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139755-83-2

139755-83-2

Identification

  • Product Name:Sildenafil

  • CAS Number: 139755-83-2

  • EINECS:200-659-6

  • Molecular Weight:474.584

  • Molecular Formula: C22H30N6O4S

  • HS Code:38220090

  • Mol File:139755-83-2.mol

Synonyms:4-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,8,9-tetrazabicyclo[4.3.0]nona-3,7,10-trien-2-one;Piperazine,1-[[3-(4,7-dihydro-1-methyl-7- oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin- 5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-;Serum Albumin Iodine;Sildenafil Mesylate;Hongdenafil (Acetildenafil);

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Safety information and MSDS view more

  • Pictogram(s):Xi,T,F

  • Hazard Codes:Xi,T,F

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Sildenafil
  • Packaging:5mg
  • Price:$ 355
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  • Manufacture/Brand:TRC
  • Product Description:Sildenafil
  • Packaging:2.5mg
  • Price:$ 55
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  • Manufacture/Brand:TRC
  • Product Description:Sildenafil
  • Packaging:10mg
  • Price:$ 70
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Sildenafil solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
  • Packaging:1 mL
  • Price:$ 86.6
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Sildenafil solution 1.0mg/mL in methanol, ampule of 1mL, certified reference material
  • Packaging:010-1ml
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Sildenafil >98%
  • Packaging:1 g
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  • Manufacture/Brand:DC Chemicals
  • Product Description:Sildenafil >98%
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  • Manufacture/Brand:Crysdot
  • Product Description:Sildenafil 97%
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  • Manufacture/Brand:Crysdot
  • Product Description:Sildenafil 97%
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  • Manufacture/Brand:Chemtos
  • Product Description:SildenafilLabeledd8Dihydrochloride
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Relevant articles and documentsAll total 43 Articles be found

Polymer-supported reagents for multi-step organic synthesis: Application to the synthesis of sildenafil

Baxendale, Ian R.,Ley, Steven V.

, p. 1983 - 1986 (2000)

Sildenafil 1 (Viagra(TM)), a well known and commercially important pharmaceutical drug, has been prepared using polymer-supported reagents in a multi-step, convergent process resulting in a clean and efficient preparation without the need for conventional purification methods. (C) 2000 Elsevier Science Ltd.

Molecular and crystal structure of sildenafil base

Stepanovs, Dmitrijs,Mishnev, Anatoly

, p. 491 - 494 (2012)

Sildenafil citrate monohydrate, well known as Viagra , is a drug for the treatment of erectile dysfunction. Here we present the X-ray crystal structure of the sildenafil base, C22H30N 6O4S. The compound crystallizes in the monoclinic system, space group P21/c with the unit cell parameters a = 17:273(1), b=17:0710(8), c=8:3171(4) A° , β =99:326(2), Z = 4, V = 2420:0(3) A°3. A comparison with the known crystal structures of sildenafil citrate monohydrate and sildenafil saccharinate is also presented.

Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation

Laha, Joydev K.,Gulati, Upma,Saima,Gupta, Anjali,Indurthi, Harish Kumar

supporting information, p. 2643 - 2648 (2021/02/16)

An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan

, p. 14866 - 14882 (2021/10/25)

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

Improved synthesis process of sildenafil

-

Paragraph 0039-0042; 0050-0052, (2021/06/21)

The invention discloses an improved synthesis process of sildenafil, belonging to the technical field of preparation of drug intermediates. In the process, high-concentration chlorosulfonic acid is prevented from being used as a reaction solvent and reagent, and 3-5 equivalent chlorosulfonic acid is used as a reaction reagent. Compared with the prior art, the process has the characteristics of economical performance, environmental protection, safety and the like, for example, equipment cannot be corroded, the post-treatment of reaction becomes simpler, the solvent is single and can be reused, product purity is high, and the like.

Preparation method of sildenafil citrate

-

, (2021/04/07)

The invention discloses a preparation method of sildenafil. The method comprises the following steps: activating an intermediate compound B in an aprotic solvent by using thionyl chloride, reducing with 1-methyl-4-nitro-3-propyl-1H-pyrazole-5-formamide in a zinc powder-ammonium chloride system in the presence of an acid-binding agent to obtain an intermediate compound E, and condensing to obtain an intermediate compound C; and cyclizing the intermediate compound C in an alcohol solvent under an alkaline condition to prepare sildenafil. The preparation method disclosed by the invention is short in reaction time, greatly shortens the production period so as to reduce the production cost, and is simple in operation and suitable for large-scale production.

Sulphonated graphene oxide catalyzed continuous flow synthesis of pyrazolo pyrimidinones, sildenafil and other PDE-5 inhibitors

Karra, Purushotham Reddy,Mahajan, Bhushan,Pabbaraja, Srihari,Singh, Ajay K.,Sthalam, Vinay Kumar

, p. 326 - 330 (2022/01/19)

Sulphonated graphene oxide was used for cascade condensation and cyclization reactions towards accessing substituted pyrazolo pyrimidinones. Further, sulphonation and amination reactions were integrated through continuous flow chemistry to access PDE-5 inhibitors. Herein, we report a simple continuous synthetic platform that reduce tedious manual operations and accelerate the synthesis of several potent inhibitors of phosphodiesterase type-5. The developed platform enabled us to perform one-flow multi-step, multi-operational process to synthesize the PDE-5 inhibitors such as sildenafil and its analogues in 32.3 min of the reaction time, with minimal human intervention and single solvent.

