Naproxen supplier | CasNO.22204-53-1

Name
Naproxen
EINECS 244-838-7
CAS No. 22204-53-1
Article Data203
CAS DataBase
Density 1.197 g/cm³
Solubility Insoluble in water.
Melting Point 152-154 °C(lit.)
Formula C₁₄H₁₄O₃
Boiling Point 403.888 °C at 760 mmHg
Molecular Weight 230.263
Flash Point 154.529 °C
Transport Information UN 2811 6.1/PG 3
Appearance White or almost white crystalline powder
Safety 36/37
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 2-Naphthaleneacetic acid, 6-methoxy-α-methyl-, (S)-;Naprontag;(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid;Nafasol;Proxen LE;(+)-2-(Methoxy-2-naphthyl)-propionic acid;Artrixen;Tohexen;Rahsen;(S)-6-Methoxy-.alpha.-methyl-2-naphthaleneacetic acid;(S)-(+)-Naproxen;(S)-2-(6-Methoxy-2-naphthyl)propionic acid;(+)-2-(Methoxy-2-naphthyl)-propionic acid;
PSA 46.53000
LogP 3.03650

Synthetic route

: (R)-praziquanacetamide (S)-naproxen salt

A: (R)-praziquanacetamide hydrochloride

B: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In water	A 100% B n/a

: 23981-80-8
naproxen

A: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

B: 23979-41-1
(R)-2-(6-methoxy-2-naphthyl)propionic acid

Conditions

Conditions	Yield
With 1-deoxy-1-(octylamino)-d-glucitol In acetonitrile for 6h; Heating;	A 99% B n/a
With phosphate buffer; sodium dodecyl-sulfate; vancomycin at 20℃; Product distribution; electrophoretic enantioseparations, various substrates;
With ammonium acetate Purification / work up; Resolution of racemate;

toluene-MeOH: toluene-MeOH

: 27602-79-5
2-(6-methoxynaphth-2-yl)acrylic acid

: 7440-44-0
pyrographite

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With triethylamine	98%

...Expand

: 26159-34-2
Naprelan

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃;	98%
With hydrogenchloride In water pH=< 2; Inert atmosphere;	94.3%

: (R)-praziquanammonium (S)-2-(6-methoxy-naphthalen-2-yl)-propionate

A: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

B: 55375-92-3
(R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 0.5h; pH=1;	A 97.9% B n/a

: 27602-79-5
2-(6-methoxynaphth-2-yl)acrylic acid

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With C48H50Cl4N2O2P2Ru3; hydrogen; sodium hydrogencarbonate In methanol at 20℃; under 3750.38 Torr; for 24h; Autoclave; enantioselective reaction;	97%
With hydrogen; (S)-Ru(OAc)2-BINAP In methanol at 15 - 30℃; under 102600 Torr; for 12h;	92%
With C42H48CoP2; hydrogen; triethylamine; zinc In methanol at 50℃; under 25858.1 Torr; for 16h; enantioselective reaction;	91%

: 2-(1-bromoethyl)-2-(6-methoxylnaphth-2-yl)-5,5-dimethyl-1,3-epoxyhexane

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
Stage #1: 2-(1-bromoethyl)-2-(6-methoxylnaphth-2-yl)-5,5-dimethyl-1,3-epoxyhexane With zinc 2-(6-methoxylnaphthyl)propionate In toluene for 5.5h; Reflux; Stage #2: With sodium hydroxide In toluene for 3.5h; Reflux; Stage #3: With water; pyrographite In toluene for 0.5h; Reflux;	96.9%

: (S)-3-methyl-2-phenylbutylammonium (S)-2-(6-methoxy-2-naphthyl)propionate

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In water	96.3%

: 23981-47-7
6-methoxy-2-naphthylacetic acid

: 74-88-4
methyl iodide

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
Stage #1: 6-methoxy-2-naphthylacetic acid With n-butyllithium; N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine In tetrahydrofuran; hexanes at 0℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexanes at -90℃; for 0.0333333h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	96%
Stage #1: 6-methoxy-2-naphthylacetic acid With n-butyllithium; N1,N3-bis((R)-1-phenyl-2-(piperidin-1-yl)ethyl)propane-1,3-diamine In tetrahydrofuran; hexane at -78 - 0℃; for 0.333333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 0.0333333h; Inert atmosphere; enantioselective reaction;	94%

