| Identification | More | [Name]
4-Bromoisoquinoline | [CAS]
1532-97-4 | [Synonyms]
4-BROMOISOQUINOLINE
LABOTEST-BB LT01143353
4-bromoisoqunoline
4-Bromoisquinoline
4-Isoquinolinyl Bromide
NSC 56333
4-Bromoisoquinoline ,98% | [EINECS(EC#)]
216-244-8 | [Molecular Formula]
C9H6BrN | [MDL Number]
MFCD00006904 | [Molecular Weight]
208.05 | [MOL File]
1532-97-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [Melting point ]
40-43 °C (lit.) | [Boiling point ]
280-285 °C (lit.) | [density ]
1.5617 (rough estimate) | [refractive index ]
1.6641 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Refrigerator (+4°C) | [solubility ]
Chloroform, Methanol | [form ]
Crystalline Solid | [pka]
3.30±0.10(Predicted) | [color ]
White to light beige | [Usage]
Shows selective inhibition of cAMP-dependent protein kinase | [Detection Methods]
HPLC,NMR,GC | [BRN ]
114431 | [InChI]
InChI=1S/C9H6BrN/c10-9-6-11-5-7-3-1-2-4-8(7)9/h1-6H | [InChIKey]
SCRBSGZBTHKAHU-UHFFFAOYSA-N | [SMILES]
C1C2=C(C=CC=C2)C(Br)=CN=1 | [CAS DataBase Reference]
1532-97-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Isoquinoline, 4-bromo-(1532-97-4) |
| Safety Data | Back Directory | [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 .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Uses]
Shows selective inhibition of cAMP-dependent protein kinase | [Preparation]
2-Alkynyl benzyl azides could smoothly undergo an electrocyclic reaction catalyzed by palladium to afford either 4-bromoisoquinoline or 4-bromoisquinolones selectively under different conditions. 4-Bromoisoquinoline was synthesised in the presence of PdBr2/CuBr2/LiBr in MeCN, and 4-bromoisoquinolone was selectively produced with PdBr2/CuBr2/HOAc in CH2ClCH2Cl[1].
| [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 10, p. 409, 1973 DOI: 10.1002/jhet.5570100326 | [Synthesis]
Synthesis of Intermediate-12: 3-Bromoisoquinoline: To a stirred solution of isoquinoline (24 g, 186 mmol) in acetic acid (50 mL) was slowly added N-bromosuccinimide (NBS, 36.2 g, 204.6 mmol) at room temperature. The reaction mixture was heated to 100 °C and the reaction was stirred at this temperature overnight. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (eluent: 5% ethyl acetate/hexane) to give 4-bromoisoquinoline (9.2 g, 23.8% yield) as an oil. | [References]
[1] Hong-ping Zhang, Hongzhan Xiao, Hong‐Yan Li. “A Selective Synthesis of 4-Bromoisoquinoline and 4-Bromoisquinolone.” Journal of Chemical Research-s (2013).
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