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619-19-2

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619-19-2 Usage

Chemical Properties

White to yellow crystalline powder

Uses

Different sources of media describe the Uses of 619-19-2 differently. You can refer to the following data:
1. 4-Nitrosalicylic Acid is a metabolite in the degradation pathway of 2-chloro-4-nitrobenzoic acid by acinetobacter strain RKJ12.
2. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

General Description

2-Hydroxy-4-nitrobenzoic acid is metabolized to 2,4-dihydroxybenzoic acid (2,4-DHBA) by a mono-oxygenase with the concomitant release of chloride and nitrite ions.

Safety Profile

Poison by intraperitoneal route.Moderately toxic by ingestion. When heated todecomposition it emits toxic vapors of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 619-19-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 619-19:
(5*6)+(4*1)+(3*9)+(2*1)+(1*9)=72
72 % 10 = 2
So 619-19-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO5/c9-6-3-4(8(12)13)1-2-5(6)7(10)11/h1-3,9H,(H,10,11)

619-19-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Nitrosalicylic acid

1.2 Other means of identification

Product number -
Other names 2-hydroxy-4-nitrobenzoic acid

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:619-19-2 SDS

619-19-2Synthetic route

4-nitro-o-anisic acid
2597-56-0

4-nitro-o-anisic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With boron tribromide In dichloromethane97%
With sulfuric acid
With hydrogen bromide
With hydrogen bromide; acetic acid at 90℃; for 72h;
4-nitro-o-anisic acid
2597-56-0

4-nitro-o-anisic acid

boron tribromide
10294-33-4

boron tribromide

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 2h;97%
2-chloro-4-nitrobenzoic acid
99-60-5

2-chloro-4-nitrobenzoic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With pyridine; water; potassium carbonate; copper for 0.25h; sonication;96%
With pyridine; copper; potassium carbonate In water for 2h; Heating;90%
With quicklime; water; copper at 160 - 170℃;
With copper(l) iodide; copper; potassium carbonate
With calcium hydroxide; copper diacetate In water at 160℃; for 7h;
2-(hydroxymethyl)-5-nitrophenol
57356-40-8

2-(hydroxymethyl)-5-nitrophenol

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sodium hypochlorite; water at 25℃; for 0.5h;96%
With oxygen In acetonitrile at 20℃; for 8.5h; Catalytic behavior;85%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; under 3800.26 Torr; for 15h;91%
With oxygen; potassium acetate; p-benzoquinone; palladium diacetate In ISOPROPYLAMIDE at 115℃; under 3800.26 Torr; for 15h; Product distribution / selectivity;91%
With [Fe(II)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethylenediamine)(CH3CN)2](ClO4)2; dihydrogen peroxide In water; acetonitrile at 20℃; Inert atmosphere; regioselective reaction;68 %Spectr.
salicylic acid
69-72-7

salicylic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sodium perborate hexahydrate; hydroquinone; sodium nitrite In neat (no solvent) for 0.0333333h; Molecular sieve; Microwave irradiation; regioselective reaction;75%
With potassium hydrogensulfate; potassium metaperiodate; silica gel; sodium nitrite In neat (no solvent) for 0.0833333h; Reagent/catalyst; Solvent; Microwave irradiation;69%
With potassium hydrogensulfate; potassium metaperiodate; sodium nitrite In water; acetonitrile at 44.84℃; Kinetics; Temperature;
2-hydroxy-4-nitro-benzoic acid methyl ester
13684-28-1

2-hydroxy-4-nitro-benzoic acid methyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

A

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

B

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
Stage #1: 4-nitro-benzoic acid With potassium carbonate In N,N-dimethyl acetamide at 90℃; for 0.5h;
Stage #2: 2-hydroxy-4-nitro-benzoic acid methyl ester at 90℃; for 24h;
A 32%
B n/a
2-methyl-5-nitrophenol
5428-54-6

