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4-Acetamidophenol

Antipyretic analgesic Chemical property Pharmacological Actions Pharmacokinetics Preparation method Usage and Dosage Adverse reaction Taboo Notes Drug interactions Administration nursing care point Usage Production
4-Acetamidophenol
4-Acetamidophenol
CAS No.
103-90-2
Chemical Name:
4-Acetamidophenol
Synonyms
G 1;APAP;Dirox;Dypap;Exdol;Fevor;Hedex;Korum;NAPAP;Panex
CBNumber:
CB1413658
Molecular Formula:
C8H9NO2
Formula Weight:
151.16
MOL File:
103-90-2.mol

4-Acetamidophenol Properties

Melting point:
168-172 °C(lit.)
Density 
1,293 g/cm3
Flash point:
11 °C
storage temp. 
Store at RT
solubility 
ethanol: soluble0.5M, clear, colorless
form 
Crystals or Crystalline Powder
color 
White
PH
5.5-6.5 (H2O, 20℃)(saturated solution)
explosive limit
15%(V)
Water Solubility 
14 g/L (20 ºC)
Merck 
14,47
BRN 
2208089
InChIKey
RZVAJINKPMORJF-UHFFFAOYSA-N
CAS DataBase Reference
103-90-2(CAS DataBase Reference)
NIST Chemistry Reference
Acetaminophen(103-90-2)
EPA Substance Registry System
Acetamide, N-(4-hydroxyphenyl)-(103-90-2)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xn,T,F
Risk Statements  22-36/37/38-52/53-36/38-40-39/23/24/25-23/24/25-11
Safety Statements  26-36-61-37/39-22-45-36/37-16-7
WGK Germany  1
RTECS  AE4200000
TSCA  Yes
HS Code  29242930
Hazardous Substances Data 103-90-2(Hazardous Substances Data)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H341 Suspected of causing genetic defects Germ cell mutagenicity Category 2 Warning P201,P202, P281, P308+P313, P405,P501
H370 Causes damage to organs Specific target organ toxicity, single exposure Category 1 Danger P260, P264, P270, P307+P311, P321,P405, P501
H371 May cause damage to organs Specific target organ toxicity, single exposure Category 2 Warning P260, P264, P270, P309+P311, P405,P501
H372 Causes damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 1 Danger P260, P264, P270, P314, P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
H402 Harmful to aquatic life Hazardous to the aquatic environment, acute hazard Category 3
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
H412 Harmful to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 3 P273, P501
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P311 Call a POISON CENTER or doctor/physician.
P330 Rinse mouth.
P391 Collect spillage. Hazardous to the aquatic environment
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P307+P311 IF exposed: call a POISON CENTER or doctor/physician.
P405 Store locked up.
P501 Dispose of contents/container to..…

4-Acetamidophenol price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1003009 Acetaminophen United States Pharmacopeia (USP) Reference Standard 103-90-2 400mg $348.4 2017-11-08 Buy
Sigma-Aldrich 8.22325 4'-Hydroxyacetanilide for synthesis 103-90-2 1EA $35 2017-11-08 Buy
TCI Chemical H0190 4'-Hydroxyacetanilide >98.0%(HPLC)(N) 103-90-2 25g $16 2017-11-08 Buy
TCI Chemical H0190 4'-Hydroxyacetanilide >98.0%(HPLC)(N) 103-90-2 500g $56 2017-11-08 Buy
Alfa Aesar A11240 4-Acetamidophenol, 98% 103-90-2 250g $45 2017-11-08 Buy

4-Acetamidophenol Chemical Properties,Uses,Production

Antipyretic analgesic

The chemiacal name of 4-acetaminophen is N-(4-hydroxy phenyl) acetamide and the trade name is paracetamol belonging to acetanilide antipyretic analgesics. It was first synthesized by Morse in 1878 and first used in clinic by VonMering in 1893. It has become an over the counter drug in the USA since 1955 and our country started production at the end of the 1950’s. 4-acetaminophen is a white crystalline or a crystalline powder in appearance with melting point from 168℃ to 172℃, odorless, slightly bitter taste, freely soluble in hot water or ethanol, dissolved in acetone, practically insoluble in cold water and petroleum ether. It is stable below 45℃ but will be hydrolyzed into p-aminophenol when exposed to humid air, then oxidized further. The color grades gradually from pink to brown then to black, so it should be sealed and stored in a cool and dry place.
4-Acetamidophenol has the antipyretic activity by inhibiting the synthesis of hypothalamic thermoregulation prostaglandins and its strength of antipyretic effect is similar to aspirin. On the other hand, 4-Acetamidophenol can produce analgesic effect by inhibiting the synthesis of prostaglandins in the central nervous system and blocking impulses of nociceptive nerve endings, but weaker than aspirin. Compared with aspirin, 4-Acetamidophenol has minor irritation, few allergic reactions and other advantages. Its antipyretic and analgesic effect is similar to phenacetin, and   the use of 4-acetaminophen increases due to limiting or banning using phenacetin in many countries.
In clinical, it is mainly used for fever and headache caused by cold and relieving mild to moderate pain such as joint pain, muscle pain, neuralgia, migraine, dysmenorrhea, cancer pain, postoperative analgesia and so on. It can be used for patients who are allergic to aspirin, intolerant of aspirin, or unsuited for aspirin, such as patients with varicella, hemophilia and other hemorrhagic disease (patients having anticoagulant therapy included), as well as patients with slight peptic ulcer and gastritis. In addition, it also can be used for the synthesis of benorylate and used as asymmetric synthetic intermediates, photographic chemicals and stabilizer of hydrogen peroxide.

