45754-12-9

Basic information

• Product Name: 2,3-BIS(CHLOROMETHYL)PYRIDINE
• Synonyms: 2,3-BIS(CHLOROMETHYL)PYRIDINE;Pyridine, 2,3-bis(chloroMethyl)-
• CAS NO: 45754-12-9
• Molecular Formula: C₇H₇Cl₂N
• Molecular Weight: 176.04
• Mol File: 45754-12-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 264.48 ºC at 760 mmHg
• Flash Point: 139.294 ºC
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 0.016mmHg at 25°C
• Refractive Index: 1.548
• PKA: 2.94±0.22(Predicted)
• CAS DataBase Reference: 2,3-BIS(CHLOROMETHYL)PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-BIS(CHLOROMETHYL)PYRIDINE(45754-12-9)
• EPA Substance Registry System: 2,3-BIS(CHLOROMETHYL)PYRIDINE(45754-12-9)

Safety Data

• Hazardous Substances Data: 45754-12-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Bis(chloromethyl)pyridine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of drugs with potent antimicrobial and antifungal effects, addressing a range of infections and diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3-Bis(chloromethyl)pyridine is utilized as a precursor in the production of pesticides, capitalizing on its strong antimicrobial properties to protect crops from a variety of fungal and microbial threats, thereby enhancing agricultural productivity.
Used in Organic Synthesis:
2,3-Bis(chloromethyl)pyridine also serves as a building block in the synthesis of other organic compounds, leveraging its reactivity to facilitate the creation of diverse chemical entities for various applications across different industries.

InChI:InChI=1/C7H7Cl2N/c8-4-6-2-1-3-10-7(6)5-9/h1-3H,4-5H2

Synthetic route

2,3-bis(hydroxymethyl)pyridine hydrochloride (423169-40-8) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
With thionyl chloride In toluene	89%

2,3-bis(hydroxymethyl)pyridine (38070-79-0) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
With thionyl chloride In dichloromethane at 45℃; Cooling with ice;	40%
With thionyl chloride In dichloromethane at 75℃; for 1h;	26%
With thionyl chloride In dichloromethane Heating / reflux;	24%

2,3-diethyl pyridinedicarboxylate (2050-22-8) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether Erwaermen des Reaktionsprodukts mit Thionylchlorid;

Pyridine-2,3-dicarboxylic acid (89-00-9) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / conc. H2SO4 / 20 h / Heating 2: 85 percent / NaBH4 / ethanol / 17 h / Heating 3: 26 percent / SOCl2 / CH2Cl2 / 1 h / 75 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid 2: sodium tetrahydroborate; hydrogenchloride / ethanol 3: thionyl chloride / toluene View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / Heating / reflux 2: sodium tetrahydroborate / ethanol; water / 20 °C 3: thionyl chloride / dichloromethane / Heating / reflux View Scheme

dimethyl 2,3-pyridinedicarboxylate (605-38-9) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / NaBH4 / ethanol / 17 h / Heating 2: 26 percent / SOCl2 / CH2Cl2 / 1 h / 75 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; hydrogenchloride / ethanol 2: thionyl chloride / toluene View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol; water / 20 °C 2: thionyl chloride / dichloromethane / Heating / reflux View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 80 °C / Cooling with ice 2: thionyl chloride / dichloromethane / 45 °C / Cooling with ice View Scheme

2,3-Lutidine (583-61-9) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

2,3-bis(chloromethyl)pyridine hydrochloride (27221-49-4) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
With sodium carbonate In dichloromethane; water pH=7.5 - 8;

2,3-bis(chloromethyl)-pyridine (45754-12-9) + trimethylsilyl cyanide (7677-24-9) → C9H7N3

Conditions	Yield
Stage #1: trimethylsilyl cyanide With cesium fluoride In acetonitrile at 10 - 20℃; for 0.5h; Stage #2: 2,3-bis(chloromethyl)-pyridine In acetonitrile at 10 - 40℃; for 12h; Temperature; Reagent/catalyst;	98.6%

2,3-bis(chloromethyl)-pyridine (45754-12-9) + sodium p-toluenesulfonamide (18522-92-4) → 6-(toluene-4-sulfonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (204593-50-0)

