610-27-5

Basic information

• Product Name: 4-Nitrophthalic acid
• Synonyms: 5-NITROPHTHALIC ACID;AKOS B028755;4-NITROBENZENE-1,2-DICARBOXYLIC ACID;4-NITROPHTHALIC ACID;LABOTEST-BB LT00848072;RARECHEM AL BO 1138;4-nitro-2-benzenedicarboxylicacid;p-Nitro Phthalic Acid 4-Nitro Phthalic Acid
• CAS NO: 610-27-5
• Molecular Formula: C₈H₅NO₆
• Molecular Weight: 211.13
• EINECS: 210-215-3
• Product Categories: Phthalic Acids, Esters and Derivatives;Organic acids;Aromatics Compounds;Aromatics;C8;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 610-27-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 159-161 °C(lit.)
• Boiling Point: 350.79°C (rough estimate)
• Flash Point: 207.6 °C
• Appearance: Yellow to beige/Crystalline Powder
• Density: 1.6342 (rough estimate)
• Vapor Pressure: 3.09E-09mmHg at 25°C
• Refractive Index: 1.5282 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: 880g/l
• PKA: pK1:2.11 (25°C)
• Water Solubility: 880 g/l at 20 °C
• BRN: 1882262
• CAS DataBase Reference: 4-Nitrophthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophthalic acid(610-27-5)
• EPA Substance Registry System: 4-Nitrophthalic acid(610-27-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 610-27-5(Hazardous Substances Data)

Usage

Chemical Properties

Light-Beige Solid

Uses

4-Nitrophthalic Acid is an impurity of Apremilast.

General Description

The tissue-specific activity of 4-nitrophthalic acid was studied.

Purification Methods

Crystallise 4-nitrophthalic acid from Et2O, EtOAc or *C6H6 (m 166o). The amide has m 200o (from EtOH). [Beilstein 9 H 828, 9 IV 4234.]

InChI:InChI=1/C8H5NO6/c10-7(11)5-2-1-4(9(14)15)3-6(5)8(12)13/h1-3H,(H,10,11)(H,12,13)/p-2

Synthetic route

4-Nitrophthalonitrile (31643-49-9) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.45h; Green chemistry;	95%

phthalic anhydride (85-44-9) → 4-nitrophthalic acid (610-27-5) + 3-nitrophthalic acid (603-11-2)

Conditions	Yield
With sulfuric acid; nitric acid at 80 - 110℃;	A 80% B n/a
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid at 25℃;

4-nitro-o-xylene (99-51-4) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With potassium permanganate In water at 20℃; for 12h; Sonication;	50%
With potassium permanganate In water for 12h; Sonication;	50%
With nitric acid at 170 - 180℃; im geschlossenen Rohr;
Multi-step reaction with 2 steps 1: NBS, (PhCO)2O2 / CCl4 2: KMnO4, aq. K2CO3 View Scheme

phthalic anhydride (85-44-9) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid
Stage #1: phthalic anhydride With sulfuric acid for 0.166667h; Stage #2: With nitric acid at 70℃; for 1h; Temperature;

5-nitroisoindoline (46053-72-9) → 4-nitrophthalimide (89-40-7) + 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With potassium dichromate; sulfuric acid

5-nitro-3H-isobenzofuran-1-one (67081-02-1) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With nitric acid at 140℃; im geschlossenen Rohr;
With potassium permanganate; water

6-nitrotetralin (19353-86-7) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With permanganate(VII) ion anschliessend behandeln in Schwefelsaeure;

2-(carboxymethyl)-5-nitrobenzoic acid (3898-66-6) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With nitric acid

2,4,7-trinitro-1-naphthalenol (38319-14-1) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With nitric acid

6-nitroindan-1-one (24623-24-3) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With alkaline permanganate

2-cyano-5-nitrotoluene (89001-53-6) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With sodium hydroxide; permanganate(VII) ion

2-formyl-5-nitrobenzoic acid (7464-91-7) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With potassium permanganate

3-hydroxy-7-nitro-naphthalene-1-sulfonic acid (68516-57-4) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With water; permanganate(VII) ion

benzene-1,2-dicarboxylic acid (88-99-3) → 4-nitrophthalic acid (610-27-5) + 3-nitrophthalic acid (603-11-2)

Conditions	Yield
With sulfuric acid; nitric acid
With nitric acid at 30℃;
With sulfuric acid; nitric acid

1,2-bis-bromomethyl-4-nitro-benzene (6425-66-7) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With potassium permanganate; potassium carbonate

