Product Name

  • Name

    2,3-BIS(CHLOROMETHYL)PYRIDINE

  • EINECS
  • CAS No. 45754-12-9
  • Article Data9
  • CAS DataBase
  • Density 1.275 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H7 Cl2 N
  • Boiling Point 264.48 ºC at 760 mmHg
  • Molecular Weight 176.045
  • Flash Point 139.294 ºC
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 45754-12-9 (2,3-BIS(CHLOROMETHYL)PYRIDINE)
  • Hazard Symbols
  • Synonyms 2,3-Bis(chloromethyl)pyridine;
  • PSA 12.89000
  • LogP 2.55920

Synthetic route

2,3-bis(hydroxymethyl)pyridine hydrochloride
423169-40-8

2,3-bis(hydroxymethyl)pyridine hydrochloride

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

2,3-bis(chloromethyl)-pyridine

Conditions
ConditionsYield
With thionyl chloride In toluene89%
2,3-bis(hydroxymethyl)pyridine
38070-79-0

2,3-bis(hydroxymethyl)pyridine

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

2,3-bis(chloromethyl)-pyridine

Conditions
ConditionsYield
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-diethyl pyridinedicarboxylate

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

2,3-bis(chloromethyl)-pyridine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether Erwaermen des Reaktionsprodukts mit Thionylchlorid;
Pyridine-2,3-dicarboxylic acid
89-00-9

Pyridine-2,3-dicarboxylic acid

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

2,3-bis(chloromethyl)-pyridine

Conditions
ConditionsYield
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

dimethyl 2,3-pyridinedicarboxylate

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

2,3-bis(chloromethyl)-pyridine

Conditions
ConditionsYield
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-Lutidine

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

2,3-bis(chloromethyl)-pyridine

2,3-bis(chloromethyl)pyridine hydrochloride
27221-49-4

2,3-bis(chloromethyl)pyridine hydrochloride

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

2,3-bis(chloromethyl)-pyridine

Conditions
ConditionsYield
With sodium carbonate In dichloromethane; water pH=7.5 - 8;
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

C9H7N3

C9H7N3

Conditions
ConditionsYield
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

2,3-bis(chloromethyl)-pyridine

sodium p-toluenesulfonamide
18522-92-4

sodium p-toluenesulfonamide

6-(toluene-4-sulfonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine
204593-50-0

6-(toluene-4-sulfonyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70 - 80℃; for 2.5h;80.5%
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

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)-7-amino-3-oxo-1,3,9,9a-tetrahydrooxazolo[3,4-a]indol-1-yl)methyl)acetamide

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

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

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80 - 90℃;80%
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

(S)-2-(6-methoxynaphthalen-2-yl)propanamide
72337-56-5, 123675-40-1, 134282-71-6, 134356-42-6

(S)-2-(6-methoxynaphthalen-2-yl)propanamide

2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one
1558014-41-7

2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one

Conditions
ConditionsYield
With sodium hydride In toluene at 80 - 90℃; for 5h;70%
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

6,7-dihydro-5H-pyrrolo[3,4-b]pyridine
147739-88-6

6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Conditions
ConditionsYield
With methyl 2-(aminosulfonyl)benzoate; sodium hydride In N,N-dimethyl-formamide46%
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

4-fluorobenzoyl chloride
403-43-0

4-fluorobenzoyl chloride

4-amino-N-(dimethylethyl)benzenesulfonamide
209917-48-6

4-amino-N-(dimethylethyl)benzenesulfonamide

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

A

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)-7-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-6-carboxamide

B

N-(4-(N-tert-butylsulfamoyl)phenyl)-6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-7-carboxamide

N-(4-(N-tert-butylsulfamoyl)phenyl)-6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-7-carboxamide

Conditions
ConditionsYield
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%
...Expand
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

2,3-Lutidine
583-61-9

2,3-Lutidine

Conditions
ConditionsYield
With methanol; palladium on activated charcoal; Lindlar's catalyst Hydrogenation;
Tetraisopropyl methylenediphosphonate
1660-95-3

Tetraisopropyl methylenediphosphonate

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

2,3-bis(chloromethyl)-pyridine

[6-(Diisopropoxy-phosphoryl)-6,7-dihydro-5H-[1]pyrindin-6-yl]-phosphonic acid diisopropyl ester
104884-10-8

[6-(Diisopropoxy-phosphoryl)-6,7-dihydro-5H-[1]pyrindin-6-yl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
With sodium hydride 1.) DMSO, RT, 1 h 2.) 80 deg C, 1 h; Multistep reaction;
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

Tetraethyl methylenediphosphonate
1660-94-2

Tetraethyl methylenediphosphonate

[6-(Diethoxy-phosphoryl)-6,7-dihydro-5H-[1]pyrindin-6-yl]-phosphonic acid diethyl ester

