TERT-BUTYL 4-HYDROXYBUTYRATE Chemical Properties

Boiling point:

73-74 °C(Press: 2.0-3.0 Torr)

Density 

0.976 g/mL at 20 °C

refractive index 

n20/D 1.431

Flash point:

>70℃

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly), Water (Slightly)

form 

Oil

pka

14.86±0.10(Predicted)

color 

Colourless to Pale Yellow

InChI

InChI=1S/C8H16O3/c1-8(2,3)11-7(10)5-4-6-9/h9H,4-6H2,1-3H3

InChIKey

RXGFTUPFXKYRMW-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CCCO

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2915601990

TERT-BUTYL 4-HYDROXYBUTYRATE Usage And Synthesis

Uses

tert-Butyl 4-Hydroxybutanoate is used as a reagent in the synthesis of theranostic vitamin-linker-taxoid conjugates. tert-Butyl 4-Hydroxybutanoate is also used as a reagent in the synthesis of teroxazoles as α-helix mimetics.

Synthesis

General procedure for the synthesis of tert-butyl 4-hydroxybutyrate from mono-tert-butyl succinate: BH3-Me2S (2.0 M solution in THF, 6.6 mL, 13.1 mmol) was slowly added dropwise to a solution of mono-tert-butyl succinate (2.12 g, 12.2 mmol) in anhydrous THF (20 mL) that was cooled to 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 24 hours. Upon completion of the reaction, EtOAc (100 mL) was added for dilution and the organic layer was separated. The organic layer was washed sequentially with water (70 mL) and saturated saline (70 mL) and dried with anhydrous MgSO4. After filtration, the solvent was removed by concentration under reduced pressure to afford tert-butyl 4-hydroxybutyrate (1.92 g, 12.2 mmol, quantitative yield), the product was a light yellow oil, which could be used in the subsequent reaction without further purification.

References

[1] Tetrahedron, 2014, vol. 70, # 44, p. 8343 - 8347
[2] Bioconjugate Chemistry, 2010, vol. 21, # 5, p. 979 - 987
[3] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 2428 - 2441
[4] Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6679 - 6684
[5] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4004 - 4009

TERT-BUTYL 4-HYDROXYBUTYRATE(59854-12-5)Related Product Information

• Fmoc-Asp(OtBu)-OH
• DIHYDROCYTOCHALASIN B
• H-ASP(OTBU)-OTBU HCL
• N-Cbz-L-Aspartic acid 4-tert-butyl ester
• Boc-Asp-OtBu
• D-Aspartic acid 4-tert-butyl ester
• BOC-ASP(OTBU)-OSU
• L-Fmoc-Aspartic acid alpha-tert-butyl ester
• FMOC-ASP(OTBU)-OPFP
• 4-tert-Butyl N-[(tert-butoxy)carbonyl]-L-aspartate dicyclohexylamine salt
• Z-ASP(OTBU)-OH DCHA
• Boc-L-aspartic acid 4-tert-butyl ester
• Fmoc-D-Aspartic acid beta-tert-butyl ester
• L-Aspartic acid 4-tert-butyl ester
• BOC-ASP(OTBU)-ONP
• L-ASPARTIC ACID DI-TERT-BUTYL ESTER DIBENZENESULFIMIDE SALT
• N-ALPHA-BENZYLOXYCARBONYL-L-ASPARTIC ACID ALPHA-TERT-BUTYL ESTER DICYCLOHEXYLAMINE
• BOC-D-ASP(OTBU)-OH DCHA