3-Nitrophthalic anhydride Chemical Properties

Melting point:

163-165 °C (lit.)

Boiling point:

329.3°C (rough estimate)

Density 

1.6392 (rough estimate)

refractive index 

1.4700 (estimate)

storage temp. 

Store below +30°C.

form 

Crystalline Powder

color 

Beige to yellow

Water Solubility 

MAY DECOMPOSE

Sensitive 

Moisture Sensitive

BRN 

179963

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

SMILES

C1(=O)C2=C(C([N+]([O-])=O)=CC=C2)C(=O)O1

CAS DataBase Reference

641-70-3(CAS DataBase Reference)

NIST Chemistry Reference

3-Nitrophthalic anhydride(641-70-3)

EPA Substance Registry System

1,3-Isobenzofurandione, 4-nitro- (641-70-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

10-21

TSCA 

Yes

HS Code 

29173980

MSDS

• Language:English Provider:3-Nitrophthalic anhydride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Nitrophthalic anhydride Usage And Synthesis

Chemical Properties

Beige to yellow crystalline powder

Uses

An intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472). Reactions with aminoquinazolinones yield phthalimidoquinazolinones.

Uses

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.

Synthesis

General procedure for the synthesis of 3-nitrophthalic anhydride from 3-nitrophthalic acid: 474.8 g (2.25 mol) of 3-nitrophthalic acid was dissolved in 450 ml of acetic anhydride and the reaction was stirred under reflux conditions for 1 hour. Upon completion of the reaction, the reaction solution was slowly cooled to 80 °C. Subsequently, 1000 ml of methyl tert-butyl ether (MTBE) was quickly added and the mixture was cooled to 15 °C to promote crystallization. The resulting solid product was separated by filtration, washed with methyl tert-butyl ether (MTBE) and finally dried in a vacuum oven at 40 °C. The yield of the reaction was 88.8%.

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.]

References

[1] Organic Letters, 2010, vol. 12, # 21, p. 4796 - 4799
[2] Bioorganic Chemistry, 2018, vol. 81, p. 373 - 381
[3] Synthetic Communications, 2016, vol. 46, # 16, p. 1343 - 1348
[4] Patent: WO2007/6566, 2007, A1. Location in patent: Page/Page column 28; 32-33
[5] Tetrahedron Letters, 2017, vol. 58, # 32, p. 3160 - 3163

3-Nitrophthalic anhydride(641-70-3)Related Product Information

• 3-Fluorophthalic anhydride
• 4-BROMO PHTHALIC ANHYDRUS
• Dimethyl phthalate
• cis-1,2,3,6-Tetrahydrophthalic anhydride
• Isatoic Anhydride
• 2-Nitrobenzoic acid
• 2-Nitrobenzaldehyde
• CIS-BUTENEDIOIC ANHYDRIDE
• PHTHALAMIDE
• O-Phthalimide
• Dibutyl phthalate
• Phthalonitrile
• Phthalic anhydride
• 3-Nitrophthalic acid
• 3-Nitrophthalhydrazide
• 3-Nitrophthalimide
• METHYL 2-NITROBENZOATE
• 3-(METHOXYMETHYL)ANILINE