ChemicalBook > CAS DataBase List > 3-Amino-2-chloro-4-methylpyridine

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

Americas 1 Canada 3 CHINA 426 Czech Republic 1 Europe 4 Germany 6 India 46 Indonesia 1 Japan 4 Jordan 1 Russia 1 Slovakia 1 South Korea 1 Switzerland 2 Ukraine 2 United Kingdom 17 United States 53 Global 570
Hubei Guanzhongtong Technology Co.,LTD
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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

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  • CAS:133627-45-9
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  • 5411-26-1
  • C6H7C1N2
  • C7H4ClF3O4
  • Halopyridines
  • Chloropyridines
  • Building Blocks
  • C5 to C6
  • Chemical Synthesis
  • Halogenated Heterocycles
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  • API Intermediate
  • (intermediate of nevirapine)
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  • Chloropyridines
  • Halopyridines
  • Aromatics
  • Bases & Related Reagents
  • Nucleotides
  • Pyridines, Pyrimidines, Purines and Pteredines
  • pharmacetical
  • Amines