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15307-79-6

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15307-79-6 Usage

Chemical Description

Diclofenac sodium is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammation.

description

Diclofenac Sodium is the sodium salt form of diclofenac, a benzene acetic acid derivate and nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic and anti-inflammatory activity. Diclofenac sodium is a non-selective reversible and competitive inhibitor of cyclooxygenase (COX), subsequently blocking the conversion of arachidonic acid into prostaglandin precursors. This leads to an inhibition of the formation of prostaglandins that are involved in pain, inflammation and fever.

Uses

Different sources of media describe the Uses of 15307-79-6 differently. You can refer to the following data:
1. Diclofenac is a phenylacetic acid derivative belonging to the class of the non-selective non-steroidal anti-inflammatory drugs (NSAIDs). It exhibits analgesic, antipyretic and anti-inflammatory activity. Due to its poor solubility, the parenteral formulation of diclofenac sodium (Voltarol ampoules) currently available in Europe contains the solvents propylene glycol and benzyl alcohol that allows intramuscular and intravenous administration. Diclofenac sodium has long been used to treat acute pain and inflammation, and is effective in various acute forms of pain.
2. Diclofenac sodium is a nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor. Oxidation of diclofenac sodium produces the metabolite 4'-hydroxy diclofenac) which demonstrates specific inhibition of Cox-2. Inhibition of Cox by diclofenac and 4'-hydroxy diclofenac suppresses prostaglandin E2 synthesis, producing anti-inflammatory and analgesic effects. Diclofenac is also shown to stabilize the native tetrameric conformation of transthyretin (TTR) fibrils, preventing the formation of insoluble amyloidogenic TTR deposits. Diclofenac Sodium is a substrate of CYP2C9. It is also used as an inhibitor of Cox-1 and Cox-2.

Mechanisms of action

Putative mechanisms of action of diclofenac may include inhibition of leukotriene synthesis, inhibition of phospholipase A2, modulation of free arachidonic acid levels, stimulation of adenosine triphosphate-sensitive potassium channels via the L-arginine-nitric oxide-cyclic guanosine monophosphate pathway and centrally mediated and neuropathic mechanisms. Other emerging mechanisms of action may include inhibition of peroxisome proliferator activated receptor-c, reduction in plasma and synovial substance P and interleukin-6 levels, inhibition of the thromboxane-prostanoid receptor and inhibition of acid-sensing ion channels.

Clinical Application

Clinical trials have demonstrated the analgesic efficacy of diclofenac sodium in terms of relieving moderate to severe postoperative pain in patients undergoing dental surgery or minor orthopaedic surgery. Subcutaneous diclofenac sodium also effectively relieved moderate to severe neuropathic pain, related to cancer or not. Diclofenac sodium was generally well tolerated in clinical trials, with injection-site reactions among the most commonly reported adverse events.

Description

Diclofenac is a non-steroidal anti-inflammatory drug (NSAID) and COX inhibitor (IC50s = 0.9-2.7 and 1.5-20 μM, for human COX-1 and COX-2, respectively). It is also an active metabolite of diclofenac methyl ester and diclofenac amide . Diclofenac inhibits release of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) induced by A23187 in isolated rat peritoneal neutrophils and macrophages (IC50s = 60 and 10 μM, respectively). Transdermal administration of diclofenac inhibits carrageenan-induced paw edema in rats. Formulations containing diclofenac have been used in the treatment of pain associated with osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis.

Chemical Properties

Off-White Crystalline Solid

Originator

Voltaren,Fujisawa,Japan,1974

Definition

ChEBI: Diclofenac sodium is the sodium salt of diclofenac. It contains a diclofenac(1-).

Manufacturing Process

Four grams of N-chloroacetyl-N-phenyl-2,6-dichloroaniline and 4 grams of aluminum chloride are well mixed together and heated for 2 hours at 160°C. The melt is cooled and poured onto about 50 grams of ice while it is still warm. The oil which separates is dissolved in 50 ml of chloroform, the chloroform solution is washed with 10 ml of water, dried over sodium sulfate and concentrated under 11 torr. The residue is distilled. The 1-(2,6- dichlorophenyl)-2-indolinone melts at 126°-127°C.A solution of 186 grams of 1-(2,6-dichlorophenyl)-2-indolinone in 660 ml of ethanol and 660 ml of 2 N sodium hydroxide solution is refluxed for 4 hours. The solution is then cooled and left to stand for 4 hours at 0°-5°C. The crystals which form are filtered off and recrystallized from water. The sodium salt of 2-(2,6-dichloroanilino)-phenylacetic acid melts at 283°-285°C. The yield is 97% of theoretical, according to US Patent 3,558,690.

