CAS 148893-10-1

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

Description:

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, commonly referred to as HATU, is a coupling reagent widely used in peptide synthesis. This compound facilitates the formation of amide bonds between amino acids by activating carboxylic acids, making them more reactive towards nucleophilic attack by amines. HATU is characterized by its high efficiency and mild reaction conditions, which help preserve sensitive functional groups during synthesis. It is typically used in conjunction with a base, such as N,N-diisopropylethylamine (DIPEA), to promote the coupling reaction. The hexafluorophosphate counterion contributes to the solubility of HATU in organic solvents, enhancing its utility in various organic synthesis applications. Additionally, HATU is known for its stability and ease of handling, although it should be stored under dry conditions to prevent hydrolysis. Safety precautions are necessary when handling HATU, as it can be irritating to the skin and eyes. Overall, HATU is a valuable reagent in the field of organic and medicinal chemistry for the efficient synthesis of peptides and other amide-containing compounds.

Formula: C₁₀H₁₅N₆O·F₆P

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

InChI key: InChIKey=FKBFHOSFPRWJNV-UHFFFAOYSA-N

SMILES: C(N(C)C)(N(C)C)=[N+]1C=2C(N(=O)=N1)=NC=CC2.[P+5]([F-])([F-])([F-])([F-])([F-])[F-]

Synonyms:

• 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate
• 1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, 3-oxide, hexafluorophosphate(1-) (1:1)
• 1H-1,2,3-Triazolo[4,5-b]pyridinium, 1-[bis(dimethylamino)methylene]-, hexafluorophosphate(1-), 3-oxide
• 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate
• 2-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
• Hatu
• N,N,N',N'-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophospate
• N-[(dimethylamino)(3-oxido-1H-[1,2,3]triazolo[4,5-b]pyridin-1-yl)methylidene]-N-methylmethanaminium hexafluorophosphate
• N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate
• O-(7-Aza-1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
• O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate

HATU

CAS: 148893-10-1

Formula: C₁₀H₁₅F₆N₆OP

Purity: >98.0%(HPLC)

Color and Shape: White to Almost white powder to crystaline

Molecular weight: 380.24

Ref: 3B-A1797

O-(7-Aza-1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 99%

CAS: 148893-10-1

O-(7-Aza-1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 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. This Thermo Scientific Chemicals brand pro

Formula: C₁₀H₁₅F₆N₆OP

Purity: 99%

Color and Shape: White, Crystals or powder or crystalline powder

Molecular weight: 380.24

Ref: 02-H26082

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

CAS: 148893-10-1

Formula: C₁₀H₁₅F₆N₆OP

Purity: 98.0%

Color and Shape: Solid, Crystalline or Powder

Molecular weight: 380.235

Ref: 10-F023926

HATU

CAS: 148893-10-1

HATU has been successfully employed for difficult couplings.

Formula: C₁₀H₁₅N₆O·PF₆

Color and Shape: Whitish

Molecular weight: 380.23

Ref: 01-4032172

HATU

CAS: 148893-10-1

Formula: C₁₀H₁₅F₆N₆OP

Purity: 98%

Color and Shape: Solid

Molecular weight: 380.2299

Ref: IN-DA001L98

HATU

CAS: 148893-10-1

Formula: C₁₀H₁₅F₆N₆OP

Purity: ≥ 99.0%

Color and Shape: White crystalline powder

Molecular weight: 380.23

Ref: 7W-GE0156

HATU

CAS: 148893-10-1

HATU

Formula: C₁₀H₁₅N₆O·PF₆

Purity: 99%

Color and Shape: white crystalline powder

Molecular weight: 380.22987g/mol

Ref: 54-PC8718

HATU

CAS: 148893-10-1

HATU is the gold standard reagent for amide formation and peptide synthesis, both in solid and solution phase. HATU is stable, allows to achieve high yields with fast reaction rates, is extremely efficient with sterically hindered substrates and suppresses racemisation. HATU generates HOAt in situ, which forms an activated ester with a high reactivity towards amines. A side-reaction to form a guanidinium by-product may take place, and this can be suppressed by the addition of HOBt. Although HATU was originally thought to exist as an uronium salt, the X-ray structure demonstrated that it is a guanidinium N-oxide instead.

Formula: C₁₀H₁₅N₆O·F₆P

Purity: Min. 98 Area-%

Color and Shape: White Powder

Molecular weight: 380.23 g/mol

Ref: 3D-FH09243

HATU

CAS: 148893-10-1

Applications A peptide coupling reagent
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Chollet, C., et al.: Bioorg. Med. Chem., 17, 2512 (2009), Barber, C., et al.: Bioorg. Med. Chem. Lett., 19, 1499 (2009),

Formula: C₁₀H₁₅N₆O·F₆P

Color and Shape: Neat

Molecular weight: 380.23

Ref: TR-H105800

HATU

CAS: 148893-10-1

HATU

Purity: ≥98%

Molecular weight: 380.23g/mol

Ref: 54-BUP15588

HATU extrapure, 98%

CAS: 148893-10-1

Formula: C₁₀H₁₅F₆N₆OP

Purity: min. 98%

Color and Shape: White to off-white, Crystalline powder

Molecular weight: 380.23

Ref: SR-99132