169905-10-6

Basic information

• Product Name: 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE
• Synonyms: 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE;2-(CHLOROMETHYL)-3,4-DIMETHOXY PYRIDINE HCL;2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE;Pyridine, 2-(chloromethyl)-3,4-dimethoxy- (9CI);2-(ChloroMethyl)-3;4-diMethoxypyridine hydrochloride;2 - (CHLOROMETHYL) - 3, 4 - DIMETHOXY PY RIDINE PHCL
• CAS NO: 169905-10-6
• Molecular Formula: C₈H₁₀ClNO₂
• Molecular Weight: 224.08
• Product Categories: HALOMETYL;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Pantoprazole Sodium
• Mol File: 169905-10-6.mol

Chemical Properties

• Melting Point: 155 °C (dec.)(lit.)
• Boiling Point: 257.8 °C at 760 mmHg
• Flash Point: 109.7 °C
• Appearance: /
• Density: 1.185 g/cm³
• Vapor Pressure: 0.0229mmHg at 25°C
• Refractive Index: 1.511
• PKA: 4.45±0.10(Predicted)
• CAS DataBase Reference: 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE(169905-10-6)
• EPA Substance Registry System: 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE(169905-10-6)

Safety Data

• Hazard Codes: Xn,N
• Statements: 21/22-38-41-43-48/22-51/53
• Safety Statements: 26-36/37/39-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 169905-10-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE is used as a reagent in organic synthesis for its ability to contribute to the development of new pharmaceutical drugs. Its unique structure allows it to be a versatile building block in the synthesis of various medicinal compounds.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE is used as an active ingredient for its potential to combat various types of bacteria, making it a candidate for the development of new antimicrobial agents.
Used in Antiviral Applications:
2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE is also being explored for its antiviral properties, suggesting its use as a component in antiviral medications to treat a range of viral infections.
Used in Drug Target Research:
2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE is used as a potential drug target in the treatment of various diseases, indicating its importance in the discovery and development of novel therapeutics for a wide array of medical conditions.

InChI:InChI=1/C8H10ClNO2/c1-11-7-3-4-10-6(5-9)8(7)12-2/h3-4H,5H2,1-2H3

Synthetic route

2-hydroxymethyl-3,4-dimethoxypyridine (72830-08-1) → 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6)

Conditions	Yield
With thionyl chloride In dichloromethane	88%
With thionyl chloride In dichloromethane	88%
With thionyl chloride In dichloromethane at 25℃; for 2h;

3,4-dimethoxy-2-methylpyridine N-oxide (72830-07-0) → 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6)

Conditions	Yield
Stage #1: 3,4-dimethoxy-2-methylpyridine N-oxide With p-toluenesulfonyl chloride In dichloromethane at 20℃; for 1h; Stage #2: With triethylamine In dichloromethane at 20℃; for 2h;
Multi-step reaction with 3 steps 1: AcOH / 120 °C 2: 2N aq. NaOH / methanol / 2 h / 25 °C 3: SOCl2 / CH2Cl2 / 2 h / 25 °C View Scheme

2-acetoxymethyl-3,4-dimethoxypyridine (102625-99-0) → 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2N aq. NaOH / methanol / 2 h / 25 °C 2: SOCl2 / CH2Cl2 / 2 h / 25 °C View Scheme

vanillin (121-33-5) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 4-((3,4-dimethoxypyridin-2-yl)methoxy)-3-methoxybenzaldehyde

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 20℃; for 20h;	98%

4-nitro-phenol (100-02-7) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 3,4-dimethoxy-2-[(4-nitrophenoxy)methyl]pyridine

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 3h;	95.1%

C14H10N4OS2 (1166385-86-9) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → C30H28N6O5S2 (1166385-45-0)

Conditions	Yield
With sodium hydroxide In methanol for 3h; Reflux;	90.7%

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) + 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole (97963-62-7) → pantoprazole sulfide (102625-64-9)

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 20℃; for 3h;	87.8%
With sodium hydroxide In water Flow reactor;

desmethyl dibenzimidazole (884330-09-0) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → C26H27N5O2

Conditions	Yield
With sodium hydroxide In water; acetone at 50℃; for 15h;	85%

C40H30N6S (1247013-51-9) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → C48H39N7O2S (1247013-53-1)

Conditions	Yield
With sodium hydroxide In water; acetone at 25 - 30℃; for 15h;	85%

3-Cyano-4,6-dimethyl-2(1H)-pyridon (769-28-8) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 2-((3,4-dimethoxypyridin-2-yl)methoxy)-4,6-dimethylnicotinonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; zinc(II) oxide; zinc(II) chloride In 1,4-dioxane at 110℃; Inert atmosphere;	80%

(4-acetylaminophenyl)boronic acid (101251-09-6) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → C16H18N2O3 (1416422-97-3)

Conditions	Yield
With potassium phosphate; C12H10ClNPd*C16H21O3P In tetrahydrofuran; water at 60℃; for 20h;	74%

1-(phenylsulfinyl)acetophenone (6099-23-6) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 2-benzenesulfinylmethyl-3,4-dimethoxypyridine

Conditions	Yield
With potassium carbonate In acetone at 25 - 57℃; for 20h; Inert atmosphere;	60%

diphenylmethylisothiouronium bromide (90280-15-2) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 2-((benzhydrylthio)methyl)-3,4-dimethoxypyridine

