4-Iodopyrazole Chemical Properties

Melting point:

108-110 °C (lit.)

Boiling point:

291.9±13.0 °C(Predicted)

Density 

2.335±0.06 g/cm3(Predicted)

RTECS 

UQ7145000

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

12.99±0.50(Predicted)

form 

Crystalline Powder

color 

White to off-white

Water Solubility 

Soluble in water.

Sensitive 

Light Sensitive

InChI

InChI=1S/C3H3IN2/c4-3-1-5-6-2-3/h1-2H,(H,5,6)

InChIKey

LLNQWPTUJJYTTE-UHFFFAOYSA-N

SMILES

N1C=C(I)C=N1

CAS DataBase Reference

3469-69-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29331990

MSDS

• Language:English Provider:SigmaAldrich

4-Iodopyrazole Usage And Synthesis

Chemical Properties

White or off-white solid

Uses

4-Iodopyrazole is used in the synthesis of (pyrazolyl)oxobenzocycloheptapyridinyl acetamides that act as inhibitors of c-Met.

Uses

4-Iodopyrazole was used in an indium-mediated synthesis of heterobiaryls.

Definition

ChEBI: 4-iodopyrazole is a member of pyrazoles and an organoiodine compound.

General Description

4-Iodopyrazole is a valuable intermediate for the synthesis of biologically active compounds. It undergoes iodination in the presence of iodine and ammonium hydroxide to yield 3,4-di-iodo- and 3,4,5-tri-iodo-pyrazole.

Synthesis

The general procedure for the synthesis of 4-iodopyrazole from pyrazole is as follows: Example 1: Preparation of 2-amino-3-methyl-5-(1-methyl-1H-pyrazol-4-yl)-5-(3-pyrimidin-5-ylphenyl)-3,5-dihydro-4H-imidazol-4-one Step a): Preparation of compound 2 A mixture of pyrazole (3.00 g, 44.0 mmol), iodine (6.71 g, 26.4 mmol) and ceric ammonium nitrate (14.5 g, 26.4 mmol) in acetonitrile (400 mL) was stirred at room temperature for 2.5 hours. Upon completion of the reaction, the mixture was concentrated and partitioned between ethyl acetate (250 mL) and 5% aqueous sodium bisulfite (250 mL). After addition of water (150 mL), the organic layer was separated, washed with brine (250 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to afford compound 2 (7.80 g, 91% yield) as a white solid with a melting point of 105-108 °C. 1H NMR (300 MHz, CDCl3) δ 7.63 (s, 2H).

References

[1] Tetrahedron Letters, 2001, vol. 42, # 5, p. 863 - 865
[2] Heterocycles, 2003, vol. 60, # 4, p. 879 - 886
[3] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8075 - 8079
[4] Tetrahedron Letters, 2001, vol. 42, # 11, p. 2089 - 2092
[5] Russian Chemical Bulletin, 2014, vol. 63, # 2, p. 360 - 367

4-Iodopyrazole(3469-69-0)Related Product Information

• Pyrazole
• Pyraclostrobin
• Zolpidem tartrate
• 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
• Zolpidem
• 4-IODO-1,3,5-TRIMETHYL-1H-PYRAZOLE
• 3,5-DIMETHYL-4-IODO-1H-PYRAZOLE,3,5-DIMETHYL-4-IODOPYRAZOLE
• 1-(BENZYLOXY)-4-IODOPYRAZOLE
• 1-ACETYL-4-IODO-1H-PYRAZOLE,acetyl-4-iodo-1H-pyrazole
• 3,4-Diiodopyrazole
• 1-Phenyl-4-iodopyrazole
• 2-Phenyl-1,5-dimethyl-4-iodo-1H-pyrazole-3(2H)-one
• 3-Methyl-4-iodopyrazole
• benzyl-4-iodo-1H-pyrazole,1-BENZYL-4-IODO-1H-PYRAZOLE,1H-(N-BENZYL)-4-IODOPYRAZOLE
• 5-IODO-1H-PYRAZOLE
• TERT-BUTYL 4-IODOPYRAZOLE-1-CARBOXYLATE,1-BOC-4-IODOPYRAZOLE,T-BUTYL 4-IODO-1H-PYRAZOLE-1-CARBOXYLATE
• 1-METHYL-4-IODO-1H-PYRAZOLE
• (4-IODO-3-NITRO-1H-PYRAZOL-1-YL)ACETIC ACID