Diclofenac-d4

Base Information

• Chemical Name: Diclofenac-d4
• CAS No.: 153466-65-0
• Molecular Formula: C₁₄H₁₁Cl₂NO₂
• Molecular Weight: 303.097
• European Community (EC) Number: 898-691-4
• DSSTox Substance ID: DTXSID20512155
• Wikidata: Q82371274
• Mol file: 153466-65-0.mol

Synonyms:Diclofenac-d4;153466-65-0;2-[2,3,4,5-tetradeuterio-6-(2,6-dichloroanilino)phenyl]acetic acid;Diclofenac D4;Diclofenac D4 acid (phenyl D4) 100 microg/mL in Acetone;Diclofenac-d4(major);DTXSID20512155;HY-15036S;AKOS015914380;AS-6035;CS-0179736;F90758;2-((2,6-Dichlorophenyl)aminobenzeneacetic Acid-d4;J-009020;[2-(2,6-Dichloroanilino)(~2~H_4_)phenyl]acetic acid;6-[(2,6-Dichlorophenyl)amino]-benzen-2,3,4,5-d4-acetic acid;Diclofenac D4 acid (phenyl D4);Diclofenac (phenyl D4)

Chemical Property of Diclofenac-d4

Chemical Property:

• Melting Point: 157-159℃
• PSA: 49.33000
• LogP: 4.43710
• Storage Temp.: -20°C Freezer
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 299.0417910
• Heavy Atom Count: 19
• Complexity: 304

Purity/Quality:

99% ^*data from raw suppliers

Diclofenac-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC(=O)O)NC2=C(C=CC=C2Cl)Cl
• Isomeric SMILES: [2H]C1=C(C(=C(C(=C1[2H])CC(=O)O)NC2=C(C=CC=C2Cl)Cl)[2H])[2H]
• Description: Diclofenac-d4 is intended for use as an internal standard for the quantification of diclofenac (Item Nos. 70680 | 22983) by GC- or LC-MS. 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.
• Uses: Labeled Diclofenac, a nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor. 92% overall isotopic purity. A representative lot was 75% d4, 23% d3 and 2 % d2 Labelled Diclofenac, a nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor. Labelled Diclofenac is a known nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor.

Technology Process of Diclofenac-d4

There total 11 articles about Diclofenac-d4 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.6%

2-(2-(2,6-dichlorophenylamino)-3,4,5,6-(2)H4-phenyl)-N,N-dimethylacetamide (1217360-64-9) → o-<(2,6-dichlorophenyl)amino>-<2H4-phenyl>-acetic acid (153466-65-0)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 12h; Inert atmosphere; Reflux;

DOI:10.1002/jlcr.1669

Reference yield: 65.0%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → [2-(2,6-dichloro-phenylamino-[4-D])-phenyl-[3,4,5,6-D4]]-essigs?ure-[1,1-D2] (1401311-57-6,153466-65-0)

Guidance literature:

With [D]-sodium hydroxide; deuteromethanol; In water-d2; at 130 ℃; for 0.00277778h; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1002/jlcr.3103

Reference yield: 65.0%

1-(2,6-dichlorophenyl-[4-D])-1,3-dihydro-indol-2-one-[3,3,4,5,6,7-D6] (1401311-51-0) → [2-(2,6-dichloro-phenylamino-[4-D])-phenyl-[3,4,5,6-D4]]-essigs?ure-[1,1-D2] (1401311-57-6,153466-65-0)

Guidance literature:

With [D]-sodium hydroxide; deuteromethanol; In water-d2; at 130 ℃; for 0.00277778h; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.bmc.2012.06.052

upstream raw materials:

1-(2,6-dichlorophenyl)-2-<2H4>-indoline

2,6-dichloroacetanilide

N-(2,6-dichlorophenyl)-<2H5>-phenylamine

2,6-dichlorophenyl-<2H5>-phenylacetamide

Refernces

• 1、 Atzrodt,Blankenstein,Brasseur,Calvo-Vicente,Denoux,Derdau,Lavisse,Perard,Roy,Sandvoss,Schofield,Zimmermann. "Synthesis of stable isotope labelled internal standards for drug-drug interaction (DDI) studies". . p. 5658 - 5667. Retrieved 2012/10/30.
• 2、 Leroy,Richard,Godbillon. "Synthesis of deuterium-labelled diclofenac sodium". . p. 1019 - 1027. Retrieved 2007/10/02.