2-BROMOPROPIONIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

90 °C / 60mmHg

Density 

1,26 g/cm³

refractive index 

1.4380-1.4410

storage temp. 

Inert atmosphere,2-8°C

form 

clear liquid

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C7H13BrO2/c1-5(8)6(9)10-7(2,3)4/h5H,1-4H3

InChIKey

CVAWKJKISIPBOD-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)C(Br)C

Safety Information

Risk Statements 

10-36/37/38

Safety Statements 

16-26-36

RIDADR 

3272

HS Code 

2915.50.5000

2-BROMOPROPIONIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

tert-Butyl 2-Bromopropanoate is a reactant used in the synthesis 3-(1-Aryl-1H-indol-5-yl)propanoic Acids as cytosolic phospholipase A2α inhibitors.

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 4067, 1972 DOI: 10.1016/S0040-4039(01)94239-X

Synthesis

Step 1 Synthesis of tert-butyl 2-bromopropionate. Isobutene (2.4 g, 42.8 mmol) was condensed into a pressurized reaction flask at -15 °C. Dioxane (6 mL) and 2-bromopropionic acid (3.5 mL, 38.9 mmol) were then added and the mixture was stirred for 5 minutes. After slow warming to -10°C, concentrated sulfuric acid (250 μL) was added dropwise. The reaction vial was sealed and the reaction mixture was stirred at room temperature overnight. After the reaction was completed, the reaction vial was opened and the reaction mixture was poured into dichloromethane (50 mL). The organic phase was washed sequentially with 20% potassium carbonate solution (50 mL) and water (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give tert-butyl 2-bromopropionate (2.17 g, 27% yield). The product was characterized by 1H NMR (CDCl3, δ): 4.31 (1H, q, J=7.1Hz), 1.81 (3H, d, J=7.1Hz), 1.52 (9H, s).

References

[1] Journal of Medicinal Chemistry, 1986, vol. 29, # 5, p. 784 - 796
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 915 - 936
[3] Patent: US6399600, 2002, B1
[4] Journal fuer Praktische Chemie (Leipzig), 1974, vol. 316, p. 729 - 740
[5] Bulletin de la Societe Chimique de France, 1974, p. 2985 - 2986

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