61278-21-5

Basic information

• Product Name: (S)-3-Amino-1,2-propanediol
• Synonyms: (S)-3-AMino-1,2-propanediol 98%;(S)-(-)-3-AMINO-1,2-PROPANEDIOL;(S)-3-AMINO-1,2-PROPANEDIOL;(2S)-3-AMINOPROPANE-1,2-DIOL;1,2-PROPANEDIOL, 3-AMINO, (S);1,2-PROPANEDIOL, 3-AMINO-, (2S)-;(R)/(S)-3-Amino-1,2-propanediol;(S)-(-)-3-Amino-1,2-propandiol*
• CAS NO: 61278-21-5
• Molecular Formula: C₃H₉NO₂
• Molecular Weight: 91.11
• EINECS: 200-002-4
• Product Categories: chiral;CHIRAL COMPOUNDS;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 61278-21-5.mol

Chemical Properties

• Melting Point: 54-56°C
• Boiling Point: 117-119 °C0.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to white/Liquid To Low Melting Solid
• Density: 1.175 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00116mmHg at 25°C
• Refractive Index: n20/D 1.483(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 12.11±0.35(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1719122
• CAS DataBase Reference: (S)-3-Amino-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Amino-1,2-propanediol(61278-21-5)
• EPA Substance Registry System: (S)-3-Amino-1,2-propanediol(61278-21-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 61278-21-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Amino-1,2-propanediol is used as a chiral selector ligand for the development of pharmaceutical compounds. Its chiral nature allows for the selective interaction with other chiral molecules, which is crucial in the synthesis of enantiomerically pure drugs. This selective interaction is particularly important in the pharmaceutical industry, as the efficacy and safety of many drugs are highly dependent on their stereochemistry.
Used in Chemical Synthesis:
(S)-3-Amino-1,2-propanediol is used as a building block in the synthesis of various organic compounds. Its amino and hydroxyl functional groups can participate in a range of chemical reactions, such as nucleophilic substitution, making it a versatile starting material for the production of a wide array of molecules.
Used in Analytical Chemistry:
(S)-3-Amino-1,2-propanediol is used as a chiral reference standard in analytical chemistry. Its well-defined stereochemistry makes it an ideal candidate for calibrating and validating analytical methods that are designed to separate and quantify enantiomers in complex mixtures.
Used in Research and Development:
(S)-3-Amino-1,2-propanediol is employed as a research tool in the development of new chiral catalysts, ligands, and other chiral materials. Its unique properties make it a valuable compound for studying the effects of stereochemistry on molecular interactions and reactivity.

InChI:InChI=1/C3H9NO2/c4-1-3(6)2-5/h3,5-6H,1-2,4H2/t3-/m0/s1

Upstream product

• 616-30-8 3-Amino-1,2-propanediol 
• 85820-82-2 (S)-1-azido-1-deoxy-2,3-O-isopropylidene-glycerol 
• 57044-25-4 (R)-oxiranemethanol 
• 82954-65-2 [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine 
• 123356-17-2 (S)-3-Benzyloxy-2-hydroxy-propionitrile 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 

Downstream Products

• 148983-25-9 (S)-1-<(tert-butoxycarbonyl)amino>-2,3-dihydroxypropane 
• 851233-13-1 C₁₅H₂₁NO₆ 
• 1072918-57-0 (2R)-N-2,3-dihydroxypropyl-2,3,4,6-tetra-O-benzyl-D-gluconamide 
• 849473-68-3 (2S)-2-[(2,3-dihydroxypropyl)amino]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile 
• 1020192-59-9 (S)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol 
• 135582-93-3 (S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol 
• 907625-11-0 (2S)-2,3-(dinitrooxy)propan-1-ammonium nitrate 
• 935528-28-2 N-(2,3-dihydroxy-propyl)-4-phenylazo-benzamide 
• 7517-99-9 (S)-5-(hydroxymethyl)-1,3-oxazolidin-2-one 

Relevant articles and documents

Stereoselective Oxidative Cyclization ofN-Allyl Benzamides to Oxaz(ol)ines

This study presents an enantioselective oxidative cyclization ofN-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besidesN-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates, giving rise to a plethora of chiral 5-memberedN-heterocycles. By applying a multitude of further functionalizations, we finally demonstrate the high value of the observed chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.

