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103-90-2 Usage

Taboo

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

Administration nursing care point

  • Nurse according to the general principles of analgesia-antipyretic drugs.
  • The caregiver should exhort the patient to pay attention to the following things during medication period: ①No drinking, drinking may aggravate the liver toxicity of this product; ②Drink plenty of water to reduce the concentration of drug in renal tubules and reduce the occurrence of “analgesic nephropathy”; ③When taking chewing chips, chew them up; ④No unauthorized use other NSAIDS or compound preparation containing NSAIDS at the same time to avoid increasing the renal toxicity.
  • In a poisoning caused by this product, we should give patients oral antagonists, acetylcysteine (Tan Yijing) as soon as possible, not oral activated carbon, because the latter can affect the absorption of antagonists. Initial dose of acetylcysteine is 140 mg/kg, add 70 mg/kg every 4 h, 17 times totally. Intake: configure acetylcysteine into a 5% solution or add in triple drinks and take after shaking well to avoid fetid odors and irritations. For the occurrence of vomiting within 1 h after medication, resupply, if necessary, take nasal or rectal administration. In severe cases, the drug can be dissolved in 5% 200 ml glucose injection and used through intravenous drip. The antagonist should be applied as soon as possible because the effect is satisfactory in 12 h but the effect is worse over 24 h. In the treatment, it is best to monitor the blood concentration and give other therapies, such as hemodialysis or hemofiltration.

Drug interactions

  • For patients with chronic alcohol ingestion or other liver enzyme inducers, especially barbiturates or anticonvulsants, when taking long-term or a large-scale use of this product, they may have a higher risk of liver toxicity.
  • When combined with chloramphenicol, this product can prolong the latter t1/2 and enhance its toxicity.
  • When combined with anticoagulant drugs, this product can increase the anti-blood-clotting effect. So it is necessary to adjust the dosage of anticoagulant drugs.
  • When combining long-term large quantities of 4-Acetamidophenol with aspirin or other non-steroidal anti-inflammatory drugs, it will increase the risk of renal toxicity.
  • When combined with the antiviral drug, zidovudine, it can increase the toxicity. We ought to avoid using at the same time.

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.

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.

General Description

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

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.

Uses

manufacture of azo dyes, photographic chemicals.

Brand name

Acephen (G & W); Infants’ Feverall (Actavis); Injectapap (Ortho-McNeil); Neopap (Polymedica); Tylenol (McNeil).

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.

Notes

  • Allergies are disabled. Patients who are allergic to aspirin do not have allergic reactions generally. However, it has been reported that a small number of patients with asthma caused by aspirin-sensitivity can have an episode of bronchospasm after taking drugs.
  • This product may increase the risk of liver toxicity when patients suffer from alcohol poisoning, liver disease or viral hepatitis, so it should be used with caution. Patients with renal insufficiency take a lot of products regularly, leading to increasing risk of renal toxicity, so they should be careful. It is contraindicated in patients with severe liver and kidney function deficiency.
  • When taking the drug for pain, it is not allowed to take for more than 40 consecutive days. Antipyretic treatments shall not exceed 3 days, unless doctors tell you otherwise. After taking this product, patients should immediately stop taking medicine when symptoms of erythema or edema occur. This product is only a drug for symptomatic treatment, it is necessary to take other treatments to relieve reasons of pain or fever at the same time when taken.
  • This product can be passed through the placenta and secreted in milk, so pregnant women and lactating women are not recommended to use. 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. Because the development of liver and kidney function declines, t1/2 of elderly patients may increase leading to adverse reactions easily. Patients should take with caution or take a smaller amount of use appropriately.
  • The interferences of diagnosis: ① Glucose measurement, falsely low values are measured by glucose oxidase/peroxidase methods, but no effect occurs when measured by hexokinase /6-dehydrogenase methods; ② Assays for uric acid of serum, falsely high values are measured by phosphotungstic acid method; ③ Determination of urinary 5-hydroxyindoleacetic acid (5-HIAA), falsely positive results are obtained in a screening test with nitroso naphthol reagent, but quantitative test is not affected; ④Liver function tests, prothrombin time, serum bilirubin, lactic dehydrogenase and serum aminotransferase can be increased due to high doses or long-term use.
  • In case of large dosage, promote vomiting timely and give antagonists named N-acetylcysteine (140mg/kg orally given at the beginning, then 70mg/kg, take 1 times every 4h, 17 times; it can be given intravenously when serious, the drug can be dissolved in 5% 200 ml glucose injection and used through intravenous drip) or take methionine orally, which has a protective effect on the liver. Do not give activated carbon, because it can affect the absorption of drugs. The antagonist should be applied as soon as possible because the effect is satisfactory in 12 h but the effect is worse over 24 h. In the treatment, it is best to monitor the blood concentration and give other therapies, such as hemodialysis or hemofiltration.

