CAS No.112529-15-4,[5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride Suppliers

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Basic Information

Molecular Structure:
CAS No.:	112529-15-4
Name:	[5-[[4-[2-(5-Ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-] thiazolidinedione hydrochloride
Article Data:	16

Formula:	C₁₉H₂₁ClN₂O₃S
Molecular Weight:	392.906
Synonyms:	(+-)-5-(p-(2-(5-Ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione monohydrochloride;Actos;2,4-Thiazolidinedione,5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-, monohydrochloride (9CI);2,4-Thiazolidinedione, 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-,monohydrochloride, (?à)-;5-[4-[2-(5-Ethyl-2-pyridyl)ethoxy]benzyl]thiazolidine-2,4-dionehydrochloride;Pioglitazone HCl;
EINECS:	629-731-9
Density:	1.26 g/cm³
Melting Point:	193-194 ºC
Boiling Point:	575.4 ºC at 760 mmHg
Flash Point:	301.8 ºC
Solubility:	soluble in N,N-dimethylformamide, slightly soluble in anhydrous ethanol, very slightly soluble in acetone and acetonitrile, practically insoluble in water, and insoluble in ether
Appearance:	white crystals or crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/38
Safety:	22-24/25
PSA:	93.59000
LogP:	4.29040

Synthetic route

: 105355-27-9
Pioglitazone

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 10 - 65℃; for 4.25h; Product distribution / selectivity;	95%
With hydrogenchloride In ethanol; water at 10 - 65℃; for 4.25h; Product distribution / selectivity;	90%
With hydrogenchloride In methanol; water at 20℃; for 1h;	90.5%

: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-thiazolidine-2,4-dione hydrogen chloride

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Stage #1: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-thiazolidine-2,4-dione hydrogen chloride With hydrogen; palladium 10% on activated carbon In methanol; water at 50 - 60℃; under 3750.38 - 4500.45 Torr; for 15h; Stage #2: With hydrogenchloride In water at 0 - 5℃; for 3h;	84%

: 5223-06-3
5-ethyl-2-(2-hydroxyethyl)pyridine

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 63 percent / NaH / dimethylformamide 2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 4: 53 percent / NaOAc / ethanol / Heating 5: 2N HCl / 6 h / Heating 6: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme
Multi-step reaction with 10 steps 1: dihydrogen peroxide / acetic acid / 14 h / 100 °C 2: 0.5 h / 120 °C 3: sodium hydroxide / water / 2 h / 40 °C 4: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 5: N,N-dimethyl-formamide / 14 h / 80 °C 6: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 7: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 8: triethylamine / dichloromethane / 2 h / 0 °C 9: acetic acid; sodium tetrahydroborate / 15 h / 40 - 45 °C 10: hydrogenchloride / water; ethanol View Scheme
Multi-step reaction with 10 steps 1: dihydrogen peroxide / acetic acid / 14 h / 100 °C 2: 0.5 h / 120 °C 3: sodium hydroxide / water / 2 h / 40 °C 4: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 5: N,N-dimethyl-formamide / 14 h / 80 °C 6: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 7: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 8: triethylamine 9: acetic acid; sodium tetrahydroborate / 15 h / 40 - 45 °C 10: hydrogenchloride / water; ethanol View Scheme

: 85583-40-0
4-[2-(5-ethylpyridin-2-yl)ethoxy]aniline

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 2: 53 percent / NaOAc / ethanol / Heating 3: 2N HCl / 6 h / Heating 4: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

: 85583-54-6
4-(2-(5-ethyl-2-pyridyl)ethoxy)nitrobenzene

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 53 percent / NaOAc / ethanol / Heating 4: 2N HCl / 6 h / Heating 5: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

: 105355-25-7
methyl 2-bromo-3-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]phenyl}propionate

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 53 percent / NaOAc / ethanol / Heating 2: 2N HCl / 6 h / Heating 3: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

: 105355-26-8
5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2N HCl / 6 h / Heating 2: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme
With hydrogenchloride; water for 15h; Product distribution / selectivity; Heating / reflux;
Stage #1: 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2-imino-4-thiazolidinone With methanol; oxalic acid In dichloromethane at 20℃; for 0.5h; Stage #2: With hydrogenchloride; water for 12h; Product distribution / selectivity; Heating / reflux;

: 350-46-9
4-Fluoronitrobenzene

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 63 percent / NaH / dimethylformamide 2: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 3: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 4: 53 percent / NaOAc / ethanol / Heating 5: 2N HCl / 6 h / Heating 6: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

: 674798-32-4
2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propionic acid

: 17356-08-0
thiourea

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-bromo-3-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}propionic acid; thiourea With sodium acetate In ethanol for 3h; Heating / reflux; Stage #2: With hydrogenchloride In ethanol; water for 18h; Heating / reflux; Stage #3: With ammonia In ethanol; water at 20℃;

: 1034515-30-4
5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]-benzyl}-2-morpholin-4-yl-thiazol-4-one

: 112529-15-4
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; water; isopropyl alcohol for 8h; Product distribution / selectivity; Heating / reflux;

Raw Materials

Downstream Products

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Chemistry

IUPAC Name: 5-[[4-[2-(5-Ethylpyridin-2-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione hydrochloride
Molecular Formula: C₁₉H₂₁ClN₂O₃S
Molecular Weight: 392.90 g/mol
Canonical SMILES: CCC1=CN=C(C=C1)CCOC2=CC=C(C=C2)CC3C(=O)NC(=O)S3.Cl
InChI: InChI=1/C19H20N2O3S.ClH/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17;/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23);1H
Classification Code: Antidiabetic
Product Categories: Active Pharmaceutical Ingredients; Antidiabetic; Diabetes; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds;API's; Pioglitazone
H-Bond Donor: 2
H-Bond Acceptor: 4
Rotatable Bond Count: 7
Tautomer Count: 10
Exact Mass: 392.096141
MonoIsotopic Mass: 392.096141
Topological Polar Surface Area: 68.3
Heavy Atom Count: 26
Complexity: 466
Melting Point: 193-194 °C
Flash Point: 301.8 °C
Enthalpy of Vaporization: 86.19 kJ/mol
Boiling Point: 575.4 °C at 760 mmHg
Vapour Pressure of Pioglitazone HCl (CAS NO.112529-15-4): 3.03E-13 mmHg at 25 °C

Uses

Pioglitazone HCl (CAS NO.112529-15-4) is used as an antidiabetic.

Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/38
R36/38: Irritating to eyes and skin.
Safety Statements of Pioglitazone HCl (CAS NO.112529-15-4): 22-24/25
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.

Specification

Pioglitazone HCl (CAS NO.112529-15-4), its Synonyms are 2,4-Thiazolidinedione, 5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-, monohydrochloride, (+-)- ; (+-)-5-(p-(2-(5-Ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione monohydrochloride ; Pioglitazone hydrochloride ; Actos . It is colourless prisms.