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Phenacetin

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Name

Phenacetin

EINECS 200-533-0
CAS No. 62-44-2 Density 1.099 g/cm3
PSA 38.33000 LogP 2.11670
Solubility 0.076 g/100 mL in water Melting Point 133-136 °C(lit.)
Formula C10H13NO2 Boiling Point 355.1 °C at 760 mmHg
Molecular Weight 179.24 Flash Point 168.5 °C
Transport Information Appearance white crystalline powder
Safety 53-45 Risk Codes 45-22-20/21/22
Molecular Structure Molecular Structure of 62-44-2 (Acetamide,N-(4-ethoxyphenyl)-) Hazard Symbols
Synonyms

p-Acetophenetidide(8CI);4-(Acetylamino)phenetole;4-Ethoxy-1-acetylaminobenzene;4-Ethoxyacetanilide;4'-Ethoxyacetanilide;Aceto-4-phenetidine;Acetophenetidin;Acetophenetidine;Acetophenetin;Acetphenetidin;Fenidina;Fenina;Kalmin;N-(4-Ethoxyphenyl)acetamide;N-Acetyl-4-ethoxyaniline;N-Acetyl-p-ethoxyaniline;N-Acetyl-p-phenetidine;NSC 7651;Pertonal;Phenacetin;Phenacetine;Phenazetin;Phenedina;Phenidin;Phenin;p-Ethoxyacetanilide;

 

Phenacetin Synthetic route

60-35-5

acetamide

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

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

acetic anhydride

156-43-4

4-Ethoxyaniline

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
108-24-7

acetic anhydride

100-29-8

1-ethoxy-4-nitrobenzene

62-44-2

4-ethoxyacetanilide

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

4'-ethoxyacetophenone

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

108-24-7

acetic anhydride

62-44-2

4-ethoxyacetanilide

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

acetic anhydride

4-phenetidinium hydrogen sulfate

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

108-24-7

acetic anhydride

62-44-2

4-ethoxyacetanilide

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

p-ethoxyaniline hydrobromide

108-24-7

acetic anhydride

62-44-2

4-ethoxyacetanilide

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

triacetylglycerol

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

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

ethylene glycol diacetate

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

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

acetyl chloride

156-43-4

4-Ethoxyaniline

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

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%
141-78-6

ethyl acetate

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

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

4-Ethoxyaniline

123-54-6

acetylacetone

62-44-2

4-ethoxyacetanilide

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

acetaldehyde

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

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

ethyl bromide

103-90-2

4-acetaminophenol

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;
14040-11-0

tungsten hexacarbonyl

616-38-6

carbonic acid dimethyl ester

100-29-8

1-ethoxy-4-nitrobenzene

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%
64-19-7

acetic acid

103-73-1

Phenetole

62-44-2

4-ethoxyacetanilide

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

acetic acid

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

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

acetic anhydride

100-29-8

1-ethoxy-4-nitrobenzene

A

62-44-2

4-ethoxyacetanilide

B

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%
64-17-5

ethanol

103-84-4

Acetanilid

62-44-2

4-ethoxyacetanilide

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

[bis(acetoxy)iodo]benzene

N-benzyl-4-ethoxybenzenecarboximidamide

62-44-2

4-ethoxyacetanilide

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

(4-nitrobenzylidene)(4-ethoxyphenyl)amine

108-24-7

acetic anhydride

A

62-44-2

4-ethoxyacetanilide

B

555-16-8

4-nitrobenzaldehdye

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

4-Ethoxyaniline

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
108-24-7

acetic anhydride

100-29-8

1-ethoxy-4-nitrobenzene

A

62-44-2

4-ethoxyacetanilide

B

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;
108-24-7

acetic anhydride

64-19-7

acetic acid

156-43-4

4-Ethoxyaniline

62-44-2

4-ethoxyacetanilide

Conditions
ConditionsYield
for 2h; Reflux;

Phenacetin Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2A IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 310.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 (1977),p. 141.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 (1977),p. 141.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 (1980),p. 135.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 (1980),p. 135.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 (1980),p. 135.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Phenacetin Specification

Phenacetin, its cas register number is 62-44-2. It also can be called Aceto-p-phenetidin. Phenacetin is a white crystalline powder with the chemical composition C10H13NO2. Phenacetin is an analgesic, once widely used; its use has declined because of its adverse effects. In addition to its pain-reducing properties, it also has been used as a fever-reducer, a treatment for rheumatoid arthritis and a treatment for intercostal neuralgia, a rare disorder that causes pain in the nerves around the ribs. 

Physical properties about Phenacetin are: (1)ACD/LogP: 1.655; (2)ACD/LogD (pH 5.5): 1.66; (3)ACD/LogD (pH 7.4): 1.66; (4)ACD/BCF (pH 5.5): 10.67; (5)ACD/BCF (pH 7.4): 10.67; (6)ACD/KOC (pH 5.5): 189.43; (7)ACD/KOC (pH 7.4): 189.44; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.549; (12)Molar Refractivity: 51.836 cm3; (13)Molar Volume: 163.025 cm3; (14)Polarizability: 20.549 10-24cm3; (15)Surface Tension: 39.0260009765625 dyne/cm; (16)Density: 1.099 g/cm3; (17)Flash Point: 168.531 °C; (18)Enthalpy of Vaporization: 60.016 kJ/mol; (19)Boiling Point: 355.054 °C at 760 mmHg

Preparation of Phenacetin: Phenacetin may be synthesized as an example of the Williamson ether synthesis: ethyl iodide, paracetamol, and anhydrous potassium carbonate are refluxed in 2-butanone to give the crude product, which is recrystallized from water.

Preparation of Phenacetin

When you are using this chemical, please be cautious about it as the following:
1. Avoid exposure - obtain special instruction before use;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);

You can still convert the following datas into molecular structure:
(1)InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12);
(2)InChIKey=CPJSUEIXXCENMM-UHFFFAOYSA-N;
(3)SmilesCCOc1ccc(cc1)NC(=O)C

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 260mg/kg (260mg/kg)   National Technical Information Service. Vol. PB282-666,
guinea pig LD50 oral 1870mg/kg (1870mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Toxicology and Applied Pharmacology. Vol. 2, Pg. 23, 1960.
 
hamster LD50 oral 1690mg/kg (1690mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: ATAXIA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Pharmazie. Vol. 8, Pg. 572, 1953.
 
man LDLo unreported 74mg/kg (74mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LC50 inhalation 33900mg/m3 (33900mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(10), Pg. 36, 1969.
mouse LD50 intraperitoneal 540mg/kg (540mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 81, Pg. 659, 1961.
mouse LD50 oral 866mg/kg (866mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1644, 1978.
 
mouse LD50 subcutaneous 1625mg/kg (1625mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 25, 1958.
 
rabbit LD50 oral 2500mg/kg (2500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 53, 1977.
rabbit LD50 subcutaneous 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
 
rat LD50 intraperitoneal 634mg/kg (634mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 62, Pg. 11, 1966.
 
rat LD50 oral 1650mg/kg (1650mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 240, 1959.
rat LD50 oral 1650mg/kg (1650mg/kg) CARDIAC: PULSE RATE 

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 1, Pg. 240, 1959.

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