112243-65-9

Basic information

• Product Name: (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL
• Synonyms: (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL;(2S)-3-AMINO-1-PHENOXY-2-PROPANOL;2-PROPANOL, 1-AMINO-3-PHENOXY-, (2S)-;(S)-1-AMINO-3-PHENOXY-2-PROPANOL
• CAS NO: 112243-65-9
• Molecular Formula: C₉H₁₃NO₂
• Molecular Weight: 167.21
• Mol File: 112243-65-9.mol

Chemical Properties

• Boiling Point: 330.2±27.0 °C(Predicted)
• Appearance: /
• Density: 1.129±0.06 g/cm3(Predicted)
• PKA: 12.04±0.35(Predicted)
• CAS DataBase Reference: (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL(112243-65-9)
• EPA Substance Registry System: (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL(112243-65-9)

Safety Data

• Hazardous Substances Data: 112243-65-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL is used as a chiral building block for the preparation of pharmaceuticals and other biologically active compounds. Its unique stereochemistry allows for the creation of enantioselective products, which is crucial in the development of effective and safe drugs.
Used as a Resolving Agent:
In the pharmaceutical industry, (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL is used as a resolving agent for racemic mixtures. This application is essential for obtaining pure enantiomers, which can have different biological activities and are often required for the synthesis of chiral drugs.
Used as a Chiral Auxiliary:
(2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL is utilized as a chiral auxiliary in asymmetric synthesis. Its ability to induce chirality in the products of chemical reactions is valuable for the synthesis of complex molecules with specific stereochemistry, which is often necessary for biological activity.
Used in Pharmacological Research:
(2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL has been studied for its potential pharmacological properties, including its ability to interact with adrenergic receptors. This interaction could have implications for the development of drugs targeting these receptors, which play a role in various physiological processes.
Used as a Beta-Blocking Agent:
Research has also explored the potential of (2S)-(-)-1-AMINO-3-PHENOXY-2-PROPANOL as a beta-blocking agent. Beta-blockers are a class of drugs that are used to treat conditions such as hypertension, angina, and arrhythmias by blocking the effects of catecholamines on beta-adrenergic receptors.

Upstream product

• 71031-03-3 (R)-phenyl glycidyl ether 
• 140630-41-7 (S)-1-azido-3-phenoxy-2-propanol 
• 113080-12-9 (S)-phenoxyacetaldehyde cyanohydrin acetate 
• 122-60-1 Phenyl glycidyl ether 
• 119047-07-3 phenoxyacetaldehyde cyanohydrin 
• 4769-73-7 (RS)-1-chloro-3-phenyloxy-2-propanol 
• 121282-65-3 1-azido-3-phenoxypropan-2-ol 
• 140630-45-1 (R)-1-chloro-3-phenoxy-2-propanol 
• 140428-47-3 Acetic acid 1-bromomethyl-2-phenoxy-ethyl ester 
• 140630-40-6 Acetic acid (R)-1-bromomethyl-2-phenoxy-ethyl ester 
• 905988-41-2 (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 
• 4287-19-8 1-amino-3-phenoxy-isopropanol 
• 67843-74-7 (S)-epichlorohydrin 
• 108-95-2 phenol 

Downstream Products

• 437764-11-9 (2R)-N-[(2S)-2-hydroxy-3-phenoxypropyl]-6-iodo-3,4-dihydro-2H-chromene-2-carboxamide 
• 503060-21-7 C₂₆H₂₅NO₅ 
• 202650-27-9 5-[2-(2S-Hydroxy-3-phenoxy-propylamino)-propyl]-1-[4-(2.2.2-trifluoroethanesulfonylamino)-benzyl]-1H-indole-2-carboxylic Acid Ethyl Ester 
• 202650-18-8 5-[2-(2(S)-Hydroxy-3-phenoxy-propylamino)-propyl]-1-(4-nitrobenzyl)-1H-indole-2-carboxylic Acid Benzyl Ester 
• 115304-40-0 dimethyl 4-[2-[(E)-4-[[(S)-2-hydroxy-3-phenoxypropyl]amino]-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate HCl salt 
• 437764-16-4 methyl 4-[(2R)-2-({[(2S)-2-hydroxy-3-phenoxypropyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]benzoate 
• 1399841-75-8 C₈H₈O₃*C₉H₁₃NO₂ 
• 1630042-68-0 C₂₈H₂₃ClN₆O₃S 

