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6959-47-3

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6959-47-3 Usage

Uses

2-(Chloromethyl)pyridine hydrochloride was used as reagent in base catalyzed alkylation of p-tert-butylcalix[6]arene and p-tert-butylcalix[5]arene in DMF. It was used in the synthesis of Gd3+ diethylenetriaminepentaacetic acid bisamide complex, a Zn2+-sensitive magnetic resonance imaging contrast agent.

Definition

ChEBI: A hydrochloride obtained by combining 2-(chloromethyl)pyridine with one molar equivalent of hydrochloric acid.

Air & Water Reactions

Soluble in water.

Reactivity Profile

2-(Chloromethyl)pyridine hydrochloride is incompatible with strong oxidizing agents.

Fire Hazard

Flash point data for 2-(Chloromethyl)pyridine hydrochloride are not available. 2-(Chloromethyl)pyridine hydrochloride is probably combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 6959-47-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,5 and 9 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6959-47:
(6*6)+(5*9)+(4*5)+(3*9)+(2*4)+(1*7)=143
143 % 10 = 3
So 6959-47-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H6ClN.ClH/c7-5-6-3-1-2-4-8-6;/h1-4H,5H2;1H

6959-47-3 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A10226)  2-(Chloromethyl)pyridine hydrochloride, 98%   

  • 6959-47-3

  • 5g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (A10226)  2-(Chloromethyl)pyridine hydrochloride, 98%   

  • 6959-47-3

  • 25g

  • 474.0CNY

  • Detail
  • Alfa Aesar

  • (A10226)  2-(Chloromethyl)pyridine hydrochloride, 98%   

  • 6959-47-3

  • 100g

  • 1478.0CNY

  • Detail
  • Aldrich

  • (162701)  2-(Chloromethyl)pyridinehydrochloride  98%

  • 6959-47-3

  • 162701-5G

  • 171.99CNY

  • Detail
  • Aldrich

  • (162701)  2-(Chloromethyl)pyridinehydrochloride  98%

  • 6959-47-3

  • 162701-25G

  • 686.79CNY

  • Detail
  • Aldrich

  • (162701)  2-(Chloromethyl)pyridinehydrochloride  98%

  • 6959-47-3

  • 162701-100G

  • 1,786.59CNY

  • Detail

6959-47-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(chloromethyl)pyridine hydrochloride

1.2 Other means of identification

Product number -
Other names 2-(chloromethyl)pyridine,hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6959-47-3 SDS

6959-47-3Synthetic route

2-Hydroxymethylpyridine
586-98-1

2-Hydroxymethylpyridine

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

Conditions
ConditionsYield
With thionyl chloride100%
With thionyl chloride for 16h; Reflux;93%
With thionyl chloride In dichloromethane at 0℃; for 1h;93%
2-Hydroxymethylpyridine
586-98-1

2-Hydroxymethylpyridine

A

2-(1-indenylmethyl)pyridine
378797-57-0

2-(1-indenylmethyl)pyridine

B

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

Conditions
ConditionsYield
A 51%
B n/a
α-picoline
109-06-8

α-picoline

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; trichloroisocyanuric acid; N,N-dimethyl-formamide 1.) CHCl3, 2 h, heating; 2.) CHCl3; Yield given. Multistep reaction;
Multi-step reaction with 3 steps
1: acetic acid; dihydrogen peroxide / 10 h / 70 °C
2: acetic acid
3: thionyl chloride / methanol
View Scheme
α-picoline
109-06-8

α-picoline

trichloroisocyanuric acid
87-90-1

trichloroisocyanuric acid

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; chlorine In N-methyl-acetamide; chloroform; acetone
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

syn-distal-25,27-bis<(2-pyridylmethyl)oxy>-26,28-dihydroxycalix<4>arene
139584-72-8

syn-distal-25,27-bis<(2-pyridylmethyl)oxy>-26,28-dihydroxycalix<4>arene

25,26,27,28-tetrakis<(2-pyridylmethyl)oxy>calix<4>arene
123207-93-2, 139683-32-2, 139683-33-3, 139584-73-9

