| Identification | More | [Name]
5-Bromoisoquinoline | [CAS]
34784-04-8 | [Synonyms]
5-BROMOISOQUINOLINE
AKOS BBS-00003132
BUTTPARK 44\07-76
5-Bromo Isoquinolin
5-Bromoisoquinoline,98%
Isoquinoline, 5-bromo- | [EINECS(EC#)]
626-788-1 | [Molecular Formula]
C9H6BrN | [MDL Number]
MFCD01646405 | [Molecular Weight]
208.05 | [MOL File]
34784-04-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White to yellow-brown crystals | [Melting point ]
83-87 °C (lit.) | [Boiling point ]
95-97°C 0,1mm | [density ]
1.564±0.06 g/cm3(Predicted) | [Fp ]
95-97°C/0.1mm | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform, Dichloromethane, Ethyl Acetate, Methanol | [form ]
Solid | [pka]
4.39±0.13(Predicted) | [color ]
Yellow | [BRN ]
114468 | [InChI]
InChI=1S/C9H6BrN/c10-9-3-1-2-7-6-11-5-4-8(7)9/h1-6H | [InChIKey]
CYJZJGYYTFQQBY-UHFFFAOYSA-N | [SMILES]
C1C2=C(C(Br)=CC=C2)C=CN=1 | [CAS DataBase Reference]
34784-04-8(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,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R21/22:Harmful in contact with skin and if swallowed .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29334900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
5-Bromoisoquinoline is a synthetic intermediate useful for pharmaceutical synthesis. | [Chemical Properties]
White to yellow-brown crystals | [Uses]
Starting material employed in palladium-catalyzed aminomethylation1 and amination2 reactions. | [Synthesis Reference(s)]
[1] W. Brown, A. Gouliaev. “Bromination of Isoquinoline, Quinoline, Quinazoline and Quinoxaline in Strong Acid.” ChemInform 98 1 (2002). | [Synthesis]
To mechanically stirred concd H2SO4 (42.5 mL) at 0 °C, isoquinoline (1; 5 mL, 42.5 mmol) was slowly added. The mixture was cooled to –25 °C, and NBS (9.83 g, 55.2 mmol) was added at such a rate that the reaction temperature was kept between –25 °C and –22 °C. The mixture was stirred at -22±1 °C for 2 h and at -18±1 °C for 3h. The mixture was then worked up as described above to give 6.16 g (72%) as a slightly off-white solid after chromatography; mp 81–82 °C. The solid was further purified by sublimation (75 °C/0.2 mmHg) to give 5-Bromoisoquinoline as a white powder[1].
| [References]
[1] Patent: US2008/318941, 2008, A1. Location in patent: Page/Page column 22
[2] Patent: WO2009/23844, 2009, A2. Location in patent: Page/Page column 105-106
[3] Patent: US2008/200471, 2008, A1. Location in patent: Page/Page column 45; 45-46
[4] Patent: US2010/16297, 2010, A1. Location in patent: Page/Page column 25
[5] Patent: WO2010/21797, 2010, A1. Location in patent: Page/Page column 68 |
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