Uses

antiinfectant

Usage

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

Uses

dispersing agent in liquid scintillation counting

Chemical Properties

White Solid

Application in Particular Diseases

In Osteoarthritis:
  • Acetaminophen is recommended by the ACR as first-line drug therapy for pain management of OA. The dose is 325 to 650 mg every 4 to 6 hours on a scheduled basis (maximum dose 4 g/day; maximum 2 g/day if chronic alcohol intake or underlying liver disease). Comparable relief of mild to moderate OA pain has been demonstrated for acetaminophen (2.6 to 4 g/ day) compared with aspirin (650 mg four times daily), ibuprofen (1,200 or 2,400 mg daily), and naproxen (750 mg daily). However, some patients respond better to NSAIDs.
  • Acetaminophen is usually well tolerated, but potentially fatal hepatotoxicity with overdose is well documented. It should be used with caution in patients with liver disease and those who chronically abuse alcohol. Chronic alcohol users (three or more drinks daily) should be warned about an increased risk of liver damage or GI bleeding with acetaminophen. Other individuals do not appear to be at increased risk for GI bleeding. Renal toxicity occurs less frequently than with NSAIDs.

Reactivity Profile

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

Purification Methods

Recrystallise Paracetamol from water or EtOH. The 3,5-dinitrobenzamide complex gives orange crystals from hot H2O and has m 171.5o. [Beilstein 13 H 460, 13 I 159, 13 II 243, 13 III 1056, 13 IV 1091.]

Uses

Analgesic; antipyretic

Air & Water Reactions

Slightly soluble in water.

Fire Hazard

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

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.

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.

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.

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

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.
InChI:InChI=1/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)/i2D,3D,4D,5D

103-90-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A11240)  4-Acetamidophenol, 98%    103-90-2 5000g 4114.0CNY Detail
Alfa Aesar (A11240)  4-Acetamidophenol, 98%    103-90-2 1000g 1033.0CNY Detail
Alfa Aesar (A11240)  4-Acetamidophenol, 98%    103-90-2 500g 678.0CNY Detail
Alfa Aesar (A11240)  4-Acetamidophenol, 98%    103-90-2 250g 370.0CNY Detail
TCI America (H0190)  4'-Hydroxyacetanilide  >98.0%(HPLC)(N) 103-90-2 500g 570.00CNY Detail
TCI America (H0190)  4'-Hydroxyacetanilide  >98.0%(HPLC)(N) 103-90-2 25g 155.00CNY Detail

103-90-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name paracetamol

1.2 Other means of identification

Product number -
Other names APAP

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103-90-2 SDS

103-90-2Synthetic route

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

4-acetaminophenol
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%
acetic anhydride
108-24-7

acetic anhydride

4-amino-phenol
123-30-8

4-amino-phenol

4-acetaminophenol
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%
4-acetoxyacetanilide
2623-33-8

4-acetoxyacetanilide

4-acetaminophenol
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%
4-hydroxyacetophenone oxime
34523-34-7

4-hydroxyacetophenone oxime

4-acetaminophenol
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%
4-nitro-phenol
100-02-7

4-nitro-phenol

acetic acid
64-19-7

acetic acid

4-acetaminophenol
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;
p-nitrosophenol
104-91-6

p-nitrosophenol

acetic acid
64-19-7

acetic acid

4-acetaminophenol
103-90-2

4-acetaminophenol

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

acetic anhydride

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-acetaminophenol
103-90-2

4-acetaminophenol

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

4-amino-phenol

acetylacetone
123-54-6

acetylacetone

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With dihydrogen peroxide In water at 25℃; for 8h; Green chemistry;97%
(4-acetylaminophenyl)boronic acid
101251-09-6

(4-acetylaminophenyl)boronic acid

4-acetaminophenol
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;
acetamide
60-35-5

acetamide

4-amino-phenol
123-30-8

4-amino-phenol

4-acetaminophenol
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%
4-nitro-phenol
100-02-7