25,26,27,28-tetrakis<(2-pyridylmethyl)oxy>calix<4>arene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 16h;100%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

triphenylphosphine
603-35-0

triphenylphosphine

Triphenyl-2-pyridylmethylphosphonium chloride hydrochloride
38700-15-1

Triphenyl-2-pyridylmethylphosphonium chloride hydrochloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 140℃; for 20h;100%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

2-Naphthalenethiol
91-60-1

2-Naphthalenethiol

2-(2-naphthylthiomethyl)pyridine
132065-22-6

2-(2-naphthylthiomethyl)pyridine

Conditions
ConditionsYield
With sodium hydroxide at 4℃; for 10h;100%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

1,4,7-triazacyclononane
4730-54-5

1,4,7-triazacyclononane

1,4,7-tris(pyridin-2-ylmethyl)-1,4,7-triazacyclononane
102851-50-3

1,4,7-tris(pyridin-2-ylmethyl)-1,4,7-triazacyclononane

Conditions
ConditionsYield
With sodium hydroxide; hexadecylamine hydrochloride In water at 20℃; for 24h; Condensation;100%
With sodium carbonate In acetonitrile at 20℃; for 120h;83%
With triethylamine; sodium iodide In ethanol for 12h; Heating;55%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 2h; Inert atmosphere;
(CH3)3COC(O)ONH(CH2)2NH2
807614-00-2

(CH3)3COC(O)ONH(CH2)2NH2

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

C19H26N4O3

C19H26N4O3

Conditions
ConditionsYield
With sodium carbonate In ethanol for 24h; Heating / reflux;100%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

5-[(1R)-2-amino-1-methylethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

5-[(1R)-2-amino-1-methylethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

Conditions
ConditionsYield
Stage #1: 4-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-chlorophenol With benzaldehyde In DMF (N,N-dimethyl-formamide) for 0.333333h;
Stage #2: 2-chloromethylpyridine hydrochloride With potassium carbonate; 18-crown-6 ether In DMF (N,N-dimethyl-formamide) for 16h;
Stage #3: With hydrogenchloride In water
100%
1-phenyl-1,1-bis(4-hydroxyphenyl)ethane
1571-75-1

1-phenyl-1,1-bis(4-hydroxyphenyl)ethane

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

C32H28N2O2
1020725-66-9

C32H28N2O2

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In benzene at 80℃; for 48h;98.1%
sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

2-<(phenylsulfonyl)methyl>pyridine
1620-50-4

2-<(phenylsulfonyl)methyl>pyridine

Conditions
ConditionsYield
With tetra-n-propylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; for 24h;98%
With tetra-n-propylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 16h; Reflux;89%
With tetra-n-propylammonium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 16h; Reflux;89%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

syn-proximal-25,26-bis<(2-pyridylmethyl)oxy>-27,28-dihydroxycalix<4>arene
123207-98-7

syn-proximal-25,26-bis<(2-pyridylmethyl)oxy>-27,28-dihydroxycalix<4>arene

25,26,27-tris<(2-pyridylmethyl)oxy>-28-hydroxycalix<4>arene
123207-99-8

25,26,27-tris<(2-pyridylmethyl)oxy>-28-hydroxycalix<4>arene

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 6h;98%
2-chloro-4-nitrophenol
619-08-9

2-chloro-4-nitrophenol

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

2-((2-chloro-4-nitrophenoxy)methyl)pyridine
179687-79-7

2-((2-chloro-4-nitrophenoxy)methyl)pyridine

Conditions
ConditionsYield
Stage #1: 2-chloromethylpyridine hydrochloride With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: 2-chloro-4-nitrophenol With potassium iodide In N,N-dimethyl-formamide at 60℃; for 12h;
98%
With potassium carbonate; sodium iodide In acetonitrile Reflux;74%
With potassium carbonate In N,N-dimethyl-formamide at 95℃;63%
methyl 14-[(1R*,2S*)-2-fluoro-cyclohexyl]-3-hydroxy-6-isopropyl-5,6,7,8-tetrahydro-indolo[2,1-a][2,5]benzodiazocine-11-carboxylate

methyl 14-[(1R*,2S*)-2-fluoro-cyclohexyl]-3-hydroxy-6-isopropyl-5,6,7,8-tetrahydro-indolo[2,1-a][2,5]benzodiazocine-11-carboxylate

