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772828

Sigma-Aldrich

5-Norbornene-2-endo-acetic acid

Synonym(s):

Bicyclo[2.2.1]hept-5-en-2-ylacetic acid, Norbornene acetic acid

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About This Item

Empirical Formula (Hill Notation):
C9H12O2
CAS Number:
825-71-8
Molecular Weight:
152.19
UNSPSC Code:
12352106
PubChem Substance ID:
329766608
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: click chemistry
reagent type: linker

refractive index

n20/D 1.495

density

1.124 g/mL at 25 °C

functional group

carboxylic acid

SMILES string

OC(CC1C[C@@H]2C=C[C@H]1C2)=O

InChI

1S/C9H12O2/c10-9(11)5-8-4-6-1-2-7(8)3-6/h1-2,6-8H,3-5H2,(H,10,11)/t6-,7+,8?/m1/s1

InChI key

HRVGJQMCNYJEHM-KVARREAHSA-N

Application

Carboxylic acid functionalized norbornene. Carboxylic acid can be used to modify amine containing compounds such as lysine residues on proteins/peptides via standard peptide coupling methods. Norbornene has been shown to react with 1,2,4,5-tetrazines in an inverse electron demand Diels-Alder cycloaddition reaction, which is a bioorthogonal click chemistry reaction demonstrated to be useful in biological imaging applications.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H412

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Hee-Sun Han et al.
Journal of the American Chemical Society, 132(23), 7838-7839 (2010-05-21)
We present a bioorthogonal and modular conjugation method for efficient coupling of organic dyes and biomolecules to quantum dots (QDs) using a norbornene-tetrazine cycloaddition. The use of noncoordinating functional groups combined with the rapid rate of the cycloaddition leads to
Neal K Devaraj et al.
Bioconjugate chemistry, 19(12), 2297-2299 (2008-12-05)
Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast

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