Product Name

  • Name

    5-(Difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl) sulfinyl)-1H-benzimidazole sodium

  • EINECS 604-093-4
  • CAS No. 138786-67-1
  • Article Data25
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 199-202 °C
  • Formula C16H15F2N3NaO4S
  • Boiling Point 586.9oC at 760 mmHg
  • Molecular Weight 405.357
  • Flash Point 308.7oC
  • Transport Information
  • Appearance white to off-white solid
  • Safety 22-26-36/37/39-45
  • Risk Codes 20/21/22-37/38-41-48
  • Molecular Structure Molecular Structure of 138786-67-1 (5-(Difluoromethoxy)-2-(((3,4-dimethoxy-2-pyridinyl)methyl) sulfinyl)-1H-benzimidazole sodium)
  • Hazard Symbols HarmfulXn
  • Synonyms 1H-Benzimidazole,5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-, sodium salt (9CI);5-Difluoromethoxy-2-[[(3,4-dimethoxypyridin-2-yl)methyl]sulfinyl]-1H-benzimidazolesodium salt;Controloc;Pantecta;Pantoloc;Pantoprazolesodium salt;Protonix;Zurcal;1H-Benzimidazole, 6-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-, sodium salt (1:1);
  • PSA 94.68000
  • LogP 3.53580

Synthetic route

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
102625-70-7

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile at 20℃;95%
With sodium hydroxide In ethanol for 5h; Reflux;95%
With sodium hydroxide In water; ethyl acetate at 20℃; for 5.5h;92%
pantoprazole sulfide
102625-64-9

pantoprazole sulfide

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
Stage #1: pantoprazole sulfide With sodium hydroxide; tert-butylhypochlorite In dichloromethane; water at 0 - 5℃; for 1h;
Stage #2: With sodium hydroxide In water; acetone at 0 - 25℃; for 7h;		95%
Stage #1: pantoprazole sulfide With potassium tungstate dihydrate; dihydrogen peroxide at -5 - 0℃; for 4.5h; pH=3.5;
Stage #2: With sodium hydroxide In water at 20℃; Temperature; Reagent/catalyst;		78.7%
With sodium hypochlorite; sodium hydroxide In methanol; water at -20 - -5℃;
Stage #1: pantoprazole sulfide With sodium hypochlorite; sodium hydroxide In water; acetonitrile at -5 - 30℃;
Stage #2: With acetic acid In dichloromethane at 25 - 30℃; pH=8 - 8.5;
Stage #3: With sodium hydroxide In dichloromethane; water at 25 - 30℃; Concentration;
Stage #1: pantoprazole sulfide With sodium hypochlorite; water; sodium hydroxide In ethyl acetate at 0 - 10℃; for 7h;
Stage #2: With sodium thiosulfate In ethyl acetate for 0.333333h;
5-(difluoromethoxy)-2-mercapto-1H-benzimidazole
97963-62-7

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole

2-Chloromethyl-3,4-dimethoxy-pyridine; hydrochloride
72830-09-2

2-Chloromethyl-3,4-dimethoxy-pyridine; hydrochloride

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
Stage #1: 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole; 2-Chloromethyl-3,4-dimethoxy-pyridine; hydrochloride With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25 - 30℃; for 12h;
Stage #2: With sodium hydroxide; sodium hypochlorite In dichloromethane; water at 0 - 8℃; for 6h; Product distribution / selectivity;		83%
2-hydroxymethyl-3,4-dimethoxypyridine hydrochloride

2-hydroxymethyl-3,4-dimethoxypyridine hydrochloride

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole
97963-62-7

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
Stage #1: 2-hydroxymethyl-3,4-dimethoxypyridine hydrochloride With thionyl chloride In dichloromethane at 0 - 15℃; for 1h;
Stage #2: 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 10 - 30℃; for 12h; pH=10 - 11;
Stage #3: With sodium hydroxide; sodium hypochlorite In dichloromethane; water at 0 - 8℃; for 6h; Product distribution / selectivity;		79.6%
(5-difluoromethoxy)-2-[(4-chloro-3-methoxy-2-pyridinyl)methyl]thio-1H-benzimidazole
368890-20-4

