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
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)
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
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.
N-Bromosuccinimide Price
- Product number
- 708135
- Product name
- 3-Amino-2-chloro-4-methylpyridine
- Purity
- 97%
- Packaging
- 5g
- Price
- $66.1
- Updated
- 2023/06/20
- Product number
- 708135
- Product name
- 3-Amino-2-chloro-4-methylpyridine
- Purity
- 97%
- Packaging
- 1g
- Price
- $24
- Updated
- 2023/01/07
- Product number
- A1855
- Product name
- 3-Amino-2-chloro-4-methylpyridine
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $39
- Updated
- 2025/07/31
- Product number
- A1855
- Product name
- 3-Amino-2-chloro-4-methylpyridine
- Purity
- >98.0%(GC)(T)
- Packaging
- 25g
- Price
- $116
- Updated
- 2025/07/31
- Product number
- A1376-48
- Product name
- 3-Amino-2-chloro-4-methylpyridine
- Packaging
- 5g
- Price
- $382
- Updated
- 2021/12/16
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.
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View Lastest Price from 3-Amino-2-chloro-4-methylpyridine manufacturers
- 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
- 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
- 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