| Identification | More | [Name]
2-Chloro-3-amino-4-methyl pyridine | [CAS]
133627-45-9 | [Synonyms]
2-CHLORO-3-AMINO-4-METHYLPYRIDINE
2-CHLORO-3-AMINO-4-PICOLINE
2-CHLORO-4-METHYLPYRIDIN-3-AMINE
2-CHLORO-4-METHYL-PYRIDIN-3-YLAMINE
3-AMINO-2-CHLORO-4-METHYLPYRIDINE
3-AMINO-2-CHLORO-4-PICOLINE
ASINEX-REAG BAS 13794917
TIMTEC-BB SBB010194
2-Chloro-3-Amino-4-Methylpyridine,Nevirapine
2-Chloro-3-Amino-4-Methylpyrid
2-chloro-3-amino-4-methylpyridine (intermediate of nevirapine)
3-Pyridinamine,2-chloro-4-methyl-(9CI)
2-CHLORO-4-METHYLPYRIDIN-3-AMINE ,98%
3-AMINO-2-CHLORO-4-PICOLINE (3-AMINO-2-CHLORO-4-METHYLPYRIDINE)
2-chloro-4-methylpyridin-3-amine(3-AMINO-2-CHLORO-4-PICOLINE)
3-Amino-2-chloro-4-methlpyridine
3-Amino-2-chloro-4-methylpyridine ,98% | [EINECS(EC#)]
603-756-5 | [Molecular Formula]
C6H7ClN2 | [MDL Number]
MFCD00673152 | [Molecular Weight]
142.59 | [MOL File]
133627-45-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Off White Crystals | [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 | [form ]
Crystals | [pka]
3.22±0.10(Predicted) | [color ]
Off White | [Detection Methods]
GC,HPLC, | [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) | [Storage Precautions]
Heat sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
UN2811 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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]
3-Amino-2-chloro-4-methylpyridine can be obtained by reacting 2-chloro-4-methylnicotinamide with strong bases and halides.
| [Synthesis]
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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