(5-difluoromethoxy)-2-[(4-chloro-3-methoxy-2-pyridinyl)methyl]thio-1H-benzimidazole

sodium methylate
124-41-4

sodium methylate

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
In methanol at 50℃; Heating / reflux;70.8%
5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
409098-86-8

5-(difluoromethoxy)-2-[[(4-chloro-3-methoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
With sodium methylate In methanol at 50℃; Heating / reflux;70.8%
pantoprazole sulfide
102625-64-9

pantoprazole sulfide

A

5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole

5-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole

B

pantoprazole sodium
138786-67-1

pantoprazole sodium

C

Pantoprazole sulfone

Pantoprazole sulfone

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite In water; ethyl acetate at -5℃; for 1 - 1.5h; Product distribution / selectivity;A n/a
B 65%
C n/a
...Expand
5-(difluoromethoxy)-2-mercapto-1H-benzimidazole
97963-62-7

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / ethanol / 8 h / 80 °C
2: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / 0 °C
3: sodium hydroxide / ethanol / 5 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / water; methanol / 3.5 h / 40 - 55 °C
2: LACTIC ACID; peracetic acid / methanol; dichloromethane / 1 h / -25 - -20 °C
3: sodium hydroxide / water; acetone / 40 - 45 °C
View Scheme
sodium hydroxide
1310-73-2

sodium hydroxide

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
102625-70-7

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
In water; acetonitrile at 25 - 35℃; for 1h;
In ethanol; dichloromethane; water at 20℃; pH=12.5; Product distribution / selectivity;
2-chloromethyl-3,4-dimethoxypyridine hydrochloride

2-chloromethyl-3,4-dimethoxypyridine hydrochloride

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole
97963-62-7

5-(difluoromethoxy)-2-mercapto-1H-benzimidazole

pantoprazole sodium
138786-67-1

pantoprazole sodium

Conditions
ConditionsYield
Stage #1: 2-chloromethyl-3,4-dimethoxypyridine hydrochloride; 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole With sodium hydroxide In ethanol; water at 35℃; for 2h;
Stage #2: With sodium borate In ethanol at 45℃; for 2h;
Stage #3: With dihydrogen peroxide In water at 20℃; for 2.5h; Concentration; Temperature;		19.61 g
pantoprazole sodium
138786-67-1

pantoprazole sodium

zinc (S)-bis{[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)-methylsulphinyl]-1H-benzimidazolide}

zinc (S)-bis{[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)-methylsulphinyl]-1H-benzimidazolide}

Conditions
ConditionsYield
With zinc(II) chloride In water at 20℃; for 1.5h;95%
pantoprazole sodium
138786-67-1

pantoprazole sodium

magnesium {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

magnesium {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

Conditions
ConditionsYield
Stage #1: pantoprazole sodium With sodium hydroxide In water at 25℃; for 1h;
Stage #2: With magnesium chloride In water at 25℃; for 1h;		94.6%
pantoprazole sodium
138786-67-1

pantoprazole sodium

zinc(II) chloride
7646-85-7

zinc(II) chloride

zinc {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

zinc {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

Conditions
ConditionsYield
Stage #1: pantoprazole sodium With sodium hydroxide In water at 25℃; for 1h;
Stage #2: zinc(II) chloride In water at 25℃; for 20h;		94.2%
(S)-1,1,2-triphenyl-1,2-ethanediol
108998-83-0

