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11-Bromoundecanoic acid

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CAS:2834-05-1
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11-Bromoundecanoic acid Basic information
Description References
Product Name:11-Bromoundecanoic acid
Synonyms:11-bromo-undecanoicaci;Undecanoic acid, 11-bromo-;11-BROMOUNDECANOIC ACID;11-BROMOHENDECANOIC ACID;11-bromodecanoic acid;Bromoundecanoicacid;11-BromoundecanoicAcid98+%;11-Bromo-1-Undecanoic Acid
CAS:2834-05-1
MF:C11H21BrO2
MW:265.19
EINECS:220-602-9
Product Categories:Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;OLED materials,pharm chemical,electronic;Pyridines;Organic acids;omega-Bromocarboxylic Acids;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Linear hydrocarbon series;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Miscellaneous;K00001
Mol File:2834-05-1.mol
11-Bromoundecanoic acid Structure
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)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
form Crystalline Chunks
pka4.78±0.10(Predicted)
color White to beige
Water Solubility insoluble
BRN 1767205
Stability:Stable. Incompatible with bases, oxidizing agents, reducing agents.
InChIKeyIUDGNRWYNOEIKF-UHFFFAOYSA-N
CAS DataBase Reference2834-05-1(CAS DataBase Reference)
NIST Chemistry Reference11-Bromoundecanoic acid(2834-05-1)
EPA Substance Registry System11-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
8
TSCA TSCA listed
HS Code 29159000
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
11-Bromoundecanoic acid Usage And Synthesis
Description11-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.
ReferencesNavarro, 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.
https://www.trc-canada.com/product-detail/?B688880
http://www.sigmaaldrich.com/catalog/product/aldrich/165816?lang=en&region=US
Chemical Propertiesfaintly beige crystalline solid
Uses11-Bromoundecanoic acid was used in the synthesis of 11-phenoxyundecyl phosphate and 11-hydroxytetradecanoic acid.
DefinitionChEBI: 11-bromo-undecanoic acid is a medium-chain fatty acid.
General Description11-Bromoundecanoic acid reacts with potassium salt of dimethyl hydantoin to yield 4,4-dimethyl hydantoin-undecanoic acid.
Synthesis
Undecenoic acid

112-38-9

11-Bromoundecanoic acid

2834-05-1

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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