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Sigma-Aldrich

4-Azidophenyl isothiocyanate

≥97.0% (CHN)

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About This Item

Linear Formula:
N3C6H4NCS
CAS Number:
Molecular Weight:
176.20
Beilstein:
6391971
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Assay

≥97.0% (CHN)

mp

65-68 °C (lit.)
66-68 °C

storage temp.

2-8°C

SMILES string

[N-]=[N+]=Nc1ccc(cc1)N=C=S

InChI

1S/C7H4N4S/c8-11-10-7-3-1-6(2-4-7)9-5-12/h1-4H

InChI key

XMPGXADJZXSISQ-UHFFFAOYSA-N

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Other Notes

Heterobifunctional crosslinking agent which forms a crosslink over a range of 10 Å and is expected to facilitate the investigation of hydrophobically interacting sites between proteins and membrane lipids

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Methods in Enzymology, 88, 207-207 (1982)
H. Sigrist et al.
Febs Letters, 113, 307-307 (1980)
Songlin Xu et al.
International journal of pharmaceutics, 404(1-2), 205-210 (2010-11-09)
Staudinger ligation was evaluated as a strategy for synthesizing receptor targeted liposomes. First, an activated lipid derivative was synthesized by reacting dioleoyl phosphatidylethanolamine (DOPE) and 2-(diphenylphosphino) terephthalic acid 1-methyl 4-penta-fluorophenyldiester. Second, transferrin (Tf) was activated with p-azidophenyl isothiocyanate. Third, liposomes
H Sigrist et al.
European journal of biochemistry, 125(1), 197-201 (1982-06-15)
Two hydrophobic, heterobifunctional azidoarylisothiocyanates have been synthesized. The reagents are applicable for group-directed modification of membrane-integrated protein segments and subsequent photo-induced cross-linking with neighbouring membrane constituents. Both 5-isothiocyanato-1-naphthalene azide and p-azidophenylisothiocyanate are chemically characterized with respect to structure and photosensitivity.

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