Brand name

Solaraze (Bioglan); Voltaren (Novartis);Aflamin;Alfamin;Allvoran;Artren;Blesin;B-voltaren;Cgp 9194;Chlorgyl;Ct-diclo;Dichloronic;Diclo attritin;Diclo spondril;Diclo-attritin;Diclo-burg;Diclo-phlohont;Diclo-puren;Diclo-recip;Dicloreum;Diclo-spondyril;Diclo-wolf;Dolobasan;Dolotrem;Doragon;Duravolten;Duvavotten;Feloran;Fenoflam;Flogofenac;Flogogenac;Forgenac;Inflamac;Klast;Monoflam;Myogit;Neuro-effekton;Neurofenac;Neuro-voltaren;Neviodin;Olfen;Panamor;Rewodina;Rheumalgen;Rheumavincin-n;Seecoren;Shignol;Silino;Sofarin;Thicataren;Toryxil;Tsudomin;Voltarene.

Therapeutic Function

Antiinflammatory

World Health Organization (WHO)

The World Health Organization currently has no information to suggest that diclofenac is less safe than other widely available non-steroidal antiinflammatory substances of this type, or that children are particularly liable to react adversely. It is registered in many countries in several dosage forms, including a 12.5 mg suppository indicated for juvenile arthritis.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.Diclofenac is a derivative of benzeneacetic acid. It is categorized under the class of non-steroidal anti-inflammatory drugs (NSAIDs). It shows inflammatory, analgesic and antipyretic activities.

Biochem/physiol Actions

Standard NSAID and cyclooxygenase (COX) inhibitor. Major metabolites are 4′-hydroxydiclofenac and 5′-hydroxydiclofenac. Has been used as substrate selective for CYP2C9.

Clinical Use

Diclofenac sodium is indicated for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis.

Veterinary Drugs and Treatments

The equine topical cream (Surpass?) is labeled for the control of pain and inflammation associated with osteoarthritis in tarsal, carpal, metacarpophalangeal, metarsophalangeal, and proximal interphalangeal (hock, knee, fetlock, pastern) joints for use up to 10 days duration. While, theoretically, diclofenac could be used systemically (orally) in other veterinary species, there are approved and safer alternatives.

Drug interactions

Potentially hazardous interactions with other drugs antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia.Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage).Antibacterials: possibly increased risk of convulsions with quinolones; concentration reduced by rifampicin.Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban; increased risk of haemorrhage with IV diclofenac - avoid.Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine.Antidiabetic agents: effects of sulphonylureas enhanced.Antiepileptics: possibly increased phenytoin concentration.Ciclosporin: may potentiate nephrotoxicity; concentration increased by ciclosporin.Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib.

Metabolism

Diclofenac undergoes first-pass metabolism and is It is then excreted in the form of glucuronide and sulfate conjugates, mainly in the urine (about 60%) but also in the bile (about 35%). then extensively metabolised to 4′-hydroxydiclofenac, 5-hydroxydiclofenac, 3′-hydroxydiclofenac, and 4′,5-dihydroxydiclofenac by glucuronidation of the intact molecule or more commonly by single and multiple hydroxylation followed by glucuronidation.

Check Digit Verification of cas no

The CAS Registry Mumber 15307-79-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,3,0 and 7 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 15307-79:
(7*1)+(6*5)+(5*3)+(4*0)+(3*7)+(2*7)+(1*9)=96
96 % 10 = 6
So 15307-79-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H9Cl2N.C2H4O2.Na/c13-10-7-4-8-11(14)12(10)15-9-5-2-1-3-6-9;1-2(3)4;/h1-8,15H;1H3,(H,3,4);/q;;+1/p-1

15307-79-6 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D2508)  Diclofenac Sodium Salt  >98.0%(HPLC)(N)

  • 15307-79-6

  • 25g

  • 655.00CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1144)  Diclofenac sodium salt  pharmaceutical secondary standard; traceable to USP, PhEur and BP