: 32305-59-2
S-2-(6-methoxy-2-naphthyl)propionaldehyde

: 109-68-2
2-pentene

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With sodium dihydrogenphosphate; sodium chlorite In water at 20℃; for 1h;	96%

: (S)-2-(6-methoxynaphthalen-2-yl)-N-phenylpropanamide

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane; water at 80℃; for 8h;	96%

: 126899-42-1
2-(6-Methoxy-naphthalen-2-yl)-2-methyl-malonic acid

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With tris hydrochloride In water at 37℃; for 24h; pH=7.0; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	95%

: 1330660-68-8
(S)-3-(2-(6-methoxynaphthalen-2-yl)propanoyl)oxazolidin-2-one

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With water; dihydrogen peroxide; lithium hydroxide In tetrahydrofuran at 20℃; for 12h;	94%
Stage #1: (S)-3-(2-(6-methoxynaphthalen-2-yl)propanoyl)oxazolidin-2-one With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=4;

Ru((-)-T-BINAP)(O2 CCF3)2: Ru((-)-T-BINAP)(O2 CCF3)2

: 27602-79-5
2-(6-methoxynaphth-2-yl)acrylic acid

: argon

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
In methanol	93.7%

...Expand

: 72658-10-7
tert-butyl trimethylsilyl methyl ketene acetal

: 129731-74-4
6-methoxynaphthalen-2-yl trifluoromethanesulfonate

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
Stage #1: tert-butyl trimethylsilyl methyl ketene acetal; 6-methoxynaphthalen-2-yl trifluoromethanesulfonate With (R)-2-(dicyclohexylphosphino)-2'-(2-naphthylmethoxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; lithium acetate In dodecane; α,α,α-trifluorotoluene at 50℃; for 60h; Inert atmosphere; Stage #2: In dichloromethane; trifluoroacetic acid optical yield given as %ee;	93%
Stage #1: tert-butyl trimethylsilyl methyl ketene acetal; 6-methoxynaphthalen-2-yl trifluoromethanesulfonate With (N,N,N',N'-tetramethylethylenediamine)dimethylpalladium(II); (R)-2-(dicyclohexylphosphino)-2'-(2-naphthylmethoxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; lithium acetate at 50℃; for 60h; Inert atmosphere; Stage #2: With trifluoroacetic acid In dichloromethane at 25℃; for 4h;	93%

Yield

Stage #1: tert-butyl trimethylsilyl methyl ketene acetal; 6-methoxynaphthalen-2-yl trifluoromethanesulfonate With (R)-2-(dicyclohexylphosphino)-2'-(2-naphthylmethoxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; lithium acetate In dodecane; α,α,α-trifluorotoluene at 50℃; for 60h; Inert atmosphere;
Stage #2: In dichloromethane; trifluoroacetic acid optical yield given as %ee;

93%

Stage #1: tert-butyl trimethylsilyl methyl ketene acetal; 6-methoxynaphthalen-2-yl trifluoromethanesulfonate With (N,N,N',N'-tetramethylethylenediamine)dimethylpalladium(II); (R)-2-(dicyclohexylphosphino)-2'-(2-naphthylmethoxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; lithium acetate at 50℃; for 60h; Inert atmosphere;
Stage #2: With trifluoroacetic acid In dichloromethane at 25℃; for 4h;

93%

: 26159-36-4
naproxol

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water; acetone at 20℃; for 168h; Enzymatic reaction;	92%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; Schlenk technique;	90%
With chromium(VI) oxide; sulfuric acid In acetone at 0℃; for 0.5h;	69%

: 31220-35-6
(S)-6-methoxy-α-methyl-2-naphthaleneacetic acid ethyl ester

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;	92%
With monoclonal antibody N116-27; tris hydrochloride; sodium chloride In acetonitrile at 37℃; pH=8.2; Enzyme kinetics;

Ru2 Cl4 [(-)-T-BINAP]2 (NEt3): Ru2 Cl4 [(-)-T-BINAP]2 (NEt3)

: 27602-79-5
2-(6-methoxynaphth-2-yl)acrylic acid

: argon

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
In methanol	92%

...Expand

: 27655-95-4
(d,l)-2-(5-bromo-6-methoxy-2-naphthyl)propionic acid

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride; aluminium trichloride In chloroform; water; toluene; 1,3,5-trimethyl-benzene	91%
With hydrogenchloride; aluminium trichloride In chloroform; water; toluene; 1,3,5-trimethyl-benzene	91%

