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Antipyrine

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Name

Antipyrine

EINECS 200-486-6
CAS No. 60-80-0 Density 1.156 g/cm3
PSA 26.93000 LogP 1.48440
Solubility 1000 g/L (20 °C) in water Melting Point 109-111 °C(lit.)
Formula C11H12N2O Boiling Point 319 °C at 760 mmHg
Molecular Weight 188.229 Flash Point 114.8 °C
Transport Information UN 3249 Appearance White Powder
Safety 26-36-37/39 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 60-80-0 (Antipyrine) Hazard Symbols HarmfulXn
Synonyms

Antipyrine(8CI);1,5-Dimethyl-2-phenyl-1,2-dihydropyrazol-3-one;2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one;2,3-Dimethyl-1-phenyl-5-pyrazolone;Azophen;Azophene;Dentigoa N;Dimethyloxychinizin;Fenazone;Methozin;NSC7945;Oxydimethylquinazine;Parodyne;Phenazon;Phenazone;Phenazone(pharmaceutical);Phenylon;Phenylone;Pyrazophyl;Sedatin;Sedatine;

Article Data 66

Antipyrine Synthetic route

89-25-8

edaravone

77-78-1

dimethyl sulfate

60-80-0

antipyrine

Conditions
ConditionsYield
at 160℃; for 5h;71%
at 140 - 170℃;
948853-49-4

4-(2,3-dimethyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-benzoic acid

60-80-0

antipyrine

Conditions
ConditionsYield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;68%
89-25-8

edaravone

74-88-4

methyl iodide

60-80-0

antipyrine

Conditions
ConditionsYield
Stage #1: edaravone; methyl iodide In acetonitrile at 120℃;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
58%
With methanol at 100 - 120℃; im Rohr;
With sodium hydrogencarbonate In acetonitrile
In acetonitrile for 12h; Heating; Sealed tube;
67-56-1

methanol

89-25-8

edaravone

A

27349-35-5

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

B

60-80-0

antipyrine

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 20h; Ambient temperature;A 53%
B 14%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 20h; Product distribution; Ambient temperature; various solvents, various ratio of products;
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

A

27349-35-5

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

B

60-80-0

antipyrine

67-56-1

methanol

19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

60-80-0

antipyrine

Conditions
ConditionsYield
With hydrogenchloride at 120℃;
With ethyl bromide at 120℃;
74-83-9

methyl bromide

19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

60-80-0

antipyrine

Conditions
ConditionsYield
With methoxybenzene
at 132℃;
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

74-87-3

methylene chloride

60-80-0

antipyrine

Conditions
ConditionsYield
With methylpyridine at 135℃;
With antipyrine at 135℃;
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

80-48-8

methyl p-toluene sulfonate

60-80-0

antipyrine

Conditions
ConditionsYield
at 150 - 160℃;
19735-89-8

3-methyl-1-phenylpyrazolin-5(4H)-one

77-78-1

dimethyl sulfate

60-80-0

antipyrine

Conditions
ConditionsYield
With xylene at 150℃;
With calcium oxide In methanol

Antipyrine Consensus Reports

ANTIPYRINE is reported in EPA TSCA Inventory.

Antipyrine Specification

The Antipyrine is an organic compound with the formula C11H12N2O. The IUPAC name of this chemical is 1,5-dimethyl-2-phenylpyrazol-3-one. With the CAS registry number 60-80-0, it is also named as 3H-pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals; Lipid signaling. Besides, it is a white powder, which should be stored in a closed dark and dry place. It is an analgesic and antipyretic.

Physical properties about Antipyrine are: (1)ACD/LogP: 0.27; (2)ACD/LogD (pH 5.5): 0.27; (3)ACD/LogD (pH 7.4): 0.27; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 33.34; (7)ACD/KOC (pH 7.4): 33.34; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 23.55 Å2; (11)Index of Refraction: 1.585; (12)Molar Refractivity: 54.55 cm3; (13)Molar Volume: 162.7 cm3; (14)Polarizability: 21.62×10-24cm3; (15)Surface Tension: 42.7 dyne/cm; (16)Density: 1.156 g/cm3; (17)Flash Point: 114.8 °C; (18)Enthalpy of Vaporization: 56.05 kJ/mol; (19)Boiling Point: 319 °C at 760 mmHg; (20)Vapour Pressure: 0.000348 mmHg at 25°C.

Preparation: this chemical is formed by reducing diortho- dinitrodiphenyl with sodium amalgam and methyl alcohol, or by heating diphenylene-ortho-dihydrazine with hydrochloric acid to 150 °C. It crystallizes in needles which melt at 156 °C. Potassium permanganate oxidizes it to pyridazine tetracarboxylic acid.

Uses of Antipyrine: it can be used to produce N-methyl-N'-phenyl-hydrazine at temperature of 130 °C. It will need reagent alcoholic KOH-solution.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2\C=C(/N(N2c1ccccc1)C)C
(2)InChI: InChI=1/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
(3)InChIKey: VEQOALNAAJBPNY-UHFFFAOYAS
(4)Std. InChI: InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
(5)Std. InChIKey: VEQOALNAAJBPNY-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 525mg/kg (525mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 39, Pg. 177, 1930.
cat LDLo oral 1250mg/kg (1250mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 39, Pg. 177, 1930.
cat LDLo rectal 800mg/kg (800mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 33, Pg. 10, 1944.
cat LDLo subcutaneous 700mg/kg (700mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
dog LDLo oral 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
frog LDLo subcutaneous 2gm/kg (2000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
guinea pig LDLo oral 1400mg/kg (1400mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 14, 1959.
guinea pig LDLo subcutaneous 1600mg/kg (1600mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

CARDIAC: PULSE RATE
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 186, Pg. 195, 1937.
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 LD50 intraperitoneal 750mg/kg (750mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 686, 1960.
mouse LD50 oral 1310mg/kg (1310mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 45, Pg. 137, 1956.
mouse LD50 subcutaneous 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 214, 1967.
rabbit LDLo intravenous 600mg/kg (600mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 14, 1959.
rabbit LDLo subcutaneous 1gm/kg (1000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1304, 1935.
rat LD50 oral 1705mg/kg (1705mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 401, 1959.
rat LDLo subcutaneous 1570mg/kg (1570mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 186, Pg. 195, 1937.

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