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3-Bromoadamantane-1-carboxylic acid

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3-Bromoadamantane-1-carboxylic acid Basic information
Synthesis
Product Name:3-Bromoadamantane-1-carboxylic acid
Synonyms:3-ADAMANTANECARBOXYLIC ACID, 1-BROMO-;3-broMo-adaMantaine-1-carboxylic acid;1-BroMo-3-carboxyadaMantane;1-BroMoadaMantane-3-carboxylic acid;3-Bromotricyclo[3.3.1.1~3,7~]decane-1-carboxylic acid, 1-Bromo-3-carboxyadamantane;3-BroMoadaMantane-1-carboxylic acid;3-Bromoadamantane-1-carboxylic acid 97%;3-bromo-1-adamantanecarboxylate
CAS:21816-08-0
MF:C11H15BrO2
MW:259.14
EINECS:
Product Categories:Organic Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Adamantane derivatives;Building Blocks;C11 to C12;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis
Mol File:21816-08-0.mol
3-Bromoadamantane-1-carboxylic acid Structure
3-Bromoadamantane-1-carboxylic acid Chemical Properties
Melting point 147 °C
Boiling point 354.2±25.0 °C(Predicted)
density 1.665±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Solid
pka4.35±0.40(Predicted)
color Pale Brown
InChIInChI=1S/C11H15BrO2/c12-11-4-7-1-8(5-11)3-10(2-7,6-11)9(13)14/h7-8H,1-6H2,(H,13,14)
InChIKeyDJUDQBVINJIMFO-UHFFFAOYSA-N
SMILESC12(C(O)=O)CC3CC(CC(Br)(C3)C1)C2
CAS DataBase Reference21816-08-0(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37/39-37/39
WGK Germany 3
RTECS AU4452500
HazardClass IRRITANT
HS Code 2916200090
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
3-Bromoadamantane-1-carboxylic acid Usage And Synthesis
Synthesis

Synthetic Route of 3-Bromoadamantane-1-carboxylic acid

Adamantanecarboxylic acid is slowly added to liquid bromine. Under the action of anhydrous aluminum trichloride catalyst, the reaction is first carried out under reflux with stirring at 20℃-10℃ for 48-60 hours, and then the reaction is carried out at 20℃-30℃ for 5 hours to synthesize 3-Bromoadamantane-1-carboxylic acid.

Uses3-Bromo-1-adamantane Carboxylic Acid is used in the synthesis and in bioactivity of novel adamantyl derivatives, as potent MDR reversal agents.
Purification MethodsPurify the acid by recrystallising it from cyclohexane and/or subliming at 130o/10mm. It is converted to the methyl ester (diazomethane) with m 32o (from pet ether at -10o). [Stetter & Mayer Chem Ber 95 667 1962, Stetter & Wulff Chem Ber 93 1366 1960, Bayal & Lantvoev J Org Chem USSR (Engl Trans) 9 291 1973.]
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