: 1181399-48-3
(S)-phenethyl 2-(6-methoxynaphthalen-2-yl)propanoate

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate; palladium diacetate In methanol at 65℃; for 17h;	91%

: 32305-59-2
S-2-(6-methoxy-2-naphthyl)propionaldehyde

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tert.-butyl lithium In water; tert-butyl alcohol at 20℃; for 1h;	91%
With sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol for 1h;	90%
With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 20.8h;	184.7 mg

: 26159-35-3
(S)-naproxen methyl ester

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With hydrogenchloride In water; acetic acid at 85℃;	90%
Acid hydrolysis;
With sodium hydroxide for 3h; Heating;
With naproxen esterase(NP); water Enzymatic reaction;

: (4R)-4-isopropyl-3-[(2S)-2-(6-methoxynaphth-2-yl)propionyl]oxazolidin-2-one

A: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

B: 95530-58-8
(R)-4-isopropyloxazolidin-2-one

Conditions

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 12h;	A 74% B 90%

: 878194-08-2
(4R,2'S)-3-[2'-(6-methoxy-naphthalen-2-yl)propionyl]-4-phenyl-oxazolidin-2-one

A: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

B: 90319-52-1
(4R)-phenyl-2-oxazolidinone

Conditions

Conditions	Yield
Stage #1: (4R,2'S)-3-[2'-(6-methoxy-naphthalen-2-yl)propionyl]-4-phenyl-oxazolidin-2-one With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=3; Inert atmosphere;	A 90% B 89%

: 301663-72-9
(2S,3R,4S)-2,3-Dihydroxy-4-(6-methoxynaphthalen-2-yl)-2-phenylpentane

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
Stage #1: (2S,3R,4S)-2,3-Dihydroxy-4-(6-methoxynaphthalen-2-yl)-2-phenylpentane With sodium periodate In dichloromethane for 1h; Oxidation; oxidative cleavage; Stage #2: With jones reagent In acetone for 1h; Oxidation; Further stages.;	88%

: (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-hexyl ester

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
Stage #1: (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (2R,3S,4S,5S)-2,3,4,5,6-pentahydroxy-hexyl ester With hydroxyl chlorite In methanol for 2h; Heating; Stage #2: With sodium hydroxide In water	87%

: 197143-65-0
(S)-4-tert-Butyl-3-[(S)-2-(6-methoxy-naphthalen-2-yl)-propionyl]-oxazolidin-2-one

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

Conditions

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 25 - 30℃; for 1h;	85.4%

: 186581-53-3, 908094-01-9
diazomethane

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 26159-35-3
(S)-naproxen methyl ester

Conditions

Conditions	Yield
In diethyl ether	100%

: 67-56-1
methanol

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 26159-35-3
(S)-naproxen methyl ester

Conditions

Conditions	Yield
With sulfuric acid	100%
With sulfuric acid for 4h;	100%
With thionyl chloride at 20℃; for 16h; Cooling with ice; Inert atmosphere;	99%

: 64-17-5
ethanol

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 31220-35-6
(S)-6-methoxy-α-methyl-2-naphthaleneacetic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane 1.) 0 deg C, 1 h, 2.) r.t., 6 h;	91%
With sulfuric acid at 50℃; for 18h;	84%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 84236-26-0
S-(+)-2-(5-Bromo-6-Methoxy-2-Naphthyl)-Propionic Acid

Conditions

Conditions	Yield
With bromine In dichloromethane at 20℃; for 1h;	100%
With aluminum tri-bromide; [bis(acetoxy)iodo]benzene In acetonitrile at 23℃;	93%
Multi-step reaction with 4 steps 1: 53 percent / oxalyl chloride / toluene / 4 h / 90 °C 2: 85 percent / triethylamine / CH2Cl2 / 0.25 h / -10 °C 3: 85 percent / Br2 / 1,2-dichloro-ethane / 0.75 h / 0 °C 4: 95 percent / CH3COOH, concd. HCl, water / 85 °C View Scheme
With sodium hypochlorite; potassium bromide In methanol; water

: 5292-43-3
bromoacetic acid tert-butyl ester

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 646509-90-2
((tert-butyl)oxycarbonyl)methyl (2S)-2-(6-methoxy(2-naphthyl))propanoate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 48h;	100%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 48h;

