134625-72-2

Basic information

• Product Name: (1R)-2-azido-1-phenylethanol
• Synonyms: (1R)-2-Azido-1-phenylethanol; benzenemethanol, alpha-(azidomethyl)-, (alphaR)-
• CAS NO: 134625-72-2
• Molecular Formula: C₈H₉N₃O
• Molecular Weight: 163.1766
• Mol File: 134625-72-2.mol
• Article Data: 32

Chemical Properties

• CAS DataBase Reference: (1R)-2-azido-1-phenylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-2-azido-1-phenylethanol(134625-72-2)
• EPA Substance Registry System: (1R)-2-azido-1-phenylethanol(134625-72-2)

Safety Data

• Hazardous Substances Data: 134625-72-2(Hazardous Substances Data)

Usage

Description

(1R)-2-azido-1-phenylethanol is a chiral azide derivative of 1-phenylethanol with the molecular formula C8H9N3O. It is a versatile compound used as a chiral building block in organic synthesis, particularly in click chemistry reactions for the formation of triazoles. Its chiral nature also makes it a promising candidate for asymmetric synthesis in pharmaceutical research.

Uses

Used in Organic Synthesis:
(1R)-2-azido-1-phenylethanol is used as a chiral building block for the synthesis of various organic compounds. Its unique structure allows for the creation of complex molecules with specific stereochemistry.
Used in Click Chemistry:
(1R)-2-azido-1-phenylethanol is used as a reactant in click chemistry reactions, where it participates in the formation of triazoles. This makes it a valuable tool for the rapid and efficient synthesis of complex molecules.
Used in Pharmaceutical Research:
(1R)-2-azido-1-phenylethanol is used as a precursor in the synthesis of pharmaceuticals and fine chemicals. Its potential applications in this field include the development of new drugs and the improvement of existing ones.
Used in Asymmetric Synthesis:
(1R)-2-azido-1-phenylethanol is used as a chiral starting material in asymmetric synthesis, where the stereochemistry of the molecule is crucial for its biological activity and selectivity. This makes it a valuable resource for the development of enantiomerically pure compounds with specific therapeutic properties.

Upstream product

• 96-09-3 styrene oxide 
• 20780-53-4 (R)-Styrene oxide 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 56751-12-3 2-chloro-1-phenylethanol 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 108-05-4 vinyl acetate 
• 124718-87-2 2-azido-1-phenylethan-1-ol 
• 108-22-5 Isopropenyl acetate 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 4128-31-8 rac-octan-2-ol 
• 67-63-0 isopropyl alcohol 
• 73908-23-3 (R)-2-bromo-1-phenylethanol 
• 70-11-1 α-bromoacetophenone 
• 108-24-7 acetic anhydride 

Downstream Products

• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 148729-63-9 ((R)-2-Azido-1-phenyl-ethoxy)-acetic acid ethyl ester 
• 130406-45-0 -carbamic acid <2-<(2-hydroxy-2-phenylethyl)amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>-tricyclo<3.3.1.1^3,7>dec-2-yl ester 
• 148729-50-4 -8,11-dioxa-2,5-diazatridecanoic acid 3-(1H-indol-3-ylmethyl)-3-methyl-4,10-dioxo-7-phenyl-tricyclo<3.3.1.1^3,7>dec-2-yl ester 
• 148729-51-5 -8,12-dioxa-2,5-diazatetradecanoic acid 3-(1H-indol-3-ylmethyl)-3-methyl-4,11-dioxo-7-phenyl-tricyclo<3.3.1.1^3,7>dec-2-yl ester 
• 62779-70-8 (1S)-1-phenylethylene-1,2-diamine 
• 16595-77-0 (S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol 
• 144125-06-4 (S)-2-azido-1-phenyl-ethylamine 
• 1160187-20-1 (R)-(2-azido-1-(but-2-ynyloxy)ethyl)benzene 
• 1160187-19-8 (R)-(2-azido-1-(prop-2-ynyloxy)ethyl)benzene 
• 1489232-03-2 (-)-(R)-2-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylethanol 

Relevant articles and documents

Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa

Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of

A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction

An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).

Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents

Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3–57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1. The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, (S)-41, (R)-42, (S)-55 and (S)-57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium. However, none of the five molecules, 1, (S)-41, (R)-42, (S)-55 and (S)-57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4, 6, 7 and 11 showed high cytotoxicities with CC50 values of 5.87, 5.08, 6.44 and 14.04 μM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.