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Application Area

DL-Alaninol

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

A reagent used in the synthesis of polyunsaturated fatty acid amides.

Category

Amino Alcohol

Catalog number

BAT-000669

CAS number

6168-72-5

Molecular Formula

C3H9NO

Molecular Weight

75.11

IUPAC Name

2-aminopropan-1-ol

Synonyms

H-DL-Ala-ol; (±)-2-Amino-1-propanol; 2-Aminopropan-1-ol; 2-Amino-1-propanol

Appearance

A colorless to pale yellow liquid with a fishy odor. moderately toxic by ingestion and skin contact. a severe skin irritant. combustible. the compound contains both the amine group -nh2 and the alcohol group -oh and so has some properties of both. fl

Purity

98+ %

Density

0.943 g/mL at 25 °C

Melting Point

8 °C

Boiling Point

173-176 °C (lit.)

Storage

Store at 2-8 °C

InChI

InChI=1S/C3H9NO/c1-3(4)2-5/h3,5H,2,4H2,1H3

InChI Key

BKMMTJMQCTUHRP-UHFFFAOYSA-N

Canonical SMILES

CC(CO)N

DL-Alaninol, also known as 2-Amino-1-propanol, is a useful chiral amino alcohol with several applications in various fields. Here are some key applications of DL-Alaninol:

Pharmaceutical Intermediates: DL-Alaninol serves as an important intermediate in the synthesis of various pharmaceutical compounds. Its chiral nature allows for the production of enantiomerically pure drugs which is vital for the efficacy and safety of medications. One notable application is in the synthesis of beta-blockers which are widely used to manage cardiovascular diseases.

Polymers and Coatings: DL-Alaninol is employed in the production of specialty polymers and coatings. It can act as a monomer or a co-monomer imparting unique chemical properties to the resulting materials. For example it helps in enhancing the thermal stability and mechanical strength of polyurethane resins used in coatings and adhesives.

Agrochemicals: DL-Alaninol can be utilized in the synthesis of various agrochemicals including herbicides and insecticides. Its role as a building block in the creation of biologically active compounds helps protect crops from pests and diseases. This application supports more effective and sustainable agricultural practices.

Chiral Ligands in Catalysis: DL-Alaninol is used in the development of chiral ligands for asymmetric synthesis. These ligands are crucial in catalytic processes for producing enantiomerically pure substances which are important in various chemical industries. The ability to control stereochemistry is particularly beneficial in the fine chemical synthesis and pharmaceutical manufacturing.

1. Liquid chromatographic enantioseparation of (RS)-mexiletine and (RS)-fluoxetine using chiral derivatizing reagents synthesized with (S)-naproxen moiety

Sonika Batra, Ravi Bhushan Biomed Chromatogr. 2014 Jun;28(6):815-25. doi: 10.1002/bmc.3144.

Enantiomeric separation of racemic mexiletine and fluoxetine was achieved using three chiral derivatizing reagents (CDRs) based on (S)-naproxen. Diastereomers were synthesized by reaction of mexiletine or fluoxetine with the CDRs and were separated on a C18 column under reversed-phase conditions using a binary mixture of acetonitrile and triethylammonium phosphate/water, with UV detection at 230 and 226 nm. The results obtained for enantioseparation of the two drugs using the three CDRs were compiled and compared. The conditions for derivatization and chromatographic separation were optimized. The method was validated for linearity, repeatability, limit of detection and limit of quantification.

2. Indirect enantioseparation of selenomethionine by reversed-phase high-performance liquid chromatography using a newly synthesized chiral derivatizing reagent based on (S)-naproxen moiety

Ravi Bhushan, Hariom Nagar Biomed Chromatogr. 2014 Jan;28(1):106-11. doi: 10.1002/bmc.2903. Epub 2013 Mar 21.

(S)-Naproxen was reacted with N-hydroxyphthalimide in the presence of coupling reagent dicyclohexylcarbodiimide, and a new chiral derivatizing reagent, phthalimidyl-(S)-naproxen ester, was synthesized. It was characterized and was used for synthesis of diastereomers of selenomethionine via microwave irradiation or vortexing. The reaction conditions were optimized. Diastereomeric pairs synthesized by two approaches were successfully separated by reversed-phase high-performance liquid chromatography using binary mixtures of aqueous triethylammonium phosphate and acetonitrile. Detection was carried out at 231 nm. The limit of detection was found to be 0.11 and 0.10 pmol/mL for diastereomers of d- and l-SeMet, respectively. The method was validated for accuracy, precision and limit of detection. The new chiral derivatizing reagent was capable of enantioseparation of dl-SeMet in the form of diastereomers having higher stability, enhanced resolution and lower limits of detection in comparison to the diastereomers prepared with other chiral derivatizing reagents reported in the literature. Optimized structures of the two diastereomers were drawn using the Gaussian 09 Rev. A.02 program and hybrid density functional B3LYP with 6-31G basis set to explain the separation mechanism.

3. Indirect enantioseparation of proteinogenic amino acids using naproxen-based chiral derivatizing reagent and HPLC

Ravi Bhushan, Hariom Nagar Biomed Chromatogr. 2013 Jun;27(6):750-6. doi: 10.1002/bmc.2855. Epub 2012 Dec 7.

Diastereomers of 18 proteinogenic amino acids were synthesized under microwave irradiation and by vortexing using (S)-naproxen-benzotriazole as chiral derivatizing reagent. The diastereomers synthesized by two approaches were found to be identical in terms of their characterization and chromatographic data. A linear gradient of triethylammonium phosphate (pH 3.5)-acetonitrile (30-65%, within 35 min) was found to be successful using reversed-phase high-performance liquid chromatography for their separation. Detection was carried out at 231 nm and sharp peaks were obtained. The method was validated for accuracy, precision and limit of detection.