Chemical property

Obtain prism crystallization from ethanol. Melting point 169-171℃, relative density 1.293(21/4℃). Soluble in ethanol, acetone and hot water, difficult to dissolve in water, insoluble in petroleum ether and benzene. Odorless, bitter. The pH value of saturated aqueous solution is 5.5-6.5.

Pharmacological Actions

This product is used as antipyretic analgesics. It has the antipyretic activity by means of mediated peripheral vasodilation and perspiration caused by inhibiting the cyclooxygenase which selectively inhibiting the synthesis of hypothalamic thermoregulation prostaglandins, and its strength of antipyretic effect is similar to aspirin. As a peripheral analgesic, it can produce analgesic effect by inhibiting the synthesis and release of prostaglandins and increasing pain threshold. However, its action is weaker than aspirin and it is only effective for mild to moderate pain. There is no obvious anti-inflammation effect.

Pharmacokinetics

The oral absorption is rapid and complete, and the peak time occurs 0.5~2h later. The plasma protein binding rate is 25%~50%. This product is equally distributed in the body, 90%~95% is metabolized in the liver and mainly excreted from the kidney combining with glucuronic acid  and about 3% exits the body unchanged in the urine within 24h. Its half-life (t1/2) is 1~4h (average 2h). In case of renal insufficiency t1/2 is not affected, but t1/2 of patients with hepatic insufficiency, newborns or elderly patients may increase and t1/2 of children may decrease. It can be secreted by milk.

Preparation method

1. Using nitrobenzene as raw material
In the presence of concentrated sulfuric acid and sixteen alkyl methyl ammonium chloride, nitrobenzene is transformed into p-Aminophenol by catalytic hydrogenation with Pd/C as catalyst. P-acetaminophen is synthesized acetylation by one-step acylation without separation and the yield is 64.3%. The reaction is as followed:
Preparation method1
2. Using paranitrophenol as raw material
With paracetamol as raw material and Pd/C as catalyst, paracetamol is synthesized by hydroacylation on one-step method. The optimum solvent is acetic acid of which the dosage is 2 to 5 times of paranitrophenol and the yield of paracetamol is up to 95%. When Pd-La/C is used as catalyst instead, the yield can reach 97%. The reaction is as followed:
  Preparation method 2
3. Using p-aminophenol as raw material
Under these conditions of using p-aminophenol and acetic anhydride as raw materials, zinc powder as the antioxidant, activated carbon as the decolorizing agent and dilute acetic acid as the reaction medium, paracetamol is synthesized by microwave irradiation technology and the yield is up to81.2%. The reaction is as followed:
Preparation method 3
4. Using p-Hydroxyacetophenone as raw material
First oximate p-Hydroxyacetophenone and then rearrange it to obtain paracetamol by means of Beckmann. Under this method, the yield of 4-hydroxyacetophenone oxime obtained by oximating p-Hydroxyacetophenone is 93.5%. Then we use Hβ molecular sieve as catalyst and acetone as the solvent to obtain acetaminophen by rearrangement and the yield is 81.2 %. In the rearrangement reaction, acetone is used as the solvent and Al-MCM-41 molecular sieve is used as the catalyst. The yield is the highest when the content of phosphoric acid in the catalyst is 30%. The reaction is as followed:
  Preparation method 4
5. Using  phenol as raw material
Phenol is used as the raw material and synthesizes paracetamol after acetylation, Fries rearrangement, oxime and Beckmann rearrangement. The yields are 82%, 68.6%, 50.5%,
respectively. The reaction is as followed:
Preparation method 5