3,4-bis(trifluoromethyl)nitrobenzene (1978-20-7) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With sulfuric acid at 195 - 205℃;

4-nitrophthalimide (89-40-7) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With potassium hydroxide; nitric acid 1.) reflux, 10 min, 2.) reflux, 3 min; Yield given. Multistep reaction;

1,1,2,2-Tetrachlor-4-nitro-benzocyclobuten (64726-12-1) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With sulfuric acid; sulfur trioxide

6-nitrophthalide (610-93-5) + nitric acid (7697-37-2) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
at 140℃;

phthalic anhydride (85-44-9) + HNO3+H2SO4 → 4-nitrophthalic acid (610-27-5) + 3-nitrophthalic acid (603-11-2)

hydrogenchloride (7647-01-0) + 6-nitro-2,3-dihydrophthalazine-1,4-dione (3682-19-7) → 4-nitrophthalic acid (610-27-5) + hydrazine (302-01-2)

Conditions	Yield
at 150℃; im Rohr;

5-nitroisoindoline (46053-72-9) + diluted Cr2O3-H2SO4 → 4-nitrophthalic acid (610-27-5) + <4-nitro-phthalic acid >-imide

nitric acid (7697-37-2) + benzene-1,2-dicarboxylic acid (88-99-3) → 4-nitrophthalic acid (610-27-5) + 3-nitrophthalic acid (603-11-2)

Conditions	Yield
at 30℃; Product distribution;

benzene-1,2-dicarboxylic acid (88-99-3) + HNO3+H2SO4 → 4-nitrophthalic acid (610-27-5) + 3-nitrophthalic acid (603-11-2)

4-nitro-homophthalic acid → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With nitric acid

5-nitro-indanone-(2) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With nitric acid

<4-nitro-phthalic acid >-imide → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
With sodium hydroxide; water versetzen mit Salpetersaeure;

5-nitroindane (7436-07-9) + alkaline permanganate solution → 4-nitrophthalic acid (610-27-5)

4-nitro-o-xylene (99-51-4) + nitric acid (7697-37-2) → 4-nitrophthalic acid (610-27-5)

Conditions	Yield
at 170 - 180℃;

methanesulfonic acid (75-75-2) + 4-nitrophthalic acid (610-27-5) → 4-amino-phthalic acid dimethyl ester (51832-31-6)

Conditions	Yield
Stage #1: methanesulfonic acid; 4-nitrophthalic acid In methanol Reflux; Stage #2: With palladium on activated charcoal; hydrogen In methanol; water at 37℃; for 9h;	100%

4-nitrophthalic acid (610-27-5) → (4-nitro-1,2-phenylene)dimethanol (22162-19-2)

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane	99%
With borane-THF In tetrahydrofuran at 0 - 20℃;	98%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 0.001875h; Inert atmosphere;	98%

ethanol (64-17-5) + 4-nitrophthalic acid (610-27-5) → 4-nitrophthalic acid diethyl ester (2050-19-3)

Conditions	Yield
With sulfuric acid In ethanol at 100℃; for 24h;	98%
With sulfuric acid for 15h; Dean-Stark; Reflux;	97%
With hydrogenchloride at 80℃; for 72h; Esterification;	78%

propan-1-ol (71-23-8) + 4-nitrophthalic acid (610-27-5) → 4-nitrophthalic acid di-n-propyl ester (53577-25-6)

Conditions	Yield
With sulfuric acid for 15h; Dean-Stark; Reflux;	97%

4-nitrophthalic acid (610-27-5) → 4-aminophthalic acid (5434-21-9)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In ethanol at 20℃; for 3h;	96%
With hydrogen; 5%-palladium/activated carbon In ethanol at 20℃; for 3h;	96%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h;	93%

4-nitrophthalic acid (610-27-5) + 4-amino-benzoic acid (150-13-0) → 4-(5-nitro-1,3-dioxoisoindolin-2-yl)benzoic acid (148149-88-6)

Conditions	Yield
In acetonitrile at 180℃; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere; Sealed tube;	96%

4-nitrophthalic acid (610-27-5) + butan-1-ol (71-36-3) → 4-nitrophthalic acid di-n-butyl ester (3164-72-5)

Conditions	Yield
With sulfuric acid for 15h; Dean-Stark; Reflux;	96%

4-nitrophthalic acid (610-27-5) → 4-nitrophthalic anhydride (5466-84-2)

Conditions	Yield
With acetic anhydride	93%
With acetic anhydride 1) 60 deg C, 1 h; 2) reflux, 10 min;	90%
With acetic anhydride for 0.333333h; Heating;	88%

