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
• Article Data: 14

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

Chemical Properties

Colorless flakes

Uses

(S)-(-)-3-Amino-1,2-propanediol is used as a chiral selector ligand, used subsequently for a nucleophilic substitution with the dimethoxytrityl (DMT)-protected

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

Upstream product

• 85820-82-2 (S)-1-azido-1-deoxy-2,3-O-isopropylidene-glycerol 
• 616-30-8 3-Amino-1,2-propanediol 
• 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 
• 1020192-59-9 (S)-(2-(4-nitrophenyl)-4,5-dihydrooxazol-5-yl)methanol 
• 1072918-57-0 (2R)-N-2,3-dihydroxypropyl-2,3,4,6-tetra-O-benzyl-D-gluconamide 
• 851233-13-1 C₁₅H₂₁NO₆ 
• 1177420-46-0 N-[(2S)-2,3-Dihydroxypropyl]-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrole-2-carboxamide 
• 1177421-37-2 N-[(2S)-2,3-dihydroxypropyl]-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrole-2-carboxamide 
• 1177422-07-9 N-[(2S)-2,3-Dihydroxypropyl]-5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(triisopropylsilyl)oxy]phenyl}-1H-pyrrole-2-carboxamide 
• 7517-99-9 (S)-5-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 135582-93-3 (S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol 

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.

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.

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.