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50-78-2

Basic Information
CAS No.: 50-78-2
Name: Benzoicacid, 2-(acetyloxy)-
Article Data: 154
Cas Database
Molecular Structure:
Molecular Structure of 50-78-2 (Benzoicacid, 2-(acetyloxy)-)
Formula: C9H8O4
Molecular Weight: 180.16
Synonyms: Rhodine(7CI);Salicylic acid acetate (8CI);2-(Acetyloxy)benzoic acid;AC 5230;Acetophen;Acetysal;Acimetten;Acisal;Saletin;Solpyron;Supac;Temperal;Toldex;Trombyl;Yasta;o-(Acetyloxy)benzoic acid;Acetyl Salicylic Acid;Adiro;Asaflow;Asagran;Asatard;Ascoden 30;Ascriptin;Aspalon;Aspirdrops;Aspirin;Aspirin Protect 300;Aspirin-Direkt;Aspro;Aspropharm;Astrix;Benaspir;Bialpirinia;Caprin;Coricidin D;Dolean pH 8;Easprin;Ecotrin;Endosprin;Entericin;Ewin;Extren;Gelprin;
EINECS: 200-064-1
Density: 1.35
Melting Point: 134-136 °C(lit.)
Boiling Point: 321.4 °C at 760 mmHg
Flash Point: 131.1 °C
Solubility: water: 3.3 g/L (20 °C)
Appearance: white solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26-36/37/39
Transport Information: UN 1851
PSA: 63.60000
LogP: 1.31010
Synthetic route
108-24-7

acetic anhydride

69-72-7

salicylic acid

50-78-2

aspirin

Conditions
ConditionsYield
In neat (no solvent) Molecular sieve; Microwave irradiation; Green chemistry;100%
With erbium(III) chloride for 0.2h; Heating;99%
With SO42-/ZrO2*graphene oxide solid super acid catalyst at 70℃; for 5h; Reagent/catalyst; Green chemistry;97.1%
302353-24-8

methylene-benzo[1,3]dioxin-4-one

50-78-2

aspirin

Conditions
ConditionsYield
With water at 25℃; for 1h; pH=7;100%
64-19-7

acetic acid

69-72-7

salicylic acid

50-78-2

aspirin

Conditions
ConditionsYield
at 80 - 90℃;95%
With sulfuric acid at 70℃; for 5h; Reagent/catalyst;95.7%

2-thioacetoxy-benzoic acid

50-78-2

aspirin

Conditions
ConditionsYield
With thionyl chloride; dihydrogen peroxide In ethanol at 25℃; for 0.0166667h;95%
With chloro-trimethyl-silane; dihydrogen peroxide In ethanol; water at 25℃; for 0.0666667h; regioselective reaction;88%
With Oxone for 0.583333h;58%
75-36-5

acetyl chloride

69-72-7

salicylic acid

50-78-2

aspirin

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;86%
With pyridine; sulfuric acid Cooling with ice;59.23%

methoxymethyl 2-acetoxybenzoate

50-78-2

aspirin

Conditions
ConditionsYield
With bismuth(III) chloride; water In acetonitrile at 50℃; for 1h;85%
533-18-6

2-methylphenyl acetate

50-78-2

aspirin

Conditions
ConditionsYield
With zinc(II) oxide In N,N-dimethyl-formamide for 0.15h; microwave irradiation;80%
With potassium permanganate; benzyl(triethyl)ammoniumpermanganate In acetic acid at 30℃; for 72h;24%
With 2,2'-azobis(isobutyronitrile); oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; cobalt(II) acetate; manganese(II) acetate In acetic acid at 150℃; under 760 Torr; for 14h;9%
85515-88-4

C16H16N2O5S

50-78-2

aspirin

Conditions
ConditionsYield
With copper dichloride In tetrahydrofuran; water for 24h; Ambient temperature;80%
108-24-7

acetic anhydride

15402-17-2

4'-Methoxy-flavyliumchlorid

A

100-09-4

4-methoxybenzoic acid

B

50-78-2

aspirin

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) acetic ester, water, 20 min : decomposition reaction;A 79%
B 52%
With ruthenium(IV) oxide; sodium periodate 1) 5 h, room temp., pyridine; 2) water, acetic ester, 20 min; Yield given. Multistep reaction. Yields of byproduct given;
925681-78-3

