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Safety Information

746118

Sigma-Aldrich

Sodium difluoroheptylazidosulfinate

95%

Synonym(s):

Baran DAAS-Na Reagent, Sodium 1,1-difluoro-7-azido-heptylsulfinate, Sodium 7-azido-1,1-difluoroheptanesulfinate

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About This Item

Empirical Formula (Hill Notation):
C7H12F2N3NaO2S
CAS Number:
1450912-63-6
Molecular Weight:
263.24
UNSPSC Code:
12352125
PubChem Substance ID:
329765744
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation
reagent type: linker

storage temp.

2-8°C

SMILES string

[Na+].[O-]S(=O)C(F)(F)CCCCCCN=[N+]=[N-]

InChI

1S/C7H13F2N3O2S.Na/c8-7(9,15(13)14)5-3-1-2-4-6-11-12-10;/h1-6H2,(H,13,14);/q;+1/p-1

InChI key

FFNHIEJQAMGBCZ-UHFFFAOYSA-M

Related Categories

Application

Within heteroarene platforms, DAAS-Na allows for the direct introduction of a difluoroalkyl chain carrying an azide group, which is designed for the purpose of bioconjugation. Through a Huisgen cycloaddition (a "click" reaction), the azide moiety can then be reacted with a terminal alkyne that is bound to a functional molecule such as biomacromolecules. This effectively allows for a covalent linkage between a heteroarene and any target molecule, for example, between a heteroarene-containing drug and an antibody. This reagent was developed by the Baran Group and is one of several reagents for the direct alkylation of heterocycles.

Learn More at the Professor and Product Portal of Professor Phil S. Baran.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

746118-BULK:
746118-VAR:
746118-100MG:

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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Qianghui Zhou et al.
Journal of the American Chemical Society, 135(35), 12994-12997 (2013-08-21)
A general C-H functionalization method for the tagging of natural products and pharmaceuticals is described. An azide-containing sulfinate reagent allows the appendage of azidoalkyl chains onto heteroaromatics, the product of which can then be attached to a monoclonal antibody by
Direct synthesis of fluorinated heteroarylether bioisosteres.
Qianghui Zhou et al.
Angewandte Chemie (International ed. in English), 52(14), 3949-3952 (2013-03-06)
Fionn O'Hara et al.
Journal of the American Chemical Society, 135(32), 12122-12134 (2013-07-19)
Radical addition processes can be ideally suited for the direct functionalization of heteroaromatic bases, yet these processes are only sparsely used due to the perception of poor or unreliable control of regiochemistry. A systematic investigation of factors affecting the regiochemistry

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