| Identification | More | [Name]
5-BROMOINDOLINE | [CAS]
22190-33-6 | [Synonyms]
5-BROMO-2,3-DIHYDRO-1H-INDOLE
5-BROMOINDOLINE
AKOS BC-0891
5-Bromoindoline,98+% | [EINECS(EC#)]
629-063-8 | [Molecular Formula]
C8H8BrN | [MDL Number]
MFCD00027410 | [Molecular Weight]
198.06 | [MOL File]
22190-33-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White to brown low melting solid | [Melting point ]
36-40 °C (lit.) | [Boiling point ]
114-115°C 5mm | [density ]
1.5240 g/cm3 | [refractive index ]
1.63 | [Fp ]
>230 °F
| [storage temp. ]
-20°C | [solubility ]
DMSO, Methanol | [form ]
Solid | [pka]
4.35±0.20(Predicted) | [color ]
Off-White | [Detection Methods]
HPLC | [BRN ]
121590 | [InChI]
InChI=1S/C8H8BrN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-2,5,10H,3-4H2 | [InChIKey]
QEDCHCLHHGGYBT-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(Br)C=C2)CC1 | [CAS DataBase Reference]
22190-33-6(CAS DataBase Reference) | [Storage Precautions]
Air 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:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [PackingGroup ]
III | [HS Code ]
29339900 | [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 low melting solid | [Uses]
5-Bromoindoline is a brominated indoline derivative and a product of biocatalyzed halogenation of nucleobase analogs. 5-Bromoindoline is used in the synthetic preparation of biologically active compou
nds such as selective human β3 adrenergic receptor agonists. | [Synthesis]
A) 38 g (0.16 mol) of 1-acetyl-5-bromoindoline, 31 g of concentrated hydrochloric acid and 41 g of ethanol were added to the reaction flask and stirred thoroughly to obtain reaction mixture I; B) reaction mixture I was reacted at 78 °C for 4 h. Complete disappearance of the raw materials was confirmed by chromatographic monitoring; C) the reaction mixture was neutralized using 55 g of sodium hydroxide solution; D) the organic phase J and the aqueous phase K were separated; E) the organic phase J was extracted three times using 445 g of chloroform. K; E) Organic phase J was extracted three times with 445 g of chloroform. The organic layers were combined and the solvent was recovered to give 30.74 g of 5-bromodihydroindole in 98.04% yield and ≥99% purity. | [References]
[1] Patent: CN106432040, 2017, A. Location in patent: Paragraph 0108-0113; 0135-0140; 0162-0167
[2] European Journal of Medicinal Chemistry, 2006, vol. 41, # 1, p. 88 - 100
[3] Tetrahedron Letters, 2004, vol. 45, # 25, p. 4827 - 4830
[4] Patent: CN106966950, 2017, A. Location in patent: Paragraph 0022
[5] Patent: US2011/98311, 2011, A1 |
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