| Identification | More | [Name]
1,3-Dichloroisoquinoline | [CAS]
7742-73-6 | [Synonyms]
1,3-DICHLOROISOQUINOLINE
TIMTEC-BB SBB003563
4-(AMINOMETHYL)-4-HYDROXY-1-METHYLPIPERIDINE | [EINECS(EC#)]
627-814-4 | [Molecular Formula]
C9H5Cl2N | [MDL Number]
MFCD00034750 | [Molecular Weight]
198.05 | [MOL File]
7742-73-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White to brown crystalline powder | [Melting point ]
121-122 °C (lit.) | [Boiling point ]
307°C(lit.) | [density ]
1.407±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
-1.49±0.50(Predicted) | [color ]
Light yellow to Brown to Dark green | [InChI]
InChI=1S/C9H5Cl2N/c10-8-5-6-3-1-2-4-7(6)9(11)12-8/h1-5H | [InChIKey]
BRGZEQXWZWBPJH-UHFFFAOYSA-N | [SMILES]
C1(Cl)C2=C(C=CC=C2)C=C(Cl)N=1 | [CAS DataBase Reference]
7742-73-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [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:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29163990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White to brown crystalline powder | [Uses]
1,3-Dichloroisoquinoline may be used in the facile synthesis of 1,3,4-trisubstituted isoquinoline derivatives. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 80, p. 5481, 1958 DOI: 10.1021/ja01553a042 | [General Description]
1,3-Dichloroisoquinoline undergoes Pd(PPh3)4 catalyzed regioselective coupling with arylboronic acids to afford to 1-aryl-3-chloroisoquinolines. Reaction of amine with 1,3-dichloroisoquinoline has been studied. Regioselectivity of the Stille coupling reaction of (1-ethoxyvinyl)tri(n-butyl)stannane with 1,3-dichloroisoquinoline has been investigated. | [Synthesis]
Example 60B Synthesis of 1,3-dichloroisoquinoline: The product of Example 60A, 1,3-[2H,4H]-isoquinolinedione (6.5 g, 40.4 mmol) was mixed with phenylphosphinic acid dichloride (11.5 mL, 81.1 mmol) and the reaction was heated for 3 hours at 160 °C. After the reaction was completed, it was cooled to room temperature and left to stand overnight. The reaction mixture was dissolved in tetrahydrofuran (200 mL) and hydrolyzed by adding water (60 mL), followed by concentration under reduced pressure to remove the tetrahydrofuran. The resulting aqueous phase was neutralized with concentrated NH4OH, followed by extraction with ethyl acetate. The organic phases were combined, washed sequentially with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 1,3-dichloroisoquinoline as a yellow flaky solid (6.92 g, 74% yield). | [References]
[1] Patent: US2005/113576, 2005, A1. Location in patent: Page/Page column 30
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3651 - 3660
[3] Patent: US6340759, 2002, B1. Location in patent: Example 17
[4] Patent: WO2010/127855, 2010, A1. Location in patent: Page/Page column 136; 137 |
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