Usage and Dosage

Usage
This product is antipyretic and analgesic whose international nonproprietary name is Paracetamol. It is the most common non anti-inflammatory analgesia-antipyretic drugs without anti inflammatory and anti rheumatism action. Its antipyretic effect is similar to aspirin, but analgesic effect is weak. It is the best of breed of acetanilid drugs. The product is especially suitable for patients who cannot use carboxylic acids drugs. It is used for cold and toothache. Acetaminophen is also used as organic synthesis intermediates, stabilizer of hydrogen peroxide, photographic chemicals.
Dosage   
1. Oral (1) Paracetamol tablets or paracetamol capsules: adults take 300~600mg at a time and 3~4 times a day according to the need. The daily dosage should not be greater than 2g. Defervescence treatment is generally less than 3 days and the administration of pain relief lasts less than 10 days. Children take 10~15mg/kg every 4~ 6 hours. The dosage of children under the age of 12 does not exceed 5 times a day, a five-day course at most. This product should not be taken for a long time.
2. Dispersible tablets: When take tablets, disperse them in warm water dispersion. The commonly used amount of children is 10~15mg/kg every 4~ 6 hours. The dosage of children under the age of 12 does not exceed 5 times a day, a five-day course at most. Children under 3 years old cut back on the amount.

Adverse reaction

1. Allergic reactions: This product has less and slight side effects a dose treatment except for occasional rashes, hives and other allergic reactions. Methemoglobinemia may occur in a few cases.
2. Hepatorenal damage: A large number of long-term use,  hepatorenal damages and thrombocytopenia may occur, even jaundice, oliguria, acute severe hepatitis, which could lead to coma, and death. Using at high dosage may cause nausea, vomiting, stomach pain, stomach cramps, diarrhea, anorexia, sweating, etc.
3. For children under the age of 3, the development of liver and kidney function is not mature with poor detoxification and excretory function, so they should try to avoid using this product. In addition, patients with liver and kidney insufficiency and pregnant women should use cautiously. The long-term drug users should regularly check renal function and hemogram.

Taboo

It is contraindicated in patients allergic to the product and patients with severe liver and kidney function deficiency.

Notes

Drug interactions

Administration nursing care point

Usage

Organic synthesis intermediates, stabilizer of hydrogen peroxide, photographic chemicals, non anti-inflammatory analgesia-antipyretic drugs.

Production

Produced by acetylation of p-aminophenol. Method 1: add p-aminophenol into dilute acetic acid, then add glacial acetic acid, heat up to 150℃and react for 7h, add acetic anhydride and react for 2h, check the end point and cool to 25℃ after the acceptance, shake it and filter, water until no acetic acid flavor exists, dry to get crude products. Method 2: distill p-aminophenol, acetic acid and acid industrial containing more than 50% acid together, the speed of distilling dilute acid for is 1/10 of the total distillate in one hour, check the residue of p-aminophenol less than 2.5% aminophenol by sampling inspection when inner temperature rises up to 130℃, add dilute acid (content of more than 50%), cool to get crystallization. After shaking and filter, first use a small amount of dilute acid to wash, and then use a large number of water till filtrate is near colourless to get crude products. The yield of method 1 is 90%, but the yield of method 2 is 90-95%. Refining methods: add the crude product when the water is heated to near boiling. Heat up to the total dissolution, add activated carbon soaked in water, use dilute acetic acid to adjust till pH=4.2-4.6, boil for 10min. Filter press, add a small amount of sodium bisulfite into the filtrate. Cool to below 20℃, separate crystals out. After shaking and filter, wash and dry to get active ingredients, paracetamol finished products. Other methods of production are as followed: (1) p-nitrophenol is reduced by zinc in acetic acid, and acetaminophen is obtained by acetylation at the same time; (2) put the hydrazone generated from p-hydroxyacetophenone in acid solution containing sulfuric acid, and then add sodium nitrite to get acetaminophen by renversement.

Chemical Properties

White Solid

Uses

antiinfectant

Uses

dispersing agent in liquid scintillation counting

Uses

Analgesic; antipyretic

General Description

Odorless white crystalline solid. Bitter taste. pH (saturated aqueous solution) about 6.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

4-Acetamidophenol is sensitive to light. Incompatible with strong oxidizers. .

Fire Hazard

Flash point data for 4-Acetamidophenol are not available; however, 4-Acetamidophenol is probably combustible.

Biological Activity

Cyclooxygenase inhibitor; may be selective for COX-3 (IC 50 values are 460, > 1000 and > 1000 μ M for canine COX-3, and murine COX-1 and COX-2 respectively). Widely used analgesic and antipyretic agent.

4-Acetamidophenol Preparation Products And Raw materials

Raw materials

Preparation Products


4-Acetamidophenol Suppliers

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