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80382-23-6

Basic Information
CAS No.: 80382-23-6
Name: Loxoprofen sodium
Article Data: 10
Molecular Structure:
Molecular Structure of 80382-23-6 (Loxoprofen sodium)
Formula: C15H17NaO3
Molecular Weight: 268.288
Synonyms: Benzeneaceticacid, a-methyl-4-[(2-oxocyclopentyl)methyl]-,sodium salt (9CI);CS 600;CS 600 (antiinflammatory);Loxonin;Loxoprofensodium;Sodium 2-[4-[(2-Oxocyclopentyl)methyl]phenyl]propionate;Sodiumloxoprofen;
EINECS: 1806241-263-5
Boiling Point: 417.9 °C at 760 mmHg
Flash Point: 220.7 °C
PSA: 57.20000
LogP: 1.45170
Synthetic route
Conditions
ConditionsYield
With sodium hydroxide In ethanol; water for 2h; Reflux;96.6%
With methanol; sodium hydroxide for 1h;95%
With sodium hydroxide In ethanol at 50℃; for 2h;90.3%
111128-12-2

2-(4-(bromomethyl)phenyl)propanoic acid

611-10-9

2-ethoxycarbonyl-1-cyclopentanone

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Stage #1: 2-[4-(bromomethyl)phenyl]propanoic acid; 2-ethoxycarbonyl-1-cyclopentanone With sodium hydroxide In N,N-dimethyl-formamide under 760.051 Torr; for 8h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=5 - 6; Further stages;
92%
2362-36-9

1-(1-chloroethyl)-4-methylbenzene

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: magnesium / tetrahydrofuran / 1.5 h / 20 - 30 °C / Inert atmosphere
2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / dichloromethane / Reflux
3: sulfuric acid / 16 h / 0 - 5 °C
4: sodium periodate / N,N-dimethyl-formamide / 150 °C
5: hydrogenchloride / water / 4.5 h / Reflux
6: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 10 - 15 °C / 1125.11 Torr / Autoclave
7: sodium hydroxide / ethanol / 1 h / Reflux
View Scheme
938-94-3

(R,S)-2-(4'-methylphenyl) propionic acid

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / dichloromethane / Reflux
2: sulfuric acid / 16 h / 0 - 5 °C
3: sodium periodate / N,N-dimethyl-formamide / 150 °C
4: hydrogenchloride / water / 4.5 h / Reflux
5: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 10 - 15 °C / 1125.11 Torr / Autoclave
6: sodium hydroxide / ethanol / 1 h / Reflux
View Scheme
111128-12-2

2-(4-(bromomethyl)phenyl)propanoic acid

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid / 16 h / 0 - 5 °C
2: sodium periodate / N,N-dimethyl-formamide / 150 °C
3: hydrogenchloride / water / 4.5 h / Reflux
4: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 10 - 15 °C / 1125.11 Torr / Autoclave
5: sodium hydroxide / ethanol / 1 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sulfuric acid / toluene / 35 °C
1.2: 5 h / 281 °C
2.1: sodium methylate / toluene; dimethyl sulfoxide; methanol / 1.5 h / 2 - 5 °C
2.2: 5 - 18 °C
3.1: acetic acid; sulfuric acid / water / 2 h / 110 °C
4.1: sodium hydroxide / acetone / 30 °C / pH 7.2
View Scheme
Multi-step reaction with 4 steps
1: sulfuric acid / 6 h / 0 - 5 °C
2: potassium carbonate / toluene / 12 h / Reflux
3: hydrogen bromide; acetic acid / 8 h / Reflux
4: sodium hydroxide / ethanol; water / 3 h / 20 °C / pH 7 - 8
View Scheme
Multi-step reaction with 4 steps
1: sulfuric acid / 6 h / Cooling with ice
2: toluene / 12 h / 110 °C
3: sodium hydroxide; water / toluene / 2 h / 80 °C
4: sodium hydroxide / ethanol / 2 h / 50 °C
View Scheme
99807-54-2

2-(4-bromomethylphenyl)propionic acid methyl ester

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium periodate / N,N-dimethyl-formamide / 150 °C
2: hydrogenchloride / water / 4.5 h / Reflux
3: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 10 - 15 °C / 1125.11 Torr / Autoclave
4: sodium hydroxide / ethanol / 1 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium methylate / toluene; dimethyl sulfoxide; methanol / 1.5 h / 2 - 5 °C
1.2: 5 - 18 °C
2.1: acetic acid; sulfuric acid / water / 2 h / 110 °C
3.1: sodium hydroxide / acetone / 30 °C / pH 7.2
View Scheme
Multi-step reaction with 2 steps
1.1: sodium carbonate / acetone
2.1: hydrogenchloride / acetic acid / Reflux
2.2: Reflux
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / toluene / 12 h / Reflux
2: hydrogen bromide; acetic acid / 8 h / Reflux
3: sodium hydroxide / ethanol; water / 3 h / 20 °C / pH 7 - 8
View Scheme
Multi-step reaction with 3 steps
1: toluene / 12 h / 110 °C
2: sodium hydroxide; water / toluene / 2 h / 80 °C
3: sodium hydroxide / ethanol / 2 h / 50 °C
View Scheme
63476-54-0

