4-Acetamidophenol

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.
 

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%.

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: