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133238-87-6

Basic Information
CAS No.: 133238-87-6
Name: 2-Butyl-5-nitrobenzofuran
Article Data: 12
Molecular Structure:
Molecular Structure of 133238-87-6 (2-Butyl-5-nitrobenzofuran)
Formula: C12H13NO3
Molecular Weight: 219.24
Synonyms: benzofuran, 2-butyl-5-nitro-;
EINECS: 603-723-5
Density: 1.191 g/cm3
Boiling Point: 329.721 °C at 760 mmHg
Flash Point: 153.21 °C
Appearance: Pale yellow to yellow liquid
PSA: 58.96000
LogP: 4.20680
Synthetic route
772-33-8

Koshlands reagent I

638-29-9

n-valeryl chloride

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Stage #1: Koshlands reagent I With triphenylphosphine In dichloromethane for 1h; Reflux;
Stage #2: n-valeryl chloride With triethylamine In dichloromethane for 3h; Reflux;
94%

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

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With sulfuric acid In ethanol for 4h; Heating / reflux;80%
With hydrogenchloride In methanol; water at 90 - 95℃; for 5h;7.6 g
1068753-61-6

2-(hex-2-en-1-yl)-4-nitrophenol

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With sodium carbonate; p-benzoquinone; bis(benzonitrile)palladium(II) dichloride In 1,4-dioxane at 80℃; for 3h;50%
335153-21-4

2-(2-formyl-4-nitrophenoxy)hexanoic acid

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
With sodium acetate; acetic anhydride; acetic acid for 3h; Heating;
5445-19-2

methyl 2-bromohexanoate

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C
2: 80 percent / NaOH / Heating
3: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating
View Scheme
97-51-8

5-Nitrosalicylaldehyde

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C
2: 80 percent / NaOH / Heating
3: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating
View Scheme
847869-79-8

methyl 2-(2-formyl-4-nitrophenoxy)butanoate

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaOH / 0.5 h / 90 °C
2: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C
3: 80 percent / NaOH / Heating
4: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating
View Scheme
847869-80-1

methyl 2-(2-formyl-4-nitrophenoxy)pentanoate

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaOH / 2 h / 50 °C
2: 87 percent / K2CO3 / dimethylformamide / 3.5 h / 92 - 94 °C
3: 80 percent / NaOH / Heating
4: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating
View Scheme
335153-23-6

methyl 2-(2-formyl-4-nitrophenoxy)hexanoate

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / NaOH / Heating
2: acetic anhydride; sodium acetate; acetic acid / 3 h / Heating
View Scheme
100-02-7

4-nitro-phenol

133238-87-6

2-(n-butyl)-5-nitrobenzofuran

Conditions
ConditionsYield
Multi-step reaction with 8 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
View Scheme
Multi-step reaction with 3 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
View Scheme
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Specification

The systematic name of this chemical is 2-butyl-5-nitro-1-benzofuran. With the CAS registry number 133238-87-6, it is also named as benzofuran, 2-butyl-5-nitro-. 2-Butyl-5-nitrobenzofuran is pale yellow to yellow liquid which is used as intermediate of dronedarone hydrochloride. In addition, it must be sealed in the container.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 4; (5)ACD/BCF (pH 5.5): 1429; (6)ACD/BCF (pH 7.4): 1429; (7)ACD/KOC (pH 5.5): 6310; (8)ACD/KOC (pH 7.4): 6310; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.586; (13)Molar Refractivity: 61.756 cm3; (14)Molar Volume: 184.016 cm3; (15)Polarizability: 24.482×10-24 cm3; (16)Surface Tension: 45.049 dyne/cm; (17)Density: 1.191 g/cm3; (18)Flash Point: 153.21 °C; (19)Enthalpy of Vaporization: 54.952 kJ/mol; (20)Boiling Point: 329.721 °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)c2cc1c(oc(c1)CCCC)cc2;
2. InChI: InChI=1/C12H13NO3/c1-2-3-4-11-8-9-7-10(13(14)15)5-6-12(9)16-11/h5-8H,2-4H2,1H3.