5-BROMOPENTANOIC ACID, T-BUTYL ESTER

5-BROMOPENTANOIC ACID, T-BUTYL ESTER Property

Boiling point:

93 °C(Press: 1.6 Torr)

Density 

1.223±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C9H17BrO2/c1-9(2,3)12-8(11)6-4-5-7-10/h4-7H2,1-3H3

InChIKey

UYDIIUHJHUZDME-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CCCCBr

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

5-BROMOPENTANOIC ACID, T-BUTYL ESTER Chemical Properties,Usage,Production

Uses

tert-Butyl 5-Bromovalerate is a reactant used in synthetic preparation of haptens for production of monoclonal antibodies for pyraclostrobin ELISA.

Synthesis

5-Bromovaleric acid (5 g, 27.62 mmol) was dissolved in anhydrous dichloromethane (DCM), and the solution was brought to room temperature and stirred under cooling in an ice bath. N,N'-dimethylaminopyridine (DMAP, 1.68 g, 13.75 mmol) and dicyclohexylcarbodiimide (DCC, 6.83 g, 33.15 mmol) were added sequentially. After half an hour of reaction, tert-butanol (15.8 ml, 165.75 mmol) was added to the mixture. The reaction solution was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with dichloromethane and washed sequentially with water and brine. The organic layer was separated, dried over anhydrous sodium sulfate and evaporated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with hexane-ethyl acetate (1%) as eluent to give pure tert-butyl 5-bromopentanoate 4.1 g (62.6% yield) as a light yellow liquid.

References

[1] Patent: WO2015/6740, 2015, A2. Location in patent: Page/Page column 182; 183
[2] Patent: WO2016/154241, 2016, A1. Location in patent: Paragraph 670; 671
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 37, p. 5180 - 5192
[4] Patent: KR101569966, 2015, B1. Location in patent: Paragraph 0145; 0146
[5] Patent: WO2011/53519, 2011, A1. Location in patent: Page/Page column 27-28