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554-84-7 Usage

Chemical Properties

yellow to brown crystalline powder

Uses

Different sources of media describe the Uses of 554-84-7 differently. You can refer to the following data:
1. 3-Nitrophenol is a chemical reagent used in various organic syntheses. Used in the synthesis of RAGE inhibitors via the etherification of phenols. Also used in the synthesis of kinase inhibitors again st epidermal growth factor receptor T790M mutation.
2. As indicator in 0.3% solution in 50% alcohol. pH: 6.8 colorless, 8.6 yellow.
3. 3-Nitrophenol is a chemical reagent used in various organic syntheses. Used in the synthesis of RAGE inhibitors via the etherification of phenols. Also used in the synthesis of kinase inhibitors against epidermal growth factor receptor T790M mutation.

Definition

ChEBI: A member of the class of 3-nitrophenols that is phenol in which one of the hydrogens that is meta to the hydroxy group has been replaced by a nitro group.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 5117, 1995 DOI: 10.1016/0040-4039(95)00963-D

General Description

Colorless to pale yellow crystalline solid. Sinks in and mixes with water.

Air & Water Reactions

Water insoluble.

Reactivity Profile

3-Nitrophenol is a light-yellow, crystalline material, toxic and irritant. When heated to decomposition 3-Nitrophenol emits toxic fumes of oxides of nitrogen [Lewis, 3rd ed., 1993, p. 941]. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases.

Hazard

Toxic by ingestion.

Health Hazard

INHALATION: Inhalation or ingestion causes headaches, drowsiness, nausea, and blue color in lips, ears, and finger nails (cyanosis). EYES: Contact with eyes causes irritation. SKIN: Can be absorbed through intact skin to give same symptoms as for inhalation.

Fire Hazard

Special Hazards of Combustion Products: Dangerous toxic fumes of NO x

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic by skin contact. A skin and severe eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also other nitrophenol entries.

Purification Methods

Crystallise 3-nitrophenol from water, CHCl3, CS2, EtOH or pet ether (b 80-100o), and dry it under vacuum over P2O5 at room temperature. It can also be distilled at low pressure. The 4-nitrobenzoate had m 174o (from EtOH). [Beilstein 6 IV 1269.]

Check Digit Verification of cas no

The CAS Registry Mumber 554-84-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 4 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 554-84:
(5*5)+(4*5)+(3*4)+(2*8)+(1*4)=77
77 % 10 = 7
So 554-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H

554-84-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A15312)  3-Nitrophenol, 98+%   

  • 554-84-7

  • 10g

  • 641.0CNY

  • Detail
  • Alfa Aesar

  • (A15312)  3-Nitrophenol, 98+%   

  • 554-84-7

  • 50g

  • 1807.0CNY

  • Detail
  • Alfa Aesar

  • (A15312)  3-Nitrophenol, 98+%   

  • 554-84-7

  • 250g

  • 7666.0CNY

  • Detail

554-84-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-nitrophenol

1.2 Other means of identification

Product number -
Other names 3-nitro-phenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:554-84-7 SDS

554-84-7Synthetic route

m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With dihydrogen peroxide In water at 30℃; Green chemistry;99%
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique;98%
With water; 3-chloro-benzenecarboperoxoic acid In ethanol at 20℃; for 6h;97%
trifluoromethanesulfonic acid 3-nitrophenyl ester
32578-25-9

trifluoromethanesulfonic acid 3-nitrophenyl ester

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With tetraethylammonium hydroxide In 1,4-dioxane at 20℃; for 1h;99%
With caesium carbonate In toluene at 80℃; for 15h;85%
m-iodonitrobenzene
645-00-1

m-iodonitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
Stage #1: m-iodonitrobenzene With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 70℃; for 5h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;
98%
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique;97%
Stage #1: m-iodonitrobenzene With copper(l) iodide; 8-Hydroxyquinoline-N-oxide In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With cesiumhydroxide monohydrate In water; dimethyl sulfoxide at 100℃; for 15h; Inert atmosphere;
88%
potassium 3-nitrophenyltrifluoroborate

potassium 3-nitrophenyltrifluoroborate

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0333333h;98%
1-allyloxy-3-nitro-benzene
58621-55-9