O-acetylsalicylic acid acid 2-oxo-1,2,2-triphenylethyl ester

A

201-68-3

13-oxa-indeno[1,2-l]phenanthrene

B

50-78-2

aspirin

Conditions
ConditionsYield
With air In ethanol; acetonitrile Irradiation;A n/a
B 79%
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    Product Name Acetylsalicylic acid Synonyms O-ACETYLSALICYLIC ACID;O-ACETOXYBENZOIC ACID;ACETICYL;ACETOXYBENZOIC ACID CAS 50-78-2 MF C9H8O4

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Chemistry

IUPAC Name: 2-Acetyloxybenzoic acid
Canonical SMILES: CC(=O)OC1=CC=CC=C1C(=O)O
InChI: InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
Molecular Formula: C9H8O4
Molecular Weight: 180.16 g/mol
EINECS: 200-064-1
Classification Code: Analgesic; Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory agents, non-steroidal; Antipyretic; Antirheumatic; Antirheumatic Agents; Cardiovascular Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Fibrin Modulating Agents; Fibrinolytic agents; Hematologic Agents; Human Data; Mutation data; Peripheral Nervous System Agents; Platelet aggregation inhibitors; Reproductive Effect; Sensory System Agents
Stability: Stable. Keep dry. Incompatible with strong oxidizing agents, strong bases, strong acids, various other compounds such as iodides, iron salts, quinine salts, etc.
storage temp.: Store at RT.
solubility: H2O: 10 mg/mL at 37 °C
Water Solubility: 3.3 g/L (20 °C)
Melting Point: 134-136 °C(lit.)
Index of Refraction: 1.55
Molar Refractivity: 44.52 cm3
Molar Volume: 139.5 cm3
Surface Tension: 49.8 dyne/cm
Density: 1.29 g/cm3
Flash Point: 131.2 °C
Enthalpy of Vaporization: 59.45 kJ/mol
Boiling Point: 321.4 °C at 760 mmHg
Vapour Pressure of Aspirin (CAS NO.50-78-2): 0.000124 mmHg at 25 °C

History

 Medicines containing derivatives of salicylic acid, structurally similar to aspirin, have been in medical use long long ago. Salicylate-rich willow bark extract became recognized for its specific effects on fever, pain and inflammation in the mid-eighteenth century. By the nineteenth century pharmacists were experimenting with and prescribing a variety of chemicals related to salicylic acid, the active component of willow extract.
French chemist Charles Frederic Gerhardt was the first to prepare acetylsalicylic acid in 1853,he mixed acetyl chloride with a sodium salt of salicylic acid ,during his work on the synthesis and properties of various acid anhydrides.A reaction ensued,the resulting melt  solidified quickly.So the compound was called "salicylic-acetic anhydride" by Gerhardt. But he did not pursue it further. In 1859, Von Gilm obtained analytically pure acetylsalicylic acid. In 1897,Bayer began selling aspirin around the world.

