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62-23-7 Usage

Description

p-Nitrobenzoic acid, also known as 4-Nitrobenzoic Acid, is a chemical compound belonging to the class of nitrobenzoic acids. It is characterized by an odorless pale yellow crystalline structure with the nitro group positioned at the 4-position on the benzene ring. This light yellow crystalline powder exhibits specific chemical properties that make it suitable for various applications across different industries.

Uses

1. Used in Pharmaceutical Industry:
p-Nitrobenzoic acid is used as a synthetic intermediate for the development of anti-Trypanosoma cruzi agents. These agents are crucial in the treatment of Chagas disease, a life-threatening illness caused by the parasite Trypanosoma cruzi. p-Nitrobenzoic acid plays a significant role in the synthesis of these therapeutic agents, contributing to the fight against this devastating disease.
2. Used in Chemical Synthesis:
As a light yellow crystalline powder, p-Nitrobenzoic acid serves as a valuable building block in the synthesis of various organic compounds. Its unique chemical properties allow it to be utilized in the creation of a wide range of products, from pharmaceuticals to specialty chemicals, making it an essential component in the chemical synthesis process.
3. Used in Research and Development:
Due to its distinct chemical structure and properties, p-Nitrobenzoic acid is often employed in research and development activities. It can be used as a reference compound or a starting material for the synthesis of novel molecules with potential applications in various fields, including medicine, materials science, and environmental science.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 2387, 1985 DOI: 10.1016/S0040-4039(00)94834-2Journal of the American Chemical Society, 72, p. 5012, 1950 DOI: 10.1021/ja01167a051

Air & Water Reactions

Insoluble in water.

Reactivity Profile

p-Nitrobenzoic acid is incompatible with strong oxidizers. p-Nitrobenzoic acid is also incompatible with strong bases (potassium hydroxide). p-Nitrobenzoic acid may react with cyanides.

Fire Hazard

p-Nitrobenzoic acid is combustible.

Purification Methods

Purify it as for 3-nitrobenzoic acid above. The amide has m 201.6o (from H2O). [Beilstein 9 III 1537, 9 IV 1072.]

Check Digit Verification of cas no

The CAS Registry Mumber 62-23-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 2 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 62-23:
(4*6)+(3*2)+(2*2)+(1*3)=37
37 % 10 = 7
So 62-23-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)/p-1

62-23-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A14738)  4-Nitrobenzoic acid, 99%   

  • 62-23-7

  • 250g

  • 276.0CNY

  • Detail
  • Alfa Aesar

  • (A14738)  4-Nitrobenzoic acid, 99%   

  • 62-23-7

  • 1000g

  • 484.0CNY

  • Detail
  • Alfa Aesar

  • (A14738)  4-Nitrobenzoic acid, 99%   

  • 62-23-7

  • 5000g

  • 2310.0CNY

  • Detail

62-23-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-nitrobenzoic acid

1.2 Other means of identification

Product number -
Other names p-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:62-23-7 SDS

62-23-7Synthetic route

4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite In acetonitrile at 35℃; pH 6.7;100%
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; water; acetonitrile at 35℃; pH=6.7; Green chemistry;100%
With gold oxide; oxygen; copper(II) oxide; sodium hydroxide; silver(l) oxide In water at 40℃; under 750.075 Torr; for 16h;100%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With sodium perborate In acetic acid for 1.5h; steam bath;100%
With phosphate-buffered silica gel supported KMnO4 In cyclohexane at 65℃;100%
With [Cu2C6H4(CHNCH2CH2N(CH2C5H4N)2)2](2+)*2ClO4(1-)=C36H38Cu2N8(ClO4)2; oxygen In acetone at -90.16℃;100%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

carbon monoxide
201230-82-2

carbon monoxide

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 50℃; under 760 Torr; for 3h;100%
With amphiphilic resin-supported phosphine-palladium; water; potassium carbonate at 25℃; under 760 Torr; for 12h; hydroxycarbonylation;100%
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 50℃; for 3h; Product distribution; effect of different catalysts;100%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation;99%
With sodium hypochlorite; bis(2,2'-bipyridine)dichloronickel(II) In acetonitrile for 1h; Ambient temperature;98%
With oxygen; nitric acid at 230℃; under 4500.45 - 15001.5 Torr; for 14h; Autoclave; Green chemistry;97.1%
4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;99%
With methanesulfonic acid; 1-methylimidazolium hydrobromide at 120℃; for 2h;96%
With iron(III) sulfate; water In toluene at 110℃; for 4h; Ionic liquid;95%
tert-butyl 4-nitrobenzoate
19756-72-0

tert-butyl 4-nitrobenzoate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;99%
With ytterbium(III) triflate In nitromethane at 45 - 50℃; for 8h;98%
With sodium hydroxide In methanol; dichloromethane at 20℃; for 5.5h; Solvent;93%
4-nitrobenzanilide
3460-11-5

4-nitrobenzanilide

A

aniline
62-53-3

aniline

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With 40% potassium fluoride/alumina for 0.0666667h; Microwave irradiation; Neat (no solvent);A 90%
B 99%
3-(4-nitrophenyl)acrylic acid n-butyl ester
131061-15-9, 86622-84-6

3-(4-nitrophenyl)acrylic acid n-butyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With sodium periodate; 2C16H13N2O10Ru2(1-)*Ca(2+) In water at 45℃; for 16h; Green chemistry;99%
4-nitrobenzoylacetone
4023-82-9

4-nitrobenzoylacetone

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;99%
ethyl 4-nitrobenzoate
99-77-4

ethyl 4-nitrobenzoate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;98%
Stage #1: ethyl 4-nitrobenzoate With iron(III) chloride In tetrachloromethane at 85℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrachloromethane Inert atmosphere;
96%
With potassium hydroxide In methanol at 35℃; for 0.166667h;83%
4-methyl-N'-(1-(4-nitrophenyl)ethylidene)benzenesulfonohydrazide
41780-82-9

4-methyl-N'-(1-(4-nitrophenyl)ethylidene)benzenesulfonohydrazide

A

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With silica-supported selenamide; dihydrogen peroxide In tert-butyl alcohol at 55℃; for 20h;A 98%
B 2%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

A

N-acetoxy-1,8-naphthalenedicarboximide

N-acetoxy-1,8-naphthalenedicarboximide

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With acetic acid In titaniumA n/a
B 98%
4-((tert-butyldimethylsilyl)oxy)benzyl 4-nitrobenzoate

4-((tert-butyldimethylsilyl)oxy)benzyl 4-nitrobenzoate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;98%
2-p-nitrobenzoyl-2-acetamido-1,3-propanediol
58561-10-7

2-p-nitrobenzoyl-2-acetamido-1,3-propanediol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With nitric acid In water at 100℃; for 6h;97.8%
polymer, Merrifield resin, 3-hydroxybenzaldehyde bound, adduct with 2-phenyl-1,3-dithiane, 4-nitrobenzoyl ester, dithiane-deprotected

polymer, Merrifield resin, 3-hydroxybenzaldehyde bound, adduct with 2-phenyl-1,3-dithiane, 4-nitrobenzoyl ester, dithiane-deprotected

A

polymer, Merrifield resin, 3-hydroxybenzaldehyde bound, adduct with 2-phenyl-1,3-dithiane, benzoyl ester, dithiane-deprotected, photolysis product

polymer, Merrifield resin, 3-hydroxybenzaldehyde bound, adduct with 2-phenyl-1,3-dithiane, benzoyl ester, dithiane-deprotected, photolysis product

B

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 1h; Cyclization; Irradiation;A 97%
B n/a
(4-Nitrophenyl)acetylene
937-31-5

(4-Nitrophenyl)acetylene

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: (4-Nitrophenyl)acetylene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h;
Stage #2: With hydrogenchloride In water at 20℃;
97%
With carbon tetrabromide; water; oxygen In ethyl acetate for 40h; Irradiation;97%
Multi-step reaction with 3 steps
1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 25 °C / Inert atmosphere
2.1: potassium carbonate / methanol; dichloromethane / 1 h / 25 °C
2.2: 4 h / 145 °C / Inert atmosphere
3.1: dihydrogen peroxide / 25 °C / pH 7.4 / aq. phosphate buffer
View Scheme
diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With lithium trimethylsilanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; Glovebox;97%
benzyl 4-nitrobenzoate
14786-27-7

benzyl 4-nitrobenzoate

toluene
108-88-3

toluene

A

1-methyl-3-(phenylmethyl)-benzene
620-47-3

1-methyl-3-(phenylmethyl)-benzene

B

1-methyl-4-(phenylmethyl)benzene
620-83-7

1-methyl-4-(phenylmethyl)benzene

C

2-benzyltoluene
713-36-0

2-benzyltoluene

D

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;A n/a
B n/a
C n/a
D 97%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With potassium trimethylsilonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h;96%
(1S,2S)-1,2-bis(4-nitrophenyl)ethane-1,2-diol
1609430-93-4