1-allyloxy-3-nitro-benzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 9h;97%
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating;90%
3-(2-tetrahydropyranyloxy)nitrobenzene
28659-20-3

3-(2-tetrahydropyranyloxy)nitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With acid-washed bentonite In acetone at 40 - 50℃; for 0.833333h;97%
With montmorillonite K-10 In methanol at 40 - 50℃; for 0.4h;96%
3-nitrophenyl acetate
1523-06-4

3-nitrophenyl acetate

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
silica gel; toluene-4-sulfonic acid In water; toluene at 80℃; for 8h;96%
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;70%
With water In acetonitrile for 3h; Irradiation;
p-Nitrophenylvinylether
1441-07-2

p-Nitrophenylvinylether

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With acetic acid; trifluoroacetic acid In water for 0.75h; Reflux;95%
3-(benzyloxy)nitrobenzol
24318-00-1

3-(benzyloxy)nitrobenzol

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With thiophene; sodium hydrogen sulfate; silica gel for 5h; Heating;94%
With methyl-phenyl-thioether; trifluoroacetic acid In toluene at 20℃; for 36h;75%
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃;
1-ethoxy-3-nitrobenzene
621-52-3

1-ethoxy-3-nitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 200 - 220℃; for 0.416667h; Microwave irradiation; Inert atmosphere;94%
3-nitro-aniline
99-09-2

3-nitro-aniline

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite at 12.5 - 90℃;92.3%
Stage #1: 3-nitro-aniline With sulfuric acid In water at 15 - 95℃;
Stage #2: With sulfuric acid In water at 90 - 99℃; for 0.416667h; Temperature;
82%
Stage #1: 3-nitro-aniline With sulfuric acid at 20℃; Cooling with ice;
Stage #2: With sodium nitrite In water Reflux;
75%
diethyl-carbamic acid 3-nitro-phenyl ester
915394-31-9

diethyl-carbamic acid 3-nitro-phenyl ester

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With zirconocene dichloride In tetrahydrofuran at 20℃; Inert atmosphere;91%
Carbonic acid 3-nitro-phenyl ester 2-trimethylsilanyl-ethyl ester
78687-53-3

Carbonic acid 3-nitro-phenyl ester 2-trimethylsilanyl-ethyl ester

A

ethene
74-85-1

ethene

B

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

C

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.166667h; deprotection of TMSEC derivat with various catalyst;A n/a
B n/a
C 90%
3-Bromonitrobenzene
585-79-5

3-Bromonitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
Stage #1: m-nitrobromobenzene With copper(l) iodide; tetra(n-butyl)ammonium hydroxide In water at 60℃; for 24h; Inert atmosphere; Sealed tube;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h; Inert atmosphere; chemoselective reaction;
87%
Stage #1: m-nitrobromobenzene With copper(l) iodide; 8-Hydroxyquinoline-N-oxide In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With cesiumhydroxide monohydrate In water; dimethyl sulfoxide at 110℃; for 15h; Inert atmosphere;
85%
Stage #1: m-nitrobromobenzene With copper(l) iodide; cesiumhydroxide monohydrate; 1,3-diphenylpropanedione In water; dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride In dichloromethane; water; dimethyl sulfoxide at 20℃; Inert atmosphere; chemoselective reaction;
78%
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;78%
Stage #1: m-nitrobromobenzene With copper(ll) sulfate pentahydrate; water; sodium L-ascorbate; potassium hydroxide In dimethyl sulfoxide at 120℃; for 24h; Schlenk technique; Green chemistry;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.5h; pH=2 - 3; Catalytic behavior; Schlenk technique; Green chemistry;
75%
3-nitrophenyl benzenesulfonate
41076-06-6

