tert-Butyl 4-iodobenzoate Chemical Properties

Melting point:

107-110 °C(Solv: hexane (110-54-3))

Boiling point:

310.2±25.0 °C(Predicted)

Density 

1.528±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

DMSO, Methanol

form 

Oil

color 

Pale Yellow

tert-Butyl 4-iodobenzoate Usage And Synthesis

Uses

4-iodo substituted benzoic acid derivative used as a building block for the synthesis of various of biologically active compounds.

Synthesis

The general procedure for the synthesis of tert-butyl p-iodobenzoate from 4-iodobenzoic acid and potassium tert-butoxide was as follows: first, thionyl chloride (2.30 mL, 32.30 mmol) and N,N-dimethylformamide (DMF) (0.02 mL, 0.20 mmol) were added to 4-iodobenzoic acid (1.00 g, 4.00 mmol). Subsequently, the air in the reaction system was displaced with nitrogen and the mixture was heated to 75 °C and kept at reflux while stirring for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (THF) (5 mL), and then a 1 M THF solution of potassium tert-butanolate (4.5 mL) was slowly added at low temperature and stirring was continued for 30 min. After that, the reaction solution was again concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate and washed sequentially with water and brine. The organic layer was collected, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. Finally, the concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate = 9:1) to afford the target product tert-butyl p-iodobenzoate (14.00 g, 99.9% yield). The product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 7.77 (2H, d, J = 7.5 Hz, aromatic), 7.69 (2H, d, J = 8.0 Hz, aromatic), 1.59 (9H, s, (CH3)3).

References

[1] Patent: EP3327000, 2018, A1. Location in patent: Paragraph 0116
[2] Bioconjugate Chemistry, 2015, vol. 26, # 2, p. 197 - 200

tert-Butyl 4-iodobenzoate(120363-13-5)Related Product Information

• T-BUTYL 4-FLUOROBENZOATE
• (4-IODO-BENZYL)-CARBAMIC ACID TERT-BUTYL ESTER
• TERT-BUTYL 4-IODOBUTYLCARBAMATE
• 1,3-Butanediol
• Dibutyl phthalate
• Itaconic acid
• Benzoyl peroxide
• Zinc stearate
• Magnesium oxide
• Chlorine dioxide
• 2,2-Dimethoxy-2-phenylacetophenone
• 4-Methyl-benzoic acid tert-butyl ester
• 4-FORMYL-BENZOIC ACID MONO TERT-BUTYL ESTER
• TERT-BUTYL-4-CHLORO-3-OXOBUTANOATE
• TERT-BUTYL 4-ETHYNYLBENZOATE
• tert-Butyl 4-ethynylbenzylcarbamate
• TERT-BUTYL 4-METHYL-3-OXOPENTANOATE
• BETA-OXO-4-(TRIFLUOROMETHYL)-BENZENEPROPANOIC ACID 1,1-DIMETHYLETHYL ESTER