(1S,2S)-1,2-bis(4-nitrophenyl)ethane-1,2-diol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: (1S,2S)-1,2-bis(4-nitrophenyl)ethane-1,2-diol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 2h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; chemoselective reaction;
96%
2-(hydroxymethyl)-5-nitrophenol
57356-40-8

2-(hydroxymethyl)-5-nitrophenol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With 3-methyl-butan-2-one; samarium(III) oxide at 55 - 69℃; for 2.16667h; Temperature;96%
carbon dioxide
124-38-9

carbon dioxide

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: para-nitrophenyl bromide With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 7h; Schlenk technique; Sealed tube;
96%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 60℃; for 0.416667h; Schlenk technique;
Stage #2: para-nitrophenyl bromide With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 10h; Schlenk technique;
96%
Stage #1: para-nitrophenyl bromide With iodine; magnesium; methyl iodide In tetrahydrofuran at 50℃; for 3h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran for 2h; Inert atmosphere;
13.5 g
With triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 24h; Irradiation;
carbon dioxide
124-38-9

carbon dioxide

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With C26H30B10Cl2P2Pd In toluene at 60℃; under 760.051 Torr; for 10h;96%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: 4-chlorobenzonitrile With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 14h; Schlenk technique; Sealed tube;
60%
With triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 24h; Irradiation;
4-nitrobenzyl trimethylsilyl ether
14856-73-6

4-nitrobenzyl trimethylsilyl ether

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With aluminium trichloride; silver bromate In acetonitrile for 0.35h; Product distribution; Heating; other primary trimethylsilyl ethers, var. time;95%
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
In acetone at 22℃; for 0.5h;95%
4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With sodium periodate; dibenzo-18-crown-6; N-benzyl-N,N,N-triethylammonium chloride In ethanol for 1.5h; Heating;95%
With sodium percarbonate In water; acetone for 2h; Irradiation;85%
With sodium hydroxide; potassium chloride; potassium hexacyanoferrate(III) In water; acetonitrile at 10℃; Rate constant;
With sodium percarbonate In water; acetone for 1h; Irradiation; other α-haloketones, var. time; also thermal cleavage;
4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With silica-supported selenamide; dihydrogen peroxide In tetrahydrofuran at 55℃; for 37h;95%
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 38h; Heating;94%
With [hydroxy(tosyloxy)iodo]benzene; water In dimethyl sulfoxide at 20℃; for 24h;82%
trans-4,4'-dinitrostilbene
736-31-2

trans-4,4'-dinitrostilbene

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With Oxone; osmium(VIII) oxide In N,N-dimethyl-formamide; tert-butyl alcohol at 20℃; for 3h;95%
Multi-step reaction with 2 steps
1.1: potassium carbonate; potassium hexacyanoferrate(III) / tert-butyl alcohol; water / 20 °C / Inert atmosphere
2.1: sodium t-butanolate; oxygen / tetrahydrofuran / 2 h / 20 °C / 760.05 Torr
2.2: pH 1
View Scheme
allyl 4-nitrobenzoate
15727-80-7

allyl 4-nitrobenzoate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide for 0.333333h; Heating;95%
With toluene-4-sulfonic acid for 0.0666667h; microwave irradiation;70%
aniline
62-53-3

aniline

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzanilide
3460-11-5

4-nitrobenzanilide

Conditions
ConditionsYield
With diphosphorus tetraiodide In tetrachloromethane; dichloromethane Heating;100%
Stage #1: 4-nitro-benzoic acid With pyridine; iodine; phosphorous acid trimethyl ester In tetrahydrofuran at -10℃; for 0.166667h; Green chemistry;
Stage #2: aniline In tetrahydrofuran at -10 - 20℃; for 2.16667h; Reagent/catalyst; Solvent; Green chemistry;
99%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;97%
benzyl alcohol
100-51-6

