641-70-3

Basic information

• Product Name: 3-Nitrophthalic anhydride
• Synonyms: 1,3-Isobenzofurandione, 4-nitro-;1,3-Isobenzofurandione,4-nitro-;3-Isobenzofurandione,4-nitro-1;4-Nitro-2-benzofuran-1,3-dione;4-nitro-3-isobenzofurandione;Phthalic anhydride, 3-nitro-;3-NITROPHTHALIC ANHYDRIDE;4-NITRO-ISOBENZOFURAN-1,3-DIONE
• CAS NO: 641-70-3
• Molecular Formula: C₈H₃NO₅
• Molecular Weight: 193.11
• EINECS: 211-373-6
• Product Categories: Phthalic Acids, Esters and Derivatives;Dyes intermediates;Amines;Aromatics;Intermediates;Anhydride Monomers;Monomers;Polymer Science;Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks;Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Chemical Synthesis;Organic Building Blocks
• Mol File: 641-70-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 163-165 °C(lit.)
• Boiling Point: 329.3°C (rough estimate)
• Flash Point: 227.5 °C
• Appearance: Beige to yellow/Crystalline Powder
• Density: 1.6392 (rough estimate)
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: Store at RT.
• Water Solubility: MAY DECOMPOSE
• Sensitive: Moisture Sensitive
• BRN: 179963
• CAS DataBase Reference: 3-Nitrophthalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitrophthalic anhydride(641-70-3)
• EPA Substance Registry System: 3-Nitrophthalic anhydride(641-70-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 641-70-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 641-70-3 differently. You can refer to the following data:
1. An intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472). Reactions with aminoquinazolinones yield phthalimidoquinazolinones.
2. 4-Nitrophthalic Anhydride is an intermediate for the synthesis of the benzimidazole PARP inhibitor I, ABT-472. It reacts with aminoquinazolinones to yield phthalimidoquinazolinones.

Preparation

3-Nitrophthalic anhydride can be prepared by heating 3-nitrophthalic acid under various conditions and by the action of acetic anhydride, essentially as in the procedure described. The direct nitration of phthalic anhydride yields 3-nitrophthalic anhydride together with the isomeric 4-nitro compound.

Purification Methods

Crystallise it from *C6H6, *C6H6/pet ether, Me2CO, AcOH, or Ac2O (m 164-165o). Dry it at 100o. [Beilstein 17 III/IV 6149, 17/11 V 266.]

InChI:InChI=1/C8H3NO5/c10-7-4-2-1-3-5(9(12)13)6(4)8(11)14-7/h1-3H

Synthetic route

3-nitrophthalic acid (603-11-2) → 3-nitrophthalic acid anhydride (641-70-3)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In cyclohexane at 5 - 10℃; for 3.83333h; Time; Reagent/catalyst; Solvent; Temperature; Vilsmeier Reaction; Reflux;	98.9%
With acetic anhydride for 2h; Reflux;	95%
With acetic anhydride for 2h; Reflux;	95.8%

benzene-1,2-dicarboxylic acid (88-99-3) → 3-nitrophthalic acid anhydride (641-70-3)

Conditions	Yield
nitration reaction;	77%
Multi-step reaction with 2 steps 1: durch Nitrierung View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; fuming nitric acid 2: durch Erhitzen auf 230grad, oder durch Sublimation bei ca. 160-170grad View Scheme

naphthalene (91-20-3) → 3-nitrophthalic acid anhydride (641-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: durch Erhitzen auf 230grad, oder durch Sublimation bei ca. 160-170grad View Scheme

phthalic anhydride (85-44-9) → 3-nitrophthalic acid anhydride (641-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: durch Nitrierung View Scheme
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 80 - 110 °C 2: acetic anhydride / Reflux View Scheme

1-Nitronaphthalene (86-57-7) → 3-nitrophthalic acid anhydride (641-70-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; CrO3 2: durch Erhitzen auf 230grad, oder durch Sublimation bei ca. 160-170grad View Scheme

3-nitrophthalic acid (603-11-2) + acetic anhydride (108-24-7) → 3-nitrophthalic acid anhydride (641-70-3)

Conditions	Yield
at 115 - 120℃; for 3h;

3-nitrophthalic acid anhydride (641-70-3) → 3-aminophthalic anhydride (17395-99-2)

Conditions	Yield
With palladium on activated carbon; hydrogen; magnesium sulfate In ethyl acetate under 760.051 Torr; for 18h;	100%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran under 15001.5 Torr; for 18h;	13%
With nickel; magnesium sulfate; acetone Hydrogenation;
With hydrogen; magnesium sulfate at 50℃; under 3102.97 Torr;
With hydrogen; magnesium sulfate In acetone at 50℃; under 3102.97 Torr;

3-nitrophthalic acid anhydride (641-70-3) + 2-(2-phenylethyl)aniline (5697-85-8) → C22H16N2O4 (1259938-74-3)

Conditions	Yield
With acetic acid for 3h; Reflux;	100%

3-nitrophthalic acid anhydride (641-70-3) + 4-[2-(4-methoxyphenyl)ethyl]aniline (14802-10-9) → C23H18N2O5 (1259938-76-5)