2-(4-formylphenyl)propionic acid methyl ester

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 4.5 h / Reflux
2: 5%-palladium/activated carbon; hydrogen / methanol / 14 h / 10 - 15 °C / 1125.11 Torr / Autoclave
3: sodium hydroxide / ethanol / 1 h / Reflux
View Scheme
81762-92-7

loxoprofen methyl ester

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 1h; Reflux;35.36 g

C14H19BrO2

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium; iodine / tetrahydrofuran / 20 - 25 °C
1.2: 0 - 20 °C
2.1: hydrogenchloride / methanol; water / 0 °C / Reflux
2.2: 0 °C / Reflux
3.1: sodium hydroxide; methanol / 1 h
View Scheme
589-15-1

1-bromomethyl-4-bromobenzene

80382-23-6

sodium 2-<4-<(2-oxocyclopentyl)methyl>phenyl>propionate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium methylate / methanol / Reflux
2.1: acetic acid; hydrogenchloride / water / Reflux
3.1: pyridinium p-toluenesulfonate / methanol / 45 - 50 °C
4.1: magnesium; iodine / tetrahydrofuran / 20 - 25 °C
4.2: 0 - 20 °C
5.1: hydrogenchloride / methanol; water / 0 °C / Reflux
5.2: 0 °C / Reflux
6.1: sodium hydroxide; methanol / 1 h
View Scheme
Raw Materials
68767-14-6
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    Name: Loxoprofen Sodium CAS:80382-23-6 MF: C15H17NaO3 Appearance:White Powder Storage:Store in cool and dry place, away from sun light. Package:25kg Application:API Transportation:By sea or by air Port:Qingdao Port

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    1.Prompt Goods; 2.Flexible payment terms; 3.Documents & Certificate support. Name: Loxoprofen sodium Molecular Structure: Formula: C15H17NaO3 Molecular Weight : 268.28 Synonyms: alpha-methyl-4-((2-oxocyclopentyl)methyl)benzeneacetatesodiu

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 Loxoprofen (CAS NO.80382-23-6) Market Research Report 2009

Specification

The Loxoprofen sodium, with the CAS registry number 80382-23-6, is also known as Benzeneaceticacid, a-methyl-4-[(2-oxocyclopentyl)methyl]-,sodium salt (9CI). It belongs to the product categories of APIS; Aromatics; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C15H17NaO3 and molecular weight is 268.28. What's more, its systematic name is Sodium 2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoate.

Physical properties about Loxoprofen sodium (CAS 80382-23-6) are: (1)ACD/LogP: 1.866; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5): 0.73; (4)ACD/LogD (pH 7.4):  -1.07; (5)ACD/BCF (pH 5.5):  1.12; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  17.90; (8)ACD/KOC (pH 7.4):  1.00; (9)#H bond acceptors:  3; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  4; (12)Polar Surface Area:  54.37 Å2; (13)Flash Point:  220.7 °C; (14)Enthalpy of Vaporization:  70.78 kJ/mol; (15)Boiling Point:  417.9 °C at 760 mmHg; (16)Vapour Pressure:  9.92E-08 mmHg at 25°C.

Preparation of Loxoprofen sodium (CAS 80382-23-6): it can be produced by ethyl 2-oxocyclopentanecarboxylate (I) with ethyl 2-(4-chloromethylphenyl)propionate (II) by means of KOH in hot DMF. The reaction gives ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionate (III), which is then hydrolyzed and decarboxylated by treatment with 47% HBr in refluxing dioxane.

Loxoprofen sodium can be produced by ethyl 2-oxocyclopentanecarboxylate (I) and ethyl 2-(4-chloromethylphenyl)propionate.

Uses of Loxoprofen sodium (CAS 80382-23-6): it is a non-steroidal anti-inflammatory drug which is used for chronic and wet arthritis, deformability arthropathy, waist pain and periarthritis of shoulder. It's the sodium salt of Loxoprofen marketed in Brazil, Mexico and Japan by Sankyo.

You can still convert the following datas of Loxoprofen sodium (CAS 80382-23-6) into molecular structure:
(1) SMILES:[Na+].O=C2C(Cc1ccc(cc1)C(C([O-])=O)C)CCC2
(2) Std. InChI:InChI=1S/C15H18O3.Na/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16;/h5-8,10,13H,2-4,9H2,1H3,(H,17,18);/q;+1/p-1
(3) Std. InChIKey:WORCCYVLMMTGFR-UHFFFAOYSA-M