benzyl alcohol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

benzyl 4-nitrobenzoate
14786-27-7

benzyl 4-nitrobenzoate

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;100%
With [bis(acetoxy)iodo]benzene; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 16h; Mitsunobu reaction;100%
Stage #1: 4-nitro-benzoic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h; Cooling;
Stage #2: benzyl alcohol With triethylamine In dichloromethane at 20℃; for 0.333333h;
98%
methanol
67-56-1

methanol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
Stage #1: 4-nitro-benzoic acid With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 0.0833333h; Garegg-Samuelsson type reaction;
Stage #2: methanol In dichloromethane at 20℃; Garegg-Samuelsson type reaction;
100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;100%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 50℃; for 0.0833333h; Green chemistry;100%
With hydrogen In ethanol; water at 25℃; under 11251.1 Torr; for 6h; chemoselective reaction;99%
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;99%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

Conditions
ConditionsYield
With thionyl chloride In ethyl acetate for 2h; Heating;100%
With thionyl chloride for 1h; Reflux;100%
With thionyl chloride; N,N-dimethyl-formamide for 5h; Reflux;100%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

azobenzene-4,4'-dicarboxylic acid
586-91-4

azobenzene-4,4'-dicarboxylic acid

Conditions
ConditionsYield
With D-glucose; acetic acid; sodium hydroxide In water at 50℃;100%
With D-glucose; sodium hydroxide In water at 50℃; for 12h;91%
With D-glucose; sodium hydroxide In water at 70℃; for 12h; pH=5 - 6;81%
tert-butyl alcohol
75-65-0

tert-butyl alcohol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

tert-butyl 4-nitrobenzoate
19756-72-0

tert-butyl 4-nitrobenzoate

Conditions
ConditionsYield
With pyridine; p-toluenesulfonyl chloride at 0 - 20℃; for 18h; Esterification;100%
With pyridine; p-toluenesulfonyl chloride at 20℃; for 72h;99%
With pyridine; 2,4,6-trinitrochlorobenzene for 3h;88%
n-heptan1ol
111-70-6

n-heptan1ol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

heptyl 4-nitrobenzoate
14309-44-5

heptyl 4-nitrobenzoate

Conditions
ConditionsYield
With Candida antarctica lipase B immobilised in a macroporous DVB crosslinked polymer (Novozym 435) In cyclohexane at 80℃; for 24h; Enzymatic reaction;100%
With diphenylphosphinopolystyrene; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 4h;84%
(2S,3S,4R,5R,6S)-5-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-4,6-dimethoxy-tetrahydro-pyran-2-carboxylic acid

(2S,3S,4R,5R,6S)-5-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-4,6-dimethoxy-tetrahydro-pyran-2-carboxylic acid

Isopropyl isocyanate
1795-48-8

Isopropyl isocyanate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

Trityl-linked Tentagel-OCOCH(NHFmoc)CH2CHMe2

Trityl-linked Tentagel-OCOCH(NHFmoc)CH2CHMe2

2-{[(2S,3S,4R,5R,6S)-3-Isopropylcarbamoyloxy-4,6-dimethoxy-5-(4-nitro-benzoylamino)-tetrahydro-pyran-2-carbonyl]-amino}-4-methyl-pentanoic acid

2-{[(2S,3S,4R,5R,6S)-3-Isopropylcarbamoyloxy-4,6-dimethoxy-5-(4-nitro-benzoylamino)-tetrahydro-pyran-2-carbonyl]-amino}-4-methyl-pentanoic acid

Conditions
ConditionsYield
Multistep reaction;100%
benzyl (3R*,6S*,7S*)-3-hydroxy-7-(3-oxononyl)-1-azaspiro[5.5]undecane-1-carboxylate

benzyl (3R*,6S*,7S*)-3-hydroxy-7-(3-oxononyl)-1-azaspiro[5.5]undecane-1-carboxylate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

(3R,6R,7R)-3-(4-Nitro-benzoyloxy)-7-(3-oxo-nonyl)-1-aza-spiro[5.5]undecane-1-carboxylic acid benzyl ester

