ACETYLSALICYLIC ANHYDRIDE

ACETYLSALICYLIC ANHYDRIDE Property

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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ACETYLSALICYLIC ANHYDRIDE Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

Acetylsalicylic Acid Impurity D

Uses

Acetylsalicylic Acid (A187780) 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