Mono-tert-butyl succinate

Mono-tert-butyl succinate Property

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2917198090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Mono-tert-butyl succinate Chemical Properties,Usage,Production

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