3-Amino-2-chloro-4-methylpyridine

Product Name: 3-Amino-2-chloro-4-methylpyridine
CAS No.: 133627-45-9
Chemical Name: 3-Amino-2-chloro-4-methylpyridine
Synonyms: 2-CHLORO-4-METHYLPYRIDIN-3-AMINE;2-CHLORO-3-AMINO-4-METHYLPYRIDINE;Capic;CAS:133627-45-9;TIMTEC-BB SBB010194;3-Amino-2-chloro-4-p;ASINEX-REAG BAS 13794917;2-CHLORO-3-AMINO-4-PICOLINE;3-AMINO-2-CHLORO-4-PICOLINE;2-Chloro-3-Amino-4-Methylpyrid
CBNumber: CB5240863
Molecular Formula: C6H7ClN2
Formula Weight: 142.59
MOL File: 133627-45-9.mol

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3-Amino-2-chloro-4-methylpyridine Property

Melting point:: 65-70 °C
Boiling point:: 283.3±35.0 °C(Predicted)
Density: 1.260±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,2-8°C
solubility: Chloroform, Ethanol
pka: 3.22±0.10(Predicted)
form: Crystals
color: Off White
InChI: InChI=1S/C6H7ClN2/c1-4-2-3-9-6(7)5(4)8/h2-3H,8H2,1H3
InChIKey: UOBCYTOUXLAABU-UHFFFAOYSA-N
SMILES: C1(Cl)=NC=CC(C)=C1N
CAS DataBase Reference: 133627-45-9(CAS DataBase Reference)

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Safety

Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-41-37/38-22
Safety Statements: 26-36/37/39-36-39
RIDADR: UN2811
WGK Germany: 3
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
HS Code: 29333990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 708135
Product name: 3-Amino-2-chloro-4-methylpyridine
Purity: 97%
Packaging: 5g
Price: $66.1
Updated: 2023/06/20

Sigma-Aldrich

Product number: 708135
Product name: 3-Amino-2-chloro-4-methylpyridine
Purity: 97%
Packaging: 1g
Price: $24
Updated: 2023/01/07

TCI Chemical

Product number: A1855
Product name: 3-Amino-2-chloro-4-methylpyridine
Purity: >98.0%(GC)(T)
Packaging: 5g
Price: $39
Updated: 2025/07/31

TCI Chemical

Product number: A1855
Product name: 3-Amino-2-chloro-4-methylpyridine
Purity: >98.0%(GC)(T)
Packaging: 25g
Price: $116
Updated: 2025/07/31

Usbiological

Product number: A1376-48
Product name: 3-Amino-2-chloro-4-methylpyridine
Packaging: 5g
Price: $382
Updated: 2021/12/16

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3-Amino-2-chloro-4-methylpyridine Chemical Properties,Usage,Production

Chemical Properties

Off White Crystals

Uses

3-Amino-2-chloro-4-methylpyridine, also known as CAPIC, is a key intermediate in the production of nevirapine, a non-nucleosidic reverse transcriptase inhibitor that has been established to be clinically useful for the treatment of infection by HIV-1.

Preparation

An improved and commercially valuable process is developed by Ge et al. for the scalable synthesis of 2-chloro-3-amino-4-methylpyridine (CAPIC), a key intermediate of Nevirapine. The synthesis was accomplished in four steps, featuring condensation starting from 4,4-dimethoxyl-2-butanone and cyanoacetamide with ammonium acetate and acetic acid as catalysts. Specifically, a stirred solution of NaOH (15.6 g, 0.39 mol) and water (85 g) at 10 ℃ was added, 10% NaClO (96.8 g, 0.13 mol) and ethanol (80 g). 2-Chloro-3-amido-4- methylpyridine 7 (22 g, 0.13 mol) was added to the reaction mixture, stirring for 1 h. The mixture was heated to 60 ℃ and held for 3 h. After ethanol was removed in a vacuum, the mixture was cooled with an ice-water bath for 15–20 min to precipitate solid. Then, the mixture was filtered, washed with water, and dried to give 15.8 g (85.1% yield) of light yellow solid. 14.7 g of the white solid 2 was obtained via recrystallization in toluene.

Synthesis

152362-01-1

133627-45-9

General procedure for the synthesis of 2-chloro-3-amino-4-methylpyridine from 2-chloro-4-methylnicotinamide: 61.5 g of calcium hypochlorite was added to the reaction mixture in batches, and after the addition was completed, stirring was continued for 30 minutes at a maintained reaction temperature of 50 °C. Subsequently, 50 mL of 40 wt% aqueous calcium oxide solution was added in batches, the temperature was controlled not to exceed 10 °C, and the reaction lasted for 2 to 3 hours. Upon completion of the reaction, the cooled reaction mixture was slowly added dropwise to 150 mL of water, and the temperature was controlled not to exceed 100 °C during the dropwise addition. After the dropwise addition, the reaction was continued at 70 to 80°C for 2 hours. After the reaction solution was cooled to 5°C, the pH was adjusted to 6.5~7 with concentrated hydrochloric acid. filtration was carried out and the filter cake was washed with ice water. The filter cake was resuspended in 75 mL of water, heated to 60-70°C, stirred for 30 minutes, and then slowly cooled to 0~5°C to precipitate crystals. It was filtered again and the filter cake was washed with ice water and finally dried under vacuum. This process yielded 41.5 g of 2-chloro-3-amino-4-methylpyridine with 99.9% HPLC purity.

References

[1] Xin Ge. “A concise synthesis of 2-chloro-3-amino-4-methylpyridine.” Research on Chemical Intermediates 37 6 (2011): 599–604.

3-Amino-2-chloro-4-methylpyridine Preparation Products And Raw materials

Raw materials

Hydrogen peroxide Hydrochloric acid 3-Amino-4-methylpyridine

Preparation Products

Nevirapine

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3-Amino-2-chloro-4-methylpyridine Suppliers

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View Lastest Price from 3-Amino-2-chloro-4-methylpyridine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: 3-Amino-2-chloro-4-methylpyridine 133627-45-9
Price: US $0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 1000kg
Release date: 2021-09-18

Henan Aochuang Chemical Co.,Ltd.

Product: 3-Amino-2-chloro-4-methylpyridine 133627-45-9
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-09-22

Shaanxi Dideu New Materials Co. Ltd

Product: 3-Amino-2-chloro-4-methylpyridine 133627-45-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-02-23

133627-45-9, 3-Amino-2-chloro-4-methylpyridineRelated Search:

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CAS:133627-45-9

133627-45-9

133627-45

33627-45-9

5411-26-1

C6H7C1N2

C7H4ClF3O4

Halopyridines

Chloropyridines

Building Blocks

C5 to C6

Chemical Synthesis

Halogenated Heterocycles

Heterocyclic Building Blocks

API Intermediate

(intermediate of nevirapine)

Aromatics Compounds

Chloropyridines

Halopyridines

Aromatics

Bases & Related Reagents

Nucleotides

Pyridines, Pyrimidines, Purines and Pteredines

pharmacetical

Amines