5-BROMOINDOLINE Chemical Properties

Melting point:

36-40 °C (lit.)

Boiling point:

114-115°C 5mm

Density 

1.5240 g/cm3

refractive index 

1.63

Flash point:

>230 °F

storage temp. 

-20°C

solubility 

DMSO, Methanol

form 

Solid

pka

4.35±0.20(Predicted)

color 

Off-White

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-BROMOINDOLINE Usage And Synthesis

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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