126923-25-9

Basic information

• Product Name: Benzeneethanol, b-azido-, (S)-
• CAS NO: 126923-25-9
• Molecular Formula: C8H9N3O
• Molecular Weight: 163.179
• Mol File: 126923-25-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzeneethanol, b-azido-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, b-azido-, (S)-(126923-25-9)
• EPA Substance Registry System: Benzeneethanol, b-azido-, (S)-(126923-25-9)

Safety Data

• Hazardous Substances Data: 126923-25-9(Hazardous Substances Data)

Upstream product

• 96-09-3 styrene oxide 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 104762-37-0 4-Phenyl-2,2,2-triphenyl-1,3,2λ⁵-dioxaphospholane 
• 104762-38-1 (S)-4-methyl-2,2,2-triphenyl-1,2,2λ⁵-dioxaphospholane 
• 86030-83-3 1-(4-Methylbenzenesulfonyloxy)-1-phenyl-2-ethanol 
• 20780-53-4 (R)-Styrene oxide 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 133522-24-4 (R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide 

Downstream Products

• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 
• 1160187-16-5 (S)-(1-azido-2-(but-2-ynyloxy)ethyl)benzene 
• 1160187-15-4 (S)-(1-azido-2-(prop-2-ynyloxy)ethyl)benzene 
• 1204508-42-8 (S)-(2-azido-2-phenylethoxy)(tert-butyl)dimethylsilane 
• 20989-17-7 (2S)-2-phenylglycinol 
• 25260-42-8 cis-2-Phenyl-aziridin 
• 1202553-54-5 2-methyl-2,4,6-triphenyl-2H-1,3-oxazine 
• 1202553-60-3 1,3-bis[2,6-diphenyl-2-methyl-2H-1,3-oxazin-4-yl]benzene 
• 1202553-56-7 2-methyl-4-naphthalen-2-yl-2-phenyl-6-thiophen-3-yl-2H-1,3-oxazine 
• 1202553-55-6 6-biphenyl-4-yl-2-methyl-4-naphthalen-2-yl-2-phenyl-2H-1,3-oxazine 
• 1202553-58-9 6-(3-methoxy-phenyl)-2-methyl-2,4-diphenyl-2H-1,3-oxazine 

Relevant articles and documents

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes

(Figure presented) Enantioenriched allenylsilanes are used in three-component propargylatlon reactions with aldehydes and silyl ethers to form syn-homopropargylic ethers that contain an imbedded azide. These materials then undergo thermally Induced intram

The regioselective and stereospecific substitution of unsymmetrical 1,2-diols using the 1,3,2λ5-dioxaphospholane methodology

Stereo specific tosylate (-OTs) or azide (N3-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2λ5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either P-toluenesulfonic acid (P-TsOH) in tetrahydrofuran solvent or P-TsOH/sodium azide in acetonitrile solvent, respectively.