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761540

Dibenzocyclooctyne-amine

for Copper-free Click Chemistry

Synonym(s):

DBCO-NH2, DBCO-amine

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Size/SKUAvailabilityPrice
10 mg
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$71.90
100 mg
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$536.00

About This Item

Empirical Formula (Hill Notation):
C18H16N2O
CAS Number:
Molecular Weight:
276.33
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352116
MDL number:
Assay:
≥94.5 %
Form:
solid

$71.90


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Quality Segment

assay

≥94.5 %

form

solid

reaction suitability

reaction type: click chemistry, reagent type: linker

mp

86-96 °C

functional group

amine

storage temp.

−20°C

SMILES string

NCCC(N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3)=O

InChI

1S/C18H16N2O/c19-12-11-18(21)20-13-16-7-2-1-5-14(16)9-10-15-6-3-4-8-17(15)20/h1-8H,11-13,19H2

InChI key

OCCYFTDHSHTFER-UHFFFAOYSA-N

General description

Dibenzocyclooctyne-amine (DBCO-NH2), is a heterobifunctional linker containing a DBCO moiety commonly used for the site-specific functionalization of nanobodies, enabling the addition of reactive DBCO groups for subsequent click chemistry reactions.

Application

Dibenzocyclooctyne-amine can be used as a :
  • Linker to link azide-containing functional groups. It facilitates the formation of linkages through Strain-promoted azide-alkyne cycloaddition reactions (SPAAC)
  • Reagent in the synthesis of N-heterocyclic carbene metal thiolates. It functionalizes the metal complexes and increases their reactivity in the strain-promoted alkyne–azide cycloaddition (SPAAC) reactions
  • Amine functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.

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This Item
760668764019762040
assay

≥94.5 %

assay

-

assay

≥90%

assay

≥90.0 %

reaction suitability

reaction type: click chemistry, reagent type: linker

reaction suitability

reaction type: click chemistry, reagent type: cross-linking reagent

reaction suitability

reaction type: click chemistry, reagent type: linker

reaction suitability

reaction type: click chemistry, reagent type: linker

mp

86-96 °C

mp

-

mp

-

mp

240-260 °C

form

solid

form

solid

form

paste

form

solid

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

functional group

amine

functional group

maleimide

functional group

NHS ester

functional group

-


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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