HATU

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HATU
Names
IUPAC name
O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
Other names
  • 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate
  • N-[(Dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.103.434 Edit this at Wikidata
UNII
  • InChI=1S/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
    Key: JNWBBCNCSMBKNE-UHFFFAOYSA-N
  • InChI=1/C10H15N6O.F6P/c1-14(2)10(15(3)4)17-16-9-8(12-13-16)6-5-7-11-9;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
    Key: JNWBBCNCSMBKNE-UHFFFAOYAG
  • CN(C)C(=[N+](C)C)On1c2c(cccn2)nn1.F[P-](F)(F)(F)(F)F
Properties
C10H15F6N6OP
Molar mass 380.235 g·mol−1
Appearance White crystalline solid
Melting point 183–185 °C (361–365 °F; 456–458 K)[1]
Hazards
GHS labelling:[2]
GHS07: Exclamation markGHS02: Flammable
Danger
H228, H303+H313, H315, H319, H335
P210, P240, P241, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, P501
NFPA 704 (fire diamond)
[2]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
3
3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

HATU (Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium) is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid. HATU is used along with Hünig's base (N,N-diisopropylethylamine), or triethylamine to form amide bonds. Typically dimethylformamide is used as solvent, although other polar aprotic solvents can also be used.[3]

HATU was first reported by Louis A. Carpino in 1993 as an efficient means of preparing active esters derived from 1-hydroxy-7-azabenzotriazole (HOAt).[4] HATU is commonly prepared from HOAt and TCFH under basic conditions[5] and can exist as either the uronium salt (O-form) or the less reactive iminium salt (N-form). HATU was initially reported as the O-form using the original preparation reported by Carpino; however, X-ray crystallographic and NMR studies revealed the true structure of HATU to be the less reactive guanidinium isomer.[6] It is, however, possible to obtain the uronium isomer by preparing HATU using KOAt in place of HOAt and working up the reaction mixture quickly to prevent isomerisation.

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Safety

References

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