2-IODO-5-NITROBENZOIC ACID

2-IODO-5-NITROBENZOIC ACID Property

Melting point:

197-198 °C

Boiling point:

394.2±37.0 °C(Predicted)

Density 

2.156±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.16±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C7H4INO4/c8-6-2-1-4(9(12)13)3-5(6)7(10)11/h1-3H,(H,10,11)

InChIKey

JSSFIFUXHORXJX-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC([N+]([O-])=O)=CC=C1I

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-IODO-5-NITROBENZOIC ACID Chemical Properties,Usage,Production

Uses

2-iodo-5-nitrobenzoic acid is a useful reactant for the synthesis of 2-?Arylquinazolines and Tetracyclic Isoindolo[1,?2-?a]?quinazoline.

Synthesis

During this preparation, up to 25 mmol of I2 is generated. therefore, the synthesis operation must be carried out in a well-ventilated fume hood. The preparation was carried out with reference to the literature method [10]. 2-Iodobenzoic acid (4.10 g, 40.3 mmol, 1 equiv) was added to a mixed solution of HNO3 (35 mL, 65%) and H2SO4 (85 mL, 95%). The reaction mixture was heated to 135 °C and stirred at this temperature for 1 hour. Upon completion of the reaction, the resulting brown slurry was poured on ice, filtered to collect the gray precipitate, and washed with plenty of water. Subsequently, the filter cake was suspended in water (100 mL), heated to 100 °C and a solution consisting of KI (8.5 g, 51.2 mmol, 1.3 eq.) and H2SO4 (5 drops) dissolved in water (10 mL) was added in the process and the reaction was continued for 1 hour. Finally, the brown suspension was filtered while hot and washed with cold water to give the pure product 2-iodo-5-nitrobenzoic acid (5 g, 42% yield) as a brown solid. If the product is impure, it can be purified by boiling in water and then hot filtering.

References

[1] Journal of Organic Chemistry, 2005, vol. 70, # 12, p. 4778 - 4783
[2] Synlett, 2013, vol. 24, # 13, p. 1707 - 1711
[3] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1 - 6
[4] Organic Letters, 2011, vol. 13, # 3, p. 518 - 521
[5] Helvetica Chimica Acta, 1930, vol. 13, p. 310,311