  • 15307-79-6

  • PHR1144-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001635)  Diclofenac for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 15307-79-6

  • Y0001635

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (S0765000)  Diclofenac sodium  European Pharmacopoeia (EP) Reference Standard

  • 15307-79-6

  • S0765000

  • 1,880.19CNY

  • Detail
  • USP

  • (1188800)  Diclofenac sodium  United States Pharmacopeia (USP) Reference Standard

  • 15307-79-6

  • 1188800-200MG

  • 4,662.45CNY

  • Detail
  • Sigma

  • (D6899)  Diclofenac sodium salt  

  • 15307-79-6

  • D6899-10G

  • 671.58CNY

  • Detail
  • Sigma

  • (D6899)  Diclofenac sodium salt  

  • 15307-79-6

  • D6899-25G

  • 1,456.65CNY

  • Detail
  • Sigma

  • (D6899)  Diclofenac sodium salt  

  • 15307-79-6

  • D6899-100G

  • 4,002.57CNY

  • Detail
  • Sigma-Aldrich

  • (93484)  Diclofenac sodium salt  analytical standard

  • 15307-79-6

  • 93484-100MG

  • 458.64CNY

  • Detail

15307-79-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name diclofenac sodium

1.2 Other means of identification

Product number -
Other names KROPLEX

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:15307-79-6 SDS

15307-79-6Synthetic route

2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester
15307-78-5

2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
With sodium hydroxide In water; N,N-dimethyl-formamide at 80℃; for 24h;96.1%
1-(2,6-dichlorophenyl)indolin-2-one
15362-40-0

1-(2,6-dichlorophenyl)indolin-2-one

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water for 4h; Heating;93%
With sodium dithionite; water; sodium hydroxide for 6h; Reflux;92.3%
With sodium hydroxide In ethanol for 3h; Heating;85%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In toluene for 10h; Reflux;83.6%
With sodium hydroxide for 2h; Temperature; Reflux;4.035 g
C22H17Cl2NO3

C22H17Cl2NO3

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
With water; sodium hydroxide In methanol for 6h; Solvent; Reflux;86%
potassium 2-iodophenylacetate
100754-92-5

potassium 2-iodophenylacetate

2,6-Dichloroaniline
608-31-1

2,6-Dichloroaniline

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; copper; potassium carbonate at 120℃; for 22h;56%
2'-chloro-benzeneacetic acid
2444-36-2

2'-chloro-benzeneacetic acid

2,6-Dichloroaniline
608-31-1

2,6-Dichloroaniline

butan-1-ol
71-36-3

butan-1-ol

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
With sodium hydroxide; potassium iodide; copper(I) iodide; potassium carbonate In N,N-dimethyl-formamide42.9%
2'-chloro-benzeneacetic acid
2444-36-2

2'-chloro-benzeneacetic acid

2,6-Dichloroaniline
608-31-1

2,6-Dichloroaniline

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Stage #1: 2'-chloro-benzeneacetic acid; 2,6-Dichloroaniline With copper(l) iodide; iodine; potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 12h; Inert atmosphere; Schlenk technique; Reflux;
Stage #2: With sodium hydroxide In water for 4h; Reflux;
31%
2-(2-((2,6-dichlorophenyl)amino)phenyl)-2-oxoacetic acid
66156-75-0

2-(2-((2,6-dichlorophenyl)amino)phenyl)-2-oxoacetic acid

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
With sodium methylate; hydrazine hydrate In 2-methoxy-ethanol 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h; Yield given;
N-phenyl-2,6-dichloroaniline
15307-93-4

N-phenyl-2,6-dichloroaniline

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: benzene / 6 h / Heating
2: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature
3: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating
4: 97 percent / Zn / acetic acid / 4 h / Heating
5: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
Multi-step reaction with 5 steps
1: benzene / 6 h / Heating
2: N-chlorosuccinimide / CCl4 / 1 h / Ambient temperature
3: SnCl4 / CCl4 / 0.83 h / Ambient temperature
4: 97 percent / Zn / acetic acid / 4 h / Heating
5: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: benzene / 2 h / Ambient temperature
2: AlCl3 / various solvent(s) / 20 h / Ambient temperature
3: 1 N NaOH / ethanol; H2O / 0.17 h / Heating
4: hydrazine hydrate, NaOCH3 / 2-methoxy-ethanol / 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h
View Scheme
Multi-step reaction with 3 steps
1: 66 percent / 16 h / Heating
2: 75.4 percent / AlCl3 / 2 h / 160 °C
3: 93 percent / 2 N NaOH / ethanol; H2O / 4 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: toluene / 3 h / 120 °C
2: triethylamine hydrochloride-aluminum trichloride / 4.5 h / 20 - 60 °C
3: sodium hydroxide / 2 h / Reflux
View Scheme
N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide
83281-93-0