3-nitrophenyl benzenesulfonate

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere;87%
m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;82%
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h;71%
With caro's acid
With 2A, 3B, 2D, 3E-tetra-O-formylmethyl-2B, C, E-G, 3A,C, D, F, G, 6A-G-heptakaideca-O-methyl-β-CD; dihydrogen peroxide In aq. phosphate buffer at 25℃; pH=7; Kinetics; Reagent/catalyst;
m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

A

meta-nitrophenol
554-84-7

meta-nitrophenol

B

3-nitro-aniline
99-09-2

3-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide; potassium nitrate In water at 20℃; for 2h; Electrochemical reaction; chemoselective reaction;A n/a
B 81%
(R)-Octan-2-ol
5978-70-1

(R)-Octan-2-ol

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

A

(S)- [4-(1-methylheptyloxy)-3-nitrophenyl]-benzoate

(S)- [4-(1-methylheptyloxy)-3-nitrophenyl]-benzoate

B

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; waterA 80%
B n/a
sodium 3-nitrobenzenesulfonate
127-68-4

sodium 3-nitrobenzenesulfonate

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With potassium hydroxide; sodium hydroxide In water for 0.0166667h; microwave irradiation;78%
2-(3-nitrophenoxy)ethanamine
26646-35-5

2-(3-nitrophenoxy)ethanamine

A

C8H9N2O3(1-)

C8H9N2O3(1-)

B

meta-nitrophenol
554-84-7

meta-nitrophenol

C

N-(2-hydroxyethyl)-3-nitroaniline
55131-09-4

N-(2-hydroxyethyl)-3-nitroaniline

D

ethanolamine
141-43-5

ethanolamine

Conditions
ConditionsYield
With deuteriated sodium hydroxide In water-d2 at 20℃; for 0.833333h; Smiles rearrangement; UV-irradiation;A 15%
B n/a
C 73%
D n/a
3-nitroanisole
555-03-3

3-nitroanisole

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With 1-butylpyridinium bromide for 0.0666667h; microwave irradiation;71%
With lithium chloride In N,N-dimethyl-formamide for 6h; Heating;50%
With sodium hydroxide In water Quantum yield; Irradiation; other reagent, reagents ratio;
3-nitrophenyl benzoate
1523-13-3

3-nitrophenyl benzoate

A

meta-nitrophenol
554-84-7

meta-nitrophenol

B

benzyl alcohol
100-51-6

benzyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;A 70%
B n/a
C10H14N4O2
20942-49-8

C10H14N4O2

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With water; sulfonic acid resin (H+ form) In acetonitrile Heating;68%
3-Chloronitrobenzene
121-73-3

3-Chloronitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
Stage #1: 3-Nitrochlorobenzene With copper(ll) sulfate pentahydrate; water; sodium L-ascorbate; potassium hydroxide In dimethyl sulfoxide at 120℃; for 24h; Schlenk technique; Green chemistry;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.5h; pH=2 - 3; Catalytic behavior; Schlenk technique; Green chemistry;
66%
With steam at 420℃; Leiten ueber aktivierte Kieselsaeure;
2-(3-nitrophenoxy)pyridine
28355-48-8

2-(3-nitrophenoxy)pyridine

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
Stage #1: 2-(3-nitrophenoxy)pyridine With methyl trifluoromethanesulfonate In toluene at 100℃; for 2h; Inert atmosphere;
Stage #2: With sodium In methanol for 0.25h; Inert atmosphere; Reflux;
65%
nitrobenzene
98-95-3

nitrobenzene

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

meta-nitrophenol
554-84-7

meta-nitrophenol

C

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

Conditions
ConditionsYield
With Fe2(N,N-bis(pyridin-2-ylmethyl)prop-2-yn-1-amine)2(μ2-Cl)2Cl2; dihydrogen peroxide In acetonitrile at 70℃; for 2h;A 28%
B 62%
C 13%
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Product distribution; pH 6.8 buffer;A 4%
B 4%
C 1%
With [(4-bromophenyl)diazenyl](phenyl)methyl hydroperoxide; oxygen for 3h; Product distribution; Irradiation; reaction under Ar, reaction in acetonitrile; isomer ratio of nitrophenols obtained; isomer ratio distribution in the reaction of aromatics with the hydroxy radical under argon or oxygen gas;
4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane
68716-48-3

