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62-44-2 Usage

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenacetin react with oxidizing agents, iodine and nitrating agents.

Brand name

[Names previously used: Acetophenetidin; Acetphenetidin.].

Side Effects

Long term use may cause renal papillary necrosis and interstitial nephritis, and even induce renal pelvic cancer and bladder cancer. Phenacetin also makes the hemoglobin to form methemoglobin, decreasing blood oxygen carrying capacity, causing cyanosis. In addition, Phenacetin can cause hemolysis and hemolytic anemia, and is toxic to the retina. Long term use may cause also lead to dependence. Countries including America, Britain, German, and Japan have banned Phenacetin, or required packaging to note that it is “not indicated for long-term usage or large doses.”

Fire Hazard

Flash point data for Phenacetin are not available but Phenacetin is probably combustible.

Uses

Analgesic, antipyretic. Component of APC tablets, analgesic mixture also containing aspirin and caffeine. Phenacetin is reasonably anticipated to be a human carcinogen; analgesic mixtures containing Phenacetin are listed as known human carcinogens.

Purification Methods

Crystallise it from H2O or EtOH, and its solubility in H2O is 0.08% (at ~10o) and 1.2% (at ~100o), and in EtOH it is 6.7% (at ~10o) and 36% (at ~100o). Alternatively it can be purified by solution in cold dilute alkali and re-precipitating by addition of acid to neutralisation point. Dry it in air. [Beilstein 13 H 461, 13 IV 1092.]

General Description

Odorless fine white crystalline solid with a lightly bitter taste. Used as an analgesic medicine.

Uses

glycosylation inhibitor

Chemical Properties

white crystalline powder

Mechanisms of Action

On its own, phenacetin has no antipyretic or analgesic effects. In vivo, acetaminophen and paracetamol are metabolized and decomposed to create the antipyretic and analgesic effects. Its decomposites with ammonia and phenyl either not only have no antipyretic and analgesic effects, but also are major factors in its side effects.

Indications and Usage

Phenacetin is mainly used as an antipyretic analgesic, with slow and lasting effects, treating headaches, neuralgia, joint pain, and fever, and weakly resisting rheumatism and inflammation. Because of toxic side effects and the rapid development of similar drugs, however, it is no longer used alone, only as a raw material in combination with other drugs. Commonly combined with aspirin and caffeine to form a less toxic compound aspirin used to treat the common cold. Can make chlorpheniramine cold tablets by adding a small amount of chlorpheniramine to the above compound, used to treat colds with headache, neuralgia, rheumatism, etc. Can be used as a material for organic synthesis or a pharmaceutical intermediate.

Definition

ChEBI: A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a 4-ethoxyphenyl group.
InChI:InChI=1/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)

62-44-2 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (77440)  Phenacetin  ≥98.0% (HPLC) 62-44-2 77440-1KG 1,304.55CNY Detail
Aldrich (77440)  Phenacetin  ≥98.0% (HPLC) 62-44-2 77440-250G 320.58CNY Detail
Aldrich (77440)  Phenacetin  ≥98.0% (HPLC) 62-44-2 77440-50G 180.18CNY Detail
Vetec (V900730)  Phenacetin  Vetec reagent grade, 98% 62-44-2 V900730-500G 480.87CNY Detail
Vetec (V900730)  Phenacetin  Vetec reagent grade, 98% 62-44-2 V900730-100G 109.98CNY Detail
USP (1514008)  Phenacetin Melting Point Standard  United States Pharmacopeia (USP) Reference Standard 62-44-2 1514008-1G 2,882.88CNY Detail
Alfa Aesar (A11200)  4'-Ethoxyacetanilide, 97%    62-44-2 500g 550.0CNY Detail
Alfa Aesar (A11200)  4'-Ethoxyacetanilide, 97%    62-44-2 100g 191.0CNY Detail

62-44-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name phenacetin

1.2 Other means of identification

Product number -
Other names p-Acetophenetidide

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:62-44-2 SDS

62-44-2Synthetic route

acetamide
60-35-5

acetamide

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With dipotassium peroxodisulfate In water at 100℃; for 0.166667h; Microwave irradiation; Green chemistry;94%
acetic anhydride
108-24-7

acetic anhydride

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With water for 0.25h;88%
With sulfuric acid
With (2S)-N-methyl-1-phenylpropan-2-amine hydrate
acetic anhydride
108-24-7

acetic anhydride

1-ethoxy-4-nitrobenzene
100-29-8

1-ethoxy-4-nitrobenzene

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With hydrogen; AV-17-8-Pd anion exchanger In ethanol at 45℃; under 760 Torr;87.8%
4'-ethoxyacetophenone
1676-63-7

4'-ethoxyacetophenone

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With pyridine; ammonium hydroxide; hydrogen sulfide In water62%
Multi-step reaction with 2 steps
2: phosphorus (V)-chloride; diethyl ether
View Scheme
p-ethoxyaniline acetate

p-ethoxyaniline acetate

acetic anhydride
108-24-7

acetic anhydride

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
In aq. acetate buffer at 102℃; for 5h; pH=4 - 5; Large scale;94.6%
acetic anhydride
108-24-7

acetic anhydride

4-phenetidinium hydrogen sulfate

4-phenetidinium hydrogen sulfate

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
In aq. acetate buffer at 95 - 100℃; for 6h; pH=4 - 5; Large scale;95%
4-ethoxyanilinium dihydrogenphosphate

