5-Azidopentanoic acid Chemical Properties

Boiling point:

85°C/0.01mmHg(lit.)

Density 

1.142

refractive index 

1.4640-1.4680

storage temp. 

-20°C

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml

form 

clear liquid

color 

Colorless to Red to Green

BRN 

1706398

InChI

InChI=1S/C5H9N3O2/c6-8-7-4-2-1-3-5(9)10/h1-4H2,(H,9,10)

InChIKey

SBZDIRMBQJDCLB-UHFFFAOYSA-N

SMILES

C(C(O)=O)CCCN=[N+]=[N-]

Safety Information

Hazard Codes 

Xn

Risk Statements 

40

Safety Statements 

36/37

WGK Germany 

3

HS Code 

29299090

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

Hazard Classifications

Carc. 1B
Self-react. C

5-Azidopentanoic acid Usage And Synthesis

Chemical Properties

Yellow liquid

Uses

5-Azidopentanoic acid can be used to synthesize:

• Chitosan-poly(ethylene glycol) hydrogels by azide–alkyne click chemistry.
• 5-iodo-1,2,3-triazole containing macrocycles.
• Bivalent quinine dimers intervening triazole ring used as inhibitors of P-glycoprotein (P-gp) mediated cellular efflux.

Synthesis

C7H13N302 C5H9N302 29.1 mmol Lithium hydroxide monohydrate as a 1 M solution in Water, 90 ml THF and 90 ml methanol was added to 15.4 mmol Ethyl-5-Azido pentanoate in a flask and stirred at room temperature for 18 hours. The solvent was removed in vacuo and a small amount of water and HCI 37 % was added till pH 1 . After that the reaction mixture was extracted with Ethyl acetate (250 ml) and the combined organic phase was dried over Na2SO4. The solvent was removed in vacuo leaving 2.18 g of 5-Azidopentanoic acid (15.2 mmol, yield = 99 %).^[1]

References

[1] Duval, S. , &  Kindermann, M. . Azido alkanoic acids and derivatives thereof in feed for reducing methane formation emanating from the digestive activities of ruminants. WO, WO/2011/045418.

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