HATU
- CAS No.
- 148893-10-1
- Chemical Name:
- HATU
- Synonyms
- 2-(7-AZA-1H-BENZOTRIAZOLE-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE;O-(7-AZABENZOTRIAZOL-1-YL)-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE;1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, ChemDoseTM tablets;2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V);1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate;2-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate;N-[(DIMETHYLAMINO)-1H-1,2,3-TRIAZOLO[4,5-B]PYRIDINO-1-YLMETHYLENE]-N-METHYLMETHANAMINIUM HEXAFLUOROPHOSPHATE N-OXIDE;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
- CBNumber:
- CB0122630
- Molecular Formula:
- C10H15F6N6OP
- Molecular Weight:
- 380.24
- MDL Number:
- MFCD00274639
- MOL File:
- 148893-10-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Product description | Number | Pack Size | Price |
| HATU 97% | 445460 | 1g | $70.8 |
| HATU Novabiochem? | 8.51013 | 25g | $567 |
| HATU 97% | 445460 | 5g | $131 |
| HATU Novabiochem? | 8.51013 | 100g | $811 |
| O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium Hexafluorophosphate >98.0%(HPLC) | A1797 | 5g | $111 |
| More product size | |||
| 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 Application | peptide synthesis |
| 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
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 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Gloves | |||||||||
| 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 | |||||||||
| Storage Class | 4.1A - Other explosive hazardous materials | |||||||||
| Hazard Classifications | Resp. Sens. 1 Skin Sens. 1A |
|||||||||
| REACH Registrations | Inactive | |||||||||
| NFPA 704 |
|
HATU price More Price(118)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 445460 | HATU 97% | 148893-10-1 | 1g | $70.8 | 2026-04-30 | Buy |
| Sigma-Aldrich | 8.51013 | HATU Novabiochem? | 148893-10-1 | 25g | $567 | 2026-04-30 | Buy |
| Sigma-Aldrich | 445460 | HATU 97% | 148893-10-1 | 5g | $131 | 2026-04-30 | Buy |
| Sigma-Aldrich | 8.51013 | HATU Novabiochem? | 148893-10-1 | 100g | $811 | 2026-04-30 | Buy |
| TCI Chemical | A1797 | O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium Hexafluorophosphate >98.0%(HPLC) | 148893-10-1 | 5g | $111 | 2026-04-30 | 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.
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 CHCl/DMF (4:1) after the deprotection of the tert-butyl group in TFA/CHCl.
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 × 103 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.
HATU Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Suzhou Highfine Biotech Co.,Ltd. | +86-0512-68071238 +86-13771819922 | june@highfine.com | China | 489 | 58 |
| HANGZHOU LEAP CHEM CO., LTD. | +86-571-87711850 | market18@leapchem.com | China | 24597 | 58 |
| Jiangsu Vcan Advanced Material Co., Ltd. | +86-17306299870 +86-18652789875 | vcanam@vcanam.com | China | 49 | 58 |
| Hebei Chuanghai Biotechnology Co., Ltd | +8615350571055 | Sibel@chuanghaibio.com | China | 8738 | 58 |
| Wuhan Fortuna Chemical Co., Ltd | +86-27-59207850 | info@fortunachem.com | China | 5983 | 58 |
| Hebei Chuanghai Biotechnology Co,.LTD | +86-86-13131129325 +8613131129325 | sales1@chuanghaibio.com | China | 5231 | 58 |
| XINXIANG RUNYU MATERIAL CO., LTD. | +86-13592593621; +8613592593621 | sales@runvmat.com | China | 457 | 58 |
| Hebei Fengjia New Material Co., Ltd | +86-0311-87836622 +86-18712993135 | sales01@tairunfaz.com | China | 8051 | 58 |
| Henan Bao Enluo International TradeCo.，LTD | +86-17331933971 | deasea125996@gmail.com | China | 2472 | 58 |
| Hebei Zhuanglai Chemical Trading Co.,Ltd | +8613343047651 | admin@zlchemi.com | China | 3692 | 58 |
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- The effect of HATU on human health
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