| Identification | More | [Name]
2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate | [CAS]
94790-37-1 | [Synonyms]
1-[BIS(DIMETHYLAMINO)METHYLENE]-1H-BENZOTRIAZOLIUM 3-OXIDE HEXAFLUOROPHOSPHATE
2-(1H-BENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
2-(1H-BENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYLURONOIUM HEXAFLUORPHOSPHATE
2-(1H-BENZOTRIAZOLE-1-YL)-1,1,3,3-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
BENZOTRIAZOL-1-YL-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
HBTU
HBTU POLYMER BOUND
HBTU-REAGENT
HEXAFLUOROPHOSPHATE HBTU
N-[(1-H-BENZOTRIAZOL-1-YL)(DIMETHYLAMINO)METHYLENE]-N-METHYLMETHANAMINIUM HEXAFLUOROPHOSPHATE N-OXIDE
N,N,N',N'-TETRAMETHYL-O-(1H-BENZOTRIAZOL-1-YL)URONIUM HEXAFLUOROPHOSPHATE
N,N,N',N'-TETRAMETHYL-O-(BENZOTRIAZOL-1-YL)URONIUM HEXAFLUOROPHOSPHATE
O-(1H-BENZOTRIAZOL-1-YL)-1,1,3,3-TETRAMETHYL-URONIUM HEXAFLUOROPHOSPHATE
O-(1H-BENZOTRIAZOL-1-YL)-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
O-(BENZOTRIAZOL-1-YL)-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
O-(BENZOTRIAZOL-1-YL)-N-N-N ,N-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
O-BENZOTRIAZOL-1-YL-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE POLYMER BOUND
O-BENZOTRIAZOL-1-YL-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
O-BENZOTRIAZOLE-1-YL-N,N,N',N'-TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE
O-BENZOTRIAZOLE-N,N,N',N'-TETRAMETHYL-URONIUM | [EINECS(EC#)]
423-020-5 | [Molecular Formula]
C11H17F6N5OP | [MDL Number]
MFCD00075445 | [Molecular Weight]
380.25 | [MOL File]
94790-37-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow powder | [Melting point ]
200 °C (dec.)(lit.)
| [Fp ]
200°C | [storage temp. ]
2-8°C
| [solubility ]
acetonitrile: 0.1 g/mL, clear
| [form ]
Powder | [color ]
White to Off-White | [PH]
4.1 (1.6g/l, H2O) | [Stability:]
Stable. Incompatible with oxidizing agents. | [Water Solubility ]
1.6g/L | [Decomposition ]
200 ºC | [Detection Methods]
HPLC,NMR | [BRN ]
7328329 | [InChI]
InChI=1S/C11H16N5O.F6P/c1-13(2)11(14(3)4)15-9-7-5-6-8-10(9)16(17)12-15;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1 | [InChIKey]
UQYZFNUUOSSNKT-UHFFFAOYSA-N | [SMILES]
[P+5]([F-])([F-])([F-])([F-])([F-])[F-].C(=[N+]1/N=N(=O)C2=CC=CC=C/12)(\N(C)C)/N(C)C | [CAS DataBase Reference]
94790-37-1(CAS DataBase Reference) | [EPA Substance Registry System]
1H-Benzotriazolium, 1-[bis(dimethylamino)methylene]-, 3-oxide, hexafluorophosphate(1-) (1:1) (94790-37-1) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
8-10-21 | [Hazard Note ]
Irritant | [HS Code ]
29339900 | [Toxicity]
LD50 orally in Rabbit: > 2000 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow powder | [Uses]
HBTU is a coupling reagent used in peptide synthesis. HBTU has been shown to effectively suppress racemization. | [Uses]
peptide coupling reagent that reduces racemization | [Uses]
Peptide coupling reagent which suppresses racemization. | [reaction suitability]
reaction type: Coupling Reactions | [Biological Activity]
hbtu (2-(1h-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexauorophosphate), a coupling reagent commonly used in solid phase peptide synthesis. after being introduced in 1978, this agent shows popularity in chemistry and industry use due to its mild activating properties. moreover, it also shows resistance against racemization. low tendency for racemization is a key requirement for peptide synthesis. especially for solid phase peptide synthesis, quantitative yields with short reaction times are crucial in order to make the synthesis of large peptides feasible. [1] | [Synthesis]
HBTU is synthesized by reaction of HOBt with TCFH under basic conditions.
| [in vitro]
peptide synthesis relied mostly on efficient and safe coupling reagents. hbtu was proved to transform carboxylic acids into azides efficiently and practically. the process might be applied to a wide range of carboxylic acids including n-protected amino acids. in addition, hbtu was of great value in one-pot synthesis of dipeptidyl urea esters, ureas, and carbamates from acids. the advantages of hbtu included the following points: 1) non-explosive and therefore more suitable for solution/solid phase peptide synthesis. 2) high solubility and stability in classical solvents. 3) feasible for colorimetric reaction monitoring. [2] | [Purification Methods]
Wash the salt with H2O (3x), CH2Cl2 (3x), dry and recrystallise it from MeCN. Dry it in a vacuum and store it cold in the dark [Dourtoglou et al. Tetrahedron Lett 1269 1978, NMR: Dourtoglou and Gross Synthesis 572 1984]. Benzoxazolinone (2 -hydroxybenzoxazole) [59 -49 -4] M 135.1, m 137 -139o, 142 -143o(corrected), b 121-213o/17mm, 335-337o/760mm. Benzoxazolinone is purified by recrystallisation from aqueous Me2CO followed by distillation at atmospheric pressure, then in a vacuum. The methyl mercury salt recrystallises from aqueous EtOH and has m 156-158o. [Bywater et al. J Am Chem Soc 67 905 1945, Beilstein 27 III/IV 2677.] | [References]
[1]adam s. hbtu: a mild activating ageiw of muramic acid. bioorg med chem lett. 1992 mar; 2(6): 571-4.
[2]knorr r, trzeciak a, bannwarth w and gillessen d. new coupling reagents in peptide chemistry. tetrahedron lett. 1989; 30(15): 1927-30. |
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