4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride In ethanol at 20℃; for 48h;52%
nitrobenzene
98-95-3

nitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With dihydrogen peroxide; bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt In ethanol; water at 20℃; for 1h;50%
With Pt/titania; water for 3h; Reactivity; Reagent/catalyst; Wavelength; Photolysis; regioselective reaction;
1-but-3-enyloxy-3-nitrobenzene
374588-08-6

1-but-3-enyloxy-3-nitrobenzene

meta-nitrophenol
554-84-7

meta-nitrophenol

Conditions
ConditionsYield
With gold(III) chloride; silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;50%
meta-nitrophenol
554-84-7

meta-nitrophenol

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

Conditions
ConditionsYield
With hydrogen In ethanol at 60℃; under 7500.75 Torr; for 2h;100%
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12h;100%
With sodium tetrahydroborate In methanol; water at 20℃; for 3h;100%
meta-nitrophenol
554-84-7

meta-nitrophenol

acetic anhydride
108-24-7

acetic anhydride

3-nitrophenyl acetate
1523-06-4

3-nitrophenyl acetate

Conditions
ConditionsYield
With SBA-15-Ph-Pr-SO3H at 20℃; for 0.75h;100%
With silver trifluoromethanesulfonate at 60℃; for 0.0166667h; neat (no solvent);99%
Montmorillonite KSF for 5h; Ambient temperature;98%
meta-nitrophenol
554-84-7

meta-nitrophenol

1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

Dimethyl-(3-nitro-phenoxy)-silane
79516-19-1

Dimethyl-(3-nitro-phenoxy)-silane

Conditions
ConditionsYield
100%
meta-nitrophenol
554-84-7

meta-nitrophenol

(3R)-1-methoxycarbonylpyrrolidin-2-ol
125787-05-5

(3R)-1-methoxycarbonylpyrrolidin-2-ol

methyl (3S)-3-(3-nitrophenoxy)pyrrolidine-1-carboxylate
741290-76-6

methyl (3S)-3-(3-nitrophenoxy)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;100%
3-bromopropanol methyl ether
36865-41-5

3-bromopropanol methyl ether

meta-nitrophenol
554-84-7

meta-nitrophenol

1-(3-methoxypropoxy)-3-nitrobenzene
1041399-44-3

1-(3-methoxypropoxy)-3-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90℃;100%
Stage #1: meta-nitrophenol With sodium hydride In N,N-dimethyl-formamide for 0.166667h;
Stage #2: 3-bromopropanol methyl ether In N,N-dimethyl-formamide at 20℃; for 18.0833h;
83%
meta-nitrophenol
554-84-7

meta-nitrophenol

3-methyl-1-(morpholin-4-ylcarbonyl)-1H-imidazol-3-ium iodide

3-methyl-1-(morpholin-4-ylcarbonyl)-1H-imidazol-3-ium iodide

C11H12N2O5
501104-91-2

C11H12N2O5

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 16h;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

meta-nitrophenol
554-84-7

meta-nitrophenol

1-but-3-enyloxy-3-nitrobenzene
374588-08-6

1-but-3-enyloxy-3-nitrobenzene

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran100%
2-(4-bromobutyl)isoindoline-1,3-dione
5394-18-3