N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature
2: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating
3: 97 percent / Zn / acetic acid / 4 h / Heating
4: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: N-chlorosuccinimide / CCl4 / 1 h / Ambient temperature
2: SnCl4 / CCl4 / 0.83 h / Ambient temperature
3: 97 percent / Zn / acetic acid / 4 h / Heating
4: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
1-(2,6-dichlorophenyl)-3-(methylthio)oxindole
83281-94-1

1-(2,6-dichlorophenyl)-3-(methylthio)oxindole

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / Zn / acetic acid / 4 h / Heating
2: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
N-(2,6-dichlorophenyl)-α-(methylsulfinyl)acetanilide
83281-96-3

N-(2,6-dichlorophenyl)-α-(methylsulfinyl)acetanilide

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating
2: 97 percent / Zn / acetic acid / 4 h / Heating
3: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
α-chloro-N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide

α-chloro-N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: SnCl4 / CCl4 / 0.83 h / Ambient temperature
2: 97 percent / Zn / acetic acid / 4 h / Heating
3: 85 percent / 20percent NaOH / ethanol / 3 h / Heating
View Scheme
1-(2,6-Dichlorphenyl)-2,3-indoldion
24542-74-3

1-(2,6-Dichlorphenyl)-2,3-indoldion

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1 N NaOH / ethanol; H2O / 0.17 h / Heating
2: hydrazine hydrate, NaOCH3 / 2-methoxy-ethanol / 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h
View Scheme
[(2,6-Dichloro-phenyl)-phenyl-amino]-oxo-acetyl chloride
24542-55-0

[(2,6-Dichloro-phenyl)-phenyl-amino]-oxo-acetyl chloride

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: AlCl3 / various solvent(s) / 20 h / Ambient temperature
2: 1 N NaOH / ethanol; H2O / 0.17 h / Heating
3: hydrazine hydrate, NaOCH3 / 2-methoxy-ethanol / 1.) from 60 deg C to 150 deg C, 2.) 150 deg C, 1 h
View Scheme
2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide
15308-01-7

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75.4 percent / AlCl3 / 2 h / 160 °C
2: 93 percent / 2 N NaOH / ethanol; H2O / 4 h / Heating
View Scheme
N-(2,6-dichlorophenyl)phenylacetamide

N-(2,6-dichlorophenyl)phenylacetamide

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tert-butylhypochlorite / dichloromethane / 10 h / 25 °C / Cooling with ice
2: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Cooling with ice
3: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / toluene / 10 h / Reflux
View Scheme
2,6-Dichloroaniline
608-31-1

2,6-Dichloroaniline

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: calcium chloride; pyridine / 4 h / Reflux; Cooling with ice
2: tert-butylhypochlorite / dichloromethane / 10 h / 25 °C / Cooling with ice
3: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Cooling with ice
4: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / toluene / 10 h / Reflux
View Scheme
phenylacetyl chloride
103-80-0

phenylacetyl chloride

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: calcium chloride; pyridine / 4 h / Reflux; Cooling with ice
2: tert-butylhypochlorite / dichloromethane / 10 h / 25 °C / Cooling with ice
3: aluminum (III) chloride / dichloromethane / 12 h / 20 °C / Cooling with ice
4: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / toluene / 10 h / Reflux
View Scheme
(2-benzoylamino-phenyl)-acetic acid methyl ester
3559-26-0

