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09668

Sigma-Aldrich

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate

≥99.0% (TLC/N)

Synonym(s):

O-(N-Succinimidyl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, HSTU

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About This Item

Empirical Formula (Hill Notation):
C9H16F6N3O3P
CAS Number:
265651-18-1
Molecular Weight:
359.21
MDL number:
MFCD01863753
UNSPSC Code:
12352101
PubChem Substance ID:
329748793
NACRES:
NA.22

Assay

≥99.0% (TLC/N)

form

crystals

reaction suitability

reaction type: Coupling Reactions

mp

218-221 °C (dec.)

solubility

acetonitrile: 0.5 g/mL, slightly hazy, colorless

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

F[P-](F)(F)(F)(F)F.CN(C)C(\ON1C(=O)CCC1=O)=[N+](\C)C

InChI

1S/C9H16N3O3.F6P/c1-10(2)9(11(3)4)15-12-7(13)5-6-8(12)14;1-7(2,3,4,5)6/h5-6H2,1-4H3;/q+1;-1

InChI key

STWZCCVNXFLDDD-UHFFFAOYSA-N

General description

N,N,N′,N′-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate can be used to prepare N-succinimidyl 4-[18F]fluorobenzoate ([18F]-SFB), a prosthetic group for the fluorination of biomolecules for PET imaging.

Application

Reactant for:
Synthesis of liposomal contrast agents for magnetic resonance imaging
Synthesis of thiol-reactive Cy5 derivatives
Synthesis of protein labeling molecules

Other Notes

Coupling reagent for peptide synthesis and the formation of other amides. Even in aqueous solution yields are excellent

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC4951V
1399967V
1406800V
1399967
1406800

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