DL-Alaninol

Base Information

• Chemical Name: DL-Alaninol
• CAS No.: 6168-72-5
• Deprecated CAS: 189328-44-7,78-91-1
• Molecular Formula: C3H9NO
• Molecular Weight: 75.1106
• Hs Code.: 29221980
• European Community (EC) Number: 228-207-3,201-156-4
• NSC Number: 1360
• UN Number: 2735
• UNII: E8V71RA4B5
• DSSTox Substance ID: DTXSID50865762
• Nikkaji Number: J10.507D
• Wikipedia: Alaninol
• Wikidata: Q27277018
• Metabolomics Workbench ID: 71477
• ChEMBL ID: CHEMBL116663
• Mol file: 6168-72-5.mol

Synonyms:2-aminopropanol;2-aminopropanol, (+-)-isomer;2-aminopropanol, (S)-isomer;alaninol

Chemical Property of DL-Alaninol

Chemical Property:

• Appearance/Colour: clear colorless to light yellow viscous liquid
• Vapor Pressure: 0.373mmHg at 25°C
• Melting Point: 8 °C
• Refractive Index: n20/D 1.450
• Boiling Point: 174.5 °C at 760 mmHg
• PKA: pK1: 9.469(+1) (25°C)
• Flash Point: 83.9 °C
• PSA: 46.25000
• Density: 0.943 g/cm³
• LogP: 0.02620
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: Chloroform, Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 75.068413911
• Heavy Atom Count: 5
• Complexity: 22.9
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

DL-Alaninol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amino Alcohols, Other
• Canonical SMILES: CC(CO)N
• Uses: DL-Alaninol has been used in the synthesis of N6-α-(I-hydroxypropyl) lysine, diastereomers of DL-β-amino alcohols, enantiopure and racemic samples of 2-methyl-N-tosylaziridine, (±)-3-(5-dimethylcarbamoyl-pent-1-enyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide.

Technology Process of DL-Alaninol

There total 40 articles about DL-Alaninol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-NITROPROPANOL (2902-96-7) → 2-Amino-1-propanol (6168-72-5)

Guidance literature:

With trichlorosilane; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 15 ℃; for 30h;

Reference yield: 82.6%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Nitroethane (79-24-3) → 2-Amino-1-propanol (6168-72-5)

Guidance literature:

formaldehyd; Nitroethane; With triethanolamine; In water; at 50 ℃; for 105h;

With Fe/Ni; hydrogen; at 70 ℃; for 4h; under 22502.3 Torr; Reagent/catalyst; Temperature; Pressure;

Reference yield: 71.5%

hydroxy-2-propanone (116-09-6) → 2-Amino-1-propanol (6168-72-5)

Guidance literature:

hydroxy-2-propanone; With ammonia; In water; at 0 - 20 ℃; for 1 - 1.5h;

With hydrogen; nickel; In water; at 85 ℃; under 57647.8 Torr; Product distribution / selectivity;

upstream raw materials:

AlaOEt

dl-alanylglycine

ethyl 2-acetamidopropanoate

1-hydroxy-2-propanone oxime

Downstream raw materials:

2-(dimethylamino)propan-1-ol

2-(2,4-dinitro-anilino)-propan-1-ol

2-isopropylamino-1-propanol

rac-Ala-OH

Refernces

Double Heck Route to a Dibenzoxepine and Convergent Suzuki Cross-Coupling Strategy for the Synthesis of an MR Antagonist

10.1021/acs.oprd.6b00368

The research describes the development of a practical pilot plant synthesis for the mineralocorticoid receptor (MR) antagonist LY2623091, which is used as a treatment for resistant hypertension. The synthesis involves a convergent approach, with key steps including the stereoselective synthesis of an E-vinyl bromide via a sequential double Heck reaction, Suzuki-Miyaura cross-coupling, selective nitro reduction, and cyanamide hydrolysis to the urea. The double Heck reaction was particularly crucial for achieving the desired geometric isomer of the vinyl bromide. The synthesis also involved the use of a chiral alaninol derivative as a building block and the optimization of various steps to improve yield and processing efficiency. The final API was obtained in multi-kilogram quantities to support clinical trials.