(2-benzoylamino-phenyl)-acetic acid methyl ester

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: thionyl chloride / 3 h / Reflux
1.2: 3 h / Cooling with ice; Reflux
2.1: diphenylether / 3 h / Reflux
3.1: sodium hydroxide; water / methanol / 6 h / Reflux
View Scheme
methyl (2-nitrophenyl)acetate
30095-98-8

methyl (2-nitrophenyl)acetate

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: palladium on activated charcoal; hydrogen / toluene / 5 °C / 760.05 Torr
2.1: triethylamine / toluene / 2 h / 0 °C
3.1: thionyl chloride / 3 h / Reflux
3.2: 3 h / Cooling with ice; Reflux
4.1: diphenylether / 3 h / Reflux
5.1: sodium hydroxide; water / methanol / 6 h / Reflux
View Scheme
benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: nitric acid / dichloromethane / 24 h / 0 - 20 °C
2.1: palladium on activated charcoal; hydrogen / toluene / 5 °C / 760.05 Torr
3.1: triethylamine / toluene / 2 h / 0 °C
4.1: thionyl chloride / 3 h / Reflux
4.2: 3 h / Cooling with ice; Reflux
5.1: diphenylether / 3 h / Reflux
6.1: sodium hydroxide; water / methanol / 6 h / Reflux
View Scheme
2-aminophenylacetic acid methyl ester
35613-44-6

2-aminophenylacetic acid methyl ester

diclofenac sodium
15307-79-6

diclofenac sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine / toluene / 2 h / 0 °C
2.1: thionyl chloride / 3 h / Reflux
2.2: 3 h / Cooling with ice; Reflux
3.1: diphenylether / 3 h / Reflux
4.1: sodium hydroxide; water / methanol / 6 h / Reflux
View Scheme
didecyldimethylammonium chloride
7173-51-5

didecyldimethylammonium chloride

diclofenac sodium
15307-79-6

diclofenac sodium

diclofenac didecyldimethylammonium salt
934544-42-0

diclofenac didecyldimethylammonium salt

Conditions
ConditionsYield
In water at 20℃; for 0.5h; Product distribution / selectivity;100%
diclofenac sodium
15307-79-6

diclofenac sodium

cadmium(II) chloride
10108-64-2

cadmium(II) chloride

{Cd(C6H3Cl2NHC6H4CH2COO)2(H2O)}
149753-43-5

{Cd(C6H3Cl2NHC6H4CH2COO)2(H2O)}

Conditions
ConditionsYield
With H2O; KOH In water byproducts: NaCl; mixing aq. soln. of the components, adjusting to pH 5.5-7.5 with KOH and stirring at room temp. for 4-6 h; filtn., washing with water, drying over silica gel (vac.) and over P4O10 at 90°C (vac.);100%
diclofenac sodium
15307-79-6

diclofenac sodium

zinc(II) chloride
7646-85-7

zinc(II) chloride

{Zn(C6H3Cl2NHC6H4CH2COO)2(H2O)}
149753-42-4

{Zn(C6H3Cl2NHC6H4CH2COO)2(H2O)}

Conditions
ConditionsYield
With H2O; KOH In water byproducts: NaCl; mixing aq. soln. of the components, adjusting to pH 5.5-7.5 with KOH and stirring at room temp. for 4-6 h; filtn., washing with water, drying over silica gel (vac.) and over P4O10 at 90°C (vac.);100%
diclofenac sodium
15307-79-6

diclofenac sodium

[2-(2,6-dichloroanilino)phenyl]acetic acid
15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20 - 45℃; for 3h; pH=1.4 - 1.6; Solvent;99%
With hydrogenchloride In water Cooling with ice;90%
With hydrogenchloride In water at 0 - 20℃;70%
diclofenac sodium
15307-79-6

diclofenac sodium

1-(2,6-dichlorophenyl)-1,3-dihydro-indol-2-one-[3,3,5,7-D4]
1401311-49-6

1-(2,6-dichlorophenyl)-1,3-dihydro-indol-2-one-[3,3,5,7-D4]

Conditions
ConditionsYield
With water-d2; hydrogen chloride at 160℃; for 0.333333h; Microwave irradiation;96%
choline chloride
67-48-1

choline chloride

diclofenac sodium
15307-79-6

diclofenac sodium

(2-hydroxyethyl)tri-methylammonium [o-(2,6-dichloroanilino)phenyl]acetate
148439-51-4

(2-hydroxyethyl)tri-methylammonium [o-(2,6-dichloroanilino)phenyl]acetate

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;96%
diclofenac sodium
15307-79-6

diclofenac sodium

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

1-O-<2-<(2,6-dichlorophenyl)amino>phenylacetyl>-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
87906-12-5

