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742678

Sigma-Aldrich

(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylmethanol

for Copper-free Click Chemistry

Synonym(s):

(1α,8α,9β)-Bicyclo[6.1.0]non-4-yne-9-methanol, endo-9-Hydroxymethylbicyclo[6.1.0]non-4-yne, BCN-OH

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
1263166-90-0
Molecular Weight:
150.22
Beilstein:
21037713
MDL number:
MFCD26142970
UNSPSC Code:
12352209
PubChem Substance ID:
329765586
NACRES:
NA.22

form

powder

composition

carbon content, 79.96%
hydrogen content, 9.39%

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

hydroxyl

storage temp.

−20°C

SMILES string

[H][C@@]12[C@@]([C@H]2CO)([H])CCC#CCC1

InChI

1S/C10H14O/c11-7-10-8-5-3-1-2-4-6-9(8)10/h8-11H,3-7H2/t8-,9+,10-

InChI key

NSVXZMGWYBICRW-ILWJIGKKSA-N

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Application

Alcohol functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This strained cyclooctyne will react with azide functionalized compounds or biomolecules without the need for a copper catalyst to result in a stable triazole linkage.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dibenzocyclooctyne-maleimide for Copper-free Click Chemistry

Sigma-Aldrich

760668

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Sigma-Aldrich

QBD11372

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Xifeng Liu et al.
Biomacromolecules, 20(9), 3352-3365 (2019-08-10)
A new PPF-BCN/hyPCL32-N3 injectable system that can be cross-linked by catalyst-free, strain promoted alkyne-azide cycloaddition (SPAAC) click chemistry was developed for tissue engineering applications. The system consisted of two components: PPF-BCN, poly(propylene fumarate) (PPF) functionalized with (1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN-OH), and hyPCL32-N3
Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells.
Jan Dommerholt et al.
Angewandte Chemie (International ed. in English), 49(49), 9422-9425 (2010-09-22)

Articles

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

Click Chemistry in Drug Discovery

Drug discovery process by utilizing chemistry reaction of Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of terminal alkynes with organoazides to yield 1,4-disubstituted 1,2,3-triazoles.

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