| Identification | Back Directory | [Name]
Methyl 3-(4-Iodophenyl)propanoate | [CAS]
33994-44-4 | [Synonyms]
Methyl 3-(4-Iodophenyl)propanoate
3-(4-iodophenyl)propionic acid methyl ester
Benzenepropanoic acid, 4-iodo-, methyl ester | [Molecular Formula]
C10H11IO2 | [MDL Number]
MFCD18399500 | [MOL File]
33994-44-4.mol | [Molecular Weight]
290.1 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C(protect from light) | [Appearance]
White to light yellow Solid | [InChI]
InChI=1S/C10H11IO2/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-3,5-6H,4,7H2,1H3 | [InChIKey]
LDCXVBUZHUHPAJ-UHFFFAOYSA-N | [SMILES]
C1(CCC(OC)=O)=CC=C(I)C=C1 |
| Hazard Information | Back Directory | [Uses]
Methyl 3-(4-Iodophenyl)propanoate is used as a reactant in the preparation of HKGreen-1, a highly selective fluorescent probe for the detection of peroxynitrite in living cells. | [Synthesis]
Methanol (5 mL) was cooled to 0°C under nitrogen protection and acetyl chloride (0.4 mL, 5.63 mmol) was added slowly and dropwise. After stirring the reaction for 10 min, 3-(4-iodophenyl)propionic acid (498 mg, 1.80 mmol) was slowly added. The reaction mixture was stirred at room temperature for VA h and subsequently concentrated under vacuum. The concentrate was redissolved in methanol and concentrated again to give 512 mg (98% yield) of pure white solid product methyl 3-(4-iodophenyl)propionate. Thin layer chromatography (TLC) Rf value was 0.39 (unfolding agent ratio: ethyl acetate:hexane = 1:4). Nuclear magnetic resonance hydrogen spectrum (1H NMR, CDCl3) δ 7.61-7.59 (m, 2H), 6.97-6.94 (m, 2H), 3.66 (s, 3H), 2.92-2.87 (t, 2H, J=7.5 Hz), 2.63-2.58 (t, 2H, J=7.5 Hz). Nuclear magnetic resonance carbon spectrum (13C NMR, CDCl3) δ 173.0, 140.1, 137.5, 130.4, 91.4, 51.7, 35.4, 30.4. electron bombardment mass spectrum (EI-MS) m/z 290.0 (MH+). | [References]
[1] Organic Letters, 2008, vol. 10, # 12, p. 2597 - 2600
[2] Patent: WO2009/137322, 2009, A2. Location in patent: Page/Page column 15
[3] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17500 - 17521
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7061 - 7064
[5] Patent: WO2010/12650, 2010, A1. Location in patent: Page/Page column 39 |
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