Conditions	Yield
With acetic acid for 3h; Reflux;	100%

3-nitrophthalic acid anhydride (641-70-3) + 3-aminopiperidine-2,6-dione hydrochloric acid salt → 4-NT (19171-18-7)

Conditions	Yield
With potassium acetate; acetic acid at 90℃; for 16h;	99.5%
With sodium acetate In acetic acid at 130℃; for 48h;	92%
Stage #1: 3-nitrophthalic acid anhydride; 3-amino-piperidine-2,6-dione hydrogen chloride With triethylamine In toluene for 8h; Reflux; Stage #2: With 1,1'-carbonyldiimidazole In toluene at 20 - 25℃; for 2h;	84.2%
Stage #1: 3-amino-piperidine-2,6-dione hydrogen chloride With acetic acid at 25 - 35℃; Stage #2: 3-nitrophthalic acid anhydride at 25 - 35℃; Stage #3: With triethylamine at 25℃; Reflux;	141.60 g

4-(difluoromethoxy)-2-methylaniline + 3-nitrophthalic acid anhydride (641-70-3) → N-(4-difluoromethoxy-2-methylphenyl)-3-nitrophthalimide

Conditions	Yield
In acetic acid	98%
In acetic acid	98%

4-(1,1,2,3,3,3-hexafluoropropoxy)-1-methylaniline + 3-nitrophthalic acid anhydride (641-70-3) → N-[4-(1,1,2,3,3,3-hexafluoropropoxy)-1-methylphenyl]-3-nitrophthalimide

Conditions	Yield
In hexane; acetic acid	98%

glutamic acid dimethyl ether (6525-53-7, 16422-27-8, 40149-68-6) + 3-nitrophthalic acid anhydride (641-70-3) → 2-(1,3-dihydro-4-nitro-1,3-dioxo-2H-isoindol-2-yl)-glutaric acid dimethyl ester

Conditions	Yield
With sodium acetate; acetic acid for 7h; Reagent/catalyst; Reflux;	97.6%

3-nitrophthalic acid anhydride (641-70-3) + 4-(trifluoromethoxy)aniline (461-82-5) → N-(4-trifluoromethoxyphenyl)-3-nitrophthalimide

Conditions	Yield
In acetic acid	97%

L-Aspartic acid (56-84-8) + 3-nitrophthalic acid anhydride (641-70-3) → 2-(4-nitro-1,3-dioxoisoindolin-2-yl)succinic acid

Conditions	Yield
With pyridine; acetic acid at 20℃; Reflux;	97%

3-nitrophthalic acid anhydride (641-70-3) + 4-amino-n-butyric acid (56-12-2) → 4-(o-nitrophthalimido)butyric acid (10264-75-2)

Conditions	Yield
With acetic acid at 100℃; for 3h;	96.5%
at 20 - 185℃; for 0.183333h; Microwave irradiation;	92%
	0.57 g (79%)

methanol (67-56-1) + 3-nitrophthalic acid anhydride (641-70-3) → 2-(methoxycarbonyl)-3-nitrobenzoic acid (6744-85-0)

Conditions	Yield
for 7h; Heating;	96%
for 16h; Reflux;	71%

3-nitrophthalic acid anhydride (641-70-3) + (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester (31140-42-8) → 4-NT (19171-18-7)

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	95%
With sodium acetate; acetic acid for 6h; Reflux;

3-nitrophthalic acid anhydride (641-70-3) + 4-Nitrophenyl isocyanate (100-28-7) → 4-nitro-2-(4-nitro-phenyl)-isoindoline-1,3-dione (53555-13-8)

Conditions	Yield
In N,N-dimethyl acetamide for 0.0416667h;	94%

1,6-Hexanediamine (124-09-4) + 3-nitrophthalic acid anhydride (641-70-3) → C22H18N4O8

Conditions	Yield
With acetic acid Heating;	94%

3-nitrophthalic acid anhydride (641-70-3) → 3-nitrophthalamide (96385-50-1)

Conditions	Yield
Stage #1: 3-nitrophthalic acid anhydride With ammonia In water at 0 - 60℃; for 12h; Stage #2: With hydrogenchloride In water	94%

3-nitrophthalic acid anhydride (641-70-3) → 5-nitro-2,3-dihydro-phthalazine-1,4-dione (3682-15-3)

Conditions	Yield
With hydrazine hydrate; acetic acid at 110℃; for 0.5h;	93.7%
With hydrazine hydrate In acetic acid at 110℃;	92%
With hydrazine hydrate In water; ethylene glycol for 1h; Reflux;	79%

GLUTAMINE (56-85-9, 585-21-7, 5959-95-5, 6899-04-3) + 3-nitrophthalic acid anhydride (641-70-3) → 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid (6383-84-2)

Conditions	Yield
With sodium acetate; acetic acid for 7h; Reagent/catalyst; Reflux;	93.2%
In acetic acid

