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| CAS No.: | 22204-53-1 |
|---|---|
| Name: | Naproxen |
| Article Data: | 203 |
| Molecular Structure: | |
|
|
|
| Formula: | C14H14O3 |
| Molecular Weight: | 230.263 |
| 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; |
| EINECS: | 244-838-7 |
| Density: | 1.197 g/cm3 |
| Melting Point: | 152-154 °C(lit.) |
| Boiling Point: | 403.888 °C at 760 mmHg |
| Flash Point: | 154.529 °C |
| Solubility: | Insoluble in water. |
| Appearance: | White or almost white crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 36/37 |
| Transport Information: | UN 2811 6.1/PG 3 |
| PSA: | 46.53000 |
| LogP: | 3.03650 |
- 483366-12-7(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
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- 82993-81-5D-threo-Ritalinic acid hydrochloride
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- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 240444-70-62,3,5,6-Tetrafluor-4-(methoxymethyl)benzyl-2,2-dimethyl-3-(prop-1-en-1-yl)cyclopropancarboxylat
- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
B
- 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
| 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 | 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; |
- 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 | Yield |
|---|---|
| With triethylamine | 98% |
- 26159-34-2
Naprelan
- 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol at 20℃; | 98% |
| With hydrogenchloride In water pH=< 2; Inert atmosphere; | 94.3% |
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 | 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 | 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% |
- 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
| 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% |
- 22204-53-1
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
| 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 | 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 | Yield |
|---|---|
| With sodium dihydrogenphosphate; sodium chlorite In water at 20℃; for 1h; | 96% |
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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.jpg)
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.png)
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.