2-methyl-5-nitrophenol

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate
7-nitro-4H-benzo[1,3]dioxine
50603-43-5

7-nitro-4H-benzo[1,3]dioxine

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate; acetic acid
2-hydroxy-4-nitro-benzonitrile
39835-14-8

2-hydroxy-4-nitro-benzonitrile

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid Siedetemperatur;
With hydrogenchloride at 160℃; Reinigung ueber das Barium-Salz;
With sulfuric acid; acetic acid Siedetemperatur;
2-bromo-4-nitrobenzoic acid
16426-64-5

2-bromo-4-nitrobenzoic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With barium dihydroxide; sodium hydroxide; copper (I) acetate
7-nitro-3-phenyl-benz[e][1,2]oxazin-4-one

7-nitro-3-phenyl-benz[e][1,2]oxazin-4-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

B

benzonitrile
100-47-0

benzonitrile

2-methoxy-4-nitrobenzonitrile
101084-96-2

2-methoxy-4-nitrobenzonitrile

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid
With sulfuric acid; hydrogen bromide; acetic acid
2-(2,4-dinitro-phenoxy)-4-nitro-benzoic acid

2-(2,4-dinitro-phenoxy)-4-nitro-benzoic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium carbonate
4-Nitroanthranilic acid
619-17-0

4-Nitroanthranilic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
Diazotization;
With sulfuric acid; sodium nitrite Diazotization;
2-(2-Hydroxy-4-nitro-benzoylamino)-2-methyl-propionic acid
129973-05-3

2-(2-Hydroxy-4-nitro-benzoylamino)-2-methyl-propionic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid 1) reflux, 2) 3 deg C; Yield given;
4-nitro-2-(octanoyloxy)benzoic acid

4-nitro-2-(octanoyloxy)benzoic acid

A

Octanoic acid
124-07-2

Octanoic acid

B

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With Tris-HCl buffer; water; calcium(II) ion; sodium chloride; Agkistrodon piscivorus piscivorus In acetonitrile at 37℃; Rate constant; pH = 8.0;
hydrogenchloride
7647-01-0

hydrogenchloride

methyl 6-nitro-1,2-benzisoxazole-3-carboxylate
5453-86-1

methyl 6-nitro-1,2-benzisoxazole-3-carboxylate

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
at 150℃;
carbon dioxide
124-38-9

carbon dioxide

meta-nitrophenol
554-84-7

meta-nitrophenol

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium carbonate at 210℃; under 29420.3 Torr;
6-nitro-benzisoxazole-carboxylic acid-(3)-methyl ester

6-nitro-benzisoxazole-carboxylic acid-(3)-methyl ester

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sulfuric acid; acetic acid
6-nitro-indoxazene-carboxylic acid-(3)-methyl ester

6-nitro-indoxazene-carboxylic acid-(3)-methyl ester

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride at 150℃;
potassium-salt of sulfuric acid mono-<2-methyl-5-nitro-phenyl ester>

potassium-salt of sulfuric acid mono-<2-methyl-5-nitro-phenyl ester>

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium permanganate
2-chloro-4-nitrobenzoic acid
99-60-5

2-chloro-4-nitrobenzoic acid

water
7732-18-5

water

quicklime

quicklime

copper powder

copper powder

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
at 160 - 170℃;
sodium-<2-chloro-4-nitro benzoate>

sodium-<2-chloro-4-nitro benzoate>

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sodium-; copper diacetate; magnesium oxide at 170℃; weiteres Reagens: Wasser;
hydrogenchloride
7647-01-0

hydrogenchloride

2-hydroxy-4-nitro-benzohydroxamic acid
98550-12-0

2-hydroxy-4-nitro-benzohydroxamic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
at 150℃;
4-Aminosalicylic acid
65-49-6

4-Aminosalicylic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With Streptomyces thioluteus para-aminobenzoate N-oxygenase
2-(4-nitrobenzoylamino)isobutyric acid
52944-16-8

