1517-05-1

Basic information

• Product Name: 2-Azidoethanol
• Synonyms: 2-Azidoethanol;Ccris 4996;2-Azido-1-ethanol;2-Hydroxyethyl azide;Azidoethanol;Ethanol, 2-azido-;Azido-PEG1-alcohol
• CAS NO: 1517-05-1
• Molecular Formula: C₂H₅N₃O
• Molecular Weight: 87.0806
• Mol File: 1517-05-1.mol

Chemical Properties

• Boiling Point: 77℃ (24 Torr)
• Flash Point: °C
• Appearance: /
• Density: 1.1460
• Refractive Index: 1.4264 (estimate)
• CAS DataBase Reference: 2-Azidoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azidoethanol(1517-05-1)
• EPA Substance Registry System: 2-Azidoethanol(1517-05-1)

Safety Data

• Hazardous Substances Data: 1517-05-1(Hazardous Substances Data)

Usage

Uses

Used in Carbohydrate Chemistry:
2-Azidoethanol is used as a reagent for the glycosylation of monoor polysaccharides. Its azide group allows for the formation of glycosidic bonds, which are crucial in the synthesis of complex carbohydrate structures. This application is particularly relevant in the fields of biochemistry and pharmaceuticals, where the study and development of carbohydrate-based drugs and vaccines are of significant interest.
Used in Molecular Biology:
In the field of molecular biology, 2-Azidoethanol is utilized as a 2'-deoxy-ethynyluridine (EdU) blocker in nuclear DNA. By preventing cross-reactivity with other antibodies, it enables researchers to study the pathways related to EdU incorporation more accurately. This application is valuable for understanding DNA replication and cell proliferation processes, which are essential for various biological and medical research areas.
Used in Chemical Synthesis:
2-Azidoethanol's azide group also makes it a useful building block in the synthesis of various organic compounds, particularly those with potential applications in pharmaceuticals, materials science, and agrochemicals. The azide group can be further modified or reacted with other molecules to create a wide range of products with different properties and functions.

Preparation

2-Azidoethanol synthesis: Sodium azide (14.6 g, 224 mmol, 1.5 eq.) was added portion wise to a stirred mixture of 2- chloroethanol (12.0 g, 149 mmol, 1 eq.) in H2O (80 mL) at 0°C. The reaction mixture was slowly warmed up to room temperature and stirred for another 4 h. Additional sodium azide (9.71 g, 149 mmol, 1 eq.) was added and the solution was heated under reflux at 80°C overnight. After completion, the mixture was extracted with Et2O (3×50 mL) and the combined organic phases were washed with Brine (1× 10 mL) and dried over MgSO4. The solvent was removed in vacuo to yield a colorless oil (10.57 g, 121.4 mmol, 81%).1 H NMR (400 MHz, CDCl3, ppm): δ=3.77 (q, 2H, CH2 OH), 3.43 (t, 2H, CH2 N3), 2.16 (s, 1H, OH). 13C NMR (101 MHz, CDCl3, ppm): δ=61.6 (CH2 OH), 53.7 (CH2 N3). 14N NMR (CDCl3, ppm): δ= 134 (Nβ), 171 (Nγ), 319 (Nα). C2H5N3O (87.08 gmol 1 ) calcd. N 48.25, C 27.59, H 5.79%; found IS: >40 J. FS: >360 N.

InChI:InChI=1/C2H5N3O/c3-5-4-1-2-6/h6H,1-2H2

Upstream product

• 107-07-3 2-chloro-ethanol 
• 540-51-2 2-bromoethanol 
• 141072-57-3 1-bromoethanol 
• 141-43-5 ethanolamine 
• 42772-85-0 2-hydroxyethyl 4-methylbenzenesulfonate 
• 624-76-0 Iodoethanol 

Downstream Products

• 53422-48-3 2-chloroethyl azide 
• 18523-48-3 2-azidoacetic acid 
• 53422-49-4 2-nitroxy-1-azidoethane 
• 141-43-5 ethanolamine 
• 7399-68-0 2-(4-chlorophenyl)-4,5-dihydro-1,3-oxazole 
• 7399-69-1 N-(2-hydroxyethyl)-3-nitrobenzamide 
• 88186-35-0 4,5-dihydro-2-(3-nitrophenyl)oxazole 
• 7127-19-7 2-phenyl-1,3-oxazoline 
• 18838-10-3 N-(2-hydroxyethyl)-benzamide 
• 20237-92-7 2-(2'-Hydroxyphenyl)-2-oxazolin 
• 475599-45-2 4-nitro-benzoic acid-(2-azido-ethyl ester) 
• 74862-19-4 2-(2-azidoethoxy)-4,6-dichloro-1,3,5-triazine 
• 15791-08-9 4,6-dichloro-2-hydroxy-1,3,5-triazine 
• 140428-83-7 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 

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