| Identification | More | [Name]
3-Nitrophthalic anhydride | [CAS]
641-70-3 | [Synonyms]
3-NITROPHTHALIC ANHYDRIDE
4-NITRO-ISOBENZOFURAN-1,3-DIONE
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-
1-Amino-2-Indolinon (CIS)
4-Nitro-1,3-iso benzofurandione
3-NITROPHTHALIC ANHYDRIDE ,99+%
3-Nitrophthalic Acid Anhydride
NSC 27006
NSC 4134 | [EINECS(EC#)]
211-373-6 | [Molecular Formula]
C8H3NO5 | [MDL Number]
MFCD00005921 | [Molecular Weight]
193.11 | [MOL File]
641-70-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Beige to yellow crystalline powder | [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 at RT. | [form ]
Crystalline Powder | [color ]
Beige to yellow | [Water Solubility ]
MAY DECOMPOSE | [Sensitive ]
Moisture Sensitive | [Usage]
An intermediate for the synthesis of a benzimidazole PARP inhibitor I (succinate salt) (ABT-472) | [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]
641-70-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 | [TSCA ]
Yes | [HS Code ]
29173980 |
| Hazard Information | Back Directory | [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. | [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 |
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