Product Name

  • Name

    OMEPRAZOLE

  • EINECS 201-212-8
  • CAS No. 119141-89-8
  • Article Data41
  • CAS DataBase
  • Density 1.37 g/cm3
  • Solubility H2O: 0.5 mg/mL
  • Melting Point
  • Formula C17H19N3O3S
  • Boiling Point 600 °C at 760 mmHg
  • Molecular Weight 345.422
  • Flash Point 316.7 °C
  • Transport Information
  • Appearance white solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 119141-89-8 (OMEPRAZOLE)
  • Hazard Symbols IrritantXi
  • Synonyms 1H-Benzimidazole,5-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- (9CI);1H-Benzimidazole-1-acetic acid,5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, (+)-;(+)-Omeprazole;(R)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole;(R)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole;(R)-Esomeprazole;1H-Benzimidazole,5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, (R)-;(R)-Omeprazole;
  • PSA 96.31000
  • LogP 3.76540

Synthetic route

omeprazole sulfide
73590-85-9

omeprazole sulfide

(R)-omeprazole
119141-89-8

(R)-omeprazole

Conditions
ConditionsYield
With C68H72N4O10Ti2; dihydrogen peroxide In water; ethyl acetate at 0℃; for 24h; Reagent/catalyst; enantioselective reaction;93.5%
With N-methyl-6-aza-5β,6β-epoxy-cholestane-3β-tert-butyldiphenylsilyloxy tetrafluoroborate In dichloromethane at -70 - 20℃; for 3h; Inert atmosphere; enantioselective reaction;86%
With tert.-butylhydroperoxide In water; toluene at -20℃; for 12h;n/a
omeprazole
73590-58-6

omeprazole

(R)-omeprazole
119141-89-8

(R)-omeprazole

Conditions
ConditionsYield
enantiomeric resolution; inclusion complexation with (R)-(+)-2,2'-dihydroxy-1,1'-binaphthyl;
omeprazole sodium

omeprazole sodium

(R)-omeprazole
119141-89-8

(R)-omeprazole

Conditions
ConditionsYield
Stage #1: omeprazole sodium With diethyl (2S,3S)-tartrate; (S)-Mandelic acid; titanium(IV)isopropoxide; triethylamine In acetone at 35 - 40℃; for 0.25 - 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane for 0.25 - 0.5h;
omeprazole
73590-58-6

omeprazole

A

(R)-omeprazole
119141-89-8

(R)-omeprazole

B

esomeprazole
119141-88-7

esomeprazole

Conditions
ConditionsYield
With triethylamine In methanol Purification / work up; Chiral supercritical fluid chromatography; Resolution of racemate;
With N,N-dimethyl-ethanamine In ethanol Purification / work up; Chiral supercritical fluid chromatography; Resolution of racemate;
With N,N-dimethyl-ethanamine In methanol Purification / work up; Chiral supercritical fluid chromatography; Resolution of racemate;
1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole
1138242-22-4

1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole

(R)-omeprazole
119141-89-8

(R)-omeprazole

Conditions
ConditionsYield
Stage #1: 1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole; 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole; 1-(S)-camphor sulfonyl-6-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole; 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole With methanol at 25℃; for 0.5h;
Stage #2: With methanol; sodium hydroxide; water at 25℃; for 3.16667h;
Stage #3: With water; acetic acid In methanol pH=6.8;
...Expand
omeprazole sulfide
73590-85-9

omeprazole sulfide

A

(R)-omeprazole
119141-89-8

(R)-omeprazole

B

esomeprazole
119141-88-7

esomeprazole

Conditions
ConditionsYield
With 1,2:4,5-di-O-cyclohexylidene-D-fructopyranose; Cumene hydroperoxide; vanadium(V) oxytripropoxide; N-ethyl-N,N-diisopropylamine In water; ethyl acetate at 20 - 55℃; for 20.1667 - 20.25h; Product distribution / selectivity;
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate; 1,2:4,5-di-O-cyclohexylidene-β-D-erythro-hexo-2,3-diulopyranose In acetonitrile at -10 - 20℃; for 3.16667 - 3.25h; Product distribution / selectivity;
Stage #1: omeprazole sulfide With diethyl (2S,3S)-tartrate; titanium(IV) isopropylate In water; toluene at 55℃; for 1h;
Stage #2: With Cumene hydroperoxide In water; toluene at 30℃; for 4.5h; Further stages. Title compound not separated from byproducts.;
omeprazole sulfide
73590-85-9

omeprazole sulfide

A

(R)-omeprazole
119141-89-8

(R)-omeprazole

B

omeprazole sulphone

omeprazole sulphone

C

esomeprazole
119141-88-7

esomeprazole

Conditions
ConditionsYield
Stage #1: omeprazole sulfide With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In water at 20 - 70℃; for 1.5h; Heating / reflux;
Stage #2: With Cumene hydroperoxide In water at 20℃; Product distribution / selectivity;
Stage #1: omeprazole sulfide With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate In dichloromethane; water at 20 - 70℃; for 1.5h; Heating / reflux;
Stage #2: With Cumene hydroperoxide In dichloromethane; water at 20℃; Product distribution / selectivity;
With dihydrogen peroxide; Mn-complex of (R,R)-1,2-bis(3,5-di-tert-butyl-2-hydroxybenzylamino)cyclohexane In water; acetonitrile at -10℃; for 5h; Product distribution / selectivity;A n/a
B n/a
C n/a
...Expand
3C8H8O3*C8H14O6*C12H28O4Ti*C17H19N3O3S

