2-IODOISOPROPYLBENZENE Chemical Properties

Boiling point:

89 °C

Density 

1.54

refractive index 

1.5801

Flash point:

110°C/20mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Clear Pale Red to Red

Sensitive 

Light Sensitive

BRN 

2351872

CAS DataBase Reference

19099-54-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50/53-41-37/38

Safety Statements 

26-36/37/39-61-60-39

Hazard Note 

Irritant/Light Sensitive

HS Code 

29039990

MSDS

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2-IODOISOPROPYLBENZENE Usage And Synthesis

Uses

2-Iodocumene acts as a reagent in the synthesis of aryliminoguanidines as NPFF1 and NPFF2 agonists.

Synthesis

General procedure for the synthesis of 2-isopropyliodobenzene from 2-isopropylaniline: 2-isopropylaniline (27.04 g, 0.2 mol) was dissolved in 25% aqueous sulfuric acid solution (w/w, 160 mL), and diazotization reaction was carried out by slowly and dropwise addition of an aqueous solution of sodium nitrite (14 g) (26 mL) at -20 °C. The resulting diazonium salt solution was transferred to an aqueous solution (100 mL) of potassium iodide (100 g) and after 18 hours of reaction, sodium hydroxide (36 g) and water (125 mL) were added to neutralize the reaction system. The reaction mixture was extracted with hexane, the organic phases were combined and purified by silica gel column chromatography, and the target product, 2-isopropyliodobenzene, was obtained after concentration in a yield of 35.8 g, 73%. The product was identified by mass spectrometry: m/z 246 (M+). 1H NMR (CDCl3) δppm: 1.23 (d, 6H, J=6.84 Hz), 3.18 (septet, 1H, J=6.84 Hz), 6.86 (m, 1H), 7.28 (m, 2H), 7.82 (dd, 1H, J=1.24 and 7.92 Hz).

References

[1] Patent: US10113065, 2018, B1. Location in patent: Page/Page column 21
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 1897,1900
[3] Bulletin of the Chemical Society of Japan, 1971, vol. 44, p. 266 - 270
[4] Journal of Organic Chemistry, 1997, vol. 62, # 16, p. 5651 - 5656
[5] Advanced Synthesis and Catalysis, 2008, vol. 350, # 14-15, p. 2179 - 2182

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