2-(4-bromobutyl)isoindoline-1,3-dione

meta-nitrophenol
554-84-7

meta-nitrophenol

2-[4-(3-Nitro-phenoxy)-butyl]-isoindole-1,3-dione
666719-64-8

2-[4-(3-Nitro-phenoxy)-butyl]-isoindole-1,3-dione

Conditions
ConditionsYield
Stage #1: meta-nitrophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 2-(4-bromobutyl)isoindoline-1,3-dione In DMF (N,N-dimethyl-formamide) at 60℃; for 4h;
100%
meta-nitrophenol
554-84-7

meta-nitrophenol

2-bromo-4-fluorobenzaldehyde
59142-68-6

2-bromo-4-fluorobenzaldehyde

2-bromo-4-(3-nitro-phenoxy)-benzaldehyde
1196474-70-0

2-bromo-4-(3-nitro-phenoxy)-benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;100%
meta-nitrophenol
554-84-7

meta-nitrophenol

2,4-dinitrophenyl benzoate
1523-15-5

2,4-dinitrophenyl benzoate

A

3-nitrophenyl benzoate
1523-13-3

3-nitrophenyl benzoate

B

potassium 2,4-dinitrophenolate
14314-69-3

potassium 2,4-dinitrophenolate

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 5h;A 100%
B n/a
2,4-dichloro-pyrrolo[2,1-f][1,2,4]triazine
918538-05-3

2,4-dichloro-pyrrolo[2,1-f][1,2,4]triazine

meta-nitrophenol
554-84-7

meta-nitrophenol

2-chloro-4-(3-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine
1313036-56-4

2-chloro-4-(3-nitrophenoxy)pyrrolo[2,1-f][1,2,4]triazine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;100%
With potassium carbonate In tetrahydrofuran; methanol at 20℃;
(R)-Methyl lactate
17392-83-5

(R)-Methyl lactate

meta-nitrophenol
554-84-7

meta-nitrophenol

methyl (R)-2-(3-nitrophenoxy)propanoate
153546-07-7

methyl (R)-2-(3-nitrophenoxy)propanoate

Conditions
ConditionsYield
Stage #1: (R)-Methyl lactate; meta-nitrophenol With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Mitsunobu Displacement;
Stage #2: With diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 8h; Mitsunobu Displacement;
100%
(S)-Methyl lactate
27871-49-4

(S)-Methyl lactate

meta-nitrophenol
554-84-7

meta-nitrophenol

methyl (S)-2-(3-nitrophenoxy)propanoate

methyl (S)-2-(3-nitrophenoxy)propanoate

Conditions
ConditionsYield
Stage #1: (S)-Methyl lactate; meta-nitrophenol With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Mitsunobu Displacement;
Stage #2: With diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 8h; Mitsunobu Displacement;
100%
meta-nitrophenol
554-84-7

meta-nitrophenol

3,4-bis(4-methoxyphenyl)-6-chloropyridazine
67820-94-4

3,4-bis(4-methoxyphenyl)-6-chloropyridazine

3,4-bis(4-methoxyphenyl)-6-(3-nitrophenoxy)pyridazine

3,4-bis(4-methoxyphenyl)-6-(3-nitrophenoxy)pyridazine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 17h;99.9%
at 150℃; for 17h;99.9%
meta-nitrophenol
554-84-7

meta-nitrophenol

benzyl halide

benzyl halide

3-(benzyloxy)nitrobenzol
24318-00-1

3-(benzyloxy)nitrobenzol

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone Reflux;99.81%
1-bromo-butane
109-65-9