3C8H8O3*C8H14O6*C12H28O4Ti*C17H19N3O3S

(R)-omeprazole
119141-89-8

(R)-omeprazole

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.5h; Product distribution / selectivity;
1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R/S)-sulfinyl]-1H-benzimidazole

1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R/S)-sulfinyl]-1H-benzimidazole

A

(R)-omeprazole
119141-89-8

(R)-omeprazole

B

esomeprazole
119141-88-7

esomeprazole

Conditions
ConditionsYield
Stage #1: 1-(S)-camphor sulfonyl-5-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R/S)-sulfinyl]-1H-benzimidazole With water; sodium hydroxide at 25℃; for 6.5h;
Stage #2: With hydrogenchloride In dichloromethane; water pH=7.0; Product distribution / selectivity;
omeprazole sodium

omeprazole sodium

A

(R)-omeprazole
119141-89-8

(R)-omeprazole

B

esomeprazole
119141-88-7

esomeprazole

Conditions
ConditionsYield
Stage #1: omeprazole sodium With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate; water; triethylamine In acetone at 35 - 40℃;
Stage #2: With (S)-Mandelic acid In acetone at 35 - 40℃; for 2h;
Stage #3: With sodium hydrogencarbonate In dichloromethane; water for 0.5h; Concentration;		A n/a
B n/a
(R)-omeprazole
119141-89-8

(R)-omeprazole

5-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole sodium salt

5-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole sodium salt

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 0.5h;95%
With sodium hydroxide In methanol at 5 - 10℃; for 0.75 - 1.5h;
(R)-omeprazole
119141-89-8

(R)-omeprazole

(R)-esomeprazole potassium salt

(R)-esomeprazole potassium salt

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 0.5h; Product distribution / selectivity;94.1%
With potassium hydroxide In methanol at 5 - 10℃; for 0.75 - 1.5h;
(R)-omeprazole
119141-89-8

(R)-omeprazole

esomeprazole magnesium dihydrate

esomeprazole magnesium dihydrate

Conditions
ConditionsYield
With magnesium chloride In methanol; water at 20℃; for 0.5h;90%
chloromethyl (1R)-endo-(+)-fenchyl ether

chloromethyl (1R)-endo-(+)-fenchyl ether

(R)-omeprazole
119141-89-8

(R)-omeprazole

A

5-Methoxy-2-((R)-4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1-((1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxymethyl)-1H-benzoimidazole

5-Methoxy-2-((R)-4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1-((1R,2R,4S)-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yloxymethyl)-1H-benzoimidazole

B

6-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-(R)-sulfinyl}-1-({[(1R-endo)-1,3,3-trimethylbicyclo[2.2.1]hept-=2-yl]oxy}methyl)-1H-benzimidazole

6-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-(R)-sulfinyl}-1-({[(1R-endo)-1,3,3-trimethylbicyclo[2.2.1]hept-=2-yl]oxy}methyl)-1H-benzimidazole

...Expand
(R)-omeprazole
119141-89-8

(R)-omeprazole

(-)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulphinyl]-1H-benzimidazole magnesium

(-)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulphinyl]-1H-benzimidazole magnesium

Conditions
ConditionsYield
Stage #1: With magnesium In methanol; dichloromethane for 1 - 2h;
Stage #2: (R)-omeprazole In methanol; dichloromethane at 5 - 10℃; for 0.25 - 0.5h;
(R)-omeprazole
119141-89-8

(R)-omeprazole

magnesium R-omeprazole

magnesium R-omeprazole

Conditions
ConditionsYield
Stage #1: (R)-omeprazole With magnesium ethylate In methanol; ethanol for 48h;
Stage #2: With water In methanol for 1h;
(R)-omeprazole
119141-89-8

(R)-omeprazole

S-omeprazole magnesium

S-omeprazole magnesium

Conditions
ConditionsYield
With magnesium methanolate In methanol at 20℃; for 0.5h;n/a

1H-Benzimidazole,6-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- Specification

The 1H-Benzimidazole,6-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- is an organioc compound with the formula C17H19N3O3S. The IUPAC name of this chemical is 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole. With the CAS registry number 119141-89-8, it is also named as Omeprazole. The product's categories are Chiral Reagents; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals. It is white solid.

The other characteristics of 1H-Benzimidazole,6-methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- can be summarized as: (1)ACD/LogP: 2.17; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.11; (4)ACD/LogD (pH 7.4): 2.17; (5)ACD/BCF (pH 5.5): 22.95; (6)ACD/BCF (pH 7.4): 26.19; (7)ACD/KOC (pH 5.5): 315.1; (8)ACD/KOC (pH 7.4): 359.55; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 85.45 Å2; (13)Index of Refraction: 1.669; (14)Molar Refractivity: 94.02 cm3; (15)Molar Volume: 251.8 cm3; (16)Surface Tension: 75.1 dyne/cm; (17)Enthalpy of Vaporization: 89.31 kJ/mol; (18)Vapour Pressure: 2.35E-14 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Tautomer Count: 2; (21)Exact Mass: 345.114712; (22)MonoIsotopic Mass: 345.114712; (23)Topological Polar Surface Area: 96.3; (24)Heavy Atom Count: 24; (25)Complexity: 453.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=S(c2nc1ccc(OC)cc1n2)Cc3ncc(c(OC)c3C)C
2. InChI:InChI=1/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20) 
3. InChIKey:SUBDBMMJDZJVOS-UHFFFAOYAZ

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