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

methyl 14-[(1R*,2S*)-2-fluoro-cyclohexyl]-3-(pyridin-2-ylmethoxy)-6-isopropyl-5,6,7,8-tetrahydro-indolo[2,1-a][2,5]benzodiazocine-11-carboxylate

methyl 14-[(1R*,2S*)-2-fluoro-cyclohexyl]-3-(pyridin-2-ylmethoxy)-6-isopropyl-5,6,7,8-tetrahydro-indolo[2,1-a][2,5]benzodiazocine-11-carboxylate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 5h;98%
ethyl 4-[(4-fluorophenyl)sulfonyl]piperidine-4-carboxylate hydrochloride

ethyl 4-[(4-fluorophenyl)sulfonyl]piperidine-4-carboxylate hydrochloride

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

C20H23FN2O4S
1243734-67-9

C20H23FN2O4S

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 24h;98%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

1-t-Butoxycarbonylpiperazine
57260-71-6

1-t-Butoxycarbonylpiperazine

1-(tert-butoxycarbonyl)-4-((2-pyridyl)methyl)piperazine
77278-93-4

1-(tert-butoxycarbonyl)-4-((2-pyridyl)methyl)piperazine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;98%
5-(4-chlorophenyl)-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one
225666-36-4

5-(4-chlorophenyl)-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

5-(4-chlorophenyl)-6-[4-(methylthio)phenyl]-2-(pyridin-2-ylmethyl)-2H-pyridazin-3-onePotassium carbonate

5-(4-chlorophenyl)-6-[4-(methylthio)phenyl]-2-(pyridin-2-ylmethyl)-2H-pyridazin-3-onePotassium carbonate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;97.5%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

(Z)-5-(4-ethoxybenzylidene)-3-(pyridin-2-ylmethyl)thiazolidine-2,4-dione
1438409-40-5

(Z)-5-(4-ethoxybenzylidene)-3-(pyridin-2-ylmethyl)thiazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: (Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 0℃; for 0.333333h;
Stage #2: 2-chloromethylpyridine hydrochloride In N,N-dimethyl-formamide at 20℃;
97.5%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

thiourea
17356-08-0

thiourea

2-(2-pyridylmethyl)isothiourea dihydrochloride
1822-49-7

2-(2-pyridylmethyl)isothiourea dihydrochloride

Conditions
ConditionsYield
In ethanol for 1.5h; Heating;97%
In methanol for 0.166667h; Ambient temperature;77%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

2-(1H-pyrazol-3-yl)pyridine
75415-03-1

2-(1H-pyrazol-3-yl)pyridine

2-(3-(2'-pyridyl)pyrazol-1-ylmethyl)pyridine
546142-85-2

2-(3-(2'-pyridyl)pyrazol-1-ylmethyl)pyridine

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide; water In benzene for 8h; Heating;97%
2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

1-(4-piperidinyl)-1H-indole
118511-81-2

1-(4-piperidinyl)-1H-indole

1-(1-(pyridin-2-ylmethyl)piperidin-4-yl)-1H-indole
594827-31-3

1-(1-(pyridin-2-ylmethyl)piperidin-4-yl)-1H-indole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 5h;97%

6959-47-3Relevant articles and documents

Synthesis method of 2-chloromethylpyridine hydrochloride

-

Paragraph 0018-0024, (2020/05/05)