1-O-<2-<(2,6-dichlorophenyl)amino>phenylacetyl>-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions
ConditionsYield
citrimide In water; 1,2-dichloro-ethane Ambient temperature;95%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

diclofenac sodium
15307-79-6

diclofenac sodium

2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester
139272-68-7

2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium iodide In ethanol at 61 - 65℃; for 3h; Temperature; Large scale;94.45%
With potassium iodide In acetonitrile at 30℃; for 0.25h; Microwave irradiation;91.6%
With tetra(n-butyl)ammonium hydrogensulfate; potassium iodide In water; acetone at 60 - 65℃; for 2h;17.3 g
In N,N-dimethyl-formamide at 20 - 45℃;
diclofenac sodium
15307-79-6

diclofenac sodium

Reaxys ID: 15741354

Reaxys ID: 15741354

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃;94%
diclofenac sodium
15307-79-6

diclofenac sodium

C14H3(2)H6Cl2NO

C14H3(2)H6Cl2NO

Conditions
ConditionsYield
With trifluoroacetic acid-d1 at 110℃; for 16h; Sealed tube;94%
4,4'-bipyridine
553-26-4

4,4'-bipyridine

diclofenac sodium
15307-79-6

diclofenac sodium

silver nitrate

silver nitrate

Ag(2-(2,6-dicholoroanilino)phenylacetic acid)(4,4'-bipyridine)

Ag(2-(2,6-dicholoroanilino)phenylacetic acid)(4,4'-bipyridine)

Conditions
ConditionsYield
In water; acetonitrile at 50℃;94%
diclofenac sodium
15307-79-6

diclofenac sodium

3-(bromomethyl)-4-methyl-1,2,5-oxadiazole-2-oxide
169614-77-1

3-(bromomethyl)-4-methyl-1,2,5-oxadiazole-2-oxide

[2-(2,6-dichlorophenylamino)-phenyl]-acetic acid 4-methyl-2-oxy-furazan-3-ylmethyl ester

[2-(2,6-dichlorophenylamino)-phenyl]-acetic acid 4-methyl-2-oxy-furazan-3-ylmethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 25℃; for 2h;93%
2-(2-Hydroxyethyl)pyridine
103-74-2

2-(2-Hydroxyethyl)pyridine

diclofenac sodium
15307-79-6

diclofenac sodium

copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

C42H36Cl4Cu2N4O6

C42H36Cl4Cu2N4O6

Conditions
ConditionsYield
In methanol at 50℃;91%
diclofenac sodium
15307-79-6

diclofenac sodium

N,N-didecyl-N,N-dimethylammonium bromide
2390-68-3

N,N-didecyl-N,N-dimethylammonium bromide

diclofenac didecyldimethylammonium salt
934544-42-0

diclofenac didecyldimethylammonium salt

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium hydroxide In methanol; water at 20℃; for 0.5h;91%
diclofenac sodium
15307-79-6

diclofenac sodium

methyl iodide
74-88-4

methyl iodide

2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester
15307-78-5

2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide90%
In acetone Heating;
copper(ll) sulfate pentahydrate

copper(ll) sulfate pentahydrate

diclofenac sodium
15307-79-6

diclofenac sodium

2C14H10Cl2NO2(1-)*Cu(2+)*2H2O

2C14H10Cl2NO2(1-)*Cu(2+)*2H2O

Conditions
ConditionsYield
In water at 20℃;90%
tert-Butyl chloroacetate
107-59-5

tert-Butyl chloroacetate

diclofenac sodium
15307-79-6

diclofenac sodium

2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester
139272-68-7

2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid tert-butyl ester

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 77 - 78℃; for 2h;89.6%
In acetonitrile for 4h; Reflux;
With potassium iodide In N,N-dimethyl-formamide for 2h; Reflux; Large scale;25.5 g
diclofenac sodium
15307-79-6

diclofenac sodium

6-bromomethyl-benzo[1,2,5]oxadiazole-1-oxide

6-bromomethyl-benzo[1,2,5]oxadiazole-1-oxide

[2-(2,6-dichlorophenylamino)-phenyl]-acetic acid 1-oxy-benzo[1,2,5]oxadiazol-6-ylmethyl ester

