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HATU

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Products Intro: Product Name:HATU; O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
CAS:148893-10-1
Purity:99.5% HPLC Package:50g;100g;500g;1kg;10kg;25kg
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Products Intro: Product Name:2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate
CAS:148893-10-1
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HATU Basic information
Product Name:HATU
Synonyms:2-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate;HATU >=98.0% (CHN);1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, ChemDoseTM tablets;O-(7-AZABENZOTRIAZOL-1-YL)URONIUM HEXAFLUORO-PHOSPHATE;O-(7-AZABENZOTRIAZOLE-1-YL)-N, N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE;O-(7-AZABENZOTRIAZOL-1-YL)-1,1,3,3-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
CAS:148893-10-1
MF:C10H15F6N6OP
MW:380.24
EINECS:604-662-7
Product Categories:peptides;carboxylic ester;HATU;Peptide Coupling Reagents;Miscellaneous Reagents;Coupling Reagent;PROTECTED AMINO ACID & PEPTIDES;Pharmaceutical Intermediates;Amino Acid Derivatives;Peptide coupling agents;Peptide;intermediate;148893-10-1
Mol File:148893-10-1.mol
HATU Structure
HATU Chemical 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.
Major Applicationpeptide synthesis
InChIInChI=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
InChIKeyKZAWCZZRROLLDL-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 Reference148893-10-1(CAS DataBase Reference)
EPA Substance Registry System1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, hexafluorophosphate(1-), 3-oxide (148893-10-1)
Safety Information
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
10-21
HazardClass 4.1
PackingGroup 
HS Code 29339999
Storage Class4.1A - Other explosive hazardous materials
Hazard ClassificationsResp. Sens. 1
Skin Sens. 1A
MSDS Information
ProviderLanguage
SigmaAldrich English
HATU Usage And Synthesis
DescriptionHATU, 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 PropertiesWhite crystalline to off-white powder
UsesHATU[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.
ReactionsHATU 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%.
reaction suitabilityreaction type: Coupling Reactions
SynthesisThe 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%).

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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 materialsN,N-Diisopropylethylamine-->Sodium hydroxide-->Ethyl acetate-->Lithium hydroxide-->Magnesium sulfate-->Triethylamine-->HOAt
Tag:HATU(148893-10-1) Related Product Information
Ammonium hexafluorophosphate Potassium hexafluorophosphate Lithium hexafluorophosphate Ribavirin 1,2,4-Triazole 5-Methyl-1H-benzotriazole Hexafluorophosphoric acid 1H-Benzotriazole HBTU N-Benzyl-DL-serine Methyl Ester Dess-Martin periodinane 3-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE N-Bromosuccinimide AM2201 Ethyl (R)-(-)-4-cyano-3-hydroxybutyate Nitrogen Azobenzene HOAt

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