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HATU

Product Name
HATU
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
Formula Weight
380.24
MOL File
148893-10-1.mol
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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)
EPA Substance Registry System
1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, hexafluorophosphate(1-), 3-oxide (148893-10-1)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
445460
Product name
HATU
Purity
97%
Packaging
1g
Price
$64.5
Updated
2024/03/01
Sigma-Aldrich
Product number
8.51013
Product name
HATU
Purity
Novabiochem?
Packaging
25g
Price
$518
Updated
2024/03/01
Sigma-Aldrich
Product number
8.51013
Product name
HATU
Purity
Novabiochem?
Packaging
100g
Price
$742
Updated
2024/03/01
Sigma-Aldrich
Product number
445460
Product name
HATU
Purity
97%
Packaging
5g
Price
$119
Updated
2024/03/01
TCI Chemical
Product number
A1797
Product name
O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium Hexafluorophosphate
Purity
>98.0%(HPLC)
Packaging
5g
Price
$111
Updated
2024/03/01
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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%.

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.

HATU Preparation Products And Raw materials

Raw materials

Preparation Products

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HATU Suppliers

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View Lastest Price from HATU manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
HATU 148893-10-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
99.5%min
Supply Ability
1000KGS
Release date
2021-06-18
Watson Biotechnology Co.,Ltd
Product
HATU 148893-10-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20MT
Release date
2024-07-29
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
HATU 148893-10-1
Price
US $58.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-05-22

148893-10-1, HATURelated Search:

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

  • 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
  • N,N,N',N'-TETRAMETHYL-O-(7-AZABENZOTRIAZOL-1-YL)URONIUM HEXAFLUOROPHOSPHATE
  • N-[(DIMETHYLAMINO)-1H-1,2,3-TRIAZOLO[4,5-B]PYRIDINO-1-YLMETHYLENE]-N-METHYLMETHANAMINIUM HEXAFLUOROPHOSPHATE N-OXIDE
  • 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
  • N-[(Dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethylaminium hexafluorophosphate
  • O-(7-Azabenzotriazol
  • [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium
  • O-(7-
  • 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-(7-AZA-1H-BENZOTRIAZOLE-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
  • 2-(1H-7-AZABENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYL URONIUM HEXAFLUOROPHOSPHATE METHANAMINIUM
  • 1-[BIS(DIMETHYLAMINO)METHYLENE]-1 H-1,2,3-TRIAZOLO(4,5-B) PYRIDINIUM 3-OXIDE HEXAFLUOROPHOSPHATE
  • 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
  • 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetraMethyluroniuM hexafluorophosphate(V)
  • O-(7-Azabenzotriazol-1-yl)-N,N,N',N`-tetraMethyluroniuM
  • N,N,N',N'-TetD23-RAMethyl-O-(7-azabenzotriazol-1-yl)uroniuM hexafluorophosphate
  • 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 impregnated tablets
  • N-[(Dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide
  • 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate impregnated tablets
  • 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 &gt
  • HATU O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate,99%
  • 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V)