Application in Particular Diseases
ChemicalBook > CAS DataBase List > 1-(2,6-Dichlorophenyl)-2-indolinone

1-(2,6-Dichlorophenyl)-2-indolinone

Application in Particular Diseases
Product Name
1-(2,6-Dichlorophenyl)-2-indolinone
CAS No.
15307-86-5
Chemical Name
1-(2,6-Dichlorophenyl)-2-indolinone
Synonyms
Diclac;Pennsaid;Rhumalgan;Voltaflan;Diciofenac;Diclofenac;Dielofenac;DicloMelan;DicloreuMa;Transfenac
CBNumber
CB5225367
Molecular Formula
C14H11Cl2NO2
Formula Weight
296.15
MOL File
15307-86-5.mol
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1-(2,6-Dichlorophenyl)-2-indolinone Property

Melting point:
156-158°
Boiling point:
412.0±45.0 °C(Predicted)
Density 
1.431±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
pka
pKa 4 (Uncertain)
Water Solubility 
1.278mg/L(30 ºC)
Merck 
14,3081
InChIKey
DCOPUUMXTXDBNB-UHFFFAOYSA-N
CAS DataBase Reference
15307-86-5(CAS DataBase Reference)
NIST Chemistry Reference
Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-(15307-86-5)
EPA Substance Registry System
Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]- (15307-86-5)
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Safety

RIDADR 
3249
RTECS 
AG6310000
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
15307-86-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
D3748
Product name
2-(2,6-Dichloroanilino)phenylacetic Acid
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$48
Updated
2021/03/22
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1-(2,6-Dichlorophenyl)-2-indolinone Chemical Properties,Usage,Production

Application in Particular Diseases

In Osteoarthritis:
Topical diclofenac in a dimethyl sulfoxide carrier (Pennsaid) is a safe and effective treatment for Osteoarthritis pain. It is thought to act primarily by local inhibition of COX-2 enzymes.

Originator

Voltaren,Fujisawa,Japan,1974

Uses

Diclofenac possesses all of the properties unique to the series of propionic acid drugs, yet in terms of anti-inflammatory and analgesic strength it exceeds that of aspirin, analgin, and ibuprofen. It is used in acute rheumatism, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, arthrosis, back pain, neuralgia, and myalgia. It rarely causes side effects. The most common synonym is voltaren.

Uses

prostaglandin synthetic inhibitor

Indications

Diclofenac (Voltaren, Cataflam) is approved for use in rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, dysmenorrhea, and topically for the treatment treatment of ocular inflammation and actinic keratosis. Diclofenac exhibits approximately equal selectivity for COX-1 and COX-2. The most common adverse reactions are GI disturbances and headache.A reversible elevation of serum transaminases occurs in 15% of patients.

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.

Therapeutic Function

Antiinflammatory

Biological Functions

Diclofenac (Voltaren) is a phenylacetic acid derivative that is a potent inhibitor of COX and that has analgesic, antiinflammatory, and antipyretic effects. Its use is accompanied by side effects similar to those of other NSAIDs. Indications for the drug include rheumatoid arthritis, osteoarthritis, and ophthalmic inflammation (use of an ophthalmic preparation).

Mechanism of action

Diclofenac is unique among the NSAIDs in that it possesses three possible mechanisms of action: 1) inhibition of the arachidonic acid cyclooxygenase system (3 to 1,000 times more potent than other NSAIDs on a molar basis), resulting in a decreased production of prostaglandins and thromboxanes; 2) inhibition of the lipoxygenase pathway, resulting in decreased production of leukotrienes, particularly the pro-inflammatory LKB4; and 3) inhibition of arachidonic acid release and stimulation of its reuptake, resulting in a reduction of arachidonic acid availability.

Pharmacokinetics

Diclofenac is rapidly and completely (~100%) absorbed on oral administration, with peak plasma levels being reached within 1.5 to 2.5 hours. The free acid (pKa = 4.0) is highly bound to serum proteins (99.5%), primarily albumin. Only 50 to 60% of an oral dose is bioavailable because of extensive hepatic metabolism.