(S)-1,1,2-triphenyl-1,2-ethanediol

pantoprazole sodium
138786-67-1

pantoprazole sodium

C20H18O2*C16H15F2N3O4S

C20H18O2*C16H15F2N3O4S

Conditions
ConditionsYield
With acetic acid In ethanol for 0.5h; pH=7 - 8; Reflux; Industrial scale;94%
pantoprazole sodium
138786-67-1

pantoprazole sodium

pantoprazole sodium sesquihydrate

pantoprazole sodium sesquihydrate

Conditions
ConditionsYield
With water In tert-butyl methyl ether at 20 - 30℃; for 12h; Product distribution / selectivity;92.4%
With water In di-isopropyl ether at 20 - 30℃; for 1 - 12h; Product distribution / selectivity;91.93%
With water In diethyl ether at 20 - 30℃; for 12h; Product distribution / selectivity;91.93%
With water at 0 - 35℃; Product distribution / selectivity;91.4%
With water In dichloromethane at 25 - 35℃; for 1.5h; Product distribution / selectivity;
pantoprazole sodium
138786-67-1

pantoprazole sodium

clcium {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

clcium {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

Conditions
ConditionsYield
Stage #1: pantoprazole sodium With sodium hydroxide In water at 25℃; for 1h;
Stage #2: With calcium chloride In water at 25℃; for 20h;		91.8%
pantoprazole sodium
138786-67-1

pantoprazole sodium

calcium bis{[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)-methylsulphinyl]-1H-benzimidazolide}

calcium bis{[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)-methylsulphinyl]-1H-benzimidazolide}

Conditions
ConditionsYield
With calcium chloride In water at 20℃; for 1.91667h;73%
pantoprazole sodium
138786-67-1

pantoprazole sodium

magnesium {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

magnesium {[5-(difluoromethoxy)]-2-[(3,4-dimethoxy-2-pyridinyl)methylsulphinyl]-1H-benzimidazolide} hydroxy

Conditions
ConditionsYield
Stage #1: pantoprazole sodium With sodium hydroxide In water at 25℃; for 0.25h;
Stage #2: With magnesium chloride In water at 25℃; for 2.5h;		52.7%
pantoprazole sodium
138786-67-1

pantoprazole sodium

magnesium bis[5-[difluoromethoxy]-2-[[3,4-dimethoxy-2-pyridinyl]-methylsulfinyl]-1H-benzimidazolide]

magnesium bis[5-[difluoromethoxy]-2-[[3,4-dimethoxy-2-pyridinyl]-methylsulfinyl]-1H-benzimidazolide]

Conditions
ConditionsYield
With magnesium chloride In water at 20 - 30℃; for 21 - 22h;
pantoprazole sodium
138786-67-1

pantoprazole sodium

pantoprazole sodium

pantoprazole sodium

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 24h; Heating / reflux;
In tert-butyl methyl ether; acetonitrile at 20℃; for 48h;
at 100℃;
3-chlorosulfonylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-72-2

3-chlorosulfonylbenzoic acid 2-(toluene-4-sulfonyl)ethyl ester

pantoprazole sodium
138786-67-1

pantoprazole sodium

A

3-[5-difluoromethoxy-2-{(3,4-dimethoxy-pyridin-2-yl)-methanesulfinyl}-benzimidazole-1-sulfonyl]benzoic acid 2-(toluene-4-sulfonyl)ethyl ester

3-[5-difluoromethoxy-2-{(3,4-dimethoxy-pyridin-2-yl)-methanesulfinyl}-benzimidazole-1-sulfonyl]benzoic acid 2-(toluene-4-sulfonyl)ethyl ester

B

3-[6-difluoromethoxy-2-{(3,4-dimethoxy-pyridin-2-yl)-methanesulfinyl}-benzimidazole-1-sulfonyl]benzoic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-78-8

3-[6-difluoromethoxy-2-{(3,4-dimethoxy-pyridin-2-yl)-methanesulfinyl}-benzimidazole-1-sulfonyl]benzoic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate; triethylamine In dichloromethane at 20℃; for 1.5h;
...Expand
(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-13-1

(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester

pantoprazole sodium
138786-67-1

pantoprazole sodium

A

4-[5-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

4-[5-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

B

4-[6-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-69-7

4-[6-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate; triethylamine In dichloromethane
With sodium hydrogencarbonate; triethylamine In dichloromethane Inert atmosphere;
...Expand
pantoprazole sodium
138786-67-1

pantoprazole sodium

A

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)-chloromethyl]sulfinyl]-1H-benzimidazole
812664-93-0

