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CAS 265651-18-1

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

Description:
N,N,N',N'-Tetramethyl-O-(N-succinimidyl)uronium hexafluorophosphate, commonly referred to as HATU, is a coupling reagent widely used in peptide synthesis and other organic reactions. It is characterized by its ability to activate carboxylic acids for amide bond formation, facilitating the coupling of amino acids in peptide synthesis. The compound is typically a white to off-white solid and is soluble in polar organic solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO). HATU is known for its efficiency and mild reaction conditions, which minimize side reactions and enhance yield. It is also favored for its stability under standard laboratory conditions, although it should be handled with care due to its reactivity and potential toxicity. The presence of the succinimidyl group allows for selective reactions with amines, making it a valuable tool in the synthesis of complex organic molecules. Proper storage in a cool, dry place away from moisture is recommended to maintain its integrity and effectiveness.
Formula:C9H16F6N3O3P
InChI:InChI=1/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
SMILES:CN(C)C(=[N+](C)C)ON1C(=O)CCC1=O.F[P-](F)(F)(F)(F)F
Synonyms:
  • Hstu
  • O-(N-Succinimidyl)-1,1,3,3-tetramethyluronium hexafluorophosphate
  • N-{(dimethylamino)[(2,5-dioxopyrrolidin-1-yl)oxy]methylidene}-N-methylmethanaminium hexafluorophosphate
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