[2-(2,6-dichlorophenylamino)-phenyl]-acetic acid 1-oxy-benzo[1,2,5]oxadiazol-6-ylmethyl ester

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20 - 25℃; for 2h;89%
diclofenac sodium
15307-79-6

diclofenac sodium

5-(bromomethyl)benzofuroxan
175609-21-9

5-(bromomethyl)benzofuroxan

given name is incorrect
883738-54-3

given name is incorrect

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In N,N-dimethyl-formamide at 25℃; for 2h;89%
2-(2-Hydroxyethyl)pyridine
103-74-2

2-(2-Hydroxyethyl)pyridine

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

diclofenac sodium
15307-79-6

diclofenac sodium

[Ni(diclofenac)2(2-pyridineethanol)2]

[Ni(diclofenac)2(2-pyridineethanol)2]

Conditions
ConditionsYield
In methanol at 50℃;89%
methanol
67-56-1

methanol

diclofenac sodium
15307-79-6

diclofenac sodium

copper(II) nitrate

copper(II) nitrate

tetrakis{μ-2-[2-(2,6-dichloroanilino)phenyl]acetato-κ2O:O'}bis(methanol-κO)copper(II)

tetrakis{μ-2-[2-(2,6-dichloroanilino)phenyl]acetato-κ2O:O'}bis(methanol-κO)copper(II)

Conditions
ConditionsYield
In water at 20℃;89%
1H-imidazole
288-32-4

1H-imidazole

diclofenac sodium
15307-79-6

diclofenac sodium

copper(II) nitrate

copper(II) nitrate

bis{2-[2-(2,6-dichloroanilino)phenyl]acetato-κ2O,O'}bis(1H-imidazole-κN3)copper(II)

bis{2-[2-(2,6-dichloroanilino)phenyl]acetato-κ2O,O'}bis(1H-imidazole-κN3)copper(II)

Conditions
ConditionsYield
In methanol; water at 20℃;89%
didecyldimethylammonium acesulfamate
934544-25-9

didecyldimethylammonium acesulfamate

diclofenac sodium
15307-79-6

diclofenac sodium

diclofenac didecyldimethylammonium salt
934544-42-0

diclofenac didecyldimethylammonium salt

Conditions
ConditionsYield
In acetone at 60℃; for 2h; Product distribution / selectivity;88%
diclofenac sodium
15307-79-6

diclofenac sodium

silver nitrate

silver nitrate

silver(I) diclofenac

silver(I) diclofenac

Conditions
ConditionsYield
In water87%
In methanol at 20℃; for 1h; Darkness;85%
With ammonia In ethanol; water at 20℃; for 0.25h; pH=8;
isopropyloxycarbonyloxymethyl iodide
258841-42-8

isopropyloxycarbonyloxymethyl iodide

diclofenac sodium
15307-79-6

diclofenac sodium

1-[(1-methylethoxy)carbonyloxy]methyl 2-[(2,6-dichlorophenyl)amino]phenylacetate
1264635-62-2

1-[(1-methylethoxy)carbonyloxy]methyl 2-[(2,6-dichlorophenyl)amino]phenylacetate

Conditions
ConditionsYield
Stage #1: diclofenac sodium With sodium carbonate In N,N-dimethyl acetamide at 30℃; for 0.166667h; Inert atmosphere;
Stage #2: isopropyloxycarbonyloxymethyl iodide In N,N-dimethyl acetamide at -10℃; for 0.75h; Inert atmosphere;
86.4%
trimethyltin(IV)chloride
1066-45-1

trimethyltin(IV)chloride

diclofenac sodium
15307-79-6

diclofenac sodium

(CH3)3SnOC(O)CH2C6H4NHC6H3Cl2

(CH3)3SnOC(O)CH2C6H4NHC6H3Cl2

Conditions
ConditionsYield
In chloroform byproducts: sodium chloride; under inert atmosphere; 1 equiv. of sodium salt of ligand refluxed withSn compd. in dry CHCl3 for 6-7 h; cooled to room temp.; filtered; solvent removed from filtrate by rotary evaporator; crystd. from CH2Cl2-hexane; elem. anal.;86%
1-(2-aminoethyl)pyrrolidine
7154-73-6