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)-chloromethyl]sulfinyl]-1H-benzimidazole

B

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)chlorohydroxymethyl]sulfinyl]-1H-benzimidazole
812664-94-1

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)chlorohydroxymethyl]sulfinyl]-1H-benzimidazole

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite In water; acetonitrile at 20℃; for 12h;
pantoprazole sodium
138786-67-1

pantoprazole sodium

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
102625-70-7

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

Conditions
ConditionsYield
Stage #1: pantoprazole sodium With ethanol
Stage #2: With water
pantoprazole sodium
138786-67-1

pantoprazole sodium

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole sodium salt monohydrate
797789-88-9

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole sodium salt monohydrate

Conditions
ConditionsYield
In acetone Purification / work up; Heating / reflux;
With water In ethyl acetate; acetone at 0 - 55℃; for 2.25h; Product distribution / selectivity;
With water In ethyl acetate at 0 - 5℃; for 2h; Product distribution / selectivity;
pantoprazole sodium
138786-67-1

pantoprazole sodium

pantoprazole sodium sesquihydrate

pantoprazole sodium sesquihydrate

Conditions
ConditionsYield
With water In ethyl acetate; acetone at 0 - 55℃; for 2.25h; Product distribution / selectivity;
With water In ethyl acetate at 0 - 5℃; for 2h; Product distribution / selectivity;
(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester
651728-13-1

(4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester

pantoprazole sodium
138786-67-1

pantoprazole sodium

A

4-[6-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid sodium salt

4-[6-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid sodium salt

B

4-[5-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid sodium salt

4-[5-difluoromethoxy-2-{(3,4-dimethoxypyridin-2-yl)methanesulfinyl}benzimidazole-1-sulfonyl]phenoxyacetic acid sodium salt

Conditions
ConditionsYield
Stage #1: (4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester; pantoprazole sodium With sodium hydrogencarbonate; triethylamine In dichloromethane Inert atmosphere;
Stage #2: With water; sodium hydrogencarbonate In acetonitrile at 65℃; for 5h; Inert atmosphere;
...Expand
pantoprazole sodium
138786-67-1

pantoprazole sodium

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C16H14F2N3O4S(1-)*C42H70O35*Na(1+)

C16H14F2N3O4S(1-)*C42H70O35*Na(1+)

Conditions
ConditionsYield
In water

Pantoprazole sodium Specification

The Pantoprazole sodium, with the CAS registry number 138786-67-1, is also known as 1H-Benzimidazole, 6-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-, sodium salt (1:1). It belongs to the product categories of Active Pharmaceutical Ingredients; Antibiotic Explorer; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Pantoprazole; Aromatics; Heterocycles; Sulfur & Selenium Compounds. This chemical's molecular formula is C16H15F2N3NaO4S and molecular weight is 406.36. What's more, its systematic name is 5-(Difluoromethoxy)-2-{[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl}-1H-benzimidazole - sodium (1:1). Its classification code is Drug / Therapeutic Agent. This chemical is an antiulcerative and a gastric pump inhibitor.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to respiratory system and skin. This substance has a risk of serious damage to eyes and has a danger of serious damage to health by prolonged exposure. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: COc1ccnc(c1OC)CS(=O)c2[nH]c3ccc(cc3n2)OC(F)F.[NaH]
(2)Std. InChI: InChI=1S/C16H15F2N3O4S.Na.H/c1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16;;/h3-7,15H,8H2,1-2H3,(H,20,21);;
(3)Std. InChIKey: WOLQSLCSAWUFCD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 395mg/kg (395mg/kg)   Drugs of the Future. Vol. 15, Pg. 801, 1990.
mouse LD50 oral > 1gm/kg (1000mg/kg)   Drugs of the Future. Vol. 15, Pg. 801, 1990.
rat LD50 intravenous 256mg/kg (256mg/kg)   Drugs of the Future. Vol. 15, Pg. 801, 1990.
rat LD50 oral 747mg/kg (747mg/kg)   Drugs of the Future. Vol. 15, Pg. 801, 1990.

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