4-nitrophthalic acid (610-27-5) → 4-nitrophthalic acid chloride (24564-72-5)

Conditions	Yield
With thionyl chloride at 78℃; for 3.25h;	93%
With phosphorus pentachloride
With thionyl chloride
With thionyl chloride

4-nitrophthalic acid (610-27-5) + N-(hydroxycarbonylmethyl)pyridinium bromide (45811-13-0) → N-(5-nitro-1H-indene-1,3(2H)-dion-2-yl)pyridinium betaine

Conditions	Yield
With acetic anhydride; triethylamine In acetonitrile Condensation; Heating;	92%

2-Ethylhexyl alcohol (104-76-7) + 4-nitrophthalic acid (610-27-5) → bis(2-ethylhexyl) 4-nitrophthalate (59986-42-4)

Conditions	Yield
With titanium(IV) isopropylate at 150℃; for 4h;	91.1%
With titanium(IV) isopropylate at 150℃; for 4h;	86%

4-nitrophthalic acid (610-27-5) + 4-amino-N-carboxymethylpyridinium bromide → N-(5-nitro-1H-indene-1,3(2H)-dion-2-yl)-4'-(4-nitrophthalimido)pyridinium betaine

Conditions	Yield
With acetic anhydride; triethylamine In acetic acid; acetonitrile Condensation; acylation; Heating;	88%

copper(ll) sulfate pentahydrate + 4-nitrophthalic acid (610-27-5) → copper(II) 2,9,16,23-tetranitrohophthalocyanine (118-20-7)

Conditions	Yield
With urea In neat (no solvent) heating a mixture of copper sulphate pentahydrate, 4-nitrophthalic aicd, a catalytic quantity of NH4Cl/(NH4)2MoO4 and an excess of urea at 185°C for 5 h; elem. anal.;	88%

1,3-diazido 2-propanol (57011-48-0) + 4-nitrophthalic acid (610-27-5) → bis(1,3-diazidopropan-2-yl) 4-nitrophthalate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;	88%

3,5-dimethyl-1H-pyrazole (67-51-6) + 4-nitrophthalic acid (610-27-5) → C5H8N2*C8H5NO6

Conditions	Yield
In methanol; ethanol	87.87%

piperidine (110-89-4) + 4-nitrophthalic acid (610-27-5) → C5H11N*C8H5NO6

Conditions	Yield
In methanol for 0.25h;	87.75%

1H-imidazole (288-32-4) + 4-nitrophthalic acid (610-27-5) → C3H4N2*C8H5NO6

Conditions	Yield
In methanol; ethanol	85.96%

ethanol (64-17-5) + 4-nitrophthalic acid (610-27-5) + water (7732-18-5) + zinc(II) acetate dihydrate (5970-45-6) + potassium hydroxide + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → 2C8H3NO6(2-)*2C12H10N2*2HO(1-)*3Zn(2+)*H2O*C2H6O

Conditions	Yield
at 120℃; for 96h; Autoclave;	85%

2-(1H-imidazol-1-yl)-1-phenylethanone (24155-34-8) + 4-nitrophthalic acid (610-27-5) → 2-(imidazolium-1-yl)-1-phenylethanone 4-nitrohydrogenphthalate

Conditions	Yield
In methanol; ethanol	83.05%

2-methylquinoline (91-63-4) + 4-nitrophthalic acid (610-27-5) → C10H9N*C8H5NO6

Conditions	Yield
In methanol	81.85%

4-nitrophthalic acid (610-27-5) + 2,6-dimethylaniline (87-62-7) → (2,6‑dimethylaniline):(4‑nitrophthalic acid)

Conditions	Yield
In methanol	81.25%

4-nitrophthalic acid (610-27-5) + bis(4-(1H-imidazol-1-yl)phenyl)methanone + zinc(II) acetate dihydrate (5970-45-6) → {[Zn(npa)(L1)]*2H2O}n

Conditions	Yield
In water; N,N-dimethyl-formamide at 95℃; for 336h;	81%

4-nitrophthalic acid (610-27-5) + 8-azidooctan-1-ol (57395-46-7) → bis(8-azidooctyl)4-nitrophthalate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;	79%