3-nitrophthalic acid anhydride (641-70-3) + glycine (56-40-6) → 2-(4-nitro-1,3-dioxoisoindolin-2-yl)acetic acid (15784-35-7)

Conditions	Yield
With acetic acid at 120℃; for 6h;	93%
With acetic anhydride Reflux;	91%
With acetic acid Reflux;	80%

3-nitrophthalic acid anhydride (641-70-3) + (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate → pomalidomide (19171-19-8)

Conditions	Yield
Stage #1: 3-nitrophthalic acid anhydride; (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate With sodium acetate; acetic acid Reflux; Stage #2: With palladium on activated charcoal; hydrogen In N,N-dimethyl-formamide at 25℃;	93%

1,3-di(aminomethyl)benzene (1477-55-0) + 3-nitrophthalic acid anhydride (641-70-3) → C24H14N4O8

Conditions	Yield
With acetic acid Heating;	92%

2-aminopyrimidine (109-12-6) + 3-nitrophthalic acid anhydride (641-70-3) → 3-nitro-N-pyrimidin-2-yl-phthalamic acid

Conditions	Yield
In ethyl acetate	91%

3-nitrophthalic acid anhydride (641-70-3) + methyl N-[5(6)-(4-aminophenylsulfanyl)benzimidazol-2-yl]carbamate (56073-96-2) → N-[4-(2-methoxycarbonylamino-1H-benzoimidazol-5-ylsulfanyl)-phenyl]-3-nitro-phthalamic acid

Conditions	Yield
In dimethyl sulfoxide at 40 - 45℃; for 2h;	91%

3-nitrophthalic acid anhydride (641-70-3) + 4-Aminoacetophenone (99-92-3) → 2-(4-acetyl-phenyl)-4-nitro-isoindoline-1,3-dione

Conditions	Yield
at 160℃; for 0.5h;	91%
With acetic acid for 18h; Reflux;	400 mg

3-nitrophthalic acid anhydride (641-70-3) + rac-α-aminoglutarimide hydrochloride (24666-56-6) → 2-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-nitrobenzoic acid

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Reagent/catalyst; Green chemistry;	91%
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;	91%
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;	91%

3-nitrophthalic acid anhydride (641-70-3) + phenyl isocyanate (103-71-9) → 3-nitro-N-phenylphthalimide (19065-85-1)

Conditions	Yield
In N,N-dimethyl acetamide for 0.0416667h;	90%

3-nitrophthalic acid anhydride (641-70-3) + phenyl isothiocyanate (103-72-0) → 3-nitro-N-phenylphthalimide (19065-85-1)

Conditions	Yield
In N,N-dimethyl acetamide for 0.0416667h;	90%

Upstream product

• 88-99-3 benzene-1,2-dicarboxylic acid 
• 91-20-3 naphthalene 
• 603-11-2 3-nitrophthalic acid 
• 108-24-7 acetic anhydride 
• 86-57-7 1-Nitronaphthalene 
• 85-44-9 phthalic anhydride 

Downstream Products

• 7335-60-6 2-benzoyl-3-nitro-benzoic acid 
• 7335-77-5 6-nitro-o-benzoylbenzoic acid 
• 6744-94-1 3-nitro-phthalic acid-2-octyl ester 
• 6828-46-2 3-nitro-phthalic acid-2-ethyl ester 
• 6744-89-4 3-nitro-phthalic acid-2-sec-butyl ester 
• 106269-58-3 (+/-)-3-nitro-phthalic acid-2-(2-methyl-butyl ester) 
• 6744-88-3 3-nitro-phthalic acid-2-isobutyl ester 
• 6744-91-8 3-nitro-phthalic acid-2-pentyl ester 

Relevant articles and documents

Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities

Synthesis of 2-(4-Acetyl-phenyl)-4-nitro-isoindole-1, 3-dione chalcones were performed by fusion of 3-nitro phthalic anhydride with p-aminoacetophenone. Then the later was grinded with different aromatic aldehydes in the presence of sodium hydroxide to produce new chalcones derivatives A3-10 without using any solvent formation of new Narylphthailimide chalcones were confirmed by FT-IR,1HNMR, 13CNMR spectroscopy and all final compounds were tested for their antifungal and antibacterial activity some of them showed more biological activity than the standard drugs.

ANTIVIRAL 1,3-DI-OXO-INDENE COMPOUNDS

The invention provides compounds of Formula (I): as described herein, along with pharmaceutically acceptable salts, pharmaceutical compositions containing such compounds, and methods to use these compounds, salts and compositions for treating viral infections.

Preparation method of 3-nitrophthalic anhydride

The invention relates to a preparation method of 3-nitrophthalic anhydride. The method includes the following steps: placing 3-nitrophthalic acid in a reaction solvent, adding a catalyst, and heatingfor reaction; and removing the reaction solvent and the catalyst from an obtained substance under negative pressure to obtain the 3-nitrophthalic anhydride. In the preparation method, the 3-nitrophthalic acid raw material can be easily obtained, the 3-nitrophthalic anhydride is synthesized by direct catalytic dehydration in one step, and the preparation method has the advantages of simple process,low cost, high yield and no by-products.