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10919

Sigma-Aldrich

Fmoc isothiocyanate

≥98.0% (CHN)

Synonym(s):

9-Fluorenylmethoxycarbonyl isothiocyanate, 9-Fluorenylmethyl isothiocyanatoformate

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About This Item

Empirical Formula (Hill Notation):
C16H11NO2S
CAS Number:
199915-38-3
Molecular Weight:
281.33
Beilstein:
7930648
MDL number:
MFCD01861169
UNSPSC Code:
12352005
PubChem Substance ID:
57646854
NACRES:
NA.22

Assay

≥85% (coupling to amines)
≥98.0% (CHN)

solubility

ethanol: soluble

fluorescence

λex 264 nm; λem 313 nm

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

SMILES string

O=C(OCC1c2ccccc2-c3ccccc13)N=C=S

InChI

1S/C16H11NO2S/c18-16(17-10-20)19-9-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15H,9H2

InChI key

DHMYULZVFHHEHE-UHFFFAOYSA-N

Related Categories

Application

Fmoc isothiocyanate can be used:
  • As a starting material in the preparation of biologically relevant pharmacophores named N-aryl-N′-carboalkoxy guanidines.
  • In one of the intermediate steps for the synthesis of N-aryl-N-thiazolyl derivatives.
  • To synthesize cyclic isothiourea derivatives as potent neuropeptide Y (NPY) Y1 receptor antagonists.
  • To prepare 2-aminothiazoles, aminobenz-imidazole conjugated thiazoles, and thiazole derived cyclopeptides.

Other Notes

Reagent for the synthesis of substituted thioureas from amines

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - 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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Solid-Phase Synthesis of N-Aryl-N′-Carboalkoxy Guanidines by the Mitsunobu Reaction of Fmoc-Guanidines
Robinson DE, et al.
Synthetic Communications, 34(15), 2743-2749 (2004)
Two-step hantzsch based macrocyclization approach for the synthesis of thiazole-containing cyclopeptides
Nefzi A, et al.
The Journal of Organic Chemistry, 75(22), 7939-7941 (2010)
Solid-Phase Synthesis of 2-Aminothiazoles.
Patrick C. Kearney et al.
The Journal of organic chemistry, 63(1), 196-200 (2001-10-25)
Diversity-oriented synthesis of N-aryl-N-thiazolyl compounds
Nefzi A and Arutyunyan S
Tetrahedron Letters, 51(37), 4797-4800 (2010)
Discovery and SAR of cyclic isothioureas as novel NPY Y1 receptor antagonists
Sun Z, et al.
Bioorganic & medicinal chemistry letters, 19(23), 6801-6805 (2009)
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