(R)-Naproxen

Base Information

• Chemical Name: (R)-Naproxen
• CAS No.: 23979-41-1
• Molecular Formula: C14H14 O3
• Molecular Weight: 230.263
• Hs Code.: 2918990090
• European Community (EC) Number: 245-966-6
• UNII: 484XV9323P
• DSSTox Substance ID: DTXSID00904711
• Nikkaji Number: J242.711G
• Wikidata: Q27166414
• Pharos Ligand ID: 6CXQUM4Y9M93
• ChEMBL ID: CHEMBL1618254
• Mol file: 23979-41-1.mol

Synonyms:(R)-Naproxen;23979-41-1;(R)-2-(6-Methoxynaphthalen-2-yl)propanoic acid;(2r)-2-(6-methoxynaphthalen-2-yl)propanoic acid;l-Naproxen;(-)-Naproxen;Naproxen, (-)-;CHEMBL1618254;UNII-484XV9323P;(R)-6-Methoxy-a-methyl-2-naphthaleneacetic acid;EINECS 245-966-6;484XV9323P;(R)-2-(2-Methoxynaphthalen-6-yl)propanoic acid;(R)-6-Methoxy-alpha-methylnaphthalene-1-acetic acid;r-naproxen;(2R)-2-(6-Methoxynaphthalen-2-yl)propanoic Acid ((R)-Naproxen);EINECS 247-485-7;NPX;(1)-2-(6-Methoxy-2-naphthyl)propionic acid;(R)-(-)-Naproxen;Prestwick0_000045;Prestwick1_000045;Prestwick2_000045;Prestwick3_000791;(2R)-2-(6-Methoxynaphth-2-yl)propanoic acid;(R)-2-(6-Methoxynaphthalen-2-yl)propanoicacid;SCHEMBL42434;BSPBio_000922;SPBio_002090;BPBio1_001016;CHEBI:94583;DTXSID00904711;HMS1568I11;BDBM50533571;MFCD00870716;AKOS016842784;CS-T-59125;CS-W019918;PS-7719;AC-25534;HY-15031;NAPROXEN IMPURITY G [EP IMPURITY];(R)-2-(6methoxynaphthalen-2-yl)propanoic acid;(R)-Naproxen, pharmaceutical impurity standard;EN300-139794;NAPROXEN SODIUM IMPURITY G [EP IMPURITY];J-015300;Q27166414;2-Naphthaleneacetic acid, 6-methoxy-?-methyl-, (?R)-;(R)-(-)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid;(-)-6-METHOXY-.ALPHA.-METHYL-2-NAPHTHALENEACETIC ACID;(R)-(-)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid, 98%;2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, (.ALPHA.R)-

Chemical Property of (R)-Naproxen

Chemical Property:

• Vapor Pressure: 3.01E-07mmHg at 25°C
• Melting Point: 156-158oC(lit.)
• Boiling Point: 403.9°Cat760mmHg
• PKA: 4.84±0.30(Predicted)
• Flash Point: 154.5°C
• PSA: 46.53000
• Density: 1.197g/cm³
• LogP: 3.03650
• Storage Temp.: Refrigerator
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Naproxen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
• Isomeric SMILES: C[C@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
• Uses: Antiinflammatory;'Cyclooxygenase inhibitor

Technology Process of (R)-Naproxen

There total 98 articles about (R)-Naproxen 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: 99.0%

naproxen (23981-80-8) → (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + (R)-2-(6-methoxy-2-naphthyl)propionic acid (23979-41-1)

Guidance literature:

With 1-deoxy-1-(octylamino)-d-glucitol; In acetonitrile; for 6h; Heating;

DOI:10.1016/S0957-4166(01)00536-5

Reference yield: 51.0%

1-(6-methoxy-2-naphthyl)ethanol (108781-65-3,119341-64-9,125712-80-3,77301-42-9) + sodium cyanide (143-33-9,25596-52-5) → 6-methoxy-2-acetylnaphthalene (3900-45-6) + (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + (R)-2-(6-methoxy-2-naphthyl)propionic acid (23979-41-1)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts;

Reference yield: 49.0%

naproxen (23981-80-8) + bis(1-naphthyl)methanol (62784-66-1) → (S)-naproxen di(1-naphthyl)methyl ester (1116086-50-0) + (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + (R)-2-(6-methoxy-2-naphthyl)propionic acid (23979-41-1)

Guidance literature:

With (-)-(S)-β-Np-BTM; p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h; optical yield given as %ee; Resolution of racemate;

DOI:10.1002/ejoc.200800942

upstream raw materials:

carbon monoxide

2-methoxy-6-vinylnapthalene

methyl 2-(6-methoxy-2-naphthyl)propionate

2-(6-methoxynaphth-2-yl)acrylic acid

Downstream raw materials:

R-naproxen β-1-O-acyl-glucuronide

1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline

1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline

(+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline

Refernces

• 1、 Ozyilmaz, Elif,Ascioglu, Sebahat,Yilmaz, Mustafa. "Preparation of One-Pot Immobilized Lipase with Fe3O4 Nanoparticles Into Metal-Organic Framework For Enantioselective Hydrolysis of (R,S)-Naproxen Methyl Ester". . p. 3687 - 3694. Retrieved 2021/06/25.
• 2、 Cleary, Leah,DeLano, Travis J.,Dibrell, Sara E.,Lacker, Caitlin R.,Pancoast, Adam R.,Poremba, Kelsey E.,Reisman, Sarah E.,Sigman, Matthew S.. "Nickel-catalyzed asymmetric reductive cross-coupling of α-chloroesters with (hetero)aryl iodides". . p. 7758 - 7762. Retrieved 2021/06/16.