126923-26-0

Basic information

• Product Name: Benzeneethanol, b-azido-, (R)-
• CAS NO: 126923-26-0
• Molecular Formula: C8H9N3O
• Molecular Weight: 163.179
• Mol File: 126923-26-0.mol

Chemical Properties

• CAS DataBase Reference: Benzeneethanol, b-azido-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, b-azido-, (R)-(126923-26-0)
• EPA Substance Registry System: Benzeneethanol, b-azido-, (R)-(126923-26-0)

Safety Data

• Hazardous Substances Data: 126923-26-0(Hazardous Substances Data)

Upstream product

• 126828-42-0 1-trimethylsilyl-2-azido-2-phenylethane 
• 4427-92-3 (4S)-4-phenyl[1,3]dioxolan-2-one 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 20780-53-4 (R)-Styrene oxide 
• 20780-54-5 (S)-styrene oxide 
• 70111-05-6 (S)-2-chloro-1-phenylethanol 
• 2425-28-7 (S)-2-bromo-1-phenylethanol 
• 532-27-4 1-chloroacetophenone 
• 70-11-1 α-bromoacetophenone 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 96-09-3 styrene oxide 
• 100-42-5 styrene 

Downstream Products

• 56613-80-0 D-2-phenylglycinol 
• 677028-16-9 4-(2'-hydroxy-1'R-phenylethyl)-2R,7S-dimethyl[1,4]oxazepan-5-one 
• 67341-01-9 (R)-N-(tert-butoxycarbonyl)phenylglycinol 

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.

Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water

A practical and convenient method for the efficient and regio- and stereoselective ring-opening of enantiopure monosubstituted epoxides by sodium azide under hydrolytic conditions is reported. The ring-opening of enantiopure styryl and pyridyl (S)-epoxides by N3- in hot water takes place preferentially at the internal position with complete inversion of configuration to produce (R)-2-azido ethanols with up to 99% enantio- and regioselectivity, while the (S)-adamantyl oxirane provides mainly the (S)-1-adamantyl-2-azido ethanol in excellent yield. In general, 1,2-amino ethanols were obtained in high yield and excellent enantiopurity by the reduction of the chiral 1,2-azido ethanols with PPh3 in water/THF, and then converted into the Boc or acetamide derivatives.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: Application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols

An enantioselective borane-mediated reduction of a variety of 2-haloketones with 10% spiroaminoborate ester 1 as catalyst is described. By a simple basic workup of 2-halohydrins, optically active epoxides are obtained in high yield and with excellent enantiopurity (up to 99% ee). Ring-opening of oxiranes with phenoxides or sodium azide is investigated under different reaction conditions affording nonracemic 1,2-hydroxy ethers and 1,2-azido alcohols with excellent enantioselectivity (99% ee) and in good to high chemical yield. 2011 American Chemical Society.

Asymmetric Schmidt reaction of hydroxyalkyl azides with ketones

An asymmetric equivalent of the Schmidt reaction permits stereocontrol in ring expansions of symmetrical cyclohexanones. The procedure involves the reaction of chiral 1,2- and 1,3-hydroxyalkyl azides with ketones under acid catalysis; the initial reaction affords an iminium ether that can be subsequently opened with base. A systematic study of this reaction is reported, in which ketone substrates, chiral hydroxyalkyl azides, and reaction conditions are varied. Selectivities as high as ca. 98:2 are possible for the synthesis of substituted caprolactams, with up to 1,7-stereoselection involved in the overall process. The fact that either possible migrating carbon is electronically identical provides an unusual opportunity to study a ring-expansion reaction controlled entirely by stereoelectronic factors. The mechanism of the reaction and the source of its stereoselectivity are also discussed.

A practical route to enantiopure 1,2-aminoalcohols

A series of enantiopure aminoalcohols were synthesized from the corresponding diols by activation of the diols as cyclic carbonates, azide opening of the carbonates, and hydrogenation of the resulting azidoalcohols. Factors affecting the azide opening of the carbonates, a simple workup procedure, and a large scale synthesis of (1R,2S)-(-)-2-amino-1,2-diphenylethanol are described.

OUVERTURE ENANTIODIVERGENTE DE L'EPOXYSTYRENE (R) PAR Me3SiN3 CATALYSEE PAR Al(O-iPr)3 ET Ti(O-iPr)4

Ring-opening of (R) epoxystyrene with Me3SiN3 in the presence of Al(O-iPr)3 gives only the (S) silylated azidohydrine.Use of Ti(O-iPr)4 leads to the enantiodivergent opening of the epoxide, depending upon the solvent used.