(3R,6R,7R)-3-(4-Nitro-benzoyloxy)-7-(3-oxo-nonyl)-1-aza-spiro[5.5]undecane-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 40℃; Mitsunobu reaction;100%
methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate
245054-32-4

methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester
321887-10-9

(2S,3S,4aR,8S,8aS)-2,3-Dimethoxy-2,3-dimethyl-8-(4-nitro-benzoyloxy)-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Acylation;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 5h; Mitsunobu reaction;
(1S,4R,5R,6R)-4,5,6-Tris-benzyloxy-cyclohex-2-enol
155155-67-2

(1S,4R,5R,6R)-4,5,6-Tris-benzyloxy-cyclohex-2-enol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-Nitro-benzoic acid (1R,4R,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enyl ester
340013-64-1

4-Nitro-benzoic acid (1R,4R,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine Mitsunobu reaction;100%
maleic anhydride
108-31-6

maleic anhydride

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

N-(4-carboxyphenyl)maleimide
17057-04-4

N-(4-carboxyphenyl)maleimide

Conditions
ConditionsYield
Multistep reaction.;100%
5-benzyloxymethyl-2-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-2-enol

5-benzyloxymethyl-2-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-2-enol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitro-benzoic acid 5-benzyloxymethyl-2-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-2-enyl ester

4-nitro-benzoic acid 5-benzyloxymethyl-2-[2-(4-methoxy-benzyloxy)-ethyl]-cyclohex-2-enyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate Mitsunobu reaction;100%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone
4231-71-4

1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 20℃; for 8.5h;100%
With thionyl chloride In dichloromethane at 20℃;91%
With thionyl chloride In dichloromethane at 20℃; for 2h;91.4%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

(2S,4R)-4-hydroxy-2-[(1R,2S)-1-methoxycarbonyl-2-vinylcyclopropylcarbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester
572922-89-5

(2S,4R)-4-hydroxy-2-[(1R,2S)-1-methoxycarbonyl-2-vinylcyclopropylcarbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-2-((1R,2S)-1-Methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
872496-94-1

(2S,4R)-2-((1R,2S)-1-Methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4.75h; Mitsunobu reaction;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h; Mitsunobu reaction;108.1 g
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

(2S,4R)-4-hydroxy-2-[(1R,2S)-1-methoxycarbonyl-2-vinylcyclopropylcarbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester
572922-89-5

(2S,4R)-4-hydroxy-2-[(1R,2S)-1-methoxycarbonyl-2-vinylcyclopropylcarbamoyl]pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-2-((1R,2S)-1-Methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
572922-90-8

(2S,4S)-2-((1R,2S)-1-Methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4.75h;100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Mitsunobu reaction;
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 17.5h; Mitsunobu reaction;
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-phenylbutyl 4-nitrobenzoate

4-phenylbutyl 4-nitrobenzoate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 25℃; for 16h; Mitsunobu reaction;100%
C10H16O2
956483-60-6

C10H16O2

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

C17H19NO5
956483-61-7

C17H19NO5

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane100%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

(2S,4S)-4-Hydroxy-2-((1R,2S)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
572922-91-9

(2S,4S)-4-Hydroxy-2-((1R,2S)-1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4S)-2-((1R,2S)-1-Methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
572922-90-8

(2S,4S)-2-((1R,2S)-1-Methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 22℃; for 4h;
3-(2,4-dichloro-benzyl)-1-(trans-4-hydroxy-cyclohexyl)-pyrrolidin-2-one

3-(2,4-dichloro-benzyl)-1-(trans-4-hydroxy-cyclohexyl)-pyrrolidin-2-one

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

cis-4-nitro-benzoic acid 4-[3-(2,4-dichloro-benzyl)-2-oxo-pyrrolidin-1-yl]-cyclohexyl ester

cis-4-nitro-benzoic acid 4-[3-(2,4-dichloro-benzyl)-2-oxo-pyrrolidin-1-yl]-cyclohexyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -20 - 20℃;100%
diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
In methanol; toluene at 20℃; for 2h;100%
In ethyl acetate60%
In methanol; diethyl ether; hexane at 20℃; for 2h; Inert atmosphere;178 mg
allyl bromide
106-95-6

allyl bromide

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

allyl 4-nitrobenzoate
15727-80-7

allyl 4-nitrobenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere;100%
With potassium carbonate In N,N-dimethyl-formamide for 24h;100%
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 72h; Inert atmosphere;88%
With potassium carbonate In N,N-dimethyl-formamide for 0.0833333h;79%
C20H21NO5
944270-01-3

