| Identification | More | [Name]
3-Iodo-2-methoxypyridine | [CAS]
112197-15-6 | [Synonyms]
3-IODO-2-METHOXYPYRIDINE
2-METHOXY-3-IODOPYRIDINE
3-IODO-2-METHOXYPYRIDINE 99% | [EINECS(EC#)]
622-890-5 | [Molecular Formula]
C6H6INO | [MDL Number]
MFCD03094946 | [Molecular Weight]
235.02 | [MOL File]
112197-15-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Cryst | [Melting point ]
66 °C(Solv: hexane (110-54-3)) | [Boiling point ]
131-133 °C (43 mmHg) | [density ]
1.831 g/mL at 25 °C | [refractive index ]
1.617-1.619
| [Fp ]
>110℃ | [storage temp. ]
2-8°C | [form ]
clear liquid | [pka]
1.38±0.10(Predicted) | [color ]
Light yellow to Brown | [Sensitive ]
Light Sensitive | [InChI]
InChI=1S/C6H6INO/c1-9-6-5(7)3-2-4-8-6/h2-4H,1H3 | [InChIKey]
BXCHJERCAUZLOE-UHFFFAOYSA-N | [SMILES]
C1(OC)=NC=CC=C1I | [CAS DataBase Reference]
112197-15-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 3334 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow Cryst | [Synthesis]
The general procedure for the synthesis of 3-iodo-2-methoxypyridine using 2-methoxypyridine as starting material was as follows: firstly, [Li(TMP)Zn(tBu)2] was prepared in 0.4 mmol scale THF solution according to the literature method. To this solution, 2-methoxypyridine (0.042 mL, 0.4 mmol) was added and the reaction mixture was stirred at room temperature for 2 h to obtain a light orange solution. Subsequently, the solution was cooled to 0°C and the reaction was quenched with I2 (508 mg, dissolved in 1 mL THF) and stirring was continued for 1 hour. Upon completion of the reaction, 10% Na2S2O3 solution was added until the solution was bleached and the product was extracted with DCM (3 x 1 mL). The organic phases were combined, dried with MgSO4 and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using heptane:DCM (20:80→40:60) as eluent to afford 3-iodo-2-methoxypyridine (2a) as a colorless oil (87.1 mg, 92% yield).1H NMR (400 MHz, CDCl3) δ ppm 4.00 (s, 3H), 6.65 (dd, J = 7.61, 4.88 Hz, 1H), 8.03 (dd, J = 7.61, 1.76 Hz, 1H), 8.13 (dd, J = 4.88, 1.76 Hz, 1H). The data obtained are in agreement with literature reports. | [References]
[1] Tetrahedron, 2016, vol. 72, # 17, p. 2196 - 2205
[2] Tetrahedron Letters, 2011, vol. 52, # 36, p. 4590 - 4594
[3] Journal of the American Chemical Society, 2004, vol. 126, # 34, p. 10526 - 10527
[4] Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1921 - 1930
[5] Chemical Communications, 2014, vol. 50, # 85, p. 12859 - 12862 |
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