: 19982-08-2
memantine*

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 1185878-08-3
memantine-(S)-naproxen salt

Conditions

Conditions	Yield
In methanol at 20℃;	100%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: (-)-tramadol

: 1112063-73-6
(1S,2S)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol (S)-naproxen salt

Conditions

Conditions	Yield
In methanol at 20℃;	100%

: 67-56-1
methanol

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 30012-51-2
methyl 2-(6-methoxy-2-naphthyl)propionate

Conditions

Conditions	Yield
With sulfuric acid for 6h; Reflux;	100%
With sulfuric acid for 18h; Reflux;	98%
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With sulfuryl dichloride In dichloromethane at 50℃; for 1h; Stage #2: methanol With triethylamine In dichloromethane at 20℃;	93%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 5680-79-5
glycine ethyl ester hydrochloride

: 847454-70-0
N-[2-(S)-(6-methoxy-2-naphthyl)propanoyl]glycine methyl ester

Conditions

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With 1,1'-carbonyldiimidazole In chloroform at 20℃; for 1h; Inert atmosphere; Stage #2: glycine ethyl ester hydrochloride In chloroform Inert atmosphere;	100%
With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	60%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile for 3h;

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 505-86-2
cetyltrimethylammonium hydroxide

: cetyltrimethylammonium naproxenate

Conditions

Conditions	Yield
In propan-1-ol	100%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 26159-35-3
(S)-naproxen methyl ester

Conditions

Conditions	Yield
With sulfuric acid In methanol at 80℃; for 8h; stereoselective reaction;	100%
With sulfuric acid In methanol at 20℃; for 12h; Inert atmosphere;	88%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: C51H51NO8

: C51H51NO8*C14H14O3

Conditions

Conditions	Yield
In acetone	99.9%

: 112-43-6
10-Undecen-1-ol

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 142634-66-0
(S)-naproxen undec-10-en-1-yl ester

Conditions

Conditions	Yield
toluene-4-sulfonic acid In benzene Heating;	99%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 26159-36-4
naproxol

Conditions

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 0.5h;	99%
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Reflux; Stage #2: With rochelle salt In tetrahydrofuran at 0℃; Inert atmosphere;	89%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 16h;	87%

: 57561-39-4
methyl(2-hydroxyethyl)carbamic acid tert-butyl ester

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 2-((tert-butoxy)-N-methylcarbonylamino)ethyl (2S)-2-(6-methoxy(2 naphthyl)) propanoate

Conditions

Conditions	Yield
With 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; dmap In dichloromethane at 0 - 20℃; for 24h;	99%

: 57-88-5
cholesterol

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 1416973-03-9
C41H58O3

Conditions

Conditions	Yield
Stage #1: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: cholesterol With dmap In dichloromethane at 0℃; for 8h;	99%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 2684-60-8
2-diazopropane

: (S)-6-methoxy-α-methyl-2-naphthaleneacetic acid isopropyl ester

Conditions

Conditions	Yield
In dichloromethane at 19℃; for 2h; chemoselective reaction;	99%

: 2,2'-dimethyl-[1,1'-biphenyl]iodonium trifluoromethanesulfonate salt

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: C28H25IO3

Conditions

Conditions	Yield
With copper diacetate; sodium carbonate; (3aR,3a'R,8aS,8a'S)-2,2'-(propane-2,2-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole) In dichloromethane; water at 30℃; for 12h; enantioselective reaction;	99%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: L-valine isopropyl ester hydrochloride

: L-valine isopropyl ester naproxenate

Conditions

Conditions	Yield
Stage #1: L-valine isopropyl ester hydrochloride With ammonium hydroxide In water Stage #2: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid In chloroform at 20℃; for 0.333333h;	98.5%

: C19H42N(1+)*C4H9O(1-)

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: cetyltrimethylammonium naproxenate

Conditions

Conditions	Yield
In methanol	98.3%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 89617-86-7
(S)-2-(1-chloro-2-methoxynaphthalen-6-yl)propanoic acid

Conditions

Conditions	Yield
With N-chloro-succinimide; dimethyl sulfoxide In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique;	98%
With sulfuryl dichloride at 20℃; for 1h;	89%
Multi-step reaction with 3 steps 1: 100 percent / diethyl ether 2: 80 percent / sodium hypochlorite, aq. HCl / CH2Cl2 / 1 h / 15 °C 3: 37percent aq. Hcl / acetone / 3 h / Heating View Scheme
With sodium hypochlorite In methanol; water