Conditions	Yield
In N,N-dimethyl-formamide at 70 - 80℃; for 2.5h;	80.5%

2,3-bis(chloromethyl)-pyridine (45754-12-9) + N-(((1S,9aS)-7-amino-3-oxo-1,3,9,9a-tetrahydrooxazolo[3,4-a]indol-1-yl)methyl)acetamide (1056039-93-0) → N-(((1S,9aS)-3-oxo-7-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-1,3,9,9a-tetrahydrooxazolo[3,4-a]indol-1-yl)methyl)acetamide (1056035-14-3)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80 - 90℃;	80%

2,3-bis(chloromethyl)-pyridine (45754-12-9) + (S)-2-(6-methoxynaphthalen-2-yl)propanamide (72337-56-5, 123675-40-1, 134282-71-6, 134356-42-6) → 2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one (1558014-41-7)

Conditions	Yield
With sodium hydride In toluene at 80 - 90℃; for 5h;	70%

2,3-bis(chloromethyl)-pyridine (45754-12-9) → 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (147739-88-6)

Conditions	Yield
With methyl 2-(aminosulfonyl)benzoate; sodium hydride In N,N-dimethyl-formamide	46%

2,3-bis(chloromethyl)-pyridine (45754-12-9) + 4-fluorobenzoyl chloride (403-43-0) + 4-amino-N-(dimethylethyl)benzenesulfonamide (209917-48-6) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → N-(4-(N-tert-butylsulfamoyl)phenyl)-7-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-6-carboxamide + N-(4-(N-tert-butylsulfamoyl)phenyl)-6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-7-carboxamide

Conditions	Yield
Stage #1: 2,3-bis(chloromethyl)-pyridine; 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 6.5h; Stage #2: With hydrogenchloride In water for 3h; Reflux; Stage #3: 4-fluorobenzoyl chloride; 4-amino-N-(dimethylethyl)benzenesulfonamide Further stages;	A 24 mg B 16%

2,3-bis(chloromethyl)-pyridine (45754-12-9) → 2,3-Lutidine (583-61-9)

Conditions	Yield
With methanol; palladium on activated charcoal; Lindlar's catalyst Hydrogenation;

Tetraisopropyl methylenediphosphonate (1660-95-3) + 2,3-bis(chloromethyl)-pyridine (45754-12-9) → [6-(Diisopropoxy-phosphoryl)-6,7-dihydro-5H-[1]pyrindin-6-yl]-phosphonic acid diisopropyl ester (104884-10-8)

Conditions	Yield
With sodium hydride 1.) DMSO, RT, 1 h 2.) 80 deg C, 1 h; Multistep reaction;

2,3-bis(chloromethyl)-pyridine (45754-12-9) + Tetraethyl methylenediphosphonate (1660-94-2) → [6-(Diethoxy-phosphoryl)-6,7-dihydro-5H-[1]pyrindin-6-yl]-phosphonic acid diethyl ester

Conditions	Yield
With sodium hydride 1.) DMSO, RT, 1 h 2.) 80 deg C, 1 h; Multistep reaction;

methanol (67-56-1) + 2,3-bis(chloromethyl)-pyridine (45754-12-9) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → methyl (+/-)-7-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate + methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate (523993-95-5)

Conditions	Yield
Multistep reaction;	A 200 mg B 1.00 g

methanol (67-56-1) + 2,3-bis(chloromethyl)-pyridine (45754-12-9) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → methyl (+/-)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate dihydrochloride + methyl (+/-)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate dihydrochloride

Conditions	Yield
Stage #1: 2,3-bis(chloromethyl)-pyridine; 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 20℃; for 14.5h; Stage #2: With hydrogenchloride for 3h; Heating; Stage #3: methanol With thionyl chloride for 20h; Heating; Title compound not separated from byproducts;

2,3-bis(chloromethyl)-pyridine (45754-12-9) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → ethyl 6-acetyl-7-ethoxycarbonyl-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate + ethyl 7-acetyl-6-ethoxycarbonyl-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 14.5h; Title compound not separated from byproducts;
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 6.5h;

2,3-bis(chloromethyl)-pyridine (45754-12-9) + 2-acetylaminomalonic acid diethyl ester (1068-90-2) → (+/-)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylic acid dihydrochloride + (+/-)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylic acid dihydrochloride

