Tiaprofenic acid supplier | CasNO.33005-95-7

Name
Tiaprofenic acid
EINECS 251-329-3
CAS No. 33005-95-7
Article Data10
CAS DataBase
Density 1.29 g/cm³
Solubility
Melting Point 96° (isopropyl ether)
Formula C₁₄H₁₂O₃S
Boiling Point 450.251 °C at 760 mmHg
Molecular Weight 260.313
Flash Point 226.104 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (RS)-Tiaprofenicacid;FC 3001;RU15060;Suralgan;Surgam;Tiaprofen;a-(5-Benzoyl-2-thienyl)propionicacid;
PSA 82.61000
LogP 3.16720

Synthetic route

: 54955-39-4
2-thiophen-2-yl-propionic acid

: 98-88-4
benzoyl chloride

: 33005-95-7
tiaprofenic acid

Conditions

Conditions	Yield
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%

: 67355-14-0
methyl α-methylthio-α-(5-benzoyl-thien-2-yl)-propionate

: 5188-07-8
sodium thiomethoxide

: 33005-95-7
tiaprofenic acid

Conditions

Conditions	Yield
In methanol; dichloromethane; water	68%

: 88-15-3
2-Acetylthiophene

: 33005-95-7
tiaprofenic acid

Conditions

Conditions	Yield
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

: 28612-98-8
2-chloro-2-(2-thienyl)ethane

: 33005-95-7
tiaprofenic acid

Conditions

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

: 115510-91-3
1-(thien-2-yl)ethanol

: 33005-95-7
tiaprofenic acid

Conditions

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

: 88701-59-1
rac-2-(thiophen-2-yl)propanenitrile

: 33005-95-7
tiaprofenic acid

Conditions

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

: 554-14-3
2-Methylthiophene

: 33005-95-7
tiaprofenic acid

Conditions

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

: 45438-73-1
2-thenyl bromide

: 33005-95-7
tiaprofenic acid

Conditions

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

: 20893-30-5
2-cyanomethylthiophene

: 33005-95-7
tiaprofenic acid

Conditions

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

: 765-50-4
2-Chloromethylthiophene

: 33005-95-7
tiaprofenic acid

Conditions

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

: 98-03-3
thiophene-2-carbaldehyde

: 33005-95-7
tiaprofenic acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrahydrofuran / 5.5 h / 50 °C 2: thionyl chloride / 3 h / 70 °C 3: potassium carbonate / acetonitrile / 10 h / 70 °C / Inert atmosphere 4: acetic acid; sulfuric acid / 6 h / 125 °C 5: aluminum (III) chloride / ethyl acetate / 5 h / 20 °C / Cooling with ice View Scheme

: 33005-95-7
tiaprofenic acid

: 6933-26-2
(5-ethyl-2-thienyl)phenylmethanone

Conditions

Conditions	Yield
In methanol at 20℃; for 24h; Irradiation;	96%
With β‐cyclodextrin In phosphate buffer pH=7.2; Quantum yield; UV-irradiation;
In aq. phosphate buffer pH=7.4; Mechanism; UV-irradiation;

: 67-56-1
methanol

: 33005-95-7
tiaprofenic acid

A: 6933-26-2
(5-ethyl-2-thienyl)phenylmethanone

B: 5912-44-7
2-benzoyl-5-acetylthiophene

C: 143379-91-3
2-Benzoyl-5-(1-hydroxyethyl)thiophene

D: 143381-62-8
[5-(1-Methoxy-ethyl)-thiophen-2-yl]-phenyl-methanone

Conditions

Conditions	Yield
With oxygen at 20℃; for 24h; Product distribution; Mechanism; Irradiation; also in the presence of O2;	A n/a B 94% C n/a D n/a

...Expand

: 33005-95-7
tiaprofenic acid

A: 6933-26-2
(5-ethyl-2-thienyl)phenylmethanone

B: 5912-44-7
2-benzoyl-5-acetylthiophene

C: 143379-91-3
2-Benzoyl-5-(1-hydroxyethyl)thiophene

Conditions

Conditions	Yield
With oxygen In methanol at 20℃; for 24h; Irradiation;	A n/a B 94% C n/a
With sodium dodecyl-sulfate In water Product distribution; Further Variations:; Reagents; Irradiation;

