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1466-82-6

Basic Information
CAS No.: 1466-82-6
Name: Acetylsalicylic anhydride
Article Data: 21
Molecular Structure:
Molecular Structure of 1466-82-6 (Acetylsalicylic anhydride)
Formula: C18H14O7
Molecular Weight: 342.305
Synonyms: Benzoicacid, 2-(acetyloxy)-, anhydride (9CI);Salicylic acid acetate, anhydride (8CI);Salicylic anhydride, diacetate (6CI,7CI);2-Acetoxybenzoic anhydride;Acetylsalicylic acid anhydride;Aspirin anhydride;Contraflu;NSC 63848;NSC 80056;Pircan;Vigal;Benzoic acid,2-(acetyloxy)-, 1,1'-anhydride;
EINECS: 215-987-5
Density: 1.306 g/cm3
Melting Point: 80-83 °C
Boiling Point: 511.2 °C at 760 mmHg
Flash Point: 226.4 °C
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26-36
PSA: 95.97000
LogP: 2.53440
Synthetic route
50-78-2

aspirin

1466-82-6

aspirin anhydride

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;100%
With iodine; triethylamine; triphenylphosphine In dichloromethane at 0 - 20℃;72%
With triethylamine; trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;71%
110-86-1

pyridine

36335-42-9

(2-acetoxy-benzoyl)-carbonic acid ethyl ester

A

1466-82-6

aspirin anhydride

B

530-75-6

acetylsalicylsalicylic acid

36335-42-9

(2-acetoxy-benzoyl)-carbonic acid ethyl ester

1466-82-6

aspirin anhydride

Conditions
ConditionsYield
im Vakuum;
With pyridine
im Vakuum;
18698-59-4

(2-acetoxy-benzoic acid )-acetic acid-anhydride

A

1466-82-6

aspirin anhydride

B

108-24-7

acetic anhydride

Conditions
ConditionsYield
Disproportionierung;

(2-acetoxy-benzoic acid )-benzoic acid-anhydride

1466-82-6

aspirin anhydride

(2-acetoxy-benzoic acid )-benzoic acid-anhydride

A

1466-82-6

aspirin anhydride

B

93-97-0

benzoic acid anhydride

50-78-2

aspirin

5538-51-2

O-acetylsalicyloyl chloride

1466-82-6

aspirin anhydride

Conditions
ConditionsYield
With toluene bei Gegenwart einer tertiaeren Base;
5538-51-2

O-acetylsalicyloyl chloride

1466-82-6

aspirin anhydride

Conditions
ConditionsYield
With α-picoline; benzene Behandeln des Reaktionsprodukts mit Wasser;
50-78-2

aspirin

A

1466-82-6

aspirin anhydride

B

(R,S)-2-(acetoxybenzoyloxy)-2-methyl-4H-1,3-benzodioxin-4-one

Conditions
ConditionsYield
With triethylamine; trifluoroacetic anhydride 1.) toluene, from 40 deg C to RT, 2.) toluene, 10 min; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With triethylamine; trifluoroacetic anhydride 1.) toluene, from 40 deg C to RT, 2.) toluene, 10 min; Yield given. Multistep reaction;
5538-51-2

O-acetylsalicyloyl chloride

acetylsalicylate sodium

acetylsalicylate sodium

1466-82-6

aspirin anhydride

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Specification

The Acetylsalicylic anhydride, with the CAS registry number 1466-82-6, is also known as 2-(Acetyloxy)benzoic anhydride. It belongs to the product categories of Impurities; Intermediates & Fine Chemicals; Pharmaceuticals. And its EINECS registry number is 215-987-5. This chemical's molecular formula is C18H14O7 and molecular weight is 342.30. What's more, its IUPAC name is (2-Acetyloxybenzoyl) 2-acetyloxybenzoate. In addition, this chemical's classification code is Mutation Data. And it is an impurity in aspirin.

Physical properties about Acetylsalicylic anhydride are: (1)ACD/LogP: 1.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.33; (4)ACD/LogD (pH 7.4): 1.33; (5)ACD/BCF (pH 5.5): 5.99; (6)ACD/BCF (pH 7.4): 5.99; (7)ACD/KOC (pH 5.5): 125.31; (8)ACD/KOC (pH 7.4): 125.31; (9)#H bond acceptors: 7; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 95.97 Å2; (13)Index of Refraction: 1.567; (14)Molar Refractivity: 85.67 cm3; (15)Molar Volume: 261.9 cm3; (16)Polarizability: 33.96×10-24 cm3; (17)Surface Tension: 49.7 dyne/cm; (18)Density: 1.306 g/cm3; (19)Flash Point: 226.4 °C; (20)Enthalpy of Vaporization: 78.21 kJ/mol; (21)Boiling Point: 511.2 °C at 760 mmHg; (22)Vapour Pressure: 1.45E-10 mmHg at 25 °C.

Preparation of Acetylsalicylic anhydride: this chemical is prepared by 2-Acetoxy-benzoic acid. This reaction needs reagents Ph3P, CCl3CN and Et3N. Meanwhile, it needs solvent Tetrahydrofuran. The reaction time is 2 hours with reaction temperature of 20 °C. The yield is about 71 %.

The Acetylsalicylic anhydride can be obtained by 2-Acetoxy-benzoic acid.

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. In addition, this chemical is harmful if swallowed. During using it, you should wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(Oc2ccccc2C(=O)OC(=O)c1ccccc1OC(=O)C)C
(2) InChI: InChI=1/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
(3) InChIKey: OAWXYINGQXLWOE-UHFFFAOYAV

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 2200mg/kg (2200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 2, Pg. 514, 1960.