Uses

  Aspirin (CAS NO.50-78-2) is one of the most frequently used drugs in the treatment of mild to moderate pain, including that of migraines and fever.It is often combined with other non-steroidal anti-inflammatory drugs and opioid analgesics in the treatment of moderate to severe pain.In high doses, aspirin and other salicylates are used in the treatment of rheumatic fever, rheumatic arthritis, and other inflammatory joint conditions. In lower doses, aspirin (or its equivalents, e.g., carbasalate calcium) also inhibits platelet aggregation, and has been shown to reduce the incidence of transient ischemic attacks and unstable angina in men, and can be used prophylactically. It is also used in the treatment of pericarditis, coronary artery disease, and acute myocardial infarction.Low doses of aspirin are also recommended for the prevention of stroke, and myocardial infarction in patients with diagnosed cardiovascular disease. It is of no value in people without proven heart disease.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 104mg/kg (104mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: HEMORRHAGE
Lancet. Vol. 2, Pg. 809, 1952.
child TDLo oral 10mg/kg/1D-I (10mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Clinical Toxicology. Vol. 18, Pg. 247, 1981.
child TDLo oral 39mg/kg/13D-I (39mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" American Journal of Diseases of Children. Vol. 139, Pg. 453, 1985.
dog LD50 intravenous 681mg/kg (681mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
dog LD50 oral 700mg/kg (700mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
guinea pig LD50 oral 1075mg/kg (1075mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 47, Pg. 479, 1958.
hamster LD50 oral 3500mg/kg (3500mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
human TDLo oral 480mg/kg/7D-I (480mg/kg) SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES
Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 281, 1975.
human TDLo oral 669mg/kg/11D (669mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED American Journal of Hospital Pharmacy. Vol. 35, Pg. 330, 1978.
human TDLo oral 1050mg/kg/14D (1050mg/kg) VASCULAR: OTHER CHANGES Clinical Pharmacology and Therapeutics Vol. 67, Pg. 530, 2000.
human TDLo oral 2880mg/kg/8W (2880mg/kg) SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 631, 1983.
infant TDLo oral 120mg/kg (120mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

KIDNEY, URETER, AND BLADDER: HEMATURIA
British Medical Journal. Vol. 1, Pg. 1081, 1979.
mammal (species unspecified) LD50 oral 1750mg/kg (1750mg/kg)   Indian Journal of Medical Research. Vol. 81, Pg. 621, 1985.
man LDLo unreported 294mg/kg (294mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo oral 857mg/kg (857mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Human Toxicology. Vol. 7, Pg. 161, 1988.
man TDLo oral 1625mg/kg (1625mg/kg) BEHAVIORAL: COMA Clinical Pediatrics Vol. 24, Pg. 678, 1985.
man TDLo oral 13036mg/kg/5Y (13036mg/kg) GASTROINTESTINAL: OTHER CHANGES

MUSCULOSKELETAL: JOINTS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Annals of Internal Medicine. Vol. 126, Pg. 665, 1997.
mouse LD50 intraperitoneal 167mg/kg (167mg/kg)   United States Patent Document. Vol. #4376771,
mouse LD50 oral 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 572, 1955.
mouse LD50 subcutaneous 1020mg/kg (1020mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 28, Pg. 1237, 1980.
mouse LD50 unreported 1350mg/kg (1350mg/kg)   United States Patent Document. Vol. #5240918,
rabbit LD50 oral 1010mg/kg (1010mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(3), Pg. 43, 1980.
rat LD50 intraperitoneal 340mg/kg (340mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 62, Pg. 11, 1966.
rat LD50 oral 200mg/kg (200mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 67, 1969.
rat LD50 rectal 790mg/kg (790mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 67, 1969.
women TDLo oral 480mg/kg/5D-I (480mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" New England Journal of Medicine. Vol. 296, Pg. 418, 1977.
women TDLo oral 525mg/kg/5D-I (525mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Annals of Internal Medicine. Vol. 80, Pg. 74, 1974.
women TDLo oral 800mg/kg (800mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

MUSCULOSKELETAL: OTHER CHANGES
American Journal of Emergency Medicine. Vol. 7, Pg. 409, 1989.
women TDLo rectal 4550mg/kg (4550mg/kg) BRAIN AND COVERINGS: ENCEPHALITIS

BEHAVIORAL: COMA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Annals of Pharmacotherpy. Vol. 28, Pg. 467, 1994.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22-36/37/38 
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 1851
WGK Germany: 1
RTECS: VO0700000
PackingGroup: III

Specification

  Aspirin (CAS NO.50-78-2), its Synonyms are Acetylsalicylic acid ; 2-(Acetyloxy)benzoic acid ; 2-Acetoxybenzoic acid ; 2-Carboxyphenyl acetate ; Acesal ; Aceticyl ; Acetilsalicilico ; Acetilum acidulatum ; Benzoic acid, 2-(acetyloxy)- ; O-Acetylsalicylic acid ; Salicylic acid, acetate . It is odorless white crystals or crystalline powder with a slightly bitter taste.