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
• Article Data: 4

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

General Description

2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE is a chemical compound that is used in the pharmaceutical industry for its potential medicinal properties. It contains a chloromethyl functional group and two dimethoxy groups attached to a pyridine ring. It is commonly used as a reagent in organic synthesis and is also being studied for its potential as a drug target in the treatment of various diseases. 2-CHLOROMETHYL-3,4-DIMETHOXY PYRIDINE HYDROCHLORIDE has been shown to possess antimicrobial and antiviral properties, and it is being explored for its potential use in the development of new pharmaceutical drugs. Its hydrochloride form is a stable and easily handled solid, making it suitable for use in laboratory and industrial settings.

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

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

Downstream Products

• 7152-24-1 2-methylsulfanylbenzimidazole 
• 107512-18-5 2-[(3,4-dimethoxy-2-pyridyl)methylthio]-1H-benzimidazole 
• 895537-14-1 (E)-2-aza-2',5,5',6-tetramethoxystilbene 
• 895537-12-9 (E)-2-aza-3',5,5',6-tetramethoxystilbene 
• 102625-64-9 pantoprazole sulfide 
• 1247013-53-1 C₄₈H₃₉N₇O₂S 
• 1416422-97-3 C₁₆H₁₈N₂O₃ 

Relevant articles and documents

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