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 154472-05-6
(2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol

: (2S)-(S)-1-phenyl-2-(piperidin-1-yl)ethyl 2-(2-methoxynaphthalen-6-yl)propanoate

Conditions

Conditions	Yield
Stage #1: (2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol With methanesulfonyl chloride; triethylamine In chloroform at 0 - 5℃; for 0.5h; Stage #2: (2S)-2-(6-methoxy(2-naphthyl))propanoic acid With triethylamine In chloroform at 5 - 20℃; for 16h; enantiospecific reaction;	98%

: 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

: 16106-20-0, 16908-90-0, 16908-91-1, 35993-37-4, 38709-03-4, 114718-64-8, 127001-76-7, 16051-77-7
isosorbide mononitrate

: 646509-45-7
(2R)-7-(nitrooxy)-4,8-dioxabicyclo(3.3.0)oct-2-yl(2S)-2-(6-methoxy (2-naphthyl)) propanoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	97.6%

Naproxen Specification

1. Introduction of Naproxen
Naproxen is one kind of white to light yellow crystal powder and belongs to the classes of Carboxylic Acids (Chiral); Chiral Building Blocks; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Intermediates & Fine Chemicals; Pharmaceuticals. The IUPAC name is (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid. In addition, the Classification Code is Analgesic; Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory; Anti-inflammatory agents, non-steroidal; Antipyretic; Antirheumatic Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Gout suppressants; Human Data; Mutation data; Peripheral Nervous System Agents; Reproductive Effect; Sensory System Agents. Naproxen can soluble in organic solvents.

2. Properties of Naproxen
Physical properties about Naproxen are:
(1)ACD/LogP: 2.88; (2)ACD/LogD (pH 5.5): 2.135; (3)ACD/LogD (pH 7.4): 0.347; (4)ACD/BCF (pH 5.5): 16.387; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 158.568; (7)ACD/KOC (pH 7.4): 2.584; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 46.53 Å²; (12)Index of Refraction: 1.609; (13)Molar Refractivity: 66.523 cm³; (14)Molar Volume: 192.25 cm³; (15)Polarizability: 26.372 ×10^-24cm³; (16)Surface Tension: 47.465 dyne/cm; (17)Density: 1.198 g/cm³; (18)Flash Point: 154.529 °C; (19)Enthalpy of Vaporization: 69.096 kJ/mol; (20)Boiling Point: 403.888 °C at 760 mmHg.

3. Structure Descriptors of Naproxen
You can still convert the following datas into molecular structure:
(1)SMILES: C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O)O
(2)InChI: InChI=1/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1
(3)InChIKey: CMWTZPSULFXXJA-VIFPVBQEBN
(4)Canonical SMILES: CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
(5)Isomeric SMILES: C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O