Conditions	Yield
Stage #1: 2,3-bis(chloromethyl)-pyridine; 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 20℃; for 14.5h; Stage #2: With hydrogenchloride for 3h; Heating; Title compound not separated from byproducts;

2,3-bis(chloromethyl)-pyridine (45754-12-9) → (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / dioxane / 25 h / 20 °C View Scheme

2,3-bis(chloromethyl)-pyridine (45754-12-9) → 6,7-dihydro-5H-1-pyrindine-6,6-bisphosphonic acid (104884-01-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMSO, RT, 1 h 2.) 80 deg C, 1 h 2: 6N HCl / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMSO, RT, 1 h 2.) 80 deg C, 1 h 2: 6N HCl / 2 h / Heating View Scheme

2,3-bis(chloromethyl)-pyridine (45754-12-9) + diethyl malonate (105-53-3) → diethyl 5,7‑dihydro‑6H‑cyclopenta[b]pyridine‑6,6‑dicarboxylate (220001-81-0)

Conditions	Yield
With sodium In ethanol for 5.08333h; Heating / reflux;

2,3-bis(chloromethyl)-pyridine (45754-12-9) + aspirin (50-78-2) → 2-acetyloxybenzoic acid 3-(nitrooxymethyl)-2-methylpyridinyl ester hydrochloride

2,3-bis(chloromethyl)-pyridine (45754-12-9) → 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine dihydrobromide

Conditions	Yield
Multi-step reaction with 2 steps 1: methyl 2-(aminosulfonyl)benzoate; sodium hydride / N,N-dimethyl-formamide 2: acetic acid; hydrogen bromide View Scheme

2,3-bis(chloromethyl)-pyridine (45754-12-9) → (4-difluoromethoxy-3-pyridin-2-ylethynyl-phenyl)-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-methanone (1253291-12-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methyl 2-(aminosulfonyl)benzoate; sodium hydride / N,N-dimethyl-formamide 2.1: acetic acid; hydrogen bromide 3.1: 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole / 1 h / 25 °C / Large scale 3.2: 4 h / 25 - 35 °C / Large scale View Scheme

2,3-bis(chloromethyl)-pyridine (45754-12-9) → C23H25NO6S2

Conditions	Yield
Multi-step reaction with 4 steps 1.1: cesium fluoride / acetonitrile / 0.5 h / 10 - 20 °C 1.2: 12 h / 10 - 40 °C 2.1: thionyl chloride / 12 h / 40 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 - 10 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 10 °C View Scheme

2,3-bis(chloromethyl)-pyridine (45754-12-9) → C21H21NO6S2

Conditions	Yield
Multi-step reaction with 4 steps 1.1: cesium fluoride / acetonitrile / 0.5 h / 10 - 20 °C 1.2: 12 h / 10 - 40 °C 2.1: thionyl chloride / 12 h / 40 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -20 - 10 °C 4.1: sodium carbonate / dichloromethane / 2 h / 0 - 30 °C View Scheme

2,3-bis(chloromethyl)-pyridine (45754-12-9) → C11H13NO4

Conditions	Yield
Multi-step reaction with 2 steps 1.1: cesium fluoride / acetonitrile / 0.5 h / 10 - 20 °C 1.2: 12 h / 10 - 40 °C 2.1: thionyl chloride / 12 h / 40 °C View Scheme

Upstream product

• 27221-49-4 2,3-bis(chloromethyl)pyridine hydrochloride 
• 605-38-9 dimethyl 2,3-pyridinedicarboxylate 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 38070-79-0 2,3-bis(hydroxymethyl)pyridine 
• 2050-22-8 2,3-diethyl pyridinedicarboxylate 
• 423169-40-8 2,3-bis(hydroxymethyl)pyridine hydrochloride 
• 583-61-9 2,3-Lutidine 

Downstream Products

• 583-61-9 2,3-Lutidine 
• 204593-50-0 6-(toluene-4-sulfonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine 
• 147739-88-6 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine 
• 1253291-12-1 (4-difluoromethoxy-3-pyridin-2-ylethynyl-phenyl)-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-methanone 
• 1211534-87-0 6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine 
• 523993-95-5 methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate 

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