Product Name

  • Name

    4-Bromo-3-nitrophenol

  • EINECS
  • CAS No. 78137-76-5
  • Article Data15
  • CAS DataBase
  • Density 1.881 g/cm3
  • Solubility
  • Melting Point 144-145 ºC
  • Formula C6H4BrNO3
  • Boiling Point 281 ºC at 760 mmHg
  • Molecular Weight 218.007
  • Flash Point 124 ºC
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 78137-76-5 (4-Bromo-3-nitrophenol)
  • Hazard Symbols
  • Synonyms 2-Bromo-5-hydroxynitrobenzene;4-Bromo-3-nitrophenol;
  • PSA 66.05000
  • LogP 2.58610

Synthetic route

meta-nitrophenol
554-84-7

meta-nitrophenol

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

Conditions
ConditionsYield
With 1-butyl-3-methylpyridinium tribromide at 20℃;98%
With 1,3-di-n-butyl-1H-imidazol-3-ium tribromide at 20℃; for 0.133333h; Neat (no solvent); regioselective reaction;95%
With 1,2-ethanediylbis(triphenylphosphonium) ditribromide In methanol; dichloromethane at 20℃; for 0.0833333h; Solvent; regioselective reaction;85%
at 120 - 140℃; Einleiten von mit CO2 verduenntem Brom-Dampf;
With hydrogenchloride; carbon dioxide; bromine
4-bromo-3-nitroanizole
5344-78-5

4-bromo-3-nitroanizole

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

Conditions
ConditionsYield
Stage #1: 4-bromo-3-nitroanizole With boron tribromide In dichloromethane at -78 - 20℃; for 31h;
Stage #2: With water In dichloromethane at 0℃;
87%
Stage #1: 4-bromo-3-nitroanizole With boron tribromide In dichloromethane at -78 - 20℃; for 31h;
Stage #2: With water In dichloromethane at 0℃;
87%
With boron tribromide In dichloromethane at -78 - 20℃;83%
4-hydroxy-2-nitroaniline
610-81-1

4-hydroxy-2-nitroaniline

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

Conditions
ConditionsYield
With hydrogen bromide Diazotization.Behandlung der Diazoniumsalz-Loesung mit Kupfer-Pulver und wss. HBr;
With sulfuric acid Diazotization.man versetzt mit einer konz. Kaliumbromidloesung und fuegt Kupferpulver hinzu;
Stage #1: 4-hydroxy-2-nitroaniline With hydrogen bromide; sodium nitrite In water at 0 - 10℃; for 1h;
Stage #2: With hydrogen bromide; copper(I) bromide at 40 - 45℃; for 1h;
13.1 g
meta-nitrophenol
554-84-7

meta-nitrophenol

bromine
7726-95-6

bromine

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

Conditions
ConditionsYield
at 120 - 140℃;
4-acetamido-3-nitrophenyl acetate
2243-69-8

4-acetamido-3-nitrophenyl acetate

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous hydrobromic acid
2: aqueous HBr / Diazotization.Behandlung der Diazoniumsalz-Loesung mit Kupfer-Pulver und wss. HBr
View Scheme
3-nitro-aniline
99-09-2

3-nitro-aniline

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Diazotization
2: 120 - 140 °C / Einleiten von mit CO2 verduenntem Brom-Dampf
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

C14H12BrNO4

C14H12BrNO4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere;100%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

vinyl zinc chloride
78389-90-9

vinyl zinc chloride

3-nitro-4-vinylphenol

3-nitro-4-vinylphenol

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 100℃; for 2h;100%
tetravinylsilane
1112-55-6

tetravinylsilane

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

3-nitro-4-vinylphenol

3-nitro-4-vinylphenol

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 80℃; for 2h;100%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