4. Toxicity of Naproxen
The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	2250mg/kg/26W (2250mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	British Journal of Rheumatology. Vol. 26, Pg. 210, 1987.
dog	LD50	oral	> 1gm/kg (1000mg/kg)		Yakkyoku. Pharmacy. Vol. 29, Pg. 861, 1978.
dog	LD50	unreported	1gm/kg (1000mg/kg)		Journal of Clinical Pharmacology. Vol. 15, Pg. 311, 1975.
guinea pig	LD50	oral	665mg/kg (665mg/kg)		Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster	LD50	oral	1400mg/kg (1400mg/kg)		Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
hamster	LD50	unreported	4110mg/kg (4110mg/kg)		Journal of Clinical Pharmacology. Vol. 15, Pg. 311, 1975.
man	TDLo	oral	54mg/kg (54mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING KIDNEY, URETER, AND BLADDER: PROTEINURIS KIDNEY, URETER, AND BLADDER: HEMATURIA	Journal of Toxicology, Clinical Toxicology. Vol. 33, Pg. 173, 1995.
man	TDLo	oral	114mg/kg/10D- (114mg/kg)	BLOOD: CHANGES IN PLATELET COUNT	Journal of Clinical Pharmacology. Vol. 40, Pg. 124, 2000.
man	TDLo	oral	214mg/kg/30D- (214mg/kg)	LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION	Postgraduate Medical Journal. Vol. 56, Pg. 368, 1980.
man	TDLo	oral	3429mg/kg/35W (3429mg/kg)	VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: CYANOSIS	Postgraduate Medical Journal. Vol. 68, Pg. 766, 1992.
mouse	LD50	intraperitoneal	500mg/kg (500mg/kg)		Bollettino Chimico Farmaceutico. Vol. 119, Pg. 600, 1980.
mouse	LD50	intravenous	435mg/kg (435mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Journal of Pharmacology and Experimental Therapeutics. Vol. 179, Pg. 114, 1971.
mouse	LD50	oral	360mg/kg (360mg/kg)		Farmaco, Edizione Scientifica. Vol. 40, Pg. 334, 1985.
mouse	LD50	subcutaneous	475mg/kg (475mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1039, 1972.
mouse	LD50	unreported	1234mg/kg (1234mg/kg)		Journal of Clinical Pharmacology. Vol. 15, Pg. 311, 1975.
rat	LD50	intraperitoneal	354mg/kg (354mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 829, 1978.
rat	LD50	oral	248mg/kg (248mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 41, Pg. 1265, 1991.
rat	LD50	subcutaneous	928mg/kg (928mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Kiso to Rinsho. Clinical Report. Vol. 17, Pg. 1272, 1983.
women	LDLo	oral	200mg/kg/10D- (200mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	American Journal of Hematology. Vol. 58, Pg. 142, 1998.
women	TDLo	oral	40mg/kg/2D-I (40mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Scandinavian Journal of Rheumatology. Vol. 15, Pg. 401, 1986.
women	TDLo	oral	70mg/kg/W-I (70mg/kg)	LIVER: "JAUNDICE, CHOLESTATIC"	New England Journal of Medicine. Vol. 295, Pg. 1201, 1976.
women	TDLo	oral	126mg/kg/3W-I (126mg/kg)	LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)" LUNGS, THORAX, OR RESPIRATION: DYSPNEA BLOOD: EOSINOPHILIA	Japanese Journal of Medicine. Vol. 30, Pg. 32, 1991.
women	TDLo	oral	315mg/kg/3W-I (315mg/kg)	BEHAVIORAL: EXCITEMENT GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING	American Journal of Medicine. Vol. 89, Pg. 526, 1990.
women	TDLo	oral	900mg/kg/9W-I (900mg/kg)	SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE	Medical Journal of Australia. Vol. 151, Pg. 167, 1989.

5. Physical Properties of Naproxen

Physical Property	Value	Units	Temp (deg C)	Source
Melting Point	153	deg C		EXP
pKa Dissociation Constant	4.15	(none)		EXP
log P (octanol-water)	3.18	(none)		EXP
Water Solubility	15.9	mg/L	25	EXP
Vapor Pressure	1.89E-06	mm Hg	25	EST
Henry's Law Constant	3.39E-10	atm-m3/mole	25	EST
Atmospheric OH Rate Constant	1.16E-10	cm3/molecule-sec	25	EST

6. Preparation of Naproxen
Naproxen can be prepared by 2-(6-Methoxy-2-naphthyl)propenoic acid. This reaction will need reagent H₂, catalyst (+)PF₆(-) and solvents methanol and acetone. The reaction time is 2 hours at reaction temperature of 25 °C.

(+)-2-(Methoxy-2-naphthyl)-propionic acid can be prepared by 2-(6-Methoxy-2-naphthyl)propenoic acid

(+)-2-(Methoxy-2-naphthyl)-propionic acid can be prepared by 2-(6-Methoxy-2-naphthyl)propenoic acid

7. Uses of Naproxen
Naproxen can react with 2-bromo-cyclohexanone to get 2-Oxocyclohexyl 2-(6-methoxy-2-naphthyl)propionat. This reaction will need reagent Et₃N and solvent acetone. The reaction time is 3 hours by heating. The yield is about 58%.

(+)-2-(Methoxy-2-naphthyl)-propionic acid can react with 2-bromo-cyclohexanone to get 2-Oxocyclohexyl 2-(6-methoxy-2-naphthyl)propionat

8. Safety information of Naproxen
When you are using this chemical, please be cautious about it as the following: This chemical is harmful if swallowed. During using it, wear suitable protective clothing and gloves.

Product Name

Naproxen

Synthetic route

Naproxen Specification

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