8-quinolinol (148-24-3) + 4-nitrophthalic acid (610-27-5) → C9H7NO*C8H5NO6

Conditions	Yield
In methanol; ethanol at 20℃;	78.58%

4-nitrophthalic acid (610-27-5) + nicotinamide (98-92-0) → C6H6N2O*C8H5NO6

Conditions	Yield
In methanol	78.02%

4-nitrophthalic acid (610-27-5) + isonicotinamide (1453-82-3) → C6H6N2O*C8H5NO6

Conditions	Yield
In methanol	78.02%

4-nitrophthalic acid (610-27-5) + 4-dimethylamino-benzaldehyde (100-10-7) → C9H11NO*C8H5NO6

Conditions	Yield
In methanol at 20℃; for 480h;	77.71%

methanol (67-56-1) + 4-nitrophthalic acid (610-27-5) → dimethyl 4-nitrophthalate (610-22-0)

Conditions	Yield
With sulfuric acid for 18.1667h; Reflux;	76%
With hydrogenchloride
With sulfuric acid

Upstream product

• 85-44-9 phthalic anhydride 
• 46053-72-9 5-nitroisoindoline 
• 67081-02-1 5-nitro-3H-isobenzofuran-1-one 
• 19353-86-7 6-nitrotetralin 
• 99-51-4 4-nitro-o-xylene 
• 3898-66-6 2-(carboxymethyl)-5-nitrobenzoic acid 
• 38319-14-1 2,4,7-trinitro-1-naphthalenol 
• 24623-24-3 6-nitroindan-1-one 
• 89001-53-6 2-cyano-5-nitrotoluene 
• 7464-91-7 2-formyl-5-nitrobenzoic acid 
• 68516-57-4 3-hydroxy-7-nitro-naphthalene-1-sulfonic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 89-40-7 4-nitrophthalimide 
• 610-93-5 6-nitrophthalide 

Downstream Products

• 610-22-0 dimethyl 4-nitrophthalate 
• 90072-77-8 4-nitro-phthalic acid-1-methyl ester 
• 89-20-3 4-chlorophthalic acid 
• 2050-19-3 4-nitrophthalic acid diethyl ester 
• 74090-07-6 2-ethyl 4-nitrophthalate 
• 74090-06-5 2-(ethoxycarbonyl)-5-nitrobenzoic acid 
• 5466-84-2 4-nitrophthalic anhydride 
• 3682-19-7 6-nitro-2,3-dihydrophthalazine-1,4-dione 
• 16426-64-5 2-bromo-4-nitrobenzoic acid 
• 5434-21-9 4-aminophthalic acid 
• 21278-45-5 3,4-dicarboxyl-(3',4'-dicarboxylazophenyl) benzene 
• 24564-72-5 4-nitrophthalic acid chloride 
• 10133-84-3 azoxybenzene-3,3',4,4'-tetracarboxylic acid 
• 53555-04-7 2-(4-chloro-phenyl)-5-nitro-isoindoline-1,3-dione 

Relevant articles and documents

CYCLIC PEPTIDE ANALOGS OF MELANOCORTIN AND AMANITIN AND METHODS OF MAKING SUCH

The invention described herein is based in part on the discovery of a protein/peptide crosslink, which introduces fluorescent properties, and which has been applied to synthesize analogues of melanocortin and amanitin as choice peptides to be explored in the context of isoindole peptides. Without limitation, it is expected that those trained in the art of peptide synthesis and stapling would appreciate the consequences of this invention such that other peptides of varied length can be similarly constrained by isoindole staples as featured herein.

Synthesis method of 2,4-diaminobenzoic acid

The present invention discloses a synthesis method of 2,4-diaminobenzoic acid, and belongs to the field of chemical synthesis. The synthesis method comprises the following steps: using phthalic anhydride as a raw material; adding concentrated sulfuric acid and fuming nitric acid to generate 4-nitrophthalic acid; adding acetic anhydride into the 4-nitrophthalic acid and heating until the solid is completely dissolved; washing ether to obtain 4-nitro phthalic anhydride; mixing and heating the 4-nitro phthalic anhydride with urea; evacuating a reaction system; then adding hydrochloric acid to obtain 4-nitro-2-formyl acetaminobenzoic acid; obtaining 2-amino-4-nitrobenzoic acid under the conditions of a sodium hypochlorite solution and an ice bath; and finally refluxing with absolute ethanol, and adding an ammonium sulfide solution to finally produce 2,4-diaminobenzoic acid by using microwave heating and other conditions.

An efficient one pot method for synthesis of carboxylic acids from nitriles using recyclable ionic liquid [bmim]HSO4 Dedicated to my mentor Professor (Mrs.) Krishna Misra on her 76th birthday

Environmentally benign ionic liquid [bmim]HSO4 was found suitable for conversion of nitriles into carboxylic acids under mild conditions with excellent purity.