ACETYLSALICYLSALICYLIC ACID Chemical Properties

Melting point:

153-160 °C

Boiling point:

361.5°C (rough estimate)

Density 

1.346

refractive index 

1.4600 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)

pka

2.94±0.36(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

20mg/L(21 ºC)

InChI

InChI=1S/C16H12O6/c1-10(17)21-14-9-5-3-7-12(14)16(20)22-13-8-4-2-6-11(13)15(18)19/h2-9H,1H3,(H,18,19)

InChIKey

DDSFKIFGAPZBSR-UHFFFAOYSA-N

SMILES

C(OC1=CC=CC=C1C(O)=O)(=O)C1=CC=CC=C1OC(C)=O

EPA Substance Registry System

2-Carboxyphenyl 2-(acetyloxy)benzoate (530-75-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25

HS Code 

29182900

MSDS

• Language:English Provider:ACROS

ACETYLSALICYLSALICYLIC ACID Usage And Synthesis

Chemical Properties

white to almost white fine crystalline powder

Uses

Antiinflammatory;Cyclooxygenase inhibitor

Uses

analgesic, antipyretic

Uses

Acetylsalicylic Acid Impurity C

Definition

ChEBI: 2-[(2-acetyloxyphenyl)-oxomethoxy]benzoic acid is a carbonyl compound.

Synthesis

To a solution of 2-((2-hydroxybenzoyl)oxy)benzoic acid (5.0 g, 19.37 mmol) in ethanoic anhydride (15.0 mL, 147.0 mmol) was added 3 drops of concentrated hydrochloric acid. The reaction mixture was stirred at room temperature for 16-20 hours. After completion of the reaction, the mixture was diluted with ice-cold water (50 mL) and the precipitated solid was collected by filtration. The solid was washed sequentially with water (2 x 10 mL) and hexane (20 mL) and dried to give 2-((2-acetoxybenzoyl)oxy)benzoic acid (5.5 g) as a white solid. Thin layer chromatography (TLC) Rf value was 0.3 (unfolding agent: 50% ethyl acetate/hexane).

Purification Methods

Crystallise the analgesic from dilute AcOH or EtOH (m 161-162o), MeOH (m 165-168o), and *C6H6/EtOH (m 163-165o). Its solubilities in boiling Et2O, *C6H6 and EtOH are 1.4%, 2.2% and 33%, respectively. [Baker et al. J Chem Soc 201 1951, Garrett et al. J Am Pharm Soc 48 684 1959, Beilstein 10 I 41, 10 II 54, 10 IV 165.]

References

[1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 5, p. 2158 - 2161
[2] Patent: US2014/357680, 2014, A1. Location in patent: Paragraph 0135-0136
[3] Patent: WO2014/195961, 2014, A1. Location in patent: Paragraph 00125; 00126

ACETYLSALICYLSALICYLIC ACID(530-75-6)Related Product Information

• 2-BENZOYLACETANILIDE
• Acetyl chloride
• 4-Hydroxybenzoic acid
• Sasapyrine
• Acetylsalicylic acid
• ACETYLSALICYLIC ANHYDRIDE
• ACETOXYVALERENIC ACID
• Acetic Aceclofenac
• 3-Hydroxybenzoic acid
• 4-amino-6-hydroxybenzene-1,3-dicarboxylic acid
• 2-Ethoxybenzoic acid
• ACETYLSALICYLIC ACID METHYL ESTER
• Methyl 2-ethoxybenzoate
• ACETYLSALICYLSALICYLIC ACID
• 2-BENZYLOXYBENZOIC ACID
• Phenyl salicylate
• 2-METHOXY-BENZOIC ACID PHENYL ESTER
• 2-BENZYLOXYBENZYL ALCOHOL