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641-70-3

Basic Information
CAS No.: 641-70-3
Name: 3-Nitrophthalic anhydride
Article Data: 43
Cas Database
Molecular Structure:
Molecular Structure of 641-70-3 (3-Nitrophthalic anhydride)
Formula: C8H3NO5
Molecular Weight: 193.116
Synonyms: 1,3-Isobenzofurandione, 4-nitro-;Phthalic anhydride, 3-nitro-;4-Nitro-isobenzofuran-1,3-dione;Phthalic anhydride, 3-nitro- (8CI);4-nitroisobenzofuran-1,3-dione;
EINECS: 211-373-6
Density: 1.687 g/cm3
Melting Point: 163-165 °C(lit.)
Boiling Point: 411.8 °C at 760 mmHg
Flash Point: 227.5 °C
Solubility: may decompose with water
Appearance: beige to yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information: N/A
PSA: 89.19000
LogP: 1.42860
Synthetic route
603-11-2

3-nitrophthalic acid

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
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%
88-99-3

benzene-1,2-dicarboxylic acid

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
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
91-20-3

naphthalene

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid
2: durch Erhitzen auf 230grad, oder durch Sublimation bei ca. 160-170grad
View Scheme
85-44-9

phthalic anhydride

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
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
86-57-7

1-Nitronaphthalene

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; CrO3
2: durch Erhitzen auf 230grad, oder durch Sublimation bei ca. 160-170grad
View Scheme
603-11-2

3-nitrophthalic acid

108-24-7

acetic anhydride

641-70-3

3-nitrophthalic acid anhydride

Conditions
ConditionsYield
at 115 - 120℃; for 3h;
641-70-3

3-nitrophthalic acid anhydride

17395-99-2

3-aminophthalic anhydride

Conditions
ConditionsYield
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;
641-70-3

3-nitrophthalic acid anhydride

5697-85-8

2-(2-phenylethyl)aniline

1259938-74-3

C22H16N2O4

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;100%
641-70-3

3-nitrophthalic acid anhydride

14802-10-9

4-[2-(4-methoxyphenyl)ethyl]aniline

1259938-76-5

C23H18N2O5

Conditions
ConditionsYield
With acetic acid for 3h; Reflux;100%
641-70-3

3-nitrophthalic acid anhydride

3-aminopiperidine-2,6-dione hydrochloric acid salt

Conditions
ConditionsYield
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
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Chemistry

Molecule structure of 3-Nitrophthalic anhydride (CAS NO.641-70-3):

IUPAC Name: 4-Nitro-2-benzofuran-1,3-dione 
Molecular Weight: 193.11312 g/mol
Molecular Formula: C8H3NO5 
Density: 1.687 g/cm3 
Melting Point: 163-165 °C(lit.)
Boiling Point: 411.8 °C at 760 mmHg 
Flash Point: 227.5 °C
Index of Refraction: 1.659
Molar Refractivity: 42.22 cm3
Molar Volume: 114.4 cm3
Polarizability: 16.74×10-24 cm3
Surface Tension: 78.1 dyne/cm 
Enthalpy of Vaporization: 66.43 kJ/mol
Vapour Pressure: 5.43E-07 mmHg at 25 °C 
Storage Temp.: store at RT.
Water Solubility: may decompose
Sensitive Moisture: sensitive
XLogP3-AA: 1.1
H-Bond Acceptor: 5
Exact Mass: 193.001122
MonoIsotopic Mass: 193.001122
Topological Polar Surface Area: 86.5
Heavy Atom Count: 14
Canonical SMILES: C1=CC2=C(C(=C1)[N+](=O)[O-])C(=O)OC2=O
InChI: InChI=1S/C8H3NO5/c10-7-4-2-1-3-5(9(12)13)6(4)8(11)14-7/h1-3H
InChIKey: ROFZMKDROVBLNY-UHFFFAOYSA-N
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

Uses

 3-Nitrophthalic anhydride (CAS NO.641-70-3) is used an an intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472).

Production

 3-Nitrophthalic anhydride is maed by the 3-nitro-phthalic acid and hot acetic anhydride.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
F: 10-21
HS Code: 29173980 

Specification

 3-Nitrophthalic anhydride (CAS NO.641-70-3) is also named as AI3-03720 ; NSC 27006 ; NSC 4134 ; 1,3-Isobenzofurandione, 4-nitro- ; Phthalic anhydride, 3-nitro- (8CI) . 3-Nitrophthalic anhydride (CAS NO.641-70-3) is beige to yellow crystalline powder. It is soluble in acetone, hot alcohol and hot acetic acid, slightly soluble in benzene, insoluble in water.