11-Bromoundecanoic acid Chemical Properties

Melting point:

45-48 °C (lit.)

Boiling point:

173-174 °C/2 mmHg (lit.)

Density 

1.2889 (rough estimate)

refractive index 

1.5120 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Chunks

pka

4.78±0.10(Predicted)

color 

White to beige

Water Solubility 

insoluble

BRN 

1767205

Stability:

Stable. Incompatible with bases, oxidizing agents, reducing agents.

InChIKey

IUDGNRWYNOEIKF-UHFFFAOYSA-N

CAS DataBase Reference

2834-05-1(CAS DataBase Reference)

NIST Chemistry Reference

11-Bromoundecanoic acid(2834-05-1)

EPA Substance Registry System

11-Bromoundecanoic acid (2834-05-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

1

F 

8

HS Code 

29159000

MSDS

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11-Bromoundecanoic acid Usage And Synthesis

Description

11-Bromoundecanoic acid is a bromo-modified undecanoic acid derivative. 11-Bromoundecanoic acid was used in the synthesis of 11-phenoxyundecyl phosphate and 11-hydroxytetradecanoic acid. It has been used as a reactant for the preparation of hydroxy-substituted naphthoquinone cations as antiplasmodial agents.

References

Navarro, I, G. Fabriás, and F. Camps. "Synthesis of [14, 14, 14-2H3] 12-hydroxytetradecanoic acid and [13,14-2H2] 11-hydroxytetradecanoic acid useful as tracers to study a (11E)-desaturation reaction in Spodoptera littoralis." Bioorganic & Medicinal Chemistry 4.3(1996):439-443.
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Chemical Properties

faintly beige crystalline solid

Uses

11-Bromoundecanoic acid was used in the synthesis of 11-phenoxyundecyl phosphate and 11-hydroxytetradecanoic acid.

Definition

ChEBI: 11-bromo-undecanoic acid is a medium-chain fatty acid.

General Description

11-Bromoundecanoic acid reacts with potassium salt of dimethyl hydantoin to yield 4,4-dimethyl hydantoin-undecanoic acid.

Synthesis

1 kg of 10-undecylenic acid having a melting point of 23° C. and a purity of more than 98.5% was used as the raw material, and it was mixed according to the ratio of the mass ratio of 10-undecylenic acid to toluene of 1:3. According to the ratio of the molar ratio of 10-undecylenic acid to hydrogen bromide of 1:1.20, hydrogen bromide gas was continuously passed through from the bottom of the charging tower, while feed liquid was continuously added to maintain the ratio. The reactor temperature was controlled at 18°C by cooling water and the reaction lasted for 1 hour. Upon completion of the reaction, toluene was recovered by distillation. The oil phase is washed 2-3 times and the system is cooled to 15?20°C to promote crystallization. After complete crystallization, vacuum filtration was performed to obtain 1.34 kg of white crystals 11-bromoundecanoic acid.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1190 - 1193
[2] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4785 - 4786
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 10, p. 1183 - 1190
[4] Bulletin of the Chemical Society of Japan, 1938, vol. 13, p. 334
[5] Journal of the Chemical Society, 1934, p. 439

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