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ChemicalBook > Product Catalog >Biochemical Engineering >Amino Acids and Derivatives >Other Amino Acid Protection >HATU

HATU

HATU Structure
CAS No.
148893-10-1
Chemical Name:
HATU
Synonyms
1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate;2-(7-AZA-1H-BENZOTRIAZOLE-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE;2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V);O-(7-AZABENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE;2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetraMethyluroniuM hexafluorophosphate(V);[bis(dimethylamino)methylidene]({3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl})oxidanium;1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, ChemDoseTM tablets;2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium;1-[BIS(DIMETHYLAMINO)METHYLENE]-1 H-1,2,3-TRIAZOLO(4,5-B) PYRIDINIUM 3-OXIDE HEXAFLUOROPHOSPHATE;N-[(Dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethylaminium hexafluorophosphate
CBNumber:
CB0122630
Molecular Formula:
C10H15F6N6OP
Molecular Weight:
380.24
MOL File:
148893-10-1.mol
Modify Date:
2024/8/21 22:41:43
Request For Quotation

HATU Properties

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)
EPA Substance Registry System 1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, hexafluorophosphate(1-), 3-oxide (148893-10-1)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Danger
Hazard statements  H317-H334
Precautionary statements  P261-P272-P280-P284-P302+P352-P304+P340+P312
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

HATU price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 8.51013 HATU Novabiochem? 148893-10-1 25G ₹37050 2022-06-14 Buy
Sigma-Aldrich(India) 8.51013 HATU Novabiochem? 148893-10-1 100G ₹59350 2022-06-14 Buy
Sigma-Aldrich(India) 8.51013 HATU Novabiochem? 148893-10-1 8510130500 ₹87710 2022-06-14 Buy
Sigma-Aldrich(India) 8.51013 HATU Novabiochem? 148893-10-1 8510131000 ₹155850 2022-06-14 Buy
Sigma-Aldrich(India) 445460 HATU 97% 148893-10-1 1G ₹8887.33 2022-06-14 Buy
Product number Packaging Price Buy
8.51013 25G ₹37050 Buy
8.51013 100G ₹59350 Buy
8.51013 8510130500 ₹87710 Buy
8.51013 8510131000 ₹155850 Buy
445460 1G ₹8887.33 Buy

HATU Chemical Properties,Uses,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.
Cyclisation of ortho-, meta- and para-arylopeptoids
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?.
Macrocyclization of the linear trimer
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%.

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%).

148893-10-1.png

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.

HATU Preparation Products And Raw materials

Raw materials

N,N-Diisopropylethylamine Sodium hydroxide Ethyl acetate Lithium hydroxide Magnesium sulfate
Triethylamine HOAt
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HATU Spectrum

HATU(148893-10-1)1HNMRHATU(148893-10-1)20FNMRHATU(148893-10-1)IRHATU(148893-10-1)FT-IR

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HATU 2-(7-AZOBENZOTRIAZOLYL-1-OXY)-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE 99% 2-(7-AZA-1H-BENZOTRIAZOLE-1-YL)-1,1,3,3- TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE (HATU) O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethylur O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N',N'-TE& O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE (HATU) O-(7-AZABENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE (HATU) O-(7-Azabenzotriazol-1-yl)-N,N,Nzzhlxy,Nzzhlxy- tetramethyluronium hexafluorophosphate (HATU) HATU 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetraMethyluroniuM hexafluorophosphate 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetraMethy O-(7-Azabenzotriazol-1-yl)-N,N,N',N`-tetraMethyluroniuM N,N,N',N'-TetD23-RAMethyl-O-(7-azabenzotriazol-1-yl)uroniuM hexafluorophosphate N-[(Dimethylamino)-1H-1,2,3-triazolo-[4,5,b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide impregnated tablets 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate impregnated tablets 2-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate HATU >=98.0% (CHN) O-(7-AZABENZOTRIAZOL-1-YL)URONIUM HEXAFLUORO-PHOSPHATE O-(7-AZABENZOTRIAZOLE-1-YL)-N, N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE N,N,N',N'-TETRAMETHYL-O-(7-AZABENZOTRIAZOL-1-YL)URONIUM HEXAFLUOROPHOSPATE N,N,N',N'-TETRAMETHYL-O-(7-AZABENZOTRIAZOL-1-YL)URONIUM HEXAFLUOROPHOSPHATE azabenzotriazolyl tetramethyluronium hexafluorophosphate HATU, N,N,Nμ,Nμ-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate HATU impregnated tablets, N,N,Nμ,Nμ-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate impregnated tablets, ChemDose(R) O-(7-Azabenzotriazol-1-yl)-N,N,Nμ,Nμ-tetramethyluronium hexafluorophosphate tablets, O-(7-Azabenzotriazol-1-yl)-N,N,Nμ,Nμ-tetramethyluronium hexafluorophosphate impregnated tablets O-(7-Azabenzotriazol-1-yl)-N,N,Nμ,Nμ-tetramethyluronium hexafluorophosphate, ChemDose(R) tablets O-(7-Aza-1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 99% O-(7-Azabenzotriazol-1-yl)-N,N,N',N'- tetramethyluronium hexaflu HATU,99% O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyl O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl uranium hexafluorophosphate HATU(o-(7-Azabenzotriazol-1-yl)uroniumhexafluoro-phosphate) O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate ,98% O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate ,99% O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate,N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate, HATU O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, ChemDose tablets,N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate impregnated tablets, O-(7-Aza O-(7-Azabenzotriazol [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium 2-(7-Aza-1H-benzotriazole-1-yl)-1 3-tetraMethyluroniuM hexafluorophosphate (HATU) HATU O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N'',N''-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N',N'-TETRAMETHYLUROINIUM HEXAFLUOROPHOSPHATE o-(7-azabenzotriazol-1-yl)-n,n,n’,n’-te-tramethyluroniumpf6 HATU 2-(1H-7-AZABENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYL URONIUM HEXAFLUOROPHOSPHATE METHANAMINIUM 1-[(dimethylamino)(dimethyliminiumyl)methyl]-3-oxo-1H,2H,3H-3λ?-[1,2,3]triazolo[5,4-b]pyridin-3-ylium-2-ide O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 99%, for synthesis O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium Hexafluorophosphate > HATU O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate,99% 2-(7-Aza-1H-benzotriazoL e-1-yL HATU USP/EP/BP HATU CAS 148893 10 1 HBTU [ 94790-37-1 o-(7-Azabenzotriazol-1-yl)-N,N,N',N'-te-tramethyluronium hex... [Dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylene]-dimethyl-ammonium hexafluorophosphate HATU extrapure, 98% O-(7- 1-[BIS(DIMETHYLAMINO)METHYLENE]-1 H-1,2,3-TRIAZOLO(4,5-B) PYRIDINIUM 3-OXIDE HEXAFLUOROPHOSPHATE 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetraMethyluroniuM hexafluorophosphate(V)