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103-90-2

Basic Information
CAS No.: 103-90-2
Name: Acetaminophen
Article Data: 344
Cas Database
Molecular Structure:
Molecular Structure of 103-90-2 (Acetaminophen)
Formula: C8H9NO2
Molecular Weight: 151.165
Synonyms: Acetamide,N-(4-hydroxyphenyl)-;Acetanilide,4'-hydroxy- (7CI,8CI);4-(Acetylamino)phenol;4-(N-Acetylamino)phenol;4-Acetamidophenol;4-Acetaminophenol;4-Hydroxyacetanilide;4'-Hydroxyacetanilide;Alpiny;Alvedon;Anhiba;Apamid;Apamide;Banesin;Ben-u-ron;Bickie-mol;Biocetamol;Cetadol;Clixodyne;Daphalgan;Datril;Dirox;Enelfa;Eu-Med;Exdol;Gattaphen T;Homoolan;Jin Gang;Korum;Lestemp;Liquagesic;Lonarid;Lyteca;Lyteca Syrup;Minoset;Minoset Plus;Momentum;Multin;N-(4-Hydroxyphenyl)acetamide;N-Acetyl-4-aminophenol;N-Acetyl-4-hydroxyaniline;Pacemo;Pacemol;Panadol;Panadol Actifast;Panadol Extend;Panaleve;Panasorb;Panets;Panodil;Paracetamol;Paracetamol DC;Paracetamole;Parageniol;Paralen;Paramol;Paraspen;Parelan;Parmol;Pasolind N;Pedric;k*e*t*a*m*i*n*e ,kush available;
EINECS: 203-157-5
Density: 1.249 g/cm3
Melting Point: 168-172 °C(lit.)
Boiling Point: 387.8 °C at 760 mmHg
Flash Point: 188.4 °C
Solubility: 14 g/L (20 °C) in water
Appearance: White crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-52/53-36/38-40
Safety: 26-36-61-37/39-22
Transport Information: N/A
PSA: 49.33000
LogP: 1.42360
Synthetic route
99-93-4

4-Hydroxyacetophenone

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With hydroxylamine hydrochloride In acetonitrile at 110℃; for 1h; Solvent; Time; chemoselective reaction;100%
With hydroxylamine hydrochloride; tetrachlorosilane at 160℃; for 0.0583333h; microwave irradiation;92%
With mesitylenesulfonylhydroxylamine In acetonitrile at 20℃; for 6h;92%
108-24-7

acetic anhydride

123-30-8

4-amino-phenol

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With sodium dodecyl-sulfate In water99%
With silica gel for 0.5h; Time; Milling;99%
With sulfuric acid supported on poly(4-vinylpyridine) (P4VP) In dichloromethane at 20℃; for 1.25h;98%
2623-33-8

4-acetoxyacetanilide

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With ammonium acetate In methanol at 20℃; for 4.5h;99%
With ytterbium(III) triflate In isopropyl alcohol for 15h; Deacetylation; Heating;96%
With sodium perborate In methanol at 25℃; for 0.5h;90%
34523-34-7

4-hydroxyacetophenone oxime

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; perfluoropinacol; 2-methoxycarbonylphenylboronic acid In nitromethane at 20℃; for 24h; Beckmann Rearrangement; chemoselective reaction;99%
With 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione In acetonitrile at 80℃; for 0.333333h; Inert atmosphere; Schlenk technique; Green chemistry;98%
With carbon tetrabromide; Eosin Y; N,N-dimethyl-formamide In acetonitrile at 20℃; for 14h; Beckmann Rearrangement; Irradiation; Inert atmosphere; Green chemistry;96%
100-02-7

4-nitro-phenol

64-19-7

acetic acid

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
at 80 - 130℃; Temperature;98%
With sodium sulfite for 16h; Reflux;83%
With Methyl formate; dodecacarbonyl-triangulo-triruthenium at 180℃; for 8h;92 % Chromat.
With hydrogen at 100℃; under 760.051 Torr; for 24h; Sealed tube;82 %Chromat.
With platinum; hydrogen at 100℃; for 24h;
104-91-6

p-nitrosophenol

64-19-7

acetic acid

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
at 80 - 130℃;98%
108-24-7

acetic anhydride

150-13-0

4-amino-benzoic acid

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With acetic acid at 80℃; for 1h; Temperature;97.13%
123-30-8

4-amino-phenol

123-54-6

acetylacetone

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With dihydrogen peroxide In water at 25℃; for 8h; Green chemistry;97%
101251-09-6