Process route upstream and downstream products

Process route

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-methylpiperazine hydrochloride
34352-59-5,50398-09-9,51545-09-6

1-methylpiperazine hydrochloride

viagra
139755-83-2

viagra

Conditions
Conditions Yield
With triethylamine; N-ethyl-N,N-diisopropylamine; In water; at 60 ℃; for 1.2h;
91.8%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

viagra
139755-83-2

viagra

Conditions
Conditions Yield
With pyridine; In water; at 50 ℃; Reagent/catalyst; Temperature;
93.9%
With triethylamine; In methanol; at 20 ℃; for 0.75h; Product distribution / selectivity;
91%
In acetone; at 20 ℃; for 3h; Sealed tube;
90%
In tetrahydrofuran; at 20 ℃; for 3h; Sealed tube;
89%
In tetrahydrofuran; at 20 ℃; for 3h;
89%
With triethylamine; In isopropyl alcohol; at 20 ℃; for 0.75h; Product distribution / selectivity;
86.1%
With sodium hydroxide; In water; ethyl acetate; at 20 ℃; for 0.75h; Product distribution / selectivity;
76.5%
With sodium hydroxide; In water; toluene; at 20 ℃; for 0.75h; Product distribution / selectivity;
75.7%
With triethylamine; In acetonitrile; at 20 ℃; for 0.75h; Product distribution / selectivity;
73%
With triethylamine; In butanone; at 20 ℃; for 0.75h; Product distribution / selectivity;
72%
With sodium hydroxide; In methanol; water; at 20 ℃; for 0.75h; Product distribution / selectivity;
70%
With triethylamine; In ethanol; at 20 ℃; for 0.75h; Product distribution / selectivity;
67.1%
With triethylamine; In acetone; at 20 ℃; for 0.75h; Product distribution / selectivity;
62.3%
With sodium hydroxide; In water; acetone; at 20 - 22 ℃; for 0.75 - 1h; Product distribution / selectivity;
57.5%
In dichloromethane; at 20 - 30 ℃; Temperature; Solvent; Concentration;
58.8 g
7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-39-0

7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
Conditions Yield
7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine; With water; sodium hydrogencarbonate; In tert-butyl alcohol; at 90 ℃; for 1.5 - 2h; Heating / reflux;
With hydrogenchloride; In water; at 0 ℃; pH=8.5 - 9.5; Product distribution / selectivity;
90%
7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine; With water; sodium hydrogencarbonate; In tert-butyl alcohol; for 2h; Reflux;
With hydrogenchloride; In water; pH=8.5 - 9.5; Product distribution / selectivity;
90%
With water; for 4h; Product distribution / selectivity; Heating / reflux;
83%
7-chloro-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine; With hydrogenchloride; water; at 60 ℃; for 2h;
With sodium hydrogencarbonate; In water; at 0 ℃; pH=8.5 - 9.5; Product distribution / selectivity;
79%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide
226956-42-9

4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
Conditions Yield
1-methyl-piperazine; 4-(5-chlorosulfonyl-2-ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide; In dichloromethane; for 2h;
With potassium carbonate; In isopropyl alcohol; for 4h; Reagent/catalyst; Reflux;
71.7%
4-[2-ethoxy-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
200575-15-1

4-[2-ethoxy-5-(4-methyl-1-piperazinylsulphonyl)benzamido]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

viagra
139755-83-2

viagra

Conditions
Conditions Yield
With sodium ethanolate; In ethanol; at 120 ℃; for 0.166667h; microwave irradiation;
100%
With potassium tert-butylate; In tert-butyl alcohol; for 8h; Reflux;
44%
With sodium hydroxide; In water; for 8h; Reflux;
280 mg
5-[2-ethoxycarbonyloxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
960009-37-4

5-[2-ethoxycarbonyloxy-5-(4-methyl-piperazine-1-sulfonyl)-phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

ethanol
64-17-5

ethanol

viagra
139755-83-2

viagra

Conditions
Conditions Yield
With dicyclohexyl-carbodiimide; at 110 ℃; for 6h; under 1324.03 - 2942.29 Torr;
With dicyclohexyl-carbodiimide; at 105 - 110 ℃; under 1324.03 - 2942.29 Torr;
5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine
1093065-15-6

5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
Conditions Yield
5-[2-ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1-hydro-7-ethoxypyrazolo[4,3-d]pyrimidine; With hydrogenchloride; water; In methanol; at 75 ℃; for 4.5h;
With sodium hydroxide; In methanol; water; pH=14;
5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine
864164-45-4

5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
Conditions Yield
5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-7-methoxy-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine; With hydrogenchloride; water; In methanol; at 75 ℃; for 4h;
With sodium hydroxide; In methanol; water; pH=14;
7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-54-9

7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine

viagra
139755-83-2

viagra

Conditions
Conditions Yield
7-bromo-1-methyl-5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)-phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine; With water; sodium hydrogencarbonate; In tert-butyl alcohol; for 2h; Heating / reflux;
With hydrogenchloride; In water; at 0 ℃; pH=8.5 - 9.5; Product distribution / selectivity;
75%
5-chloro-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one
1033443-96-7

5-chloro-1-methyl-3-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one

[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenylboronic acid
1093065-12-3

[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)]phenylboronic acid

viagra
139755-83-2

viagra

Conditions
Conditions Yield
With sodium carbonate; palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; water; Inert atmosphere; Reflux;

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