Conditions	Yield
With potassium carbonate In methanol at 20℃;	59%

5-((7-methoxynaphthalen-1-yl)methyl)-1H-tetrazole (1425498-90-3) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 3,4-dimethoxy-2-((5-((7-methoxynaphthalen-1-yl)methyl)-1H-tetrazol-1-yl)methyl)pyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃;	55%

2-mercaptothieno<3,4-d>imidazole (90070-09-0) + 2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 2-(3,4-Dimethoxy-pyridin-2-ylmethylsulfanyl)-1H-thieno[3,4-d]imidazole (122307-42-0)

Conditions	Yield
With sodium methylate In methanol at 65℃; for 1h;	27%

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) + Benzimidazol-2-thiol (134469-07-1) → 2-methylsulfanylbenzimidazole (7152-24-1) + 2-[(3,4-dimethoxy-2-pyridyl)methylthio]-1H-benzimidazole (107512-18-5)

Conditions	Yield
In methanol Heating;

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) + triethyl phosphite (122-52-1) → diethyl [3,4-dimethoxypyridin-2-ylmethylene]phosphonate (895537-11-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide at 110 - 130℃; Michaelis-Arbuzov reaction;

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-2-aza-2',5,5',6-tetramethoxystilbene (895537-14-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-2-aza-2',4',5,6-tetramethoxystilbene

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-2-aza-3',5,5',6-tetramethoxystilbene (895537-12-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-2-aza-3',5,5',6-tetrahydroxystilbene

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C 3: 98.9 percent / boron tribromide / CH2Cl2 / 25 - 35 °C View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-2-aza-2',5,5',6-tetrahydroxystilbene

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutylammonium iodide / 110 - 130 °C 2: sodium hydride / dimethylformamide / 20 °C 3: 99.7 percent / boron tribromide / CH2Cl2 / 25 - 35 °C View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 2-(3,4-Dimethoxy-pyridin-2-ylmethanesulfinyl)-1H-thieno[3,4-d]imidazole (122307-43-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 27 percent / NaOMe / methanol / 1 h / 65 °C 2: 60 percent / aq. sodium bicarbonate, m-chloroperbenzoic acid / CH2Cl2 / 0.17 h / 0 °C View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → 3,4-dimethoxy-2-formylpyridine

Conditions	Yield
With 2-nitropropane; sodium In methanol at 0 - 70℃; for 25.5h;

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) + 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole (97963-62-7) → pantoprazole

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water / Flow reactor 2: sodium hypochlorite; sodium hydroxide / water; acetonitrile / Flow reactor View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)benzohydrazide

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 - 100 °C 2: copper(l) iodide / acetonitrile / 1 h / Reflux 3: ethanol / Reflux View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-hydroxybenzohydrazide

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 - 100 °C 2: copper(l) iodide / acetonitrile / 1 h / Reflux 3: ethanol / 0.5 h / Reflux View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-methoxybenzohydrazide

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 - 100 °C 2: copper(l) iodide / acetonitrile / 1 h / Reflux 3: ethanol / 0.5 h / Reflux View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-4-(methylsulfonyl)benzohydrazide

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 - 100 °C 2: copper(l) iodide / acetonitrile / 1 h / Reflux 3: ethanol / 0.5 h / Reflux View Scheme

2-(chloromethyl)-3,4-dimethoxypyridine (169905-10-6) → (E)-N’-(4-(1-((3,4-dimethoxypyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzylidene)-3,4,5-trimethoxybenzohydrazide

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 1 h / 20 - 100 °C 2: copper(l) iodide / acetonitrile / 1 h / Reflux 3: ethanol / 0.5 h / Reflux View Scheme

Upstream product

• 72830-08-1 2-hydroxymethyl-3,4-dimethoxypyridine 
• 72830-07-0 3,4-dimethoxy-2-methylpyridine N-oxide ? 
• 102625-99-0 2-acetoxymethyl-3,4-dimethoxypyridine 

Downstream Products

• 102625-64-9 pantoprazole sulfide 
• 1247013-53-1 C₄₈H₃₉N₇O₂S 
• 1416422-97-3 C₁₆H₁₈N₂O₃ 

Relevant articles and documents

A practical one pot synthesis of 2-[2-(pridylmethyl)-thio]-1H-benzimidazoles

A combination of Et3N and pTSCl was found to be far superior than pTSCl or benzene sulfonyl chloride alone in convert ing substituted 2-picoline-N-oxides to the corresponding 2-chloromethylpyridines and has been exploited for the synthesis of a variety of 2-[2-(pyridylmethyl)-thio]-1H-benzimidazoles, key intermediates in the manufacture of H+/K+-ATPase inhibitors in a single pot.

2--1H-thienoimidazoles. A Novel Class of Gastric H+/K+-ATPase Inhibitors

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Therapeutically active chloro substituted benzimidazoles

The novel compounds of the formula I STR1 wherein Cl is in 5 or 6 position and whereby R is the group --CH2 OCOOR1, wherein R1 is a straight or branched alkyl containing 1-6 carbon atoms or benzyl, or R1 is the group --(CH2)n STR2 --(CH2)n COOH or --(CH2)n SO3 H wherein n is 1-6 and physiologically acceptable salts thereof as well as intermediates, pharmaceutical compositions containing such compounds as active ingredient, and the use of the compounds in medicine.