4-nitro-phenol

acetic anhydride
108-24-7

acetic anhydride

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With sodium tetrahydroborate; chloro-trimethyl-silane In methanol; water at 20℃; for 0.333333h; Reagent/catalyst; Irradiation;95%
With hydrogen In para-xylene at 130℃; under 750.075 Torr; for 24h; chemoselective reaction;95%
With samarium; acetic acid In methanol at 20℃; for 1.5h;80%
Stage #1: 4-nitro-phenol With sodium tetrahydroborate at 20℃; for 0.5h; Green chemistry;
Stage #2: acetic anhydride at 120℃; for 1h; Catalytic behavior; Green chemistry;
78%
With acetic acid; platinum Hydrogenation;
4-amino-phenol
123-30-8

4-amino-phenol

1-acetyl-1H-1,2,3-triazolo<4,5-b>pyridine
107866-54-6

1-acetyl-1H-1,2,3-triazolo<4,5-b>pyridine

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;95%
4-amino-phenol
123-30-8

4-amino-phenol

2-acetyl-4,5-dichloropyridazin-3(2H)-one
155164-63-9

2-acetyl-4,5-dichloropyridazin-3(2H)-one

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
In tetrahydrofuran at 17℃; for 0.2h;95%
(E)-1-(4-hydroxyphenyl)ethan-1-one oxime
198712-64-0

(E)-1-(4-hydroxyphenyl)ethan-1-one oxime

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione In acetonitrile at 80℃; for 0.333333h; Beckmann Rearrangement; Inert atmosphere; Schlenk technique;95%
With 1,1,1,3',3',3'-hexafluoro-propanol; tetrabutylammonium tetrafluoroborate; water In 1,2-dichloro-ethane at 20℃; for 0.533333h; Beckmann Rearrangement; Electrochemical reaction;92%
With cerium(III) chloride; silica gel; sodium iodide for 0.133333h; Beckmann rearrangement; microwave irradiation;82%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at 20℃; for 6h; Beckmann rearrangement;80%
4-methoxyacetanilide
51-66-1

4-methoxyacetanilide

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0℃; for 1.5h; Inert atmosphere;95%
With boron tribromide In dichloromethane at 20℃; Inert atmosphere;68%
With boron tribromide In dichloromethane Cooling with ice; Inert atmosphere;68%
With 1H-imidazole; iron (III) meso-tetrakis (2,6-dichlorophenylporphyrin-β-octabromo)chloride; 3-chloro-benzenecarboperoxoic acid In isopropyl alcohol; acetonitrile at 20℃; for 24h; Reagent/catalyst;19.2%
N-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]acetamide
103202-04-6

N-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]acetamide

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With potassium hydrogen difluoride In methanol at 20℃; for 2h;95%
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Microwave irradiation;94%
With aluminium(III) chloride hexahydrate In methanol at 100℃; for 0.25h; Solvent; Temperature; Microwave irradiation; Sealed tube; chemoselective reaction;90%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

4-amino-phenol
123-30-8

4-amino-phenol

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With 1H-imidazole; nickel oxinate at 150℃;95%
With 1,2,4-Triazole; 8-quinolinol; copper(II) choride dihydrate at 150℃;91%
With Imidazole hydrochloride at 150℃; for 4h; Sealed tube;89%
With ammonium iodide at 125℃; for 17h;29%
acetic acid
64-19-7

acetic acid

4-nitrophenol sodium salt
824-78-2

4-nitrophenol sodium salt

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
at 80 - 130℃;95%
4-amino-phenol
123-30-8

4-amino-phenol

acetic acid
64-19-7

acetic acid

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With magnesia In neat (no solvent) at 70℃; for 0.166667h; Green chemistry; chemoselective reaction;93%
at 60 - 120℃; for 11h; Product distribution / selectivity;91.6%
With Starbon-400-SO3H at 130℃; for 0.05h; Microwave irradiation; chemoselective reaction;89%
4-amino-phenol
123-30-8

4-amino-phenol

acetyl chloride
75-36-5

acetyl chloride

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With calcium oxide In 2-methyltetrahydrofuran at 20℃; for 4h; Green chemistry; chemoselective reaction;93%
With triethylamine In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere;83%
With silica gel at 20℃; for 2.5h; Green chemistry; chemoselective reaction;82%
3-((1-acetyl-1H-benzo[d][1,2,3]triazol-5-yl)methyl)-1,2-dimethyl-1H-pyrazol-2-ium hexauorophosphate

3-((1-acetyl-1H-benzo[d][1,2,3]triazol-5-yl)methyl)-1,2-dimethyl-1H-pyrazol-2-ium hexauorophosphate

