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CAS No.: | 33005-95-7 |
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Name: | Tiaprofenic acid |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C14H12O3S |
Molecular Weight: | 260.313 |
Synonyms: | (RS)-Tiaprofenicacid;FC 3001;RU15060;Suralgan;Surgam;Tiaprofen;a-(5-Benzoyl-2-thienyl)propionicacid; |
EINECS: | 251-329-3 |
Density: | 1.29 g/cm3 |
Melting Point: | 96° (isopropyl ether) |
Boiling Point: | 450.251 °C at 760 mmHg |
Flash Point: | 226.104 °C |
PSA: | 82.61000 |
LogP: | 3.16720 |
Conditions | Yield |
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With aluminum (III) chloride In ethyl acetate at 20℃; for 5h; Cooling with ice; | 94% |
With aluminum (III) chloride In ethyl acetate at 20℃; for 5.5h; Friedel-Crafts Acylation; Cooling with ice; | 94% |
With aluminum (III) chloride In ethyl acetate at 20℃; for 5h; Cooling with ice; | 94% |
With zinc(II) oxide In neat (no solvent) at 20℃; Friedel-Crafts Acylation; | 93.5% |
With zinc diacetate at 20 - 40℃; for 0.833333h; | 92% |
methyl α-methylthio-α-(5-benzoyl-thien-2-yl)-propionate
sodium thiomethoxide
tiaprofenic acid
Conditions | Yield |
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In methanol; dichloromethane; water | 68% |
2-Acetylthiophene
tiaprofenic acid
Conditions | Yield |
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Multi-step reaction with 5 steps 1: sodium tetrahydroborate; ethanol / 6 h / 20 °C 2: thionyl chloride / 3 h / 70 °C 3: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere 4: sulfuric acid; acetic acid / 6 h / 125 °C 5: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme |
2-chloro-2-(2-thienyl)ethane
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere 2: sulfuric acid; acetic acid / 6 h / 125 °C 3: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere 2: acetic acid; sulfuric acid / 6 h / 125 °C 3: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme |
1-(thien-2-yl)ethanol
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 3 h / 70 °C 2: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere 3: sulfuric acid; acetic acid / 6 h / 125 °C 4: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 4 steps 1: thionyl chloride / 3 h / 70 °C 2: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere 3: acetic acid; sulfuric acid / 6 h / 125 °C 4: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme |
rac-2-(thiophen-2-yl)propanenitrile
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid; acetic acid / 6 h / 125 °C 2: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme |
2-Methylthiophene
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: dibenzoyl peroxide; N-Bromosuccinimide / chloroform / 20 - 70 °C 2: potassium carbonate / acetonitrile / 6 h / 70 °C 3: potassium carbonate; tetrabutylammomium bromide / 7 h / 130 °C 4: acetic acid; sulfuric acid / 6 h / 125 °C 5: aluminum (III) chloride / ethyl acetate / 5.5 h / 20 °C / Cooling with ice View Scheme |
2-thenyl bromide
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 6 h / 70 °C 2: potassium carbonate; tetrabutylammomium bromide / 7 h / 130 °C 3: acetic acid; sulfuric acid / 6 h / 125 °C 4: aluminum (III) chloride / ethyl acetate / 5.5 h / 20 °C / Cooling with ice View Scheme |
2-cyanomethylthiophene
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; tetrabutylammomium bromide / 7 h / 130 °C 2: acetic acid; sulfuric acid / 6 h / 125 °C 3: aluminum (III) chloride / ethyl acetate / 5.5 h / 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate; tetrabutylammomium bromide / 7 h / 130 °C 2: sulfuric acid; acetic acid / 6 h / 125 °C 3: zinc diacetate / 0.83 h / 20 - 40 °C View Scheme |
2-Chloromethylthiophene
tiaprofenic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 10 h / 70 °C 2: potassium carbonate; tetrabutylammomium bromide / 7 h / 130 °C 3: sulfuric acid; acetic acid / 6 h / 125 °C 4: zinc diacetate / 0.83 h / 20 - 40 °C View Scheme |
IUPAC Name:2-(5-benzoylthiophen-2-yl)Propanoic acid
Synonyms : 2-[5-(Phenylcarbonyl)-2-thienyl]Propanoic acid
Molecular Structure :
Molecular Formula: C14H12O3S
Molecular Weight : 260.31
CAS Registry Number: 33005-95-7
EINECS : 251-329-3
Index of Refraction: 1.612
Surface Tension: 54 dyne/cm
Density: 1.29 g/cm3
Flash Point: 226.1 °C
Enthalpy of Vaporization: 74.72 kJ/mol
Boiling Point: 450.3 °C at 760 mmHg
Vapour Pressure: 6.8E-09 mmHg at 25°C
Surgam (33005-95-7) is used for rheumatic diseases and pain, such as ankylosing spondylitis, osteoarthritis and rheumatoid arthritis.
1. | orl-wmn TDLo:672 mg/kg/7W-I | LANCAO Lancet. 1 (1986),803. | ||
2. | orl-wmn TDLo:16 mg/kg/2D-I | CMAJAX Canadian Medical Association Journal. 137 (1987),1022. | ||
3. | orl-rat LD50:181 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 9 (1975),715. | ||
4. | ipr-rat LD50:225 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 9 (1975),715. | ||
5. | scu-rat LD50:215 mg/kg | IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. 15 (1984),688. | ||
6. | orl-mus LD50:690 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 9 (1975),715. | ||
7. | ipr-mus LD50:430 mg/kg | OYYAA2 Oyo Yakuri. Pharmacometrics. 9 (1975),715. | ||
8. | scu-mus LD50:675 mg/kg | IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. 15 (1984),688. |
Poison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx.
Usage and dosage: intramuscular injection: 0.2 ~ 0.4g / d, according to the disease, up to 0.6 / d. Oral: 0.6g / d, min 2 to 3 doses. Patients with renal insufficiency, where appropriate dose was reduced to 0.2g / times, 2 times / d.
Pharmacological effects: Surgam (33005-95-7) has effects of antipyretic, analgesic and anti-inflammatory , can reduce swelling, relieve joint stiffness. Relieve pain, improve joint movement.
Mechanism :Surgam (33005-95-7) is the inhibition of prostaglandin synthesis,play a role on blocking inflammatory mediators.
Adverse reactions: rare adverse reactions, manifested as nausea, vomiting, stomach pain, diarrhea, constipation. Also appear sleepiness, fatigue, headache and skin reactions such as rash, itching, dry skin breakdowns.