2-Chloro-3-iodopyridine Chemical Properties

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

pka

-0.70±0.10(Predicted)

form 

Crystalline Powder

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)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/22-41-22

Safety Statements 

36/37/39-26-22-36-39-37

WGK Germany 

3

Hazard Note 

Irritant/Light Sensitive

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-3-iodopyridine Usage And Synthesis

Chemical Properties

Off-white Cryst

Uses

2-Chloro-3-iodopyridine is a compound useful in organic synthesis.

Uses

2-Chloro-3-iodopyridine (cas# 78607-36-0) 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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