| Identification | Back Directory | [Name]
4-(TERT-BUTOXYCARBONYL)BENZOIC ACID | [CAS]
20576-82-3 | [Synonyms]
tert-Butyl terephthalate
mono-(tert-Butyl) terephthalate
tert-Butyl hydrogen terephthalate
4-(TERT-BUTOXYCARBONYL)BENZOIC ACID
TEREPHALIC ACID MONO TERT-BUTYL ESTER
4-[(2-methylpropan-2-yl)oxycarbonyl]benzoic Acid
4-[(2-methylpropan-2-yl)oxy-oxomethyl]benzoic acid
1,4-Benzenedicarboxylic acid, 1-(1,1-dimethylethyl) ester
4-(tert-Butoxycarbonyl)benzoic acid, tert-Butyl 4-carboxybenzoate | [Molecular Formula]
C12H14O4 | [MDL Number]
MFCD04037901 | [MOL File]
20576-82-3.mol | [Molecular Weight]
222.24 |
| Chemical Properties | Back Directory | [Melting point ]
209-212(dec.) | [Boiling point ]
351.8±25.0 °C(Predicted) | [density ]
1.173±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Ethyl Acetate (Slightly). Methanol (Slightly) | [form ]
Solid | [pka]
3.76±0.10(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Uses]
Mono-tert-Butyl Terephthalate, is used in the synthesis of pyrrolidinone analogs acting as potential 20S proteasome inhibitors. | [Synthesis]
The general procedure for the synthesis of 4-(tert-butoxycarbonyl)benzoic acid from di-tert-butyl terephthalate was as follows: 6.1 g (0.022 mol) of di-tert-butyl terephthalate was suspended in 30 mL of tert-butanol, and 22 mL (0.022 mol) of 1N KOH solution was slowly added. The reaction mixture was heated to 60°C and maintained at this temperature for 7-8 hours. After completion of the reaction, the mixture was cooled, diluted with water and extracted three times with ethyl acetate. After combining the organic phases, the aqueous phase was acidified to acidity with dilute hydrochloric acid and the product was again extracted with ethyl acetate. All ethyl acetate extracts were combined, washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure to give 4-(tert-butoxycarbonyl)benzoic acid (mono-tert-butyl terephthalate) as a white solid with a yield of 4.7 g, 96% yield, and a melting point of 100-102°C. The product was extracted with dilute hydrochloric acid. | [References]
[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 4, p. 641 - 662
[2] Patent: US5221665, 1993, A
[3] Patent: US5232928, 1993, A
[4] Patent: EP369391, 1991, A3
[5] Patent: EP369391, 1990, A2 |
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