| Identification | More | [Name]
2'-Iodoacetophenone | [CAS]
2142-70-3 | [Synonyms]
2'-IODOACETOPHENONE
2-IODOACETOPHENONE
O-IODOACETOPHENONE
2''-IODOACETOPHENONE 97%
2'-Iodoacetophenone, 98+%
2'-IODOACETOPHENONE, 99+% | [Molecular Formula]
C8H7IO | [MDL Number]
MFCD00094998 | [Molecular Weight]
246.05 | [MOL File]
2142-70-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear yellow liquid | [Boiling point ]
139-140°C 12mm | [density ]
1.72 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.618(lit.)
| [Fp ]
218 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Liquid | [color ]
Clear yellow | [Specific Gravity]
1.720 | [Sensitive ]
Light Sensitive | [BRN ]
2325078 | [InChI]
InChI=1S/C8H7IO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,1H3 | [InChIKey]
XDXCBCXNCQGZPG-UHFFFAOYSA-N | [SMILES]
C(=O)(C1=CC=CC=C1I)C | [CAS DataBase Reference]
2142-70-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29147000 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear yellow liquid | [Uses]
2′-Iodoacetophenone (2-Iodoacetophenone) may be used in the synthesis of:
indene derivatives
di-(o-acetylphenyl)acetylene
indenol derivative | [Preparation]
2'-iodoacetophenone can be prepared by diazotization of 2-acetylaniline. | [Reactions]
2'-Iodoacetophenone is a bioactive molecule that reacts with boronic acids to form aryl boronic acid derivatives. This reaction can be carried out in chlorobenzene or dihedral solvents, and it is scalable and applicable to a variety of boronic acids. The product of this reaction is an organocatalyst for the synthesis of bioactive molecules. 2'-Iodoacetophenone also reacts with dipole-containing additives to form dichlorodiphenyldichloroethane, which has been used as a fungicide, insecticide, and herbicide. | [General Description]
2′-Iodoacetophenone is a halogenated aromatic ketone. | [Synthesis]
To a round bottom flask were added phenylethanol (2 mmol), cuprous trifluoromethanesulfonate (CuOTf, 0.1 mmol, 0.05 eq.), (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 eq.), 2,2,6,6-tetramethylpiperidin-1-oxyl radical (TEMPO, 0.1 mmol, 0.05 eq.), potassium tert-butoxide (t-BuOK, 2 mmol, 1 eq.) and N,N-dimethylformamide (DMF, 5 ml). The reaction mixture was stirred and exposed to air at 25 °C until the reaction was complete (monitored by thin layer chromatography (TLC)). After completion of the reaction, the mixture was diluted with dichloromethane (CH2Cl2, 20 ml), washed with water, dried over anhydrous sodium sulfate (Na2SO4), and the solvent was evaporated in vacuum to give the crude product. The crude product was purified by column chromatography to give pure 2-iodoacetophenone. | [References]
[1] Tetrahedron, 2014, vol. 70, # 52, p. 9791 - 9796
[2] Journal of the American Chemical Society, 1996, vol. 118, # 25, p. 5904 - 5918
[3] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 372 - 381 |
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