- HATU
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- $0.00 / 1kg
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2024-08-24
- CAS:148893-10-1
- Min. Order: 1kg
- Purity: 99%
- Supply Ability: 20MT
- HATU
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- $0.00 / 1Kg/Bag
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2024-08-22
- CAS:148893-10-1
- Min. Order: 1KG
- Purity: 99.5%min
- Supply Ability: 1000KGS
- HATU
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- $480.60 / 1KG
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2024-08-21
- CAS:148893-10-1
- Min. Order: 1KG
- Purity: 99%
- Supply Ability: 5000kg
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Product Name: | HATU | Synonyms: | 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 | 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](CAS/GIF/148893-10-1.gif) |
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) |
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](/NewsImg/2024-07-29/6385785946199084013901326.png) 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](/NewsImg/2024-07-29/6385785936811151488286583.png) 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 148893-10-1.png](/NewsImg/2022-11-16/6380421456135856731519931.jpg)
| 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 |
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