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HATU

CAS No.148893-10-1
Chemical Name:HATU
CBNumber:CB0122630
Molecular Formula:C10H15F6N6OP
Formula Weight:380.24
MOL File:148893-10-1.mol

HATU Property

Melting point 183-188 °C (dec.)
RTECS XZ5633000
storage temp. 2-8°C
solubility >16mg/mL in DMSO
form powder to crystaline
color White to Almost white
Water Solubility Soluble in acetonitrile. Insoluble in water.
InChI InChI=1S/C10H15N6O.F6P/c1-13(2)10(14(3)4)15-8-6-5-7-11-9(8)16(17)12-15;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1
InChIKey KZAWCZZRROLLDL-UHFFFAOYSA-N
SMILES [P+5]([F-])([F-])([F-])([F-])([F-])[F-].C(=[N+]1/N=N(=O)C2=NC=CC=C/12)(\N(C)C)/N(C)C
CAS DataBase Reference 148893-10-1(CAS DataBase Reference)
FDA UNII B93RIH1T7E
EPA Substance Registry System 1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, hexafluorophosphate(1-), 3-oxide (148893-10-1)
UNSPSC Code 12352302
NACRES NA.22

Safety

Hazard Codes :Xi,Xn,E
Risk Statements :36/37/38-20/21/22-2
Safety Statements :26-37/39-36/37-36-35
RIDADR :1325
WGK Germany :3
F :10-21
HazardClass :4.1
PackingGroup :Ⅱ
HS Code :29339999

NFPA 704:

	2
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H317-H334
Precautionary statements P261-P272-P280-P284-P302+P352-P304+P340+P312

HATU Price More Price(23)

Brand: Sigma-Aldrich(India)
Product number: 8.51013
Product name : HATU
Purity: Novabiochem?
Packaging: 25G
Price: ₹37050
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.51013
Product name : HATU
Purity: Novabiochem?
Packaging: 100G
Price: ₹59350
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.51013
Product name : HATU
Purity: Novabiochem?
Packaging: 8510130500
Price: ₹87710
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 8.51013
Product name : HATU
Purity: Novabiochem?
Packaging: 8510131000
Price: ₹155850
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 445460
Product name : HATU
Purity: 97%
Packaging: 1G
Price: ₹8887.33
Updated: 2022/06/14
Buy: Buy

HATU Chemical Properties,Usage,Production

Description HATU, first prepared by Louis A. Carpino in 1993, is widely used in carboxylic acid amidation reactions. It acts as a facilitator of amide bond generation by activating the carboxyl group.
Chemical Properties White crystalline to off-white powder
Uses HATU[148893-10-1] is a coupling reagent and used as an additive in peptide synthesis. It is also involved efficiently to speed up the coupling process and reduces the loss of chiral integrity.
Reagent for: Synthesis of Aurora A kinase inhibitors, HPLC assay to determine D- and L- acid enantiomers in human plasma, Amide bond formation reactions.
Catalyst for: Selective acylation, Selecocyclization-oxidation deselenation sequence.
Reactions HATU is a very promising coupling agent for chemical protein synthesis.

This strategy was exploited to prepare macrocycles from the trimeric linear arylopeptoids (ortho-, meta-, and para-) containing isopropyl or ethyl side chains, synthesized as described by Hjelmgaard et al. The cyclization procedure reported for α,β-cyclopeptoids was applied. The linear arylopeptoids were cyclized in the presence of HATU and DIPEA in CH?Cl?/DMF (4:1) after the deprotection of the tert-butyl group in TFA/CH?Cl?.

After the synthesis of the Fmoc-protected monomers, the oligomers were synthesized on the 2-chlorotrityl resin with excellent yield of coupling (>98%). The trimers and tetramers of the different isomers were synthesized in good overall yield (60-84%). Then, the crude oligomers were cyclized in DMF in the presence of HATU and DIPEA in high dilution (3 × 10?3 M) to furnish the cyclized trimers and tetramers in good yields ranging between 32% and 72%.
reaction suitability reaction type: Coupling Reactions
Synthesis The synthesis of HATU is as follows:The resulting residue treated with 2-Methoxycarbonylamino-3-methyl-butyric acid (60 mg, 0.343 mmol) and HATU (130 mg, 0.343 mmol), suspended in DMF (3 mL) and cooled to 0° C. DIPEA (0.272 mL, 1.56 mmol) was added dropwise. After stirring for 4 h, NaOH (5M in H2O, 0.300 mL, 1.5 mmol) was added. This mixture was stirred for 3 h then diluted with EtOAc and washed with 1 M LiOH (2*) then brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude residue was then purified by HPLC to afford the title compound (53 mg, 44%).
References [1] CHAWLA P A, SHOME A, JHA K T. Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium (HATU): A Unique Cross-Coupling Reagent[J]. SynOpen, 2023, 66 2: 0. DOI:10.1055/s-0042-1751499.
[2] LOUIS A. CARPINO. Comparison of the Effects of 5- and 6-HOAt on Model Peptide Coupling Reactions Relative to the Cases for the 4- and 7-Isomers?,?[J]. Organic Letters, 2000, 2 15: 2253-2256. DOI:10.1021/ol006013z.