °C / Inert atmosphere
2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 24 h / 55 °C / Sealed tube
View Scheme
2-iodo-4-nitrophenol
89487-91-2

2-iodo-4-nitrophenol

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / tetrahydrofuran; dichloromethane / 4 h / 0 - 20 °C
2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / tetrahydrofuran / 5.5 h / 20 °C / Inert atmosphere
3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 24 h / 55 °C / Sealed tube
View Scheme
4-Iodophenol
540-38-5

4-Iodophenol

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C
2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 24 h / 55 °C / Sealed tube
View Scheme
Koshlands reagent I
772-33-8

Koshlands reagent I

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine / dichloromethane / 1 h / Reflux
1.2: 3 h / Reflux
2.1: tin(IV) chloride / dichloromethane / 2.5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triphenylphosphine / dichloromethane / 1 h / 40 °C / Inert atmosphere
1.2: 3 h / 110 °C / Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere
3.1: aluminum (III) chloride / chlorobenzene / 2 h / 80 °C / Inert atmosphere
View Scheme
n-valeryl chloride
638-29-9

n-valeryl chloride

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine / dichloromethane / 1 h / Reflux
1.2: 3 h / Reflux
2.1: tin(IV) chloride / dichloromethane / 2.5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: triphenylphosphine / dichloromethane / 1 h / 40 °C / Inert atmosphere
1.2: 3 h / 110 °C / Inert atmosphere
2.1: aluminum (III) chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere
3.1: aluminum (III) chloride / chlorobenzene / 2 h / 80 °C / Inert atmosphere
View Scheme
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

4-[(2-butyl-5-nitro-1-benzofuran-3-yl)carbonyl]phenyl-methanesulfonate
1448297-26-4

4-[(2-butyl-5-nitro-1-benzofuran-3-yl)carbonyl]phenyl-methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12.5h; Reflux;100%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

1,2-Epoxy-3-bromopropane
3132-64-7

1,2-Epoxy-3-bromopropane

(2-butyl-5-nitro-1-benzofuran-3-yl)[4-(oxiran-2-yl-methoxy)phenyl]methanone

(2-butyl-5-nitro-1-benzofuran-3-yl)[4-(oxiran-2-yl-methoxy)phenyl]methanone

Conditions
ConditionsYield
With sodium hydroxide In isopropyl alcohol for 1.5h; Reflux;100%
Stage #1: 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran With sodium hydroxide In isopropyl alcohol at 20℃; for 0.166667h;
Stage #2: 1,2-Epoxy-3-bromopropane In isopropyl alcohol for 1.5h; Reflux;
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

dibutyl-(3-chloro-propyl)-amine
36421-15-5

dibutyl-(3-chloro-propyl)-amine

(2-butyl-5-nitrobenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone
141645-23-0

(2-butyl-5-nitrobenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

Conditions
ConditionsYield
Stage #1: 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran With potassium carbonate In toluene at 25 - 110℃; for 0.5h; Large scale;
Stage #2: dibutyl-(3-chloro-propyl)-amine In toluene Temperature; Solvent; Reflux; Large scale;		99.5%
Stage #1: 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran With potassium carbonate In acetonitrile for 0.5h;
Stage #2: dibutyl-(3-chloro-propyl)-amine In acetonitrile Reflux;		91%
Stage #1: 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran With potassium carbonate In acetonitrile for 0.5h; Reflux;
Stage #2: dibutyl-(3-chloro-propyl)-amine In acetonitrile Reflux;		91%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

1,3-chlorobromopropane
109-70-6

1,3-chlorobromopropane

(4-(3-chloropropoxy)phenyl)(2-butyl-5-nitrobenzofuran-3-yl)methanone
1310430-03-5

(4-(3-chloropropoxy)phenyl)(2-butyl-5-nitrobenzofuran-3-yl)methanone

Conditions
ConditionsYield
With potassium carbonate In butanone at 81 - 82℃; for 4h;99.1%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 20h;88.8%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

3-chloro-1,1-diethoxy-propane
35573-93-4

3-chloro-1,1-diethoxy-propane

(2-butyl-5-nitro-1-benzofuran-3-yl)[4-(3,3-diethoxypropoxy)phenyl]methanone
1420181-01-6