1-bromo-butane

meta-nitrophenol
554-84-7

meta-nitrophenol

n-butyl 3-nitrophenylether
122329-01-5

n-butyl 3-nitrophenylether

Conditions
ConditionsYield
Stage #1: meta-nitrophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.0833333h; Inert atmosphere;
Stage #2: 1-bromo-butane In N,N-dimethyl-formamide; mineral oil at 125℃; Inert atmosphere;
99%
With potassium carbonate; acetone
With sodium hydride 1.) DMF, RT, 0.5 h, 2.) 120-140 deg C, 2 h; Yield given. Multistep reaction;
meta-nitrophenol
554-84-7

meta-nitrophenol

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

1-methoxycarbonylmethyloxy-3-nitrobenzene
81720-19-6

1-methoxycarbonylmethyloxy-3-nitrobenzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 7h;99%
With potassium carbonate In acetone at 20℃; for 5h; Inert atmosphere; Reflux;96%
With caesium carbonate In acetone at 50℃; for 1h;84.7%
2-bromo-2-(2-ethyl)dioxolane
18742-02-4

2-bromo-2-(2-ethyl)dioxolane

meta-nitrophenol
554-84-7

meta-nitrophenol

C11H13NO5
929267-27-6

C11H13NO5

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 24h;99%
1,3,5-Tris(bromomethyl)benzene
18226-42-1

1,3,5-Tris(bromomethyl)benzene

meta-nitrophenol
554-84-7

meta-nitrophenol

1,3,5-tris(3-nitrophenoxymethyl)benzene
1095314-52-5

1,3,5-tris(3-nitrophenoxymethyl)benzene

Conditions
ConditionsYield
With potassium carbonate In acetone at 0 - 70℃; Inert atmosphere;99%
With potassium carbonate In acetone at 0 - 70℃; Inert atmosphere;99%
With potassium carbonate In acetone at 0 - 20℃; Inert atmosphere;90%
meta-nitrophenol
554-84-7

meta-nitrophenol

(2-trimethylethylsilylethoxy)methyl chloride
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

C12H19NO4Si
1333239-18-1

C12H19NO4Si

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;99%
meta-nitrophenol
554-84-7

meta-nitrophenol

2,4-dichloro-5-fluoro-7-((2-(trimethyisilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
1428775-54-5

2,4-dichloro-5-fluoro-7-((2-(trimethyisilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

2-chloro-5-fluoro-4-(3-nitrophenoxy)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine
1428775-55-6

2-chloro-5-fluoro-4-(3-nitrophenoxy)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h;99%
meta-nitrophenol
554-84-7

meta-nitrophenol

benzoic acid
65-85-0

benzoic acid

3-nitrophenyl benzoate
1523-13-3

3-nitrophenyl benzoate

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h;99%
meta-nitrophenol
554-84-7

meta-nitrophenol

1,3-phenylene-3,3'-bis(2-propenoic) acid
23713-86-2

1,3-phenylene-3,3'-bis(2-propenoic) acid

C24H16N2O8

C24H16N2O8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 23℃;99%
(SP)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl phenylphosphinate
31352-60-0, 31352-61-1, 54353-18-3

(SP)-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl phenylphosphinate

meta-nitrophenol
554-84-7

meta-nitrophenol

(-)-menthyl O-3-nitrophenyl phenylphosphonate

(-)-menthyl O-3-nitrophenyl phenylphosphonate

Conditions
ConditionsYield
With triethylamine In tetrachloromethane at 20℃; for 12h; Inert atmosphere;99%
meta-nitrophenol
554-84-7

meta-nitrophenol

3-nitrophenoxysulfonyl fluoride
80858-83-9

3-nitrophenoxysulfonyl fluoride

Conditions
ConditionsYield
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; Sealed tube;99%
Stage #1: meta-nitrophenol With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere;
85%
With fluorosulfonyl fluoride; triethylamine In ethanol; water at 25℃; for 4h;
meta-nitrophenol
554-84-7

meta-nitrophenol

3-(tert-butyldiphenylsilyloxy)propyl bromide
177338-13-5

3-(tert-butyldiphenylsilyloxy)propyl bromide

C25H29NO4Si

C25H29NO4Si

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 5h;99%
2,4-dichlorothieno[3,2-d]pyrimidine
16234-14-3

