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HBTU

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HBTU Basic information

Product Name:
HBTU
Synonyms:
  • 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
  • O-BENZOTRIAZOLE-N,N,N',N'-TETRAMETHYL-URONIUM-HEXAFLUORO-PHOSPHATE
CAS:
94790-37-1
MF:
C11H16F6N5OP
MW:
379.25
EINECS:
619-076-7
Product Categories:
  • peptides
  • Peptide coupling agents
  • Starting Raw Materials & Intermediates
  • PROTECTED AMINO ACID & PEPTIDES
  • Peptide Coupling Reagents
  • Biochemistry
  • Amino Acid Derivatives
  • Condensation & Active Esterification
  • Coupling