...Expand

: 51-67-2
tyrosamine

: 33005-95-7
tiaprofenic acid

: N1-(4-hydroxyphenethyl)-2-(5-benzoyl-2-thienyl)propanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; pH=9.0 - 9.5;	86%

: 33005-95-7
tiaprofenic acid

: 263237-56-5
N-(pyren-1-ylmethyl)acetamide

: N1-(1-pyrenylmethyl)-2-(5-benzoyl-2-thienyl)propanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide pH=9.0 - 9.5;	85%

: 33005-95-7
tiaprofenic acid

: 18769-46-5
(α)-3-cholestanol

: C41H58O3S

Conditions

Conditions	Yield
Stage #1: tiaprofenic acid With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Stage #2: (α)-3-cholestanol With dmap In dichloromethane at 0℃; for 8h;	78%

: 215120-51-7
N-(1-hydroxybutan-2-yl)nicotinamide

: 33005-95-7
tiaprofenic acid

: 761416-02-8
2-(5-benzoyl-thiophen-2-yl)-propionic acid 2-[(pyridine-3-carbonyl)-amino]-butyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile	72%

: 33005-95-7
tiaprofenic acid

: 55-81-2
4-Methoxyphenethylamine

: N1-(4-methoxyphenethyl)-2-(5-benzoyl-2-thienyl)propanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; pH=9.0 - 9.5;	70%

: 6265-73-2
N-(2-hydroxyethyl)nicotinamide

: 33005-95-7
tiaprofenic acid

: 761415-94-5
2-(5-benzoyl-thiophen-2-yl)-propionic acid 2-[(pyridine-3-carbonyl)-amino]-ethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile	67%

: 33005-95-7
tiaprofenic acid

: 3144-09-0
methanesulfonamide

: N-[2-(5-benzoyl-thiophen-2-yl)-propionyl]-methanesulfonamide

Conditions

Conditions	Yield
Stage #1: tiaprofenic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 5℃; for 2h; Stage #2: methanesulfonamide With 1,2-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 4h;	65%

: 61-54-1
tryptamine

: 33005-95-7
tiaprofenic acid

: N1-[2-(1H-3-indolyl)ethyl]-2-(5-benzoyl-2-thienyl)propanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; pH=9.0 - 9.5;	60%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 33005-95-7
tiaprofenic acid

: Tiaprofensaeure-hydroxysuccinimidester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 1h;	51%

: 33005-95-7
tiaprofenic acid

: 122048-21-9
N-(2-hydroxypropyl)-3-pyridinecarboxamide

: 761415-98-9
2-(5-benzoyl-thiophen-2-yl)-propionic acid 1-methyl-2-[(pyridine-3-carbonyl)-amino]-ethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile	48%

: 33005-95-7
tiaprofenic acid

: 1080-06-4
L-Tyr-OMe

: methyl 2-(1-<5-benzoyl-2-thienyl>ethylcarboxamido)-3-(4-hydroxy-phenyl)propanoate

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide for 3h; Ambient temperature;	47%

: 33005-95-7
tiaprofenic acid

: 474-77-1
epicholesterol

A: 1019853-50-9
(S)-tiaprofenic acid-α-cholesterol

B: 1019853-49-6
(R)-tiaprofenic acid-α-cholesterol

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 8h;	A 37% B 41%

...Expand

: 33005-95-7
tiaprofenic acid

: 53676-54-3
N-(3-hydroxypropyl)nicotinamide

: 761416-06-2
2-(5-benzoyl-thiophen-2-yl)-propionic acid 3-[(pyridine-3-carbonyl)-amino]-propyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In acetonitrile	30%

: 33005-95-7
tiaprofenic acid

A: 103667-49-8
(R)-2-(5-benzoylthiophen-2-yl)propanoic acid

B: 103667-50-1
(S)-2-(5-benzoylthiophen-2-yl)propanoic acid

Conditions

Conditions	Yield
Product distribution; pharmacokinetic parameters in humans; concentration of (R)- and (S)-enantiomers in synovial fluid and plasma;
With trifluoroacetic acid In hexane; isopropyl alcohol Reagent/catalyst; Resolution of racemate;
With isopropylamine; trifluoroacetic acid In methanol; isopropyl alcohol at 35℃; under 103432 Torr; Reagent/catalyst; Resolution of racemate; Supercritical conditions;

: 33005-95-7
tiaprofenic acid

: 128-39-2
2,6-di-tert-butylphenol

: 4-<1-phenyl-1-(5-ethyl-2-thienyl)>methylidene-2,6-di-tert-butylcyclohexa-2,5-dien-1-one

Conditions

Conditions	Yield
In acetone for 0.5h; Irradiation;	31 % Chromat.