2,4-dichlorothieno[3,2-d]pyrimidine

meta-nitrophenol
554-84-7

meta-nitrophenol

2-chloro-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidine
1353553-07-7

2-chloro-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidine

Conditions
ConditionsYield
With caesium carbonate In 1,4-dioxane at 20℃; for 4h;98.7%
With caesium carbonate In N,N-dimethylsulfoneamide at 20℃; for 1h;91.8%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 70℃;
meta-nitrophenol
554-84-7

meta-nitrophenol

substituted benzyl halide

substituted benzyl halide

1-chloro-3-((3-nitrophenoxy)methyl)benzene

1-chloro-3-((3-nitrophenoxy)methyl)benzene

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In acetone Reflux;98.67%

554-84-7Relevant articles and documents

-

Calvin,Segesser

, p. 186 (1942)

-

Fittig

, p. 179 (1874)

The Rearrangement of Aromatic Nitro Compounds. Part 2. The Rearrangement os Substituted Nitrophenols in Trifluoromethanesulphonic Acid

Bullen, John V.,Ridd, John H.

, p. 1675 - 1679 (1990)

o-Nitrophenols with an additional substituent (Y = NO2, Cl, or Me) in the 3-position rearrange in trifluoromethanesulphonic acid at 100 deg C to give mainly the product with the nitro group in the opposite ortho position; no more than 1-4percent of other products are formed.The reactions give first-order kinetics, are acid-catalysed and (at least when Y = NO2) are intramolecular.The rate of rearrangement varies with the 3-substituent in the order Me > Cl > NO2.The results are discussed in terms of a rate-determining migration of the nitro group in the Wheland intermediate formed by protonation at the 2-position.A much slower rearrangement occurs with 3,4-dinitrophenol under the same conditions to give a small yield of 2,5-dinitrophenol accompanied by decomposition of the substrate.

Evaluation of 2-(piperidine-1-yl)-ethyl (PIP) as a protecting group for phenols: Stability to ortho-lithiation conditions and boiling concentrated hydrobromic acid, orthogonality with most common protecting group classes, and deprotection via Cope elimination or by mild Lewis acids

Norén, Rolf

, (2021/04/07)

A new protecting group, 2-(piperidine-1-yl)-ethyl (PIP), was evaluated as a protecting group for phenols. The PIP group was stable to ortho-lithiation conditions and refluxing with concentrated hydrobromic acid. Deprotection was accomplished by two routes, oxidation to N-oxides followed by Cope elimination (CE) and subsequent hydrolysis or ozonolysis of the vinyl ether or one-step deprotection by BBr3?Me2S. The PIP group is orthogonal to the O-benzyl, O-acetyl, O-t-butyldiphenylsilyl, O-methyl, O-p-methoxybenzyl, O-allyl, O-tetrahydropyranyl and N-t-butoxy carbonyl groups. The CE step was systematically studied and was found to give higher yields when the reaction was performed in the presence of silylating agents.

Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols

Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.

supporting information, p. 3925 - 3931 (2021/08/24)

A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.

Pyroptosis drug prodrug, preparation method thereof and pyroptosis drug

-

Paragraph 0064, (2021/06/13)

The invention discloses a pyroptosis drug prodrug, a preparation method thereof and a pyroptosis drug. The pyroptosis drug prodrug provided by the invention can cause mitochondria damage, release cytochrome c and activate Caspase3 to shear GSDME by targeting mitochondria, so that pyroptosis of cells occurs. The prodrug (NCyNH2) has selectivity to tumor cells, damage to normal cells is reduced, and the activation condition of the prodrug (NCyNH2) can be detected through recovery of self-fluorescence. After intratumor administration, the prodrug can effectively regulate the tumor immune microenvironment and activate T cell mediated anti-tumor immune response. The molecule has huge application prospects in the aspects of mitochondrial targeting, cell respiration inhibition, pyroptosis induction, tumor immune microenvironment improvement, T cell mediated anti-tumor immune response activation and the like.

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