5-CHLOROISOQUINOLINE
- Product Name
- 5-CHLOROISOQUINOLINE
- CAS No.
- 5430-45-5
- Chemical Name
- 5-CHLOROISOQUINOLINE
- Synonyms
- NSC 13799;5-CHLORISOQUINOLIN;5-Chloroisoquinolin;5-CHLOROISOQUINOLINE;isoquinoline, 5-chloro;5-CHLOROISOQUINOLINE ISO 9001：2015 REACH
- CBNumber
- CB1444694
- Molecular Formula
- C9H6ClN
- Formula Weight
- 163.6
- MOL File
- 5430-45-5.mol
5-CHLOROISOQUINOLINE Property
- Melting point:
- 69-73 °C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- color
- White
- CAS DataBase Reference
- 5430-45-5(CAS DataBase Reference)
N-Bromosuccinimide Price
- Product number
- 718238
- Product name
- 5-Chloroisoquinoline
- Purity
- 97%
- Packaging
- 1g
- Price
- $173
- Updated
- 2023/06/20
- Product number
- C367400
- Product name
- 5-Chloroisoquinoline
- Packaging
- 100mg
- Price
- $50
- Updated
- 2021/12/16
- Product number
- FC20242
- Product name
- 5-Chloroisoquinoline
- Packaging
- 500mg
- Price
- $80
- Updated
- 2021/12/16
- Product number
- 3H32-5-5Q
- Product name
- 5-Chloroisoquinoline
- Purity
- 95%
- Packaging
- 1g
- Price
- $87
- Updated
- 2021/12/16
- Product number
- W6855
- Product name
- 5-Chloroisoquinoline
- Packaging
- 1g
- Price
- $117
- Updated
- 2021/12/16
5-CHLOROISOQUINOLINE Chemical Properties,Usage,Production
Chemical Properties
White Solid
Uses
5-Chloroisoquinoline (compound 42) is an inhibitor of SARM1 (Sterile alpha and toll/interleukin receptor (TIR) motif containing protein 1), an enzyme involved in axon degeneration that catalyzes multiple activities through a ternary complex mechanism. 5-Chloroisoquinoline can be used in the study of neurodegenerative diseases or axon degeneration[1].
Synthesis
119-65-3
5430-45-5
73075-59-9
Isoquinoline (1; 12.9 g, 0.1 mol, 1.0 equiv) was slowly added to concentrated H2SO4 (100 mL) pre-cooled to 0 °C under mechanical stirring. Under vigorous stirring, TCCA (12.8 g, 55 mmol, 1.65 eq.) was added in 4 batches while the reaction temperature was controlled not to exceed 10 °C. The reaction was carried out at 10 °C for a period of 2 hours. After the reaction mixture was stirred continuously at 10 °C for 24 h, the reaction progress was monitored by GC-MS. Subsequently, the reaction mixture was poured into crushed ice (~200 g) and the precipitate was collected by filtration. The pH of the filtrate was adjusted to 2 with concentrated ammonia solution, cooled sufficiently and filtered again. The filtrate was extracted with toluene (6 x 75 mL) to remove the by-product 5,8-dichloroisoquinoline (16). The aqueous phase was further alkalized with concentrated ammonia to pH 6, at which point the precipitate precipitated was filtered, washed with water and dried at room temperature. The final product was purified by recrystallization from methylcyclohexane in 15% yield. 5-Chloroisoquinoline was obtained as 7.60 g (45% yield), melting point 70-72 °C. IR (ATR): 1580, 1489, 1371, 1267, 1204, 1140, 1065, 984, 822, 750, 687, 628, 536 cm?1. 1H NMR (400 MHz, CDCl3): δ= 9.27 (s, 1H), 8.64 (1H). 1H), 8.64 (d, J = 6.0 Hz, 1H), 8.02 (d, J = 6.0 Hz, 1H), 7.90 (d, J = 8.2 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.53 (t, J = 7.8 Hz, 1H).13C NMR (100 MHz, CDCl3): δ= 152.4, 143.9, 133.9, 133.5, 133.5 cm?1. 1H NMR (400 MHz, CDCl3): δ= 152.4, 143.9, 143.9, 133.5 cm? 143.9, 133.7, 131.0, 130.3, 129.4, 127.3, 126.7, 116.9.
References
[1] Inhibitors of SARM1. World Intellectual Property Organization, WO2019236879 A1 2019-12-12.
5-CHLOROISOQUINOLINE Preparation Products And Raw materials
Raw materials
Preparation Products
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