| Identification | Back Directory | [Name]
4-Iodo-2-nitroaniline | [CAS]
20691-72-9 | [Synonyms]
4-Iodo-2-nitroaniline
4-IODO-2-NITROANILINE 97
4-Iodo-2-nitrophenylamine
4-Iodo-2-nitroaniline 98%
2-Amino-5-iodonitrobenzene
Benzenamine, 4-iodo-2-nitro-
4-Iodo-2-nitroaniline
4-Iodo-2-nitroaniline ISO 9001：2015 REACH | [Molecular Formula]
C6H5IN2O2 | [MDL Number]
MFCD06808526 | [MOL File]
20691-72-9.mol | [Molecular Weight]
264.02 |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-43 | [Safety Statements ]
36/37 | [WGK Germany ]
2
| [HS Code ]
2921490090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Sens. 1 |
| Hazard Information | Back Directory | [Uses]
4-Iodo-2-nitroaniline can be used in organic synthesis. | [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 |
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