4-amino-phenol
123-30-8

4-amino-phenol

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With dmap In water at 100℃; for 0.25h; Microwave irradiation; Green chemistry;93%
4-amino-phenol
123-30-8

4-amino-phenol

acetonitrile
75-05-8

acetonitrile

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With aluminum oxide at 200℃; under 37503.8 Torr; for 0.45h; Sonication; Green chemistry;93%
With tert.-butylnitrite; trifluorormethanesulfonic acid; water at 60℃; for 24h;42%
4-amino-phenol
123-30-8

4-amino-phenol

thioacetic acid
507-09-5

thioacetic acid

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With Fe3O4(at)Chit-TCT-Salen-Cu(II) In water at 20℃; for 0.0833333h; chemoselective reaction;92%
With copper(II)-grafted guanidine acetic acid-modified magnetite nanoparticles In water at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;91%
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;78%
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;78%
With copper(ll) sulfate pentahydrate In methanol at 20℃; for 0.0833333h;75%
4-amino-phenol
123-30-8

4-amino-phenol

N-acetyl-1,3-oxazol-2-one
60759-49-1

N-acetyl-1,3-oxazol-2-one

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
In tetrahydrofuran for 7h; Ambient temperature;90%
4-acetamidophenyl allyl ether
6622-73-7

4-acetamidophenyl allyl ether

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 1h; Heating;90%
With potassium hydroxide; palladium on activated charcoal In methanol at 20℃; for 48h;86%
With potassium hydroxide In methanol at 20℃; for 48h;86%
With iodine In dimethyl sulfoxide at 130℃; for 0.5h;83%
N,N’-(1,2-ethanediylidene)bis-hydroxyphenylamine
24764-93-0

N,N’-(1,2-ethanediylidene)bis-hydroxyphenylamine

acetic anhydride
108-24-7

acetic anhydride

A

Glyoxal
131543-46-9

Glyoxal

B

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With water; sodium dodecyl-sulfate at 25 - 30℃; for 0.166667h;A 85%
B 90%
4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

A

4-acetaminophenol
103-90-2

4-acetaminophenol

B

4-hydroxyacetophenone oxime
34523-34-7

4-hydroxyacetophenone oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride In acetonitrile at 70℃; for 15h;A 90%
B 8%
With hydroxylamine hydrochloride at 70 - 110℃; Solvent; chemoselective reaction;
Acetanilid
103-84-4

Acetanilid

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
With formic acid; boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene at 20℃; for 0.5h; regioselective reaction;89%
With trifluoroacetic acid In ethanol; water at 20℃; for 3h; Electrochemical reaction; Green chemistry; regioselective reaction;32%
With 1H-imidazole; iron (III) meso-tetrakis (2,6-dichlorophenylporphyrin-β-octabromo)chloride; 3-chloro-benzenecarboperoxoic acid In isopropyl alcohol; acetonitrile at 20℃; for 24h; Reagent/catalyst;19.2%
4-amino-phenol
123-30-8

4-amino-phenol

3-acetylthiazolidine-2-thione
76397-53-0

3-acetylthiazolidine-2-thione

4-acetaminophenol
103-90-2

4-acetaminophenol

Conditions
ConditionsYield
In dichloromethane at 25℃; for 3h;88%
formaldehyd
50-00-0

formaldehyd

4-acetaminophenol
103-90-2

4-acetaminophenol

diethylamine
109-89-7

diethylamine

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide
121-78-8

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide

Conditions
ConditionsYield
In ethanol at 80℃; for 1.5h; Microwave irradiation;100%
In ethanol for 12h; Heating;80%
In ethanol at 80℃; for 1h; Microwave irradiation;77%
4-acetaminophenol
103-90-2

4-acetaminophenol

4-amino-phenol
123-30-8

4-amino-phenol

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 70℃; for 5h; Reagent/catalyst; Temperature; Microwave irradiation;100%
With ammonium bromide; ethylenediamine at 70℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);99%
With ammonium iodide; hydrazine hydrate at 50℃; for 12h; Inert atmosphere; Sealed tube;97%
4-acetaminophenol
103-90-2

4-acetaminophenol

S-tert-butyl cyclohexylcarbamoylthioacetate
339274-36-1

S-tert-butyl cyclohexylcarbamoylthioacetate

N-cyclohexyl-malonamic acid 4-acetylamino-phenyl ester

N-cyclohexyl-malonamic acid 4-acetylamino-phenyl ester

Conditions
ConditionsYield
With silver trifluoroacetate In tetrahydrofuran at 20℃;100%
4-acetaminophenol
103-90-2

