| Identification | More | [Name]
2-Chloro-4-iodopyridine | [CAS]
153034-86-7 | [Synonyms]
2-CHLORO-4-IODOPYRIDINE
2-CHLORO-IODOPYRIDINE
4-Iodo-2-chloropyridine
2-CHLORO-4-IODOPYRIDINE,99% | [EINECS(EC#)]
628-020-0 | [Molecular Formula]
C5H3ClIN | [MDL Number]
MFCD01861983 | [Molecular Weight]
239.44 | [MOL File]
153034-86-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
42-43 °C (lit.) | [Boiling point ]
255.5±20.0 °C(Predicted) | [density ]
2.052±0.06 g/cm3(Predicted) | [Fp ]
110 °C | [storage temp. ]
Refrigerator | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Crystals or Crystalline Flakes | [pka]
-0.03±0.10(Predicted) | [color ]
White to yellow | [Sensitive ]
Light Sensitive | [Detection Methods]
GC | [BRN ]
108668 | [InChI]
1S/C5H3ClIN/c6-5-3-4(7)1-2-8-5/h1-3H | [InChIKey]
KJKIPRQNFDUULB-UHFFFAOYSA-N | [SMILES]
Clc1cc(I)ccn1 | [CAS DataBase Reference]
153034-86-7(CAS DataBase Reference) | [Storage Precautions]
Light sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Light Sensitive | [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
2-Chloro-4-iodopyridine (cas# 153034-86-7) is a compound useful in organic synthesis. | [Synthesis]
General procedure for the synthesis of 2-chloro-4-iodopyridine from 2-chloro-3-iodopyridine: 2-chloro-3-iodopyridine (12 g, 50 mmol) was prepared as a solution by dissolving it in 20 mL of tetrahydrofuran (THF). The solution was slowly added to a pre-prepared lithium diisopropylammonium solution at -78°C (the lithium diisopropylammonium solution was prepared by reacting 1.6 M n-butyllithium hexane solution (31.25 mL, 50 mmol) with diisopropylamine (7 mL, 50 mmol) in 100 mL THF). After 3 hours of reaction, the reaction was quenched by adding 20 mL of water to the reaction mixture, followed by extraction with ether (2 x 100 mL). The organic layers were combined, dried with magnesium sulfate, filtered and concentrated under vacuum at 20 °C to give a brown solid. Purification by silica gel column chromatography (eluent: ethyl acetate/heptane=8/2) gave light yellow needle-like crystals in 95% yield (11.4 g). The structure of the product was analyzed by 1H NMR (CDCl3): δ 8.07 (d, J = 5.3 Hz, 1H), 7.76 (d, J = 1.1 Hz, 1H), 7.59 (dd, J = 5.0/0.11 Hz, 1H); 13C NMR (CDCl3): δ 151.7, 149.6, 133.0, 131.5, 106.6; MS ( EI) m/z 240 (M + 1) confirmed. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1397 - 1401
[2] Patent: WO2004/52880, 2004, A1. Location in patent: Page 30
[3] Patent: US2009/186899, 2009, A1. Location in patent: Page/Page column 45-46
[4] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[5] Patent: US2008/249128, 2008, A1. Location in patent: Page/Page column 46 |
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