(4-acetylaminophenyl)boronic acid

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With water; dihydrogen peroxide In ethanol at 20℃; for 0.0166667h; Green chemistry;97%
With Oxone; potassium phosphate; 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In water at 70℃; for 1h; chemoselective reaction;
60-35-5

acetamide

123-30-8

4-amino-phenol

103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;96%
at 150℃; for 72h; Inert atmosphere; Sealed tube; Green chemistry;96%
With air at 150℃; for 72h; Sealed tube;96%
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History

Harmon Northrop Morse had already synthesized paracetamol at Johns Hopkins University via the reduction of p-nitrophenol with tin in glacial acetic acid in 1877, but it wasn't until 1887 that clinical pharmacologist Joseph von Mering tried paracetamol on patients.
In 1893, von Mering published a paper reporting on the clinical results of paracetamol with phenacetin, another aniline derivative. Von Mering claimed that, unlike phenacetin, paracetamol had a slight tendency to produce methemoglobinemia.
Paracetamol was then quickly discarded in favor of phenacetin. The sales of phenacetin established Bayer as a leading pharmaceutical company.Overshadowed in part by aspirin, introduced into medicine by Heinrich Dreser in 1899, phenacetin was popular for many decades, particularly in widely advertised over-the-counter “headache mixtures,” usually containing phenacetin, an aminopyrine derivative or aspirin, caffeine, and sometimes a barbiturate.
In 1947 David Lester and Leon Greenberg found strong evidence that paracetamol was a major metabolite of acetanilide in human blood, and in a subsequent study they reported that large doses of paracetamol given to albino rats did not cause methemoglobinemia.
It has been suggested that contamination of paracetamol with 4-aminophenol, the substance from which it was synthesized by von Mering, may be the cause for his spurious findings.
In 1953, paracetamol was first marketed in the United States  by Sterling-Winthrop Co.,.
In 1956, 500 mg tablets of paracetamol went on sale in the United Kingdom under the trade name Panadol, produced by Frederick Stearns & Co, a subsidiary of Sterling Drug Inc.
In 1963, paracetamol was added to the British Pharmacopoeia, and has gained popularity since then as an analgesic agent with few side-effects and little interaction with other pharmaceutical agents.
Concerns about paracetamol's safety delayed its widespread acceptance until the 1970s, but in the 1980s paracetamol sales exceeded those of aspirin in many countries, including the United Kingdom.
 

Specification

The Acetaminophen with CAS registry number of 103-90-2 is also known as Acetamide,N-(4-hydroxyphenyl)-. The IUPAC name is N-(4-Hydroxyphenyl)acetamide. It belongs to product categories of Pharmaceuticals; Aromatic Phenols; Intermediates & Fine Chemicals; Lipid signaling. Its EINECS registry number is 203-157-5. In addition, the formula is C8H9NO2 and the molecular weight is 151.17. This chemical is a white crystalline powder that slightly soluble in water. It may cause damage to health and should be sealed in ventilated, cool room away from fire, heat. What's more, this chemical can be used as antipyretic, analgesic, anti-rheumatic drugs.

Physical properties about Acetaminophen are:
(1)ACD/LogP: 0.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.475; (4)ACD/LogD (pH 7.4): 0.474; (5)ACD/BCF (pH 5.5): 1.352; (6)ACD/BCF (pH 7.4): 1.348; (7)ACD/KOC (pH 5.5): 43.194; (8)ACD/KOC (pH 7.4): 43.061; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.619; (13)Molar Refractivity: 42.406 cm3; (14)Molar Volume: 120.946 cm3; (15)Surface Tension: 52.801 dyne/cm; (16)Density: 1.25 g/cm3; (17)Flash Point: 188.354 °C; (18)Enthalpy of Vaporization: 66.186 kJ/mol; (19)Boiling Point: 387.831 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Acetaminophen:
Firstly, aminophenol and glacial acetic acid are added into dilute acetic acid by turns. Then the reaction mixture is heated to 150 °C for 7 hours. Secondly, adding acetic anhydride into mixture solution for another 2 hours. At last, product is obtained by rejection filtering, washing and drying. The yield is about 90%.

Uses of Acetaminophen:
It is used to produce N-acetyl-p-vinyloxyaniline by reaction with tetravinylstannane. The reaction occurs with reagents Cu(OAc)2, O2 and solvent acetonitrile at 20 °C for 22 hours. The yield is about 90%.

Paracetamol is used to produce N-acetyl-p-vinyloxyaniline by reaction with tetravinylstannane.