3-nitro-4-vinylphenol

3-nitro-4-vinylphenol

Conditions
ConditionsYield
Stage #1: 4-bromo-3-nitrophenol; tri-n-butyl(vinyl)tin With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 4h;
Stage #2: With potassium fluoride In 1,4-dioxane at 20℃; for 2h;
100%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(4-bromo-3-nitro)phenoxy-tert-butyl-dimethyl-silane

(4-bromo-3-nitro)phenoxy-tert-butyl-dimethyl-silane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3.5h;99%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

benzyl bromide
100-39-0

benzyl bromide

2-Bromo-5-benzyloxy-nitrobenzene
4514-28-7

2-Bromo-5-benzyloxy-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In acetone; acetonitrile for 17h; Heating;95%
With potassium carbonate In acetone91%
With potassium carbonate In acetone; acetonitrile for 17h; Heating / reflux;78%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

(4-bromo-3-nitrophenoxy)(triisopropyl)silane
1380316-20-0

(4-bromo-3-nitrophenoxy)(triisopropyl)silane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 18℃; for 20h;95%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

C13H9BrClNO3

C13H9BrClNO3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere;94.8%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

2-(bromomethyl)naphthalene
3163-27-7

2-(bromomethyl)naphthalene

2-Bromo-5-(1-naphthalenylmethoxy)-nitrobenzene

2-Bromo-5-(1-naphthalenylmethoxy)-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In N-methyl-acetamide92%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

(4-bromomethyl)-phenoxy-allyl acetate

(4-bromomethyl)-phenoxy-allyl acetate

[4-(4-Bromo-3-nitro-phenoxymethyl)-phenoxy]-acetic acid allyl ester

[4-(4-Bromo-3-nitro-phenoxymethyl)-phenoxy]-acetic acid allyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 22℃; for 3h;91%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

4-bromo-3-nitrophenyl trifluoromethanesulfonate

4-bromo-3-nitrophenyl trifluoromethanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 30℃; for 0.5h; Inert atmosphere;90%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

(4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester
330793-01-6

(4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester

tert-butyl (4'-hydroxy-2'-nitro-[1,1'-biphenyl]-4-yl)carbamate

tert-butyl (4'-hydroxy-2'-nitro-[1,1'-biphenyl]-4-yl)carbamate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 110℃; for 12h;72%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 110℃; for 12h; Reflux;72%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

3-amino-4-bromophenol
100367-37-1

3-amino-4-bromophenol

Conditions
ConditionsYield
With iron(III) oxide; hydrazine hydrate In ethanol for 1.5h; Reflux;70.9%
(1,3-thiazol-2-yl)methanol
14542-12-2

(1,3-thiazol-2-yl)methanol

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

2-((4-bromo-3-nitrophenoxy)methyl)thiazole

2-((4-bromo-3-nitrophenoxy)methyl)thiazole

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In toluene at 0℃; Mitsunobu Displacement; Inert atmosphere; Reflux;69%
Trimethyl borate
121-43-7

Trimethyl borate

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

C6H6BNO5

C6H6BNO5

Conditions
ConditionsYield
Stage #1: 4-bromo-3-nitrophenol With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 1h;
Stage #3: With hydrogenchloride In tetrahydrofuran for 1h;
53%
1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1Hpyrrole-2-carbonitrile

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1Hpyrrole-2-carbonitrile

4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

5-(4-hydroxy-2-nitrophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

5-(4-hydroxy-2-nitrophenyl)-1-methyl-1H-pyrrole-2-carbonitrile

Conditions
ConditionsYield
With palladium diacetate; cesium fluoride; catacxium A In 1,4-dioxane; water at 80℃; for 1h; Suzuki Coupling; Inert atmosphere; Sealed tube;30%
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

chloroacetone
78-95-5

chloroacetone

1-(4-Bromo-3-nitro-phenoxy)-propan-2-one
78137-77-6

1-(4-Bromo-3-nitro-phenoxy)-propan-2-one

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

benzyl chloride
100-44-7

benzyl chloride

2-Bromo-5-benzyloxy-nitrobenzene
4514-28-7

2-Bromo-5-benzyloxy-nitrobenzene

Conditions
ConditionsYield
With potassium hydroxide
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

