9-Bromononanoic acid Chemical Properties

Melting point:

39°C

Boiling point:

165°C/3mm

Density 

1.282±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Soluble), DMSO (Slightly)

form 

Solid

pka

4.78±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C9H17BrO2/c10-8-6-4-2-1-3-5-7-9(11)12/h1-8H2,(H,11,12)

InChIKey

XEGRKZRPTBNSMN-UHFFFAOYSA-N

SMILES

C(O)(=O)CCCCCCCCBr

CAS DataBase Reference

41059-02-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

34

Safety Statements 

36/37/39

RIDADR 

3261

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2916399090

9-Bromononanoic acid Usage And Synthesis

Uses

9-Bromononanoic Acid is an intermediate in synthesizing Rumenic Acid (R701590), a trans fatty acid that may potentially reduce the risk of cancer and cardiovascular diseases. It may also prevent disease processes that lead to chronic inflammation, atherosclerosis, and diabetes.

Synthesis

Step 1: Synthesis of 9-bromononanoic acid To an acetone (27 ml) solution of 9-bromo-1-nonanol (1.50 g, 6.72 mmol) cooled to 0°C, saturated NaHCO3 solution (9 ml), NaBr (0.14 g, 1.34 mmol), and 2,2,6,6-tetramethyl-1-piperidinyloxy radical (TEMPO) (0.10 g, 0.67 mmol) were added sequentially. Trichloroisocyanuric acid (3.1 g, 13.44 mmol) was then added in batches. The reaction mixture was stirred at 0 °C for 30 min, then brought to room temperature and continued stirring for 3 h. The reaction was carried out at 0 °C for 2 min. After completion of the reaction, the mixture was cooled to 0 °C, 2-propanol (8 ml) was added slowly and stirring was continued at 0 °C for 30 min. A white precipitate was collected by filtration and the filtrate was concentrated under reduced pressure. H2O (10 ml) and CH2Cl2 (10 ml) were added to the residue to separate the two phases. The aqueous phase was extracted with CH2Cl2 (2 x 10 ml), the organic phases were combined, dried with Na2SO4 and concentrated under reduced pressure to give 1.60 g (yield: 100%) of 9-bromononanoic acid as a white solid.1H NMR (300 MHz, DMSO) δ 3.49 (t, 2H), 2.23-2.08 (m, 2H), 1.84-1.68 (m, 2H) , 1.57-1.14 (m, 10H).

References

[1] Tetrahedron, 1999, vol. 55, # 12, p. 3595 - 3604
[2] Journal of the American Chemical Society, 2009, vol. 131, # 30, p. 10610 - 10619
[3] Patent: WO2011/1419, 2011, A1. Location in patent: Page/Page column 17
[4] Patent: WO2013/60673, 2013, A1. Location in patent: Page/Page column 86
[5] Patent: WO2014/63923, 2014, A1. Location in patent: Page/Page column 81

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