4-acetaminophenol

methyl iodide
74-88-4

methyl iodide

4-methoxyacetanilide
51-66-1

4-methoxyacetanilide

Conditions
ConditionsYield
With potassium carbonate In acetone at 65℃; for 24h; Inert atmosphere;100%
With sodium ethanolate
4-acetaminophenol
103-90-2

4-acetaminophenol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

N-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]acetamide
103202-04-6

N-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]acetamide

Conditions
ConditionsYield
With ferric hydrogen sulphate; triethylamine at 20℃; for 60h; Inert atmosphere; chemoselective reaction;100%
With 1H-imidazole In tetrahydrofuran for 16h; Schlenk technique; Inert atmosphere;97%
With 1H-imidazole Sealed tube; Inert atmosphere;89%
5-nitro-2-fluorotoluene
455-88-9

5-nitro-2-fluorotoluene

4-acetaminophenol
103-90-2

4-acetaminophenol

C15H14N2O4

C15H14N2O4

Conditions
ConditionsYield
Stage #1: 4-acetaminophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 5-nitro-2-fluorotoluene In N,N-dimethyl-formamide at 140℃; for 5h; Solvent;
99.5%
4-acetaminophenol
103-90-2

4-acetaminophenol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonic acid 4-acetylaminophenyl ester
301337-51-9

toluene-4-sulfonic acid 4-acetylaminophenyl ester

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 2h; Green chemistry;99%
With triethylamine In dichloromethane for 16h;62%
With sodium carbonate
With pyridine In dichloromethane at 20℃;
iodomethane-d3
865-50-9

iodomethane-d3

4-acetaminophenol
103-90-2

4-acetaminophenol

N-(4-methoxy-d3-phenyl)acetamide
54536-22-0

N-(4-methoxy-d3-phenyl)acetamide

Conditions
ConditionsYield
With potassium carbonate In acetone at 20 - 25℃; for 24h;99%
With potassium carbonate In acetone at 20 - 25℃; for 24h;99%
With potassium carbonate In acetone at 20℃;479 mg
4-acetaminophenol
103-90-2

4-acetaminophenol

1-Bromopinacolon
5469-26-1

1-Bromopinacolon

N-(4-(3,3-dimethyl-2-oxobutoxy)phenyl)acetamide

N-(4-(3,3-dimethyl-2-oxobutoxy)phenyl)acetamide

Conditions
ConditionsYield
With potassium carbonate In acetone at 70℃; for 16h;99%
1-(13)C-ethyl iodide
75560-39-3

1-(13)C-ethyl iodide

4-acetaminophenol
103-90-2

4-acetaminophenol

N-4-((1-13C)Ethoxy)phenylacetamide
72156-72-0

N-4-((1-13C)Ethoxy)phenylacetamide

Conditions
ConditionsYield
With potassium carbonate In acetone for 60h;98.6%
1-bromo-octane
111-83-1

1-bromo-octane

4-acetaminophenol
103-90-2

4-acetaminophenol

N-(4-(octyloxy)phenyl)acetamide
55792-63-7

N-(4-(octyloxy)phenyl)acetamide

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 12h; Reflux;98%
With potassium carbonate In butanone at 70℃; for 18h; Williamson Ether Synthesis;91%
With potassium carbonate In acetone for 48h; Heating;80%
4-acetaminophenol
103-90-2

4-acetaminophenol

N-(4-hydroxy-3-nitrophenyl)acetamide
51288-37-0

N-(4-hydroxy-3-nitrophenyl)acetamide

Conditions
ConditionsYield
With silica gel; citric acid; sodium nitrite In hexane at 20℃; for 2.25h;98%
With Nitrite In aq. acetate buffer at 25℃; pH=5; Electrochemical reaction; Green chemistry; regioselective reaction;85%
With sulfuric acid; guanidine nitrate In water at 0 - 5℃; Inert atmosphere;84%
4-acetaminophenol
103-90-2

4-acetaminophenol

1-dodecylbromide
143-15-7

1-dodecylbromide

N-(4-(dodecyloxy)phenyl)acetamide
95705-65-0

N-(4-(dodecyloxy)phenyl)acetamide

Conditions
ConditionsYield
With potassium carbonate In butanone for 24h; Reflux;98%
With potassium carbonate In butanone at 70℃; for 18h; Williamson Ether Synthesis;86%
With potassium carbonate In acetone for 18h; Heating;72%
4-acetaminophenol
103-90-2