Relevant articles and documents

An excellent new resolving agent for the diastereomeric resolution of rac-mandelic acid

Chiral mandelic acid (S)-1, which is an important precursor for stereoselective transformations and a versatile intermediate for pharmaceuticals, was resolved with the Pope and Peachey method. Enantiopure 1-amino-3-phenoxypropan-2-ol (S)-2, a key intermediate for pharmaceuticals, was used to resolve rac-mandelic acid rac-1 successfully for the first time. The less soluble salt (S)-1·(S)-2·H2O could be obtained in 77% yield and 98% de (E 75%) using (S)-2 and LiOH in water. The crystal structure of the less soluble salt (S)-1·(S)-2·H2O showed that the water molecule played a key role in forming the crystals.

Non-enzymatic kinetic resolution of β-amino alcohols using C-12 higher carbon sugar as a chiral auxiliary

An efficient non-enzymatic kinetic resolution strategy capable of accessing optically active β-adrenergic antagonists intermediates is reported. The C-12 higher carbon sugar derived from naturally occurring sucrose was employed to probe the kinetic resolution. Excellent enantiomeric excesses (ee >99%) and high yields were obtained under very mild conditions. The chiral auxiliary could be recovered in a high reclaimed ratio (>95%) and reusable form without any decrease of the resolving ability.

2- ( (2, 3-DIHYDROXYPROPYL) AMINOMETHYL) CHROMANE DERIVATIVES FOR USE AS BETA-3 ADRENORECEPTOR AGONISTS IN THE TREATMENT OF UROLOGICAL AND INFLAMMATORY DISORDERS

This invention relates to chroman derivatives of formula (I) and salts thereof which are useful as active ingredients of pharmaceutical preparations. The chroman derivatives of the present invention have an excellent activity as BETA 3 antagonists and are useful for the prophylaxis and treatment of diseases associated with BETA 3 activity, in particular for the treatment of urological disorder or disease, such as detrusor overactivity (overactive bladder), urinary incontinence, neurogenic detrusor overactivity (detrusor hyperflexia), idiopathic detrusor overactivity (detrusor instability), benign prostatic hyperplasia, and lower urinary tract symptoms; and inflammatory disorders, such as asthma and COPD.

Resolution of β-aminoalcohols and 1,2-diamines using fractional crystallization of diastereomeric salts of dehydroabietic acid

(S)-(+)-1-Amino-3-phenyloxy-2-propanol, (R)-(-)-2-amino-1-phenylethanol, (S)-(+)-1-amino-2-propanol, (1S,2S)-(+)-2-aminocyclohexanol and (1S,2S)-(+)-1,2-diaminocyclohexane were resolved using dehydroabietic acid. It was shown that good to high enantiomeric purity, between 81～>99% ee, was obtained and that dehydroabietic acid could be easily and efficiently recovered in a reusable form.

Di-substituted aminomethyl-chroman derivative beta-3 adrenoreceptor agonists

This invention is related to novel di-substituted aminomethyl chroman derivatives which are useful in the treatment of beta-3 receptor-mediated conditions.

2-substituted thiazolidinones as beta-3 adrenergic receptor agonists

This invention provides compounds of Formula I having the structure wherein: A, X, Y, Z, R1, R2, R3, R4, R5, and R6are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

2,4-Thiazolidinediones as potent and selective human β3 agonists

Methylsulfonamide substituted 2,4-thiazolidinedione 22c is a potent (EC50 = 0.01 μM, IA = 1.19) and selective (more than 110-fold over β1 and β2 agonist activity) β3 agonist. This compound has also been proven to be active and selective in an in vivo mode.

Enzyme Assisted Preparation of Enantiomerically Pure β-Adrenergic Blockers II. Building Blocks of High Optical Purity and their Synthetic Conversion

Based on previous screening results a series of potential building blocks 2-4 for β-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolu

Formation of Optically Active Aryloxyacetaldehyde Cyanohydrin Acetates with the Aid of a Microorganism

Microorganisms that hydrolyze the one enantiomer of dl-phenoxyacetaldehyde cyanohydrin acetate were screened, and Bacillus coagulans isolated from soil was found to be the best.This bacterium was applied to the asymmetric hydrolysis of other aryloxyacetaldehyde derivatives to give satisfactory results.The effect of adding dimethyl sulfoxide to the medium is also described.