[6-(Diethoxy-phosphoryl)-6,7-dihydro-5H-[1]pyrindin-6-yl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
With sodium hydride 1.) DMSO, RT, 1 h 2.) 80 deg C, 1 h; Multistep reaction;
methanol
67-56-1

methanol

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

2,3-bis(chloromethyl)-pyridine

4-methoxy-phenyl-sulphonyl chloride
98-68-0

4-methoxy-phenyl-sulphonyl chloride

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

A

methyl (+/-)-7-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate

methyl (+/-)-7-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate

B

methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate
523993-95-5

methyl (+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate

Conditions
ConditionsYield
Multistep reaction;A 200 mg
B 1.00 g
...Expand
methanol
67-56-1

methanol

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

2,3-bis(chloromethyl)-pyridine

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

A

methyl (+/-)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate dihydrochloride

methyl (+/-)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate dihydrochloride

B

methyl (+/-)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate dihydrochloride

methyl (+/-)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate dihydrochloride

Conditions
ConditionsYield
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;
...Expand
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

A

ethyl 6-acetyl-7-ethoxycarbonyl-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate

ethyl 6-acetyl-7-ethoxycarbonyl-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylate

B

ethyl 7-acetyl-6-ethoxycarbonyl-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate

ethyl 7-acetyl-6-ethoxycarbonyl-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylate

Conditions
ConditionsYield
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;
...Expand
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

2-acetylaminomalonic acid diethyl ester
1068-90-2

2-acetylaminomalonic acid diethyl ester

A

(+/-)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylic acid dihydrochloride

(+/-)-5,6,7,8-tetrahydro[1,7]naphthylidine-6-carboxylic acid dihydrochloride

B

(+/-)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylic acid dihydrochloride

(+/-)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylic acid dihydrochloride

Conditions
ConditionsYield
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;
...Expand
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

(+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylic acid

(+/-)-6-(4-methoxybenzenesulfonyl)-5,6,7,8-tetrahydro[1,6]naphthylidine-7-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / dioxane / 25 h / 20 °C
View Scheme
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

6,7-dihydro-5H-1-pyrindine-6,6-bisphosphonic acid
104884-01-7

6,7-dihydro-5H-1-pyrindine-6,6-bisphosphonic acid

Conditions
ConditionsYield
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

2,3-bis(chloromethyl)-pyridine

diethyl malonate
105-53-3

diethyl malonate

diethyl 5,7‑dihydro‑6H‑cyclopenta[b]pyridine‑6,6‑dicarboxylate
220001-81-0

diethyl 5,7‑dihydro‑6H‑cyclopenta[b]pyridine‑6,6‑dicarboxylate

Conditions
ConditionsYield
With sodium In ethanol for 5.08333h; Heating / reflux;
2,3-bis(chloromethyl)-pyridine
45754-12-9

2,3-bis(chloromethyl)-pyridine

aspirin
50-78-2

aspirin

2-acetyloxybenzoic acid 3-(nitrooxymethyl)-2-methylpyridinyl ester hydrochloride

2-acetyloxybenzoic acid 3-(nitrooxymethyl)-2-methylpyridinyl ester hydrochloride

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

2,3-bis(chloromethyl)-pyridine

6,7-dihydro-5H-pyrrolo[3,4-b]pyridine dihydrobromide

6,7-dihydro-5H-pyrrolo[3,4-b]pyridine dihydrobromide

Conditions
ConditionsYield
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

2,3-bis(chloromethyl)-pyridine

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

(4-difluoromethoxy-3-pyridin-2-ylethynyl-phenyl)-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-methanone

Conditions
ConditionsYield
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

2,3-bis(chloromethyl)-pyridine

C23H25NO6S2

C23H25NO6S2

Conditions
ConditionsYield
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

2,3-bis(chloromethyl)-pyridine

C21H21NO6S2

C21H21NO6S2

Conditions
ConditionsYield
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

2,3-bis(chloromethyl)-pyridine

C11H13NO4

C11H13NO4

Conditions
ConditionsYield
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

Pyridine,2,3-bis(chloromethyl)- Specification

The Pyridine,2,3-bis(chloromethyl)-, with the cas registry number 45754-12-9, has the systematic name of 2,3-bis(chloromethyl)pyridine.

The characteristics of this kind of chemical are as follows: (1)ACD/LogP: 1.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 5; (6)ACD/BCF (pH 7.4): 5; (7)ACD/KOC (pH 5.5): 114; (8)ACD/KOC (pH 7.4): 115; (9)#H bond acceptors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 12.89; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 43.875 cm3; (14)Molar Volume: 138.047 cm3; (15)Polarizability: 17.394 ×10-24 cm3; (16)Surface Tension: 42.237 dyne/cm; (17)Density: 1.275 g/cm3; (18)Flash Point: 139.294 °C; (19)Enthalpy of Vaporization: 48.21 kJ/mol; (20)Boiling Point: 264.48 °C at 760 mmHg; (21)Vapour Pressure: 0.016 mmHg at 25°C.

Additionally, the following datas could be converted into the molecular structure:
(1)SMILES:ClCc1ncccc1CCl
(2)InChI:InChI=1/C7H7Cl2N/c8-4-6-2-1-3-10-7(6)5-9/h1-3H,4-5H2
(3)InChIKey:FDHDTLFJPYRSBM-UHFFFAOYAK
 

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