[4-(tert-butyl-dimethyl-silanyloxy)-2-nitro-phenyl]-(2'-nitrophenyl)-amine

[4-(tert-butyl-dimethyl-silanyloxy)-2-nitro-phenyl]-(2'-nitrophenyl)-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / Et3N / CH2Cl2 / 3.5 h / 20 °C
2: 70 percent / rac-BINAP; Cs2CO3 / Pd2(dba)3 / toluene / 0.5 h / 160 °C / microwave irradiation
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

[4-(3-Amino-4-bromo-phenoxymethyl)-phenoxy]-acetic acid allyl ester
1026914-86-2

[4-(3-Amino-4-bromo-phenoxymethyl)-phenoxy]-acetic acid allyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / K2CO3 / dimethylformamide / 3 h / 22 °C
2: 64 percent / Na2S2O4 / tetrahydrofuran; H2O / 4 h / 22 °C
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

4-Oxo-5,6,9,10-tetradehydro-4,5-secofuranoeremophilan-5,1-carbolacton
53820-33-0

4-Oxo-5,6,9,10-tetradehydro-4,5-secofuranoeremophilan-5,1-carbolacton

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: K2CO3, KI / dimethylformamide
2: 82 percent / TiCl3 / ethanol
3: 1.)NO(1+) / 1.) diazotation
4: AlH(C4H9)2 / toluene
5: 27 percent / Li / tetrahydrofuran
6: 10 percent / lithium butyl / -100 °C
7: 84 percent / hydrolysis
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

6-amino-5-brom-3-methylbenzofuran
78137-78-7

6-amino-5-brom-3-methylbenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3, KI / dimethylformamide
2: 82 percent / TiCl3 / ethanol
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

5-Bromo-3-methyl-benzofuran-6-carbonitrile
78137-79-8

5-Bromo-3-methyl-benzofuran-6-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: K2CO3, KI / dimethylformamide
2: 82 percent / TiCl3 / ethanol
3: 1.)NO(1+) / 1.) diazotation
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

5-Bromo-3-methyl-benzofuran-6-carbaldehyde
78137-80-1

5-Bromo-3-methyl-benzofuran-6-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: K2CO3, KI / dimethylformamide
2: 82 percent / TiCl3 / ethanol
3: 1.)NO(1+) / 1.) diazotation
4: AlH(C4H9)2 / toluene
View Scheme
4-bromo-3-nitrophenol
78137-76-5

4-bromo-3-nitrophenol

1-(5-Bromo-3-methyl-benzofuran-6-yl)-3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol
78137-81-2

1-(5-Bromo-3-methyl-benzofuran-6-yl)-3-(2-methyl-[1,3]dioxolan-2-yl)-propan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: K2CO3, KI / dimethylformamide
2: 82 percent / TiCl3 / ethanol
3: 1.)NO(1+) / 1.) diazotation
4: AlH(C4H9)2 / toluene
5: 27 percent / Li / tetrahydrofuran
View Scheme

4-Bromo-3-nitrophenol Chemical Properties

Empirical Formula: C6H4BrNO3
Molecular Weight: 218.0049 
Structure of Phenol,4-bromo-3-nitro- (CAS NO.78137-76-5):

Index of Refraction: 1.652
Molar Refractivity: 42.37 cm3
Molar Volume: 115.89 cm3
Polarizability: 16.797×10-24cm3
Surface Tension: 64.376 dyne/cm
Density: 1.881 g/cm3
Flash Point: 124.074 °C
Enthalpy of Vaporization: 54.125 kJ/mol 
Melting Point: 144-145 ºC
Boiling Point: 281.545 °C at 760 mmHg
Vapour Pressure: 0.002 mmHg at 25°C 
Synonyms of Phenol,4-bromo-3-nitro- (CAS NO.78137-76-5): 4-Brom-3-nitrophenol  

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