| Identification | More | [Name]
2-Chloro-3-iodopyridine | [CAS]
78607-36-0 | [Synonyms]
2-CHLORO-3-IODOPYRIDINE
3-iodo-2-chloropyridine
BUTTPARK 34\07-77
2-CHORO-3-IODOPYRIDINE
2-chloro-3-indopyridine
2-Chloro-3-iodopyridine, 98+% | [EINECS(EC#)]
675-002-3 | [Molecular Formula]
C5H3ClIN | [MDL Number]
MFCD00661298 | [Molecular Weight]
239.44 | [MOL File]
78607-36-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
90-95 °C | [Boiling point ]
261.2±20.0 °C(Predicted) | [density ]
2.052±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Crystalline Powder | [pka]
-0.70±0.10(Predicted) | [color ]
Cream yellow to salmon | [Sensitive ]
Light Sensitive | [BRN ]
4243304 | [InChI]
InChI=1S/C5H3ClIN/c6-5-4(7)2-1-3-8-5/h1-3H | [InChIKey]
OHWSWGXNZDSHLM-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC=C1I | [CAS DataBase Reference]
78607-36-0(CAS DataBase Reference) | [Storage Precautions]
Light sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/22:Harmful by inhalation 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 .
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Irritant/Light Sensitive | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
2-Chloro-3-iodopyridine (cas# 78607-36-0) is a compound useful in organic synthesis. | [Uses]
2-Chloro-3-iodopyridine is a compound useful in organic synthesis. | [Synthesis]
General procedure for the synthesis of 2-chloro-3-iodopyridine from 2-chloropyridine: 2,2,6,6-tetramethylpiperidine (17 mL, 14 g, 0.1 mol) and 2-chloropyridine (9.5 mL, 11.5 g, 0.1 mol) were sequentially added to a hexane solution of 1.6 M n-butyllithium (62.5 mL, 0.1 mol) at -78 °C with a solvent of 150 mL of tetrahydrofuran. After maintaining the reaction temperature at -78 °C with stirring for 2 h, a tetrahydrofuran solution (50 mL) of iodine (25.5 g, 0.1 mol) was added dropwise to the reaction mixture and stirring was continued for 30 min. Subsequently, the reaction mixture was partitioned between water (100 mL) and ether (3 x 50 mL). The organic layers were combined, washed with saturated aqueous sodium thiosulfate solution (2 x 50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuum to give the crude product. The crude product was purified by fast chromatography (eluent: heptane/ethyl acetate, 90/10) to give a yellow solid product in 72% yield (17.3 g). The structure of the product was analyzed by 1H NMR (CDCl3): δ 8.38 (dd, J = 4.6/1.7 Hz, 1H), 8.16 (dd, J = 8.0/0.16 Hz, 1H), 6.96 (dd, J = 8.0/4.6 Hz, 1H); 13C NMR (CDCl3): δ 154.5, 148.9, 148.8, 123.2 , 94.9; MS (EI) m/z 240 (M + 1) confirmed. | [References]
[1] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1397 - 1401
[3] Patent: WO2004/52880, 2004, A1. Location in patent: Page 29-30
[4] Tetrahedron Letters, 1994, vol. 35, # 35, p. 6489 - 6492
[5] Organic letters, 2002, vol. 4, # 13, p. 2201 - 2203 |
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