4-Iodo-2-nitroaniline Chemical Properties

Melting point:

120-123 °C (lit.)

Boiling point:

352.9±27.0 °C(Predicted)

Density 

2.101±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-1.19±0.10(Predicted)

color 

Dark Red to Dark Brown

Stability:

Air Sensitive

InChI

InChI=1S/C6H5IN2O2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H,8H2

InChIKey

QVCRSYXVWPPBFJ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

WGK Germany 

2

HS Code 

2921490090

4-Iodo-2-nitroaniline Usage And Synthesis

Uses

4-Iodo-2-nitroaniline can be used in organic synthesis.

Synthesis

2-Iodo-4-nitroaniline can be synthesized via reaction of 4-nitroaniline with iodine and silver acetate.

Synthesis

The general procedure for the synthesis of 4-iodo-2-nitroaniline from 2-nitroaniline is as follows: iodination in the presence of Na2SO3 (typical procedure). To a 100 mL round bottom flask was added a solution of 3 mmol 2-nitroaniline in 10 mL acetic acid and a solution of KI3 and Na2SO3 prepared in advance by adding 3 mmol iodine and 3 mmol Na2SO3 to the solution. A solution of 3 mmol potassium iodide in 3 mL of water was quickly added. At the same time, a solution of 3 mmol NaIO4 in 5 mL of water was added and 0.5 mL of sulfuric acid was quickly added using a pressure-balanced dropping funnel. The reaction mixture was stirred at 25 °C and the reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was poured into ice-cold water and the solid product, 4-iodo-2-nitroaniline, was isolated by vacuum filtration, washed twice with deionized water and dried under appropriate conditions.

References

[1] Monatshefte fur Chemie, 2002, vol. 133, # 10, p. 1325 - 1330
[2] Tetrahedron Letters, 2006, vol. 47, # 28, p. 4793 - 4796
[3] Russian Journal of Organic Chemistry, 2016, vol. 52, # 3, p. 433 - 436
[4] Zh. Org. Khim., 2016, vol. 52, # 3, p. 433 - 436,4
[5] Tetrahedron, 2003, vol. 59, # 14, p. 2497 - 2518

4-Iodo-2-nitroaniline(20691-72-9)Related Product Information

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• 4-NITRODIAZOAMINOBENZENE
• 2-Nitroaniline
• N-Methyl-4-nitroaniline
• 4-NITRO-2-SULFOANILINE
• 4-Nitroaniline
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• BUTTPARK 89\07-13
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