The invention belongs to the field of organic synthesis, and specifically relates to a synthesis method of 2-chloromethylpyridine hydrochloride. The synthesis method comprises the following steps: (1)taking 2-methylpyridine as a raw material and reacting 2-methylpyridine with hydrogen peroxide in the presence of acetic acid to generate oxynitride-2-methylpyridine, wherein the molar ratio of 2-methylpyridine: acetic acid: hydrogen peroxide is 1: (1-1.1): (1.3-1.5), the oxidation reaction temperature is 70-80 DEG C, and the reaction time is 10-14 h; (2) carrying out reactions between oxynitride-2-methylpyridine and glacial acetic acid to generate methyl 2-pyridylacetate; (3) hydrolyzing methyl 2-pyridylacetate to obtain 2-pyridylcarbinol; and (4) reacting 2-pyridylcarbinol with thionyl chloride to obtain the target product namely 2-chloromethylpyridine hydrochloride, wherein the molar ratio of 2-pyridylcarbinol to the thionyl chloride is 1: (1.1-1.3). The preparation method provided bythe invention is high in yield, low in cost, mild in reaction conditions and easy for industrial production.

Synthesis method of 2-chloromethylpyridine hydrochloride

-

Paragraph 0018-0024, (2019/05/28)

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 2-chloromethylpyridine hydrochloride. The synthesis method includes following steps: (1), taking 2-methylpyridine as a raw material, reacting with hydrogen peroxide in an acetic acid condition to generate nitrogen oxide-2-methylpyridine, wherein a molar ratio of 2-methylpyridine, acetic acidand hydrogen peroxide is 1:1-1.1:1.3-1.5, temperature of oxidizing reaction is 70-80 DEG C, and reaction time is 10-14h; (2), allowing nitrogen oxide 2-methylpyridine to react with glacial acetic acid to generate 2-methyl pyridylacetate; (3), hydrolyzing 2-methyl pyridylacetate into 2-pyridinemethanol; (4), allowing 2-pyridylacetate to react with thionyl chloride to obtain a target product-2-chloromethylpyridine hydrochloride, wherein a molar ratio of 2-pyridinemethanol to thionyl chloride is 1:1.1-1.3. The preparation method is high in yield, low in cost, mild in reaction condition and easyin industrial production.

Facial triad modelling using ferrous pyridinyl prolinate complexes: Synthesis and catalytic applications

Moelands, Marcel A. H.,Schamhart, Daniel J.,Folkertsma, Emma,Lutz, Martin,Spek, Anthony L.,Klein Gebbink, Robertus J. M.

, p. 6769 - 6785 (2014/05/06)

A series of new chiral pyridinyl prolinate (RPyProR) ligands and their corresponding Fe(ii) triflate and chloride complexes are reported. The ligands possess an NN′O coordination motif, as found in the active site of non-heme iron enzymes with the so-called 2-His-1-carboxylate facial triad. The coordination behaviour of these ligands towards iron turned out to be dependent on the counter ion (chloride or triflate), the crystallization conditions (coordinating or non-coordinating solvents) and the presence of substituents on the ligand. In combination with Fe(ii)(OTf)2, coordinatively saturated complexes of the type [Fe(L)2](OTf)2 are formed, in which the ligands adopt a meridional coordination mode. The use of FeCl 2 in a non-coordinating solvent leads to 5-coordinated complexes [Fe(L)(Cl)2] with a meridional N,N′,O ligand. Crystallization of these complexes from a coordinating solvent leads to 6-coordinated [Fe(L)(solv)(Cl)2] complexes (solv = methanol or acetonitrile), in which the N,N′,O ligand is coordinated in a facial manner. For RPyProR ligands bearing a 6-Me substituent on the pyridine ring, solvent coordination and, accordingly, ligand rearrangement are prevented by steric constraints. The complexes were tested as oxidation catalysts in the epoxidation of alkene substrates in acetonitrile with hydrogen peroxide as the oxidant under oxidant limiting conditions. The complexes were shown to be especially active in the epoxidation of styrene type substrates (styrene and trans-beta-methylstyrene). In the best case, complex [Fe(6-Me-PyProNH2)Cl2] (15) allowed for 65% productive consumption of hydrogen peroxide toward epoxide and benzaldehyde products. This journal is the Partner Organisations 2014.

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