4-acetaminophenol

acetyl chloride
75-36-5

acetyl chloride

4-acetoxyacetanilide
2623-33-8

4-acetoxyacetanilide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;98%
With triethylamine In dichloromethane at 0℃; for 2h;97%
4-acetaminophenol
103-90-2

4-acetaminophenol

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitrophenyl 4'-acetamidophenyl ether
2687-40-3

4-nitrophenyl 4'-acetamidophenyl ether

Conditions
ConditionsYield
With copper(l) iodide; 2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 11h; Schlenk technique; Inert atmosphere;98%
4-acetaminophenol
103-90-2

4-acetaminophenol

benzyl bromide
100-39-0

benzyl bromide

N-[4-(benzyloxy)phenyl]acetamide
41927-14-4

N-[4-(benzyloxy)phenyl]acetamide

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 40℃;98%
With potassium carbonate In acetone for 4h; Reflux;97%
With potassium carbonate In acetone at 65℃; for 4h; Inert atmosphere;97%
With potassium carbonate In acetonitrile at 70℃;
4-acetaminophenol
103-90-2

4-acetaminophenol

propargyl bromide
106-96-7

propargyl bromide

N-(4-(prop-2-yn-1-yloxy)phenyl)acetamide
26557-77-7

N-(4-(prop-2-yn-1-yloxy)phenyl)acetamide

Conditions
ConditionsYield
With caesium carbonate In acetonitrile98%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;95%
Stage #1: 4-acetaminophenol With sodium hydroxide In water at 70℃;
Stage #2: propargyl bromide With tetrabutylammomium bromide In water; toluene at 70℃; for 24h;
94%
4-acetaminophenol
103-90-2

4-acetaminophenol

2,2-dichloro-4,4,6,6-bis[spiro(2',2''-dioxy-1'',1''-biphenyl)]cyclotriphosphazene
128175-80-4

2,2-dichloro-4,4,6,6-bis[spiro(2',2''-dioxy-1'',1''-biphenyl)]cyclotriphosphazene

C40H32N5O8P3
165899-64-9

C40H32N5O8P3

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;98%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

4-acetaminophenol
103-90-2

4-acetaminophenol

C14H23NO2Si
929259-42-7

C14H23NO2Si

Conditions
ConditionsYield
With ferric hydrogen sulphate; triethylamine at 20℃; for 60h; Inert atmosphere; chemoselective reaction;98%
With triethylamine at 20℃; Inert atmosphere;80%
4-acetaminophenol
103-90-2

4-acetaminophenol

4-acetamidophenyl sulfurofluoridate
16704-37-3

4-acetamidophenyl sulfurofluoridate

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h;98%
Stage #1: 4-acetaminophenol With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h;
98%
Stage #1: 4-acetaminophenol With triethylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere;
98%
4-acetaminophenol
103-90-2

4-acetaminophenol

1,1'-spiro-<2,2'-dioxybiphenyl-1,1'>-3,3',5,5'-tetrachloro-2,4,6,1λ5,3λ5,5λ5-triazatriphosphorine
128175-79-1

1,1'-spiro-<2,2'-dioxybiphenyl-1,1'>-3,3',5,5'-tetrachloro-2,4,6,1λ5,3λ5,5λ5-triazatriphosphorine

C44H40N7O10P3
1331732-22-9

C44H40N7O10P3

Conditions
ConditionsYield
With potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;97%

103-90-2Related news

Original articleMetal complexes of azo compounds derived from 4-Acetamidophenol (cas 103-90-2) and substituted aniline08/12/2019

The Ni(II) and Cu(II) complexes of four azo compounds (H2L1–4), namely, 2-(p-X-phenylazo)-4-acetamidophenol (X = OCH3, NO2, Br, and H for H2L1, H2L2, H2L3, and H2L4, respectively) were prepared and characterized on the basis of their analytical, spectroscopic, magnetic, and conductance data. Th...detailed

Synthesis and characterization of samarium and nitrogen doped TiO2 photocatalysts for photo-degradation of 4-Acetamidophenol (cas 103-90-2) in combination with hydrodynamic and acoustic cavitation08/11/2019

In the present work, samarium (Sm) and nitrogen (N) doped TiO2 photocatalysts have been synthesized using conventional sol-gel process (CSP) and ultrasound assisted sol-gel process (USP). Detailed characterizations of catalysts have been performed using PL, UV-DRS, XPS, XRD, FTIR, FESEM, and EDX...detailed

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