(2-butyl-5-nitro-1-benzofuran-3-yl)[4-(3,3-diethoxypropoxy)phenyl]methanone

Conditions
ConditionsYield
With potassium carbonate; sodium iodide for 6h; Reflux;99%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

acrylonitrile
107-13-1

acrylonitrile

(5-nitro-2-butylbenzofuran-3-yl)-[4-(2-cyanoethoxy)phenyl]methanone
1401355-76-7

(5-nitro-2-butylbenzofuran-3-yl)-[4-(2-cyanoethoxy)phenyl]methanone

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide at 80 - 85℃; for 48h;94.2%
With N-benzyl-trimethylammonium hydroxide at 80 - 85℃; for 48h;94.2%
With N-benzyl-trimethylammonium hydroxide at 80 - 85℃; for 48h;94.2%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

1-chloro 3-di-n-butylamino propane
90050-13-8

1-chloro 3-di-n-butylamino propane

2-n-butyl 3-[4-(3-di-n-butylamino-propoxy)benzoyl] 5-nitro benzofuran
141671-42-3

2-n-butyl 3-[4-(3-di-n-butylamino-propoxy)benzoyl] 5-nitro benzofuran

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate In diethyl ether; butanone88.76%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-[(2-butyl-5-nitro-1-benzofuran-3-yl)carbonyl]phenyltrifluoromethanesulfonate
1448297-17-3

4-[(2-butyl-5-nitro-1-benzofuran-3-yl)carbonyl]phenyltrifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere;87%
With triethylamine In dichloromethane at 20℃; for 5.5h; Reflux;
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

(5-amino-2-butyl-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone
1278585-68-4

(5-amino-2-butyl-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; under 3750.38 Torr; for 6h;78.3%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

3-{ 4-[(2-butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol
1310430-11-5

3-{ 4-[(2-butyl-5-nitro-1-benzofuran-3-yl) carbonyl]phenoxy}propan-1-ol

Conditions
ConditionsYield
Stage #1: 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran With tetrabutylammomium bromide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50℃; for 0.5h;
Stage #2: 1-chloro-3-hydroxypropane In N,N-dimethyl-formamide at 80 - 85℃;		69%
With tetrabutylammomium bromide; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80 - 85℃;69%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

[4-(3-bromo-propoxy)-phenyl]-(2-butyl-5-nitro-benzofuran-3-yl)-methanone
141645-38-7

[4-(3-bromo-propoxy)-phenyl]-(2-butyl-5-nitro-benzofuran-3-yl)-methanone

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) for 5h; Reagent/catalyst; Solvent; Reflux;64%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

[2H6]-1,3-dibromopropane
120404-22-0

[2H6]-1,3-dibromopropane

[4-(3-bromo-[2H6]-propoxy)-phenyl]-(2-butyl-5-nitrobenzofuran-3-yl)-methanone
1542232-34-7

[4-(3-bromo-[2H6]-propoxy)-phenyl]-(2-butyl-5-nitrobenzofuran-3-yl)-methanone

Conditions
ConditionsYield
With sodium hydroxide In water for 8h; Solvent; Reagent/catalyst; Reflux;62%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

ethylene dibromide
106-93-4

ethylene dibromide

3-[4-(2-bromoethoxy)benzoyl] 2-n-butyl 5-nitro benzofuran
141645-36-5

3-[4-(2-bromoethoxy)benzoyl] 2-n-butyl 5-nitro benzofuran

Conditions
ConditionsYield
With potassium carbonate In butanone56%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

β-Propiolactone
57-57-8

β-Propiolactone

3-[4-(2-butyl-5-nitro-benzofuran-3-carbonyl)phenoxy]-propionic acid
1542232-29-0

3-[4-(2-butyl-5-nitro-benzofuran-3-carbonyl)phenoxy]-propionic acid

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;37%
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

2-n-butyl-3-(3,5-dibromo-4-hydroxybenzoyl)5-nitrobenzofuran

2-n-butyl-3-(3,5-dibromo-4-hydroxybenzoyl)5-nitrobenzofuran

Conditions
ConditionsYield
With bromine
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