C20H21NO5

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

C27H24N2O8
1015426-38-6

C27H24N2O8

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate Mitsunobu reaction;100%
N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester
13500-53-3

N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

C27H24N2O8
1015426-34-2

C27H24N2O8

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate Mitsunobu reaction;100%
1,4-anhdyro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-ribitol
291758-11-7

1,4-anhdyro-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-ribitol

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

1,4-anhydro-2-O-(p-nitrobenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabitol
1030358-69-0

1,4-anhydro-2-O-(p-nitrobenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-arabitol

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.333333h; Mitsunobu reaction;100%

62-23-7Relevant articles and documents

-

Wardner,Lowy

, p. 2510,2514 (1932)

-

Studies on a dithiane-protected benzoin photolabile safety catch linker for solid-phase synthesis

Hong Boon Lee,Balasubramanian

, p. 3454 - 3460 (1999)

Substituted benzoinyl systems 8a-g, differing either in the substitution pattern, type of resin matrix used, or resin loading capacity, were prepared and the kinetics of their photolytic cleavage of Fmoc-β-alanine examined on resin. The linker systems 6a-g were assembled in near-quantitative yield using Corey-Seebach dithiane addition. The dithiane group that serves as a safety catch against premature photoreaction was removed by either oxidation or alkylation. Analytical methods that include FTIR and 13C gel-phase NMR spectroscopy were used for rapid reaction monitoring and sample characterization on resin. A survey of different substituted systems 8c-f for releasing Fmoc-β-alanine confirmed that the 3-alkoxybenzoin linker photocleaves most rapidly to give the highest yield (τ(1/2) = 6.7 min; 98% yield). Lowering the resin loading from 0.59 mmol/g in 8a to 0.26 mmol/g in 8b improved the cleavage kinetics to τ(1/2) = 2.6 min, 92% yield. Tentagel resin 8g exhibits similar photocleavage kinetics in both organic and aqueous media and when compared to the polystyrene counterpart, 8a. The 3- alkoxybenzoin linker 6a was also loaded with aryl carboxylic acids (12h,i) and hindered Fmoc-protected amino acids (12j-l) with varying degrees of success (57-100%) and dithiane deprotected (70-80%, 13h-1) followed by photocleavage with comparable efficiencies (8993% after 60 min).

Disproportionation of 4-Nitroacetophenone to 4-Aminoacetophenone and 4-Nitrobenzoic Acid

Wan, Peter,Xu, Xigen

, p. 4473 - 4474 (1989)

-

2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay

Trofimov, Boris A.,Belyaeva, Kseniya V.,Nikitina, Lina P.,Afonin, Andrei V.,Vashchenko, Alexander V.

, p. 267 - 269 (2018)

2-Methylquinoline reacts with 1-(het)aryl-3-phenylprop-2-yn-1-ones under mild transition metal-free conditions (55–60 °C, 20 mol% KOH, H2O, MeCN) to afford 2-{5’-(het)aryl[1,1’: 3’,1”]terphenyl-4’-yl}quinolines in up to 35% yield. The reaction likely proceeds via the intermediate 1,3-dipole followed by the double nucleophilic vinylation of the methyl group with two molecules of ynone and subsequent elimination of (het)arenecarboxylic acid.

Hey

, p. 2636,2638 (1932)

Use of ozone for preparing 4-nitrobenzoic acid in a closed process cycle

Galstyan,Tyupalo,Patapenko,Andreev

, p. 1777 - 1779 (2001)

The possibility of preparing 4-nitrobenzoic acid in a closed process cycle by oxidation of 4-nitrotoluene with an ozone air mixture was examined. The optimal conditions of oxidation with multiple use of mother liquors were found, and the conditions for crystallization of 4-nitrobenzoic acid from the reaction mixture were determined. The effects of water, acetic anhydride, and catalyst on the oxidation performed in mother liquors after filtration of the target product were examined.

Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives

Bernard, Josephine,Capilato, Joseph N.,Hoy, Erik P.,Mattiucci, Joseph,Pellegrinelli, Peter J.,Perez, Lark J.,Philippi, Shane,Schnorbus, Logan

, p. 5298 - 5302 (2021/06/30)

The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.

Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions

Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang

, p. 319 - 330 (2021/10/29)

The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.

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