A concise stereoselective synthesis of (+)-1-deoxy-6-epi-castanospermine

A concise stereoselective synthesis of (+)-1-deoxy-6-epi-castanospermine has been developed through stereoselective approach from the chiral precursor R-Glycidol. The key steps in the synthesis involve Grignard reaction through Weinreb amide, followed by Sharpless dihydroxylation and stereoselective reduction of imine assigned the required stereochemical feature of indolizidine azasugar (+)-1-deoxy-6-epi-castanospermine.

Diversity oriented concise asymmetric synthesis of azasugars: A facile access to l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine

Diversity oriented concise asymmetric syntheses of l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine have been developed from (R)-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de. The (2R,3R,4S)-2,3-dihydroxypentanoate derivative 15 was subsequently converted to natural pyrrolidine azasugar 1 and non-natural piperidine azasugar 4 under cascade reaction conditions in good yields.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Synthesis and properties of crosslinked chiral nanoparticles via RAFT miniemulsion polymerization

Crosslinked chiral nanoparticles were successfully synthesized via reversible addition-fragmentation chain transfer (RAFT) miniemulsion polymerization of 6-O-p-vinylbenzyl-1,2:3,4di-O-isopropylidene-D-galactopyranose (VBPG) using linear poly(VBPG) as the macro-RAFT agent. The polymerization of VBPG in the absence of crosslinker was first studied and the kinetic results showed that the molecular weights of the obtained poly(VBPG) increased linearly with the monomer conversion and was in good consistency with the corresponding theoretical ones while there remained a relative narrow polydisperslty. The effect of the amount of crosslinker, divlnylbenzene, on the nanoparticle size and chiral separation properties of the obtained nanoparticles were investigated in detail using four racemates ±-3-Amino-1,2propanediol, D,L-arablnose, D,L-tartaric acid, and D,L-mandelic acid.

Nitric oxide enhancing diuretic compounds, compositions and methods of use

The invention describes novel compositions and kits comprising at least one nitric oxide enhancing diuretic compound, or pharmaceutically acceptable salts thereof, and, optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating conditions resulting from excessive water and/or electrolyte retention; (b) treating cardiovascular diseases; (c) treating renovascular diseases; (d) treating diabetes; (e) treating diseases resulting from oxidative stress; (f) treating endothelial dysfunctions; (g) treating diseases caused by endothelial dysfunctions; (h) treating cirrhosis; (j) treating pre-eclampsia; (k) treating osteoporosis; (l) treating nephropathy; (m) treating peripheral vascular diseases; (n) treating portal hypertension; (o) treating central nervous system disorders; (p) treating metabolic syndrome; (q) treating sexual dysfunctions; and (r) hyperlipidemia. The nitric oxide enhancing diuretic compounds comprise at least one nitric oxide enhancing group linked to the diuretic compound through one or more sites such as carbon, oxygen and/or nitrogen via a bond or moiety that cannot be hydrolyzed.

Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

Synthesis of orthogonally protected (2S, 4R)- and (2S, 4S)-4-hydroxyornithine was reported featuring an asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester (6) by (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine (7). Double stereoselection was examined using chiral ammonium salts as phase transfer catalysts and a substrate-directed chiral induction is documented.

PROCESS FOR THE PREPARATION OF PROTECTED 3-AMINO-1,2-DIHYDROXYPROPANE ACETAL AND DERIVATIVES THEREOF

A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.

Process for the preparation of protected 3-amino-1,2-dihydroxypropane acetal and derivatives thereof

A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.

One-pot transformation of a t-butyl carbamate to a bromoacetamide in the synthesis of the gene transfer agent pcTG201

The gene transfer agent pcTG201, a cationic lipid in which (S)-3- aminopropane-1,2-diol bears two oleoyl chains and an N,N'-permethylated diammonio polar head, has been prepared from (R)-glycidol by a short reaction sequence including a one-pot conversion of a t-butyl carbamate to a bromoacetamide and the substitution of an iodide with 3- (dimethylamino)propyltrimethylammonium iodide.