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62-44-2

Basic Information
CAS No.: 62-44-2
Name: Phenacetin
Article Data: 72
Molecular Structure:
Molecular Structure of 62-44-2 (Phenacetin)
Formula: C10H13NO2
Molecular Weight: 179.219
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;
EINECS: 200-533-0
Density: 1.099 g/cm3
Melting Point: 133-136 °C(lit.)
Boiling Point: 355.1 °C at 760 mmHg
Flash Point: 168.5 °C
Solubility: 0.076 g/100 mL in water
Appearance: white crystalline powder
Hazard Symbols:
Risk Codes: 45-22-20/21/22
Safety: 53-45
PSA: 38.33000
LogP: 2.11670
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%
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    Phenacetin Basic information Product Name: Phenacetin Synonyms: 1-ACETYL-P-PHENETIDIN;4-ACETOPHENETIDIDE;4-acetophenetidine;4'-ETHOXYACETANILIDE;4-ETHOXYACETANI

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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.

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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