Safety information of Acetaminophen:
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system, skin and is harmful if swallowed. This chemical is also harmful to aquatic organisms that may cause long-term adverse effects in the aquatic environment. However, there is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing, gloves and eye/face protection. Do not breathe dust and avoid release to the environment. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=O)NC1=CC=C(C=C1)O
2. InChI: InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
3. InChIKey: RZVAJINKPMORJF-UHFFFAOYSA-N

The toxicity data of Acetaminophen is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 50mg/kg (50mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
American Journal of Emergency Medicine. Vol. 6, Pg. 510, 1988.
child LDLo oral 140mg/kg/7D-I (140mg/kg) BEHAVIORAL: COMA

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"
Medical Journal of Australia. Vol. 171, Pg. 472, 1999.
child LDLo oral 360mg/kg/2D (360mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Journal of Pediatrics. Vol. 92, Pg. 832, 1978.
child TDLo oral 591mg/kg/2D-I (591mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

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

BLOOD: APLASTIC ANEMIA
Clinical Pediatrics Vol. 33, Pg. 42, 1994.
child TDLo oral 801mg/kg (801mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: OTHER CHANGES
Pediatrics. Vol. 61, Pg. 68, 1978.
dog LDLo intravenous 826mg/kg (826mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
dog LDLo oral 2gm/kg (2000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BLOOD: CHANGES IN SPLEEN
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 24, Pg. 602, 1993.
frog LDLo subcutaneous 50mg/kg (50mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ATAXIA
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 33, Pg. 216, 1894.
guinea pig LD50 oral 2620mg/kg (2620mg/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.
human LDLo oral 143mg/kg (143mg/kg) BEHAVIORAL: GENERAL ANESTHETIC British Medical Journal. Vol. 282, Pg. 199, 1981.
human LDLo oral 357mg/kg (357mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: COMA
Lancet. Vol. 1, Pg. 66, 1973.
infant TDLo oral 1440mg/kg/6D (1440mg/kg) BEHAVIORAL: IRRITABILITY

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
American Journal of Diseases of Children. Vol. 137, Pg. 386, 1983.
mammal (species unspecified) LD50 unreported 891mg/kg (891mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(6), Pg. 22, 1983.
mammal (species unspecified) LDLo oral 512mg/kg (512mg/kg)   United States Patent Document. Vol. #4035499,
man LDLo oral 143mg/kg/24H- (143mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
American Journal of Medicine. Vol. 74, Pg. 349, 1983.
man LDLo oral 714mg/kg (714mg/kg) LIVER: OTHER CHANGES Human Toxicology. Vol. 1, Pg. 25, 1981.
man TDLo oral 9286ug/kg (9.286mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SENSE ORGANS AND SPECIAL SENSES: OTHER: EAR

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Allergy. Vol. 50(Suppl,
man TDLo oral 714mg/kg (714mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE Postgraduate Medical Journal. Vol. 69, Pg. 52, 1993.
mouse LD50 intraperitoneal 367mg/kg (367mg/kg) BEHAVIORAL: ANALGESIA Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 520, 1965.
mouse LD50 oral 338mg/kg (338mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 20, 1971.
mouse LD50 subcutaneous 310mg/kg (310mg/kg)   Human Toxicology. Vol. 3, Pg. 13S, 1984.
pig LDLo intravenous 1gm/kg (1000mg/kg) LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Veterinary and Human Toxicology. Vol. 30, Pg. 324, 1988.
rat LD50 intraperitoneal 1205mg/kg (1205mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Studi Sassaresi, Sezione 2. Vol. 57, Pg. 561, 1979.
rat LD50 oral 1944mg/kg (1944mg/kg)   United States Patent Document. Vol. #4636513,
women LDLo oral 260mg/kg (260mg/kg) BEHAVIORAL: COMA

GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
JAMA, Journal of the American Medical Association. Vol. 236, Pg. 1874, 1976.
women LDLo oral 400mg/kg (400mg/kg) BEHAVIORAL: COMA

LIVER: LIVER FUNCTION TESTS IMPAIRED
Journal of Toxicology, Clinical Toxicology. Vol. 35, Pg. 325, 1997.
women LDLo oral 650mg/kg (650mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

VASCULAR: OTHER CHANGES
American Journal of Emergency Medicine. Vol. 6, Pg. 511, 1988.
women TDLo oral 4962ug/kg (4.962mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

BLOOD: OTHER CHANGES

LIVER: LIVER FUNCTION TESTS IMPAIRED
Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 223, 1991.
women TDLo oral 13mg/kg (13mg/kg) BEHAVIORAL: EXCITEMENT Allergy. Vol. 50(Suppl,
women TDLo oral 325mg/kg (325mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Postgraduate Medical Journal. Vol. 68, Pg. 116, 1992.
women TDLo oral 490mg/kg (490mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Southern Medical Journal. Vol. 71, Pg. 906, 1978.