dronedarone
141626-36-0

dronedarone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / butanone / 4 h / 81 - 82 °C
2: hydrogen / palladium 10% on activated carbon / ethanol / 2 h / 50 °C / 3750.38 Torr
3: pyridine / dichloromethane / 15 °C
4: sodium iodide / butanone / 16 h
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / butanone / 0.5 h / 20 °C
1.2: 12 h / 78 - 82 °C
2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 25 - 35 °C
3.1: triethylamine / dichloromethane / 0.5 h / 20 °C
3.2: 1.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetonitrile / 0.5 h
1.2: Reflux
2.1: hydrogen / Raney nickel / methanol / 45 - 50 °C / 3677.86 Torr
3.1: tetramethlyammonium chloride / toluene / Reflux
4.1: sodium hydroxide / 1 h / 0 - 5 °C
View Scheme
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

dronedarone hydrochloride

dronedarone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / butanone / 4 h / 81 - 82 °C
2: hydrogen / palladium 10% on activated carbon / ethanol / 2 h / 50 °C / 3750.38 Torr
3: pyridine / dichloromethane / 15 °C
4: sodium iodide / butanone / 16 h
5: hydrogenchloride / isopropyl alcohol; water / 5 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate; potassium iodide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.5 h / 50 °C
1.2: 80 - 85 °C
2.1: hydrogen / palladium 10% on activated carbon / water; methanol / 40 °C / 3000.3 Torr / Autoclave
3.1: pyridine / dichloromethane / 24 h / 10 - 20 °C
4.1: acetonitrile / Reflux
4.2: 2 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 25 °C
2.1: palladium 10% on activated carbon; ammonium formate / isopropyl alcohol / 0.5 h / 50 °C
3.1: sodium hydrogencarbonate / dichloromethane / 6 h / 35 °C
4.1: N,N-dimethyl-formamide / 4 h / 125 °C
4.2: 2 h / 25 °C
View Scheme
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

(4-(3-chloropropoxy)phenyl)(5-amino-2-butylbenzofuran-3-yl)methanone
1309476-89-8

(4-(3-chloropropoxy)phenyl)(5-amino-2-butylbenzofuran-3-yl)methanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / butanone / 4 h / 81 - 82 °C
2: hydrogen / palladium 10% on activated carbon / ethanol / 2 h / 50 °C / 3750.38 Torr
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 25 °C
2: palladium 10% on activated carbon; ammonium formate / isopropyl alcohol / 0.5 h / 50 °C
View Scheme
2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran
141645-16-1

2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran

N-(2-butyl-3-(4-(3-chloropropoxy)benzoyl)benzofuran-5-yl)methanesulfonamide
1310430-05-7

N-(2-butyl-3-(4-(3-chloropropoxy)benzoyl)benzofuran-5-yl)methanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / butanone / 4 h / 81 - 82 °C
2: hydrogen / palladium 10% on activated carbon / ethanol / 2 h / 50 °C / 3750.38 Torr
3: pyridine / dichloromethane / 15 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 25 °C
2: palladium 10% on activated carbon; ammonium formate / isopropyl alcohol / 0.5 h / 50 °C
3: sodium hydrogencarbonate / dichloromethane / 6 h / 35 °C
View Scheme

(2-Butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl)methanone Specification

The systematic name of this chemical is (2-butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone. With the CAS registry number 141645-16-1, it is also named as methanone, (2-butyl-5-nitro-3-benzofuranyl)(4-hydroxyphenyl)-. And this chemical is pale yellow solid which is used as intermediate of dronedarone hydrochloride. In addition, (2-Butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl)methanone must be sealed in the container.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.49; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5; (4)ACD/LogD (pH 7.4): 5; (5)ACD/BCF (pH 5.5): 4385; (6)ACD/BCF (pH 7.4): 2232; (7)ACD/KOC (pH 5.5): 14027; (8)ACD/KOC (pH 7.4): 7140; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.636; (13)Molar Refractivity: 93.43 cm3; (14)Molar Volume: 260.561 cm3; (15)Polarizability: 37.039×10-24 cm3; (16)Surface Tension: 55.562 dyne/cm; (17)Density: 1.302 g/cm3; (18)Flash Point: 292.158 °C; (19)Enthalpy of Vaporization: 87.318 kJ/mol; (20)Boiling Point: 559.472 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25°C.

People can use the following data to convert to the molecule structure. 
1. SMILES: [O-][N+](=O)c3cc1c(oc(c1C(=O)c2ccc(O)cc2)CCCC)cc3;
2. InChI: InChI=1/C19H17NO5/c1-2-3-4-17-18(19(22)12-5-8-14(21)9-6-12)15-11-13(20(23)24)7-10-16(15)25-17/h5-11,21H,2-4H2,1H3.

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