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712256

Sigma-Aldrich

5-Azidopentanoic acid

≥97.0%

Synonym(s):

5-Azidovalerianic acid

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About This Item

Empirical Formula (Hill Notation):
C5H9N3O2
CAS Number:
79583-98-5
Molecular Weight:
143.14
Beilstein:
1706398
MDL number:
MFCD11850108
UNSPSC Code:
12352100
PubChem Substance ID:
329763122
NACRES:
NA.22

Assay

≥97.0% (TLC)
≥97.0%
97.0-103.0% (calc. on dry substance, T)

form

liquid

availability

available only in USA

loss

≤10% loss on drying

functional group

azide
carboxylic acid

storage temp.

−20°C

SMILES string

OC(=O)CCCCN=[N+]=[N-]

InChI

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

InChI key

SBZDIRMBQJDCLB-UHFFFAOYSA-N

Application

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

FlameHealth hazard
GHS02,GHS08

Signal Word

Danger

Hazard Statements

H242,H350

Hazard Classifications

Carc. 1B - Self-react. C

Supplementary Hazards

EUH019

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV0359
BCBS0881V
BCBN8344V
BCBM3451V
BCBH4233V

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Synthesis of 5-iodo-1, 2, 3-triazole-containing macrocycles using copper flow reactor technology.
Bogdan AR, et al.
Organic Letters, 13(15), 4060-4063 (2011)
In situ-forming robust chitosan-poly (ethylene glycol) hydrogels prepared by copper-free azide-alkyne click reaction for tissue engineering.
Truong VX, et al.
Biomaterials Science, 2(2), 167-175 (2014)
Click chemistry-derived bivalent quinine inhibitors of P-glycoprotein-mediated cellular efflux.
Kuriakose J, et al.
Bioorganic & medicinal chemistry letters, 22(13), 4410-4412 (2012)
Ian J Huggins et al.
Molecules (Basel, Switzerland), 24(18) (2019-09-13)
Nucleic Acid Therapeutics (NATs), including siRNAs and AntiSense Oligonucleotides (ASOs), have great potential to drug the undruggable genome. Targeting siRNAs and ASOs to specific cell types of interest has driven dramatic improvement in efficacy and reduction in toxicity. Indeed, conjugation
Eliška Böhmová et al.
Pharmaceutics, 12(1) (2020-01-16)
Cell-penetrating peptides (CPPs) are commonly used substances enhancing the cellular uptake of various cargoes that do not easily cross the cellular membrane. CPPs can be either covalently bound directly to the cargo or they can be attached to a transporting
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