| Identification | More | [Name]
4-Nitrophthalic anhydride | [CAS]
5466-84-2 | [Synonyms]
4-NITROPHTHALIC ANHYDRIDE
5-NITRO-ISOBENZOFURAN-1,3-DIONE
TIMTEC-BB SBB008431
1,3-Isobenzofurandione, 5-nitro-
4-Nitrophthalic acid anhydride
4-nitrophthalicacidanhydride
4-nitro-phthalicanhydrid
5-nitro-1,3-isobenzofurandione
5-Nitro-2-benzofuran-1,3-dione
5-nitro-3-isobenzofurandione
Phthalic anhydride, 4-nitro-
4-Nitro Phthalic Anhydride p-Nitro Phthalic Anhydride
4-Nitrophthalicanhydride,95%
4-Nitro-o-phthalicanhydride
p-NitroPhthalicAnhydride
4-NITROPHTHALIC ANHYDRIDE: TECH., 90%
5-Nitrophthalic anhydride | [EINECS(EC#)]
226-776-2 | [Molecular Formula]
C8H3NO5 | [MDL Number]
MFCD00005922 | [Molecular Weight]
193.11 | [MOL File]
5466-84-2.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow-brown powder | [Melting point ]
116-120 °C(lit.)
| [Boiling point ]
197 °C / 8mmHg | [density ]
1.6392 (rough estimate) | [refractive index ]
1.4700 (estimate) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
Pale Beige | [Water Solubility ]
Hydrolysis | [Sensitive ]
Moisture Sensitive | [BRN ]
179682 | [InChI]
InChI=1S/C8H3NO5/c10-7-5-2-1-4(9(12)13)3-6(5)8(11)14-7/h1-3H | [InChIKey]
MMVIDXVHQANYAE-UHFFFAOYSA-N | [SMILES]
C1(=O)C2=C(C=C([N+]([O-])=O)C=C2)C(=O)O1 | [CAS DataBase Reference]
5466-84-2(CAS DataBase Reference) | [NIST Chemistry Reference]
4-Nitrophthalic anhydride(5466-84-2) | [EPA Substance Registry System]
5466-84-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/22:Harmful by inhalation and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [RTECS ]
TI3328000
| [F ]
10-21 | [TSCA ]
Yes | [HS Code ]
29173990 |
| Hazard Information | Back Directory | [General Description]
Yellow powder. | [Reactivity Profile]
4-NITROPHTHALIC ANHYDRIDE(5466-84-2) reacts exothermically with water. The reactions are usually slow, but might become violent if local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. | [Air & Water Reactions]
Reacts with water. The organic acids produced by this reaction are significantly more soluble in water. | [Fire Hazard]
Flash point data for this chemical are not available, however 4-NITROPHTHALIC ANHYDRIDE is probably combustible. | [Chemical Properties]
off-white to light yellow-brown powder | [Uses]
5-Nitrophthalic Anhydride is used in the preparation of phthalic acids as well as compounds with anticonvulsant activities. | [Preparation]
4-Nitrophthalic anhydride is synthesized by hydrolysis of 4-nitrophthalimide and then dehydration. The 4-nitrophthalimide was added to the sodium hydroxide solution, heated and boiled for 15min. Adjust pH to 6-8 with nitric acid, and add nitric acid to boil for 5 min. Cooling, filtering, the filtrate was extracted with ether, the extract was dried and then the ether was evaporated, that is, 4-Nitrophthalic anhydride crystals were precipitated. Yield 95%. | [Synthesis]
General procedure for the synthesis of 4-nitrophthalic anhydride from 4-nitrophthalic acid: general method: 4-nitrophthalic acid (1 mmol) was mixed with oxalyl chloride (1.2 mmol) in anhydrous toluene (5 mL), and a drop of freshly distilled DMF was added as catalyst. After the reaction vessel was purged with argon, the reaction mixture was heated under stirring for 3 hours. Upon completion of the reaction, stirring was stopped and the toluene solution was decanted from the oily residue and filtered. The volatiles were removed by evaporation to give analytically pure 4-nitrophthalic anhydride. If further purification is desired, it may be converted to a crystalline form by grinding with diethyl ether. In some cases (see ESI), an additional crystallization step or grinding with a 1:2 (v/v) hexane-toluene mixture may be used to improve the purity of the product. | [Purification Methods]
Distil the anhydride in a vacuum and/or recrystallise it from *C6H6 or Et2O/pet ether. Dry it in vacuo. It forms addition compounds with anthracene (m 118o), and phenanthrene (m 96o). [Beilstein 17 III/IV 6150, 17/11 V 267.] | [Precautions]
Moisture Sensitive. Store away from strong bases and oxidizing agents. Incompatible with water, bases, strong acids and oxidizing agents. | [References]
[1] Patent: US3979416, 1976, A
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 20, p. 2967 - 2974
[3] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1817 - 1821
[4] Tetrahedron Letters, 2017, vol. 58, # 32, p. 3160 - 3163
[5] Bulletin des Societes Chimiques Belges, 1996, vol. 105, # 1, p. 55 - 56 |
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