Clinical Use

Diclofenac is synthesized from N-phenyl-2,6-dichloroaniline. It is available in 120 different countries and, perhaps, is the most widely used NSAID in the world. It was introduced in the United States in 1989 but was first marketed in Japan in 1974. It ranks among the top prescription drugs in the United States. Diclofenac possesses structural characteristics of both arylalkanoic acid and the anthranilic acid classes of anti-inflammatory drugs, and it displays anti-inflammatory, analgetic, and antipyretic properties.

Chemical Synthesis

Diclofenac, 2-[(2,6-dichlorophenyl)-amino]-phenylacetic acid (3.2.42), is synthesized from 2-chlorobenzoic acid and 2,6-dichloroaniline. The reaction of these in the presence of sodium hydroxide and copper gives N-(2,6-dichlorophenyl)anthranylic acid (3.2.38), the carboxylic group of which undergoes reduction by lithium aluminum hydride. The resulting 2-[(2,6-dicholorphenyl)-amino]-benzyl alcohol (3.2.39) undergoes further chlorination by thionyl chloride into 2-[(2,6-dichlorophenyl)-amino]-benzylchloride (3.2.40) and further, upon reaction with sodium cyanide converts into 2-[(2,6-dicholorophenyl)-amino]benzyl cyanide (3.2.41). Hydrolysis of the nitrile group leads to diclofenac (3.2.42) [107,108].

Metabolism

Four major metabolites resulting from aromatic hydroxylation have been identified. The major metabolite via CYP3A4 is the 4′-hydroxy derivative and accounts for 20 to 30% of the dose excreted, whereas the 5-hydroxy, 3′-hydroxy, and 4′,5-dihydroxy metabolites via CYP2C9 account for 10 to 20% of the excreted dose. The remaining drug is excreted in the form of sulfate conjugates. Although the major metabolite is much less active than the parent compound, it may exhibit significant biological activity, because it accounts for 30 to 40% of all of the metabolic products.

1-(2,6-Dichlorophenyl)-2-indolinone Preparation Products And Raw materials

Raw materials

Preparation Products

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1-(2,6-Dichlorophenyl)-2-indolinone Suppliers

Shenzhen Kaimingke Biotechnology Co., Ltd.
Tel
181-26439142-
Email
1144496688@QQ.COM;
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China
ProdList
171
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Fan De(Beijing) Biotechnology Co., Ltd.
Email
liming@bio-fount.com
Country
China
ProdList
9734
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58
Shanghai Boyle Chemical Co., Ltd.
Tel
Mr Qiu:021-50182298(Demestic market) Miss Xu:021-50180596(Abroad market)
Fax
+86-21-57758967
Email
sales@boylechem.com
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China
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J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
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jkinfo@jkchemical.com;market6@jkchemical.com
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China
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
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sh@meryer.com
Country
China
ProdList
40264
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Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
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TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
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China
ProdList
24555
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BeiJing Hwrk Chemicals Limted
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0757-86329057-
Fax
0757-86311057
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sales.gd@hwrkchemical.com
Country
China
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Energy Chemical
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021-58432009-
Fax
021-58436166
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sales8178@energy-chemical.com
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China
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LGM Pharma
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1-(800)-881-8210
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615-250-9817
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inquiries@lgmpharma.com
Country
United States
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View Lastest Price from 1-(2,6-Dichlorophenyl)-2-indolinone manufacturers

Hebei Crovell Biotech Co Ltd
Product
Diclofenac 15307-86-5
Price
US $1.90/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 ton
Release date
2021-08-26
Xingtai Haoxun Import and Export Trade Co., Ltd.
Product
Diclofenac 15307-86-5
Price
US $15.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10tons
Release date
2020-07-16
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Diciofenac 15307-86-5
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-11-25

15307-86-5, 1-(2,6-Dichlorophenyl)-2-indolinoneRelated Search:


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