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Methyl 6-bromohexanoate

Product NameMethyl 6-bromohexanoate
CAS14273-90-6
MFC7H13BrO2
MW209.08
EINECS
MOL File14273-90-6.mol

Chemical Properties

Boiling point	150°C/50mmHg
Density	1.316
refractive index	1.46
storage temp.	Sealed in dry,Room Temperature
form	Liquid
color	Clear colorless to pale yellow
InChI	InChI=1S/C7H13BrO2/c1-10-7(9)5-3-2-4-6-8/h2-6H2,1H3
InChIKey	KYLVAMSNNZMHSX-UHFFFAOYSA-N
SMILES	C(OC)(=O)CCCCCBr
CAS DataBase Reference	14273-90-6(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
Hazard Note	Irritant
HS Code	29159000

Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Methyl 6-bromohexanoate serves as an alkylating reagent that reacts with dimethyl iminodiacetate in dry acetonitrile under nitrogen to afford the IDA triester[6]. It also acts as an alkylating agent in the preparation of pyrimidine-based hydroxamic acids, where 2-(alkylthio)pyrimidin-4(3H)-ones are alkylated with the ester and the resulting esters are converted to hydroxamic acids by aminolysis with hydroxylamine[7].

Synthesis

4224-70-8

14273-90-6

1. Synthesis of methyl 6-bromohexanoate: Dissolve 5.01 g (25.7 mmol) of 6-bromohexanoic acid in 250 mL of methanol and introduce hydrogen chloride gas by vigorous bubbling for 2-3 minutes. The reaction mixture was stirred at 15-25°C for 3 hours. Upon completion of the reaction, the solvent was removed by concentration to give 4.84 g of yellow oily product in 90% yield. The product was characterized by 1H NMR (DMSO-d6): δ 3.58 (3H, s), 3.51 (2H, t), 2.29 (2H, t), 1.78 (2H, pentet), 1.62-1.27 ppm (4H, m).

References

[1] Patent: US2002/15705, 2002, A1
[2] Patent: US4436746, 1984, A
[3] Patent: US4539410, 1985, A
[4] Patent: EP2425861, 2012, A1
[5] Patent: US2012/65367, 2012, A1
[6]Kalita, B., & Nicholas, K. M. (2004). Synthesis of α-substituted iminodiacetate ligands: α-hexadienyl derivatives for the selection of lipoxygenase mimics. Tetrahedron, 60(47), 10771–10778. https://doi.org/10.1016/j.tet.2004.08.029
[7]Jakubkiene, V., Valiulis, G. E., Schweipert, M., Zubriene, A., Matulis, D., Meyer-Almes, F.-J., & Tumkevicius, S. (2022). Synthesis and HDAC inhibitory activity of pyrimidine-based hydroxamic acids. Beilstein Journal of Organic Chemistry, 18, 837–844. https://doi.org/10.3762/bjoc.18.84

Methyl 6-bromohexanoate

Chemical Properties

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