Ethyl 4-iodobenzoate Chemical Properties

Melting point:

267 °C

Boiling point:

281-283 °C

Density 

1.641 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5880(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Hexane

form 

Liquid

Specific Gravity

1.66

color 

Clear colorless to yellow

Water Solubility 

insoluble

Sensitive 

Light Sensitive

BRN 

2208568

CAS DataBase Reference

51934-41-9(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 4-iodobenzoate(51934-41-9)

Safety Information

Hazard Codes 

N,Xi,C

Risk Statements 

51/53-36/37/38

Safety Statements 

61-24/25

RIDADR 

UN 3082 9/PG 3

WGK Germany 

3

F 

8

Hazard Note 

Irritant

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29163990

MSDS

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

Ethyl 4-iodobenzoate Usage And Synthesis

Chemical Properties

Light Yellow Oil

Uses

Ethyl 4-iodobenzoate can be used in the synthesis of biphenyl derivatives via Negishi cross coupling with the intermediates of the type ArMg(tmp)·2LiCl (tmp = trimethylolpropane). It can also be used as a starting material in the synthesis of p-carbomethoxyphenylmagnesium bromide, a polyfunctional organometallic reagent that can be used as building block in the synthesis of complex target molecules.

Synthesis

General procedure for the synthesis of ethyl p-iodobenzoate from ethyl 4-bromobenzoate: under nitrogen protection, Cu2O (7.2 mg, 10 mol%), L-proline (11.5 mg, 20 mol%), ethyl 4-bromobenzoate (0.50 mmol), potassium iodide (KI, 249 mg, 0.75 mmol) and ethanol (EtOH, 1.5 mL). After sealing the Schlenk tube with a PTFE valve, the reaction mixture was stirred at 110 °C and the reaction process was monitored by gas chromatography (GC) analysis. Upon completion of the reaction, the yield was determined by GC using an appropriate internal standard (e.g., chlorobenzene or 1-chloro-4-methylbenzene) for highly volatile products; or the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent ratio of petroleum ether/ethyl acetate = 10/1) to obtain the target product ethyl p-iodobenzoate.

References

[1] Catalysis Today, 2016, vol. 274, p. 129 - 132
[2] Chemical Communications, 2012, vol. 48, # 33, p. 3993 - 3995
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 263 - 266
[4] Angew. Chem., 2015, vol. 127, # 01, p. 265 - 268,4
[5] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 2110 - 2117

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