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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Solid-Phase Synthesis of 2-Aminothiazoles.
Patrick C. Kearney et al.
The Journal of organic chemistry, 63(1), 196-200 (2001-10-25)
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)
Diversity-oriented synthesis of N-aryl-N-thiazolyl compounds
Nefzi A and Arutyunyan S
Tetrahedron Letters, 51(37), 4797-4800 (2010)
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)
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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