1-(2-aminoethyl)pyrrolidine

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

diclofenac sodium
15307-79-6

diclofenac sodium

[Ni(diclofenac)2(1-(2-aminoethyl)pyrrolidine)2]
1596252-87-7

[Ni(diclofenac)2(1-(2-aminoethyl)pyrrolidine)2]

Conditions
ConditionsYield
Stage #1: nickel(II) chloride hexahydrate; diclofenac sodium In ethanol at 50℃;
Stage #2: 1-(2-aminoethyl)pyrrolidine In ethanol at 20℃;
86%
diclofenac sodium
15307-79-6

diclofenac sodium

water
7732-18-5

water

zinc(II) chloride
7646-85-7

zinc(II) chloride

C28H24Cl4N2O6Zn

C28H24Cl4N2O6Zn

Conditions
ConditionsYield
In water at 20℃; for 3h;86%

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In this study, we prepared a magnetic composite based on amine-functionalized chitosan (aminochitosan; AmCS) and Fe3O4 to remove diclofenac sodium (DS) from water. The fabricated [email protected]3O4 composite was characterized using Fourier-transform infrared spectroscopy, transmission electron...detailed

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15307-79-6Relevant articles and documents

Synthesis method of diclofenac sodium

-

, (2021/09/21)

The invention discloses a synthesis method of diclofenac sodium, which comprises the following steps: (1) toluene. An oil layer is obtained by adding 2, 6 -dichlorophenol and sodium carbonate, keeping warm and refluxing, extracting the oil layer with water, and adding an alkali heat-preserving reaction in the oil layer to obtain 2, 6 -dichloroaniline. (2) 1, 2 Dichlorodimethylaniline prepared in step (6 -) is heated and melted, chloroacetyl chloride is added dropwise, and the heat is subjected to heat preservation reaction after being heated to crystallize to obtain N - (2, 6 - dichlorophenyl) - phenyl - chloroacetamide. (3) 2 (N - 2 Dichlorophenyl) 6 - phenyl - chloroacetamide prepared in step (-) is reacted with the aluminum trichloride to give a solid 1 - (2, 6 -dichlorophenyl) -2 -indolinone. (4) 3 (1 - 2-dichlorophenyl) 6 -indolinone prepared in step (-2 -) is added to alkali liquor, stirred and heated to reflux to obtain diclofenac sodium. The synthesis method is stable, easy to operate, low in cost, high in yield and suitable for industrial production.

Preparation method of 2-[(2, 6-dichlorophenyl) amino] sodium phenylacetate

-

, (2020/05/30)

The invention belongs to the field of chemical pharmacy, and relates to a production process of a chemical bulk drug, in particular to a preparation method of 2-[(2, 6-dichlorophenyl) amino] sodium phenylacetate. The preparation method comprises the following steps: taking 2, 6-dichlorodiphenylamine and chloroacetyl chloride as initial raw materials; and completing acylation reaction, Lewis acidicionic liquid catalyzed Friedel-Crafts alkylation reaction and hydrolysis reaction by a one-pot method to finally obtain the 2-[(2, 6-dichlorophenyl) amino] sodium phenylacetate. The 2-[(2,6-dichlorophenyl) amino] sodium phenylacetate is synthesized by adopting a one-pot preparation scheme, has the advantages of short reaction time, simplicity in operation, mild conditions, high yield, good catalytic effect, high selectivity, recyclability and the like, and is beneficial to industrial production.

A double-dispain preparation method

-

, (2018/09/08)

The invention discloses a method for preparing diclofenac sodium. The method is characterized by comprising the following steps of: obtaining N-chloro-N-(2,6-dichlorophenyl)phenylacetamide (III) through reacting a chloride reagent with N-(2,6-dichlorophenyl)phenylacetamide (IV); obtaining 1-(2,6-dichlorophenyl)-2-indolinone (II) through reacting N-chloro-N-(2,6-dichlorophenyl)phenylacetamide (III) with a certain amount of Lewis acid in an organic solvent; and finally obtaining diclofenac sodium (I) through enabling the 1-(2,6-dichlorophenyl)-2-indolinone (II) to be subjected to hydrolysis reaction in a sodium hydroxide solution. The method disclosed by the invention has the characteristics of simplicity in operation, easily-available reagents, low cost, mild conditions and the like, and provides a novel processing route for the synthesis of diclofenac sodium.

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