: 33005-95-7
tiaprofenic acid

: 1080-06-4
L-Tyr-OMe

A: methyl N-[(2R)-2-(5-benzoylthien-2-yl)propanoyl]-(S)-tyrosinate

B: methyl N-[(2S)-2-(5-benzoylthien-2-yl)propanoyl]-(S)-tyrosinate

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide Condensation;
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; pH=9.0 - 9.5;

...Expand

: 33005-95-7
tiaprofenic acid

: 4299-70-1
L-tryptophan methyl ester

A: methyl N-[(2S)-2-(5-benzoylthien-2-yl)propanoyl]-3-(1H-indol-3-yl)-(S)-alaninate

B: methyl N-[(2R)-2-(5-benzoylthien-2-yl)propanoyl]-3-(1H-indol-3-yl)-(S)-alaninate

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; pH=9.0 - 9.5;

...Expand

: 33005-95-7
tiaprofenic acid

bovine serum albumin: bovine serum albumin

: 6933-26-2
(5-ethyl-2-thienyl)phenylmethanone

Conditions

Conditions	Yield
With saline phosphate buffer for 2h; pH=7.2; Irradiation;

: 33005-95-7
tiaprofenic acid

bovine serum albumin: bovine serum albumin

(tiaprofenic acid)-bovine serum albumin adduct: (tiaprofenic acid)-bovine serum albumin adduct

Conditions

Conditions	Yield
With saline phosphate buffer; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide at 20℃; for 4h; pH=8;
With saline phosphate buffer for 2h; pH=7.2; Irradiation;

: 33005-95-7
tiaprofenic acid

rabbit serum albumin: rabbit serum albumin

(tiaprofenic acid)-rabbit serum albumin adduct: (tiaprofenic acid)-rabbit serum albumin adduct

Conditions

Conditions	Yield
With saline phosphate buffer; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide at 20℃; for 4h; pH=8;

: 33005-95-7
tiaprofenic acid

: 2-(5-benzoyl-thiophen-2-yl)-propionic acid 2-[(1-methyl-1,4-dihydro-pyridine-3-carbonyl)-amino]-ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 67 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / acetonitrile 2: 55 percent / CH2Cl2; acetonitrile / 24 h / 20 °C 3: 52 percent / NaHCO3; Na2S2O4 / H2O; ethyl acetate / 0.25 h / 0 °C / pH 7 View Scheme

: 33005-95-7
tiaprofenic acid

: 3-{2-[2-(5-benzoyl-thiophen-2-yl)-propionyloxy]-ethylcarbamoyl}-1-methyl-pyridinium; iodide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / acetonitrile 2: 55 percent / CH2Cl2; acetonitrile / 24 h / 20 °C View Scheme

: 33005-95-7
tiaprofenic acid

: C22H21NO3S

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / EDC; HOBt; Et3N / dimethylformamide / 20 °C / pH 9.0 - 9.5 2: methanol / 25 °C / Flash photolysis View Scheme

: 33005-95-7
tiaprofenic acid

: C24H22N2O2S

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / EDC; HOBt; Et3N / dimethylformamide / 20 °C / pH 9.0 - 9.5 2: methanol / 25 °C / Flash photolysis View Scheme

Tiaprofenic acid Chemical Properties

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

Tiaprofenic acid Uses

Surgam (33005-95-7) is used for rheumatic diseases and pain, such as ankylosing spondylitis, osteoarthritis and rheumatoid arthritis.

Tiaprofenic acid Toxicity Data With Reference

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.

Tiaprofenic acid Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SO_x.

Tiaprofenic acid Specification

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.

Product Name

Tiaprofenic acid

Synthetic route

Tiaprofenic acid Chemical Properties

Tiaprofenic acid Uses

Tiaprofenic acid Toxicity Data With Reference

Tiaprofenic acid Safety Profile

Tiaprofenic acid Specification

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