| Identification | Back Directory | [Name]
ACETYLSALICYLIC ANHYDRIDE | [CAS]
1466-82-6 | [Synonyms]
Vigal
pircan
contraflu
NSC 63848
NSC 80056
aspirinanhydride
Aspirin IMpurity F
Aspirin Impurity 6
Aspirin EP Impurity F
Carbasalate EP Impurity A
ACETYLSALICYLIC ANHYDRIDE
ACETYLSALISYLIC ACID IMP F
2-acetoxybenzoic anhydride
O-ACETYLSALICYLIC ANHYDRIDE
acetylsalicylicacidanhydride
(Acetysalicyclclic anhydride)
2-(Acetyloxy)benzoic anhydride
salicylicacid,acetate,anhydride
ACETYLSALICYLIC ACID IMPURITY F
Bis(2-acetyloxybenzoic)anhydride
2-(acetyloxy)-benzoicacianhydride
2-(acetyloxy)benzoicacidanhydride
Carbasalate Calcium EP Impurity A
Acetylsalicylic Acid EP Impurity F
2-(Acetyloxy)benzoic Anhydride (Ace
Bis(2-acetoxybenzoic acid)anhydride
2-(Acetyloxy)benzoic Acid 1,1'-Anhydride
(2-acetyloxybenzoyl) 2-acetyloxybenzoate
Benzoic acid, 2-(acetyloxy)-, 1,1'-anhydride
Aspirin (Acetylsalicylic Acid) EP Impurity F
2-acetoxybenzoic acid (2-acetoxybenzoyl) ester
Acetylsalicylic Anhydride (Aspirin Impurity F)
(2-acetyloxyphenyl)carbonyl 2-acetyloxybenzoate
Acetylsalicylic Acid IMpurity F (Aspirin IMpurity F)
Acetylsalicylic Anhydride (Aspirin Impurity F) solution
Acetylsalicylic Acid EP Impurity F (Aspirin Impurity F)
2-acetyloxybenzoic acid [(2-acetyloxyphenyl)-oxomethyl] ester
Acetylsalicylic Acid EP Impurity F (Acetylsalicylic Anhydride)
Acetylsalicylic Acid Impurity 6（Acetylsalicylic Acid EP Impurity F）
Aspirin Impurity FQ: What is
Aspirin Impurity F Q: What is the CAS Number of
Aspirin Impurity F Q: What is the storage condition of
Aspirin Impurity F Q: What are the applications of
Aspirin Impurity F | [EINECS(EC#)]
215-987-5 | [Molecular Formula]
C18H14O7 | [MDL Number]
MFCD00013236 | [MOL File]
1466-82-6.mol | [Molecular Weight]
342.3 |
| Chemical Properties | Back Directory | [Melting point ]
80-83 °C | [Boiling point ]
511.2±35.0 °C(Predicted) | [density ]
1.306±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [color ]
White to Off-White | [BRN ]
2015320 | [Major Application]
pharmaceutical (small molecule) | [InChI]
InChI=1S/C18H14O7/c1-11(19)23-15-9-5-3-7-13(15)17(21)25-18(22)14-8-4-6-10-16(14)24-12(2)20/h3-10H,1-2H3 | [InChIKey]
OAWXYINGQXLWOE-UHFFFAOYSA-N | [SMILES]
C(=O)(OC(=O)C1C=CC=CC=1OC(C)=O)C1C=CC=CC=1OC(C)=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-36/37/38 | [Safety Statements ]
26-36 | [RIDADR ]
UN 1648 3 / PGII | [WGK Germany ]
3 | [RTECS ]
VO0710000 | [F ]
10-21 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Acetylsalicylic Acid (A187780) Impurity D. | [Uses]
Acetylsalicylic Acid Impurity D | [Synthesis]
General procedure for the synthesis of 2-(acetyloxy)benzoic anhydride from acetylsalicylic acid:
1. prepare a suspension of 2-acetoxybenzoic acid (5.0 g, 28 mmol) in 30 mL of dichloromethane.
2. a solution of N,N'-dicyclohexylcarbodiimide (DCC, 2.9 g, 13.9 mmol) in 10 mL of dichloromethane was added to the above suspension.
3. The reaction mixture was stirred at room temperature overnight.
4. After completion of the reaction, the by-product dicyclohexylurea (DCU) was filtered through a glass filter and washed with a small amount of dichloromethane.
5. The solvent was evaporated and the resulting residue was dissolved in ethyl acetate.
6. The resulting suspension was filtered through a glass filter to remove residual DCU.
7. The filtrate was evaporated to give 2-(acetyloxy)benzoic anhydride as a clear thick oil, which solidified after storage at -20 °C.
Yield: 4.6 g (quantitative).
1H NMR (CDCl3, 400 MHz): δ 8.08 (d, 2H, J = 7.9 Hz), 7.70 (t, 2H, J = 7.8 Hz), 7.40 (t, 2H, J = 7.7 Hz), 7.19 (d, 2H, J = 8.1 Hz), 2.31 (s, 6H).
13C NMR (CDCl3, 100 MHz): δ 169.42, 159.29, 151.83, 135.54, 132.24, 126.29, 124.42, 121.69, 20.89.
IR (KBr) νmax (cm-1): 3570 (w), 3491 (w), 3445 (w), 3332 (br), 3205 (w), 3100 (s, CH), 2932 (s, CH), 2855 (w), 2409 (w), 2032 (w), 1789 (br, C=O), 1728 (br, C=O) , 1603 (s, C=C), 1581 (s), 1484 (s), 1451 (s), 1369 (s), 916 (s), 506 (s).
HRMS m/z Calcd. for C18H14Na7O6: (M + Na)+ 365.0637. Found: 365.0638.
Melting point: 80-85°C. | [References]
[1] Patent: WO2015/89389, 2015, A1. Location in patent: Paragraph 0098
[2] Tetrahedron Letters, 2016, vol. 57, # 3, p. 325 - 328
[3] Synthetic Communications, 2001, vol. 31, # 3, p. 395 - 399
[4] Chemische Berichte, 1910, vol. 43, p. 2990
[5] Chem. Zentralbl., 1911, vol. 82, # I, p. 1568 |
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