Mono-tert-butyl succinate Chemical Properties

Melting point:

51-54 °C(lit.)

Boiling point:

92°C/1.5mmHg(lit.)

Density 

1.097±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Sparingly)

pka

4.46±0.17(Predicted)

form 

Solid

color 

Yellow-brown

Water Solubility 

Slightly soluble in water.

InChIKey

PCOCFIOYWNCGBM-UHFFFAOYSA-N

CAS DataBase Reference

15026-17-2

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2917198090

MSDS

• Language:English Provider:SigmaAldrich

Mono-tert-butyl succinate Usage And Synthesis

Uses

Mono-tert-butyl Succinate is a reagent used for the synthesis of fluorinated β2- and β3-amino acids, an inhibitor of α-chymotrypsin.

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 4239, 1991 DOI: 10.1016/S0040-4039(00)92137-3

General Description

mono-tert-Butyl succinate can be prepared by refluxing a mixture of succinic anhydride and N-hydroxyl succinimide in the presence of dimethylaminopyridine and triethylamine in tert-butanol and toluene.

Synthesis

Tert-butanol (10 mL) was added to a solution of toluene (100 mL) containing succinic anhydride (6.04 g, 60.40 mmol), N-hydroxysuccinimide (2.53 g, 22.01 mmol) and 4-dimethylaminopyridine (DMAP, 0.88 g, 7.23 mmol). The reaction mixture was heated under reflux conditions for 48 hours. Upon completion of the reaction, it was cooled to room temperature and two layers (brown oil and a clarified colorless solution) were observed to form in the reaction vessel. The crude product solution was diluted with ethyl acetate (EtOAc, 50 mL) and washed sequentially with 10% aqueous citric acid (2 x 50 mL) and saturated saline. The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and the solvent was evaporated under reduced pressure. The crude product was recrystallized with a solvent mixture of ethyl ether/petroleum ether (1:3, 25 mL) to obtain mono-tert-butyl succinate in quantitative yield.

References

[1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2428 - 2441
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 23, p. 10460 - 10474
[3] Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6679 - 6684
[4] Organic Letters, 2006, vol. 8, # 4, p. 713 - 716
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1643 - 1647

Mono-tert-butyl succinate(15026-17-2)Related Product Information

• tert-Butyl acetate
• Propylamine
• n-Butyllithium
• tert-Butyl methyl ether
• Disodium succinate
• 6alpha-Methylprednisolone sodium succinate
• Tetrabutylammonium bromide
• Cyhalofop-butyl
• iron succinate
• Succinic acid
• Buprofezin
• Sumatriptan
• Tris(trimethylsilyl)phosphate
• BUTYL OLEATE
• tert-Butyl peroxyacetate
• Butyl acrylate
• Succinic anhydride
• tert-Butanol