4-ethoxyanilinium dihydrogenphosphate

acetic anhydride
108-24-7

acetic anhydride

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
In aq. acetate buffer at 95 - 100℃; for 6h; pH=4 - 5; Large scale;95.5%
p-ethoxyaniline hydrobromide
108160-45-8

p-ethoxyaniline hydrobromide

acetic anhydride
108-24-7

acetic anhydride

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
In aq. acetate buffer at 90 - 93℃; for 6.5h; pH=4 - 5; Large scale;94.7%
triacetylglycerol
102-76-1

triacetylglycerol

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
sodium methylate In ethylene glycol at 120 - 125℃; for 3h; Conversion of starting material;79%
ethylene glycol diacetate
111-55-7

ethylene glycol diacetate

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
sodium methylate In ethylene glycol at 120 - 125℃; for 3h; Conversion of starting material;75%
acetyl chloride
75-36-5

acetyl chloride

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere;88%
With potassium carbonate In acetone at 0 - 30℃; for 11h;77.2%
In dichloromethane at 20℃;
1-(4-ethoxy-phenyl)-ethanone oxime

1-(4-ethoxy-phenyl)-ethanone oxime

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With aluminium trichloride; silica gel; zinc(II) chloride In dichloromethane for 0.075h; Beckmann rearrangement; microwave irradiation;93%
Stage #1: 1-(4-ethoxy-phenyl)-ethanone oxime With triethylamine In dichloromethane at 20℃; for 0.0833333h; Sealed tube;
Stage #2: With potassium hydrogen difluoride In water at 20℃; for 2h; Beckmann Rearrangement; Sealed tube;
87%
ethyl acetate
141-78-6

ethyl acetate

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
sodium methylate In ethylene glycol at 106 - 130℃; for 10h; Conversion of starting material;59%
4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

acetylacetone
123-54-6

acetylacetone

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With dihydrogen peroxide In water at 25℃; for 8h; Green chemistry;91%
acetaldehyde
75-07-0

acetaldehyde

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In acetonitrile at 80℃; for 8h;65%
ethyl bromide
74-96-4

ethyl bromide

4-acetaminophenol
103-90-2

4-acetaminophenol

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With sodium hydroxide; ethanol
With potassium carbonate In acetone for 48h; Heating;
With potassium carbonate In acetone Reflux;
With potassium carbonate In acetone Reflux;
With potassium hydroxide In ethanol for 24h; Reflux;
tungsten hexacarbonyl
14040-11-0

tungsten hexacarbonyl

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

1-ethoxy-4-nitrobenzene
100-29-8

1-ethoxy-4-nitrobenzene

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With di(rhodium)tetracarbonyl dichloride; 1,3-bis-(diphenylphosphino)propane; sodium phosphate; sodium iodide In water at 120℃; for 24h; Inert atmosphere; Sealed tube;99%
acetic acid
64-19-7

acetic acid

Phenetole
103-73-1

Phenetole

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With hydroxylamine hydrochloride at 80℃; for 2.5h;75%
acetic acid
64-19-7

acetic acid

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With hydrazine hydrate for 2.5h; Heating;95%
acetic anhydride
108-24-7

acetic anhydride

1-ethoxy-4-nitrobenzene
100-29-8

1-ethoxy-4-nitrobenzene

A

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

B

N-acetoxy-N-(4-ethoxy-phenyl)-acetamide

N-acetoxy-N-(4-ethoxy-phenyl)-acetamide

Conditions
ConditionsYield
With aluminum oxide; zinc In dichloromethane at 20℃; for 15h; Acetylation; reduction;A 55%
B 15%
ethanol
64-17-5

ethanol

Acetanilid
103-84-4

Acetanilid

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene at 20℃; for 2h; regioselective reaction;57%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

N-benzyl-4-ethoxybenzenecarboximidamide

N-benzyl-4-ethoxybenzenecarboximidamide

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
In toluene at 100℃; for 15h; Sealed tube; Inert atmosphere;94%
(4-nitrobenzylidene)(4-ethoxyphenyl)amine
15485-31-1, 97221-16-4

(4-nitrobenzylidene)(4-ethoxyphenyl)amine

acetic anhydride
108-24-7

acetic anhydride

A

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

B

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

Conditions
ConditionsYield
With water; sodium dodecyl-sulfate at 25 - 30℃; for 0.0833333h;A 95%
B 91%
4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
With carbon dioxide unter Abdestillieren des gebildeten Wassers bis auf 165grad;
With sodium acetate; acetic acid at 150℃;
Multi-step reaction with 2 steps
1: hydrogen bromide / water / 0.67 h / 30 - 35 °C / Autoclave; Large scale
2: aq. acetate buffer / 6.5 h / 90 - 93 °C / pH 4 - 5 / Large scale
View Scheme
Multi-step reaction with 2 steps
1: phosphoric acid / water / 1 h / 15 - 20 °C / Autoclave; Large scale
2: aq. acetate buffer / 6 h / 95 - 100 °C / pH 4 - 5 / Large scale
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid / water / 1 h / 15 - 20 °C / Autoclave; Large scale
2: aq. acetate buffer / 6 h / 95 - 100 °C / pH 4 - 5 / Large scale
View Scheme
acetic anhydride
108-24-7

acetic anhydride

1-ethoxy-4-nitrobenzene
100-29-8

1-ethoxy-4-nitrobenzene

A

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

B

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 45℃; under 760 Torr; Kinetics; Product distribution; Further Variations:; Catalysts; Reaction partners;
acetic anhydride
108-24-7

acetic anhydride

acetic acid
64-19-7

acetic acid

4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

4-ethoxyacetanilide
62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
for 2h; Reflux;

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