2-(4-nitrobenzoylamino)isobutyric acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) Cu(0)/O2/trimethylamine N-oxide, 2) 0.5N HCl / 1) CH3CN, 75 deg C, 1.8h
2: 15percent aq. H2SO4 / 1) reflux, 2) 3 deg C
View Scheme
4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) NaOH, 2) 5N HCl / 1) H2O/THF, a) 1 deg C, 2.5h, b) 20 deg C, 1h, 2) 0 deg C
2: 1) Cu(0)/O2/trimethylamine N-oxide, 2) 0.5N HCl / 1) CH3CN, 75 deg C, 1.8h
3: 15percent aq. H2SO4 / 1) reflux, 2) 3 deg C
View Scheme
4-nitro-2-phenoxybenzoic acid
192181-49-0

4-nitro-2-phenoxybenzoic acid

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HNO3
2: aqueous K2CO3
View Scheme
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-hydroxy-4-nitrobenzoyl chloride
39614-82-9

2-hydroxy-4-nitrobenzoyl chloride

Conditions
ConditionsYield
With thionyl chloride at 90℃; for 1h;100%
With thionyl chloride In chloroform at 0℃; for 5h; Heating / reflux;75%
With thionyl chloride; benzene
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

2-hydroxy-4-nitro-benzoic acid methyl ester
13684-28-1

2-hydroxy-4-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
In methanol; hexane; toluene at 20℃; for 1.25h;100%
In methanol; hexane; toluene at 20℃; for 1.25h;100%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

4-nitro-o-anisic acid
2597-56-0

4-nitro-o-anisic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;100%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

1-iodo-propane
107-08-4

1-iodo-propane

propyl 4-nitro-2-propoxybenzoate

propyl 4-nitro-2-propoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;100%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl 2-methoxy-4-nitrobenzoate
39106-79-1

methyl 2-methoxy-4-nitrobenzoate

Conditions
ConditionsYield
With potassium carbonate for 4h; Reflux;99%
With tetrabutylammomium bromide In dichloromethane for 10h; Ambient temperature; Yield given;
methanol
67-56-1

methanol

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-hydroxy-4-nitro-benzoic acid methyl ester
13684-28-1

2-hydroxy-4-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 65℃; for 96h; Inert atmosphere;98%
With sulfuric acid for 12h; pH=<= 1; Reflux;98%
With sulfuric acid at 70℃;96%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-(hydroxymethyl)-5-nitrophenol
57356-40-8

2-(hydroxymethyl)-5-nitrophenol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 0 - 23℃; for 18h;98%
With borane-THF98%
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 16h; Cooling with ice;97.5%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

methyl 4-aminosalicylate
4136-97-4

methyl 4-aminosalicylate

Conditions
ConditionsYield
Stage #1: 2-hydroxy-4-nitrobenzoic acid With thionyl chloride In methanol
Stage #2: With hydrogen; palladium 10% on activated carbon In ethyl acetate
98%
Multi-step reaction with 2 steps
1: 95 percent / SOCl2
2: 98 percent / H2 / Pd/C / ethyl acetate
View Scheme
Multi-step reaction with 2 steps
1: nickel-aluminium-alloy; aq. NaOH solution
2: sulfuric acid
View Scheme
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

ethyl iodide
75-03-6

ethyl iodide

2-ethoxy-4-nitro-benzoic acid ethyl ester
910572-96-2

2-ethoxy-4-nitro-benzoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In butanone at 80℃; for 16h;97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-hydroxy-4-nitro-benzoic acid methyl ester
13684-28-1

2-hydroxy-4-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride In methanol at 0℃; for 6h; Reflux;97%
With sulfuric acid In methanol
[13C2H3] methyl iodide
20710-47-8

[13C2H3] methyl iodide

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

C7(13)C2H3(2)H6NO5

C7(13)C2H3(2)H6NO5

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide97%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

4-Aminosalicylic acid
65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With aminomethyl polystyrene resin formic acid salt; zinc In methanol at 20℃; for 2h;96%
With ammoniummethyl polystyrene resin formate; palladium on activated charcoal In methanol at 20℃; for 5h;95%
With polymer-supported formate; magnesium In methanol at 20℃; for 3h;94%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

methyl 2-methoxy-4-nitrobenzoate
39106-79-1

methyl 2-methoxy-4-nitrobenzoate

Conditions
ConditionsYield
In diethyl ether at 20℃; for 4h; Methylation;96%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

allyl bromide
106-95-6

allyl bromide

2-allyloxy-4-nitrobenzoic acid allyl ester
735351-47-0

2-allyloxy-4-nitrobenzoic acid allyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 22h;90%
Stage #1: 2-hydroxy-4-nitrobenzoic acid With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;
76%
Stage #1: 2-hydroxy-4-nitrobenzoic acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.333333h;
Stage #2: allyl bromide In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;
Stage #3: With hydrogenchloride In DMF (N,N-dimethyl-formamide); water
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

methyl iodide
74-88-4

methyl iodide

2-hydroxy-4-nitro-benzoic acid methyl ester
13684-28-1

2-hydroxy-4-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2-hydroxy-4-nitrobenzoic acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 6h; Time;
90%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1h;84%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

C15H17NO5

C15H17NO5

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 8h;90%
ethanol
64-17-5

ethanol

2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-hydroxy-4-nitro-benzoic acid ethyl ester
78987-51-6

2-hydroxy-4-nitro-benzoic acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; Product distribution / selectivity; Heating / reflux;89%
With thionyl chloride Reflux;
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-hydroxy-4-nitrobenzaldehyde
2460-58-4

2-hydroxy-4-nitrobenzaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide88%
Multi-step reaction with 2 steps
1: B2H6 / tetrahydrofuran
2: MnO2 / CHCl3 / Heating
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / 4 h / Reflux
2: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C
3: dipyridinium dichromate / dichloromethane / 3 h / 40 °C
4: phosphorus tribromide / dichloromethane / 4 h / -78 - 20 °C
View Scheme
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

methyl iodide
74-88-4

methyl iodide

4-nitro-o-anisic acid
2597-56-0

4-nitro-o-anisic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;88%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

dimethyl amine
124-40-3

dimethyl amine

2-hydroxy-N,N-dimethyl-4-nitrobenzamide

2-hydroxy-N,N-dimethyl-4-nitrobenzamide

Conditions
ConditionsYield
Stage #1: 2-hydroxy-4-nitrobenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 1.5h;
Stage #2: dimethyl amine In dichloromethane
88%
Stage #1: 2-hydroxy-4-nitrobenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 1.5h;
Stage #2: dimethyl amine In dichloromethane at 20℃;
71%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

2-acetoxy-4-nitrobenzoic acid
17336-10-6

2-acetoxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With dmap; acetic anhydride; triethylamine In ethyl acetate at 80℃;87%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butyl 2-hydroxy-4-nitrobenzoate
1356600-78-6

tert-butyl 2-hydroxy-4-nitrobenzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 20h; Inert atmosphere;87%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran Reflux;81.7%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 60℃;73%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In tert-butyl alcohol at 10 - 35℃;2.3 g
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

isopropyl alcohol
67-63-0

isopropyl alcohol

2-isopropoxy-4-nitrobenzoic acid
1319746-14-9

2-isopropoxy-4-nitrobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol at 100℃; for 2h;87%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

benzyl bromide
100-39-0

benzyl bromide

2-(benzyloxy)-4-nitrobenzoic acid
5340-21-6

2-(benzyloxy)-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;83%
2-hydroxy-4-nitrobenzoic acid
619-19-2

2-hydroxy-4-nitrobenzoic acid

m,p-dichloroaniline
95-76-1

m,p-dichloroaniline

N-(3,4-dichlorophenyl)-2-hydroxy-4-nitrobenzamide

N-(3,4-dichlorophenyl)-2-hydroxy-4-nitrobenzamide

Conditions
ConditionsYield
With phosphorus trichloride Microwave irradiation; Reflux;83%

619-19-2Relevant articles and documents

Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids

Luo, Feihua,He, Shuhua,Gou, Quan,Chen, Jinyang,Zhang, mingzhong

, (2021/10/06)

A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.

Fe3O4@SiO2@Im[Cl]Mn(III)-complex as a highly efficient magnetically recoverable nanocatalyst for selective oxidation of alcohol to imine and oxime

Kazemnejadi, Milad,Alavi, Seyyedeh Ameneh,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen

, p. 230 - 249 (2019/03/28)

An efficient and environmentally friendly oxidation process for the one-pot preparation of oxime, imine and carbonyl compounds through alcohol oxidation in the presence of H2O2 and/or O2 have been developed by a melamine-Mn(III) Schiff base complex supported on Fe3O4@SiO2–Cl nanoparticles, named as Fe3O4@SiO2@Im[Cl]Mn(III)-complex nanocomposite, at room temperature. Direct oxidation of alcohol to carboxylic acid was performed using the catalyst in the presence of molecular O2 at room temperature in a different approach. The oxidation products were obtained with excellent yields and high TOFs. The properties of the catalyst were characterized by Fourier transform infrared spectroscopy (FTIR), elemental analysis (C, H, N), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), inductive coupled plasma (ICP), cyclic voltammetry (CV), nuclear magnetic resonance (1H & 13C NMR), vibration sample magnetometer (VSM), Brunauer– Emmett–Teller (BET) and differential pulse voltammetry (DPV) analyses. The mechanism of the oxidation processes was investigated for the both H2O2 and O2 oxidants. The role of the imidazolium moiety in the catalyst as a secondary functionality was investigated. Chemoselectivity behavior of the catalyst was studied by some combinations. The catalyst could be recycled from the reaction mixture by a simple external magnet and reused for several times without any considerable reactivity loss.

Potassium Periodate/NaNO2/KHSO4-Mediated Nitration of Aromatic Compounds and Kinetic Study of Nitration of Phenols in Aqueous Acetonitrile

Sriram, Y. Hemanth,Fatima, Touheeth,Rajanna,Kumar, M. Satish,Raju, R. Madhusudan

supporting information, p. 622 - 632 (2017/06/30)

Synthesis and kinetics of potassium periodate(KIO4)/NaNO2/KHSO4)-initiated nitration of aromatic compounds have been studied in aqueous acetonitrile medium. Synthesis of nitroaromatic compounds is achieved under conventional and solvent-free microwave conditions. Reaction times in microwave-assisted reaction are comparatively less than in conventional reaction. The reaction kinetics for the nitration of phenols in aqueous bisulfate and acetonitrile medium indicated first-order dependence on [phenol], [NaNO2], and [KIO4]. An increase in [KHSO4] accelerated the rate of nitration under otherwise similar conditions. The rate of nitration increased in the solvent of high dielectric media (solvents with high dielectric constant (D)). Observed results were in accordance with Amis and Kirkwood plots [log k′ vs. (1/D) and [(D ? 1)/(2D + 1)]. These observations probably indicate the participation of anionic species and molecular or (dipolar) species in the rate-determining step. In addition, the plots of (log k′) versus volume% of organic solvent were also linear, which probably indicate the importance of both electrostatic and nonelectrostatic forces, solvent–solute interactions during nitration of phenols. Reaction rates accelerated with the introduction of electron-donating groups and retarded with electron-withdrawing groups, but results could not be quantitatively correlated with Hammett's equation and depicted deviations from linearity. These deviations could probably be attributed to cumulative effects arising inductive, resonance, and steric effects. Leffler's plot (ΔH# vs. ΔS#) was found linear indicating the compensation (cumulative) effect of both enthalpy and entropy parameters in controlling the mechanism of nitration.

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