| Identification | Back Directory | [Name]
2-Iodo-4-nitroaniline | [CAS]
6293-83-0 | [Synonyms]
2-Iodo-4-nitroaniline
2-Iodo-4-nitrobenzenamine
2-Iodo-4-nitrophenylaMine
2-IODO-4-NITROANILINE 97
4-Amino-3-iodonitrobenzene | [Molecular Formula]
C6H5IN2O2 | [MDL Number]
MFCD00955758 | [MOL File]
6293-83-0.mol | [Molecular Weight]
264.02 |
| Chemical Properties | Back Directory | [Appearance]
Yellow-red cryst | [Melting point ]
105-109 °C(lit.)
| [Boiling point ]
377.6±27.0 °C(Predicted) | [density ]
2.278 g/cm3 | [storage temp. ]
Refrigerated. | [solubility ]
Methanol | [form ]
Solid | [pka]
-1.18±0.10(Predicted) | [color ]
Yellow | [λmax]
360nm(MeOH)(lit.) | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C6H5IN2O2/c7-5-3-4(9(10)11)1-2-6(5)8/h1-3H,8H2 | [InChIKey]
LOLSEMNGXKAZBZ-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C([N+]([O-])=O)C=C1I |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow-red cryst | [Uses]
2-iodo-4-nitroaniline may be used to synthesize the following:
- 2-iodo-4-nitrobenzonitrile via reaction with sodium nitrite to form a diazonium salt, which then reacts with a mixture of CuCN/KCN
- 2-iodo-p-phenylenediamine by reacting with tin(II)dihydrate in conc.HCl
| [Synthesis Reference(s)]
Synthetic Communications, 22, p. 3215, 1992 DOI: 10.1080/00397919208021135 | [General Description]
2-Iodo-4-nitroaniline can be synthesized via reaction of 4-nitroaniline with iodine and silver acetate. | [Synthesis]
General procedure for the synthesis of 2-iodo-4-nitroaniline from 4-nitroaniline: 4-nitroaniline (298.2 mg, 2.16 mmol, 1.0 eq.) was dissolved in acetonitrile (3.0 mL) at room temperature, and N-iodosuccinimide (NIS, 579.1 mg, 2.36 mmol, 1.1 eq.) and trimeshylchlorosilane ( TMSCl, 27 μL, 23.1 mg, 0.21 mmol, 0.1 equiv) and the reaction was stirred at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC) and the reaction was completed after about 20 min. Water was added to the reaction mixture and the aqueous phase was extracted three times with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and saturated aqueous sodium chloride (NaCl), dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (SiO2) with 50% ethyl acetate-hexane mixed solvent as eluent to give 545.6 mg (96% yield) of 2-iodo-4-nitroaniline as yellow crystals. | [References]
[1] Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 772 - 780
[2] Synthesis, 2004, # 11, p. 1869 - 1873
[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] Journal of Medicinal Chemistry, 2007, vol. 50, # 6, p. 1380 - 1400 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [RIDADR ]
Not available | [WGK Germany ]
3
| [HS Code ]
29214200 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
|
| Company Name: |
Jia Xing Isenchem Co.,Ltd Gold
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Shanghai Ennopharm Co., Ltd.
|
| Telephone: |
+86 (21) 6435-5022 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList13640/0_EN.htm |
| Company Name: |
Aemon Chemical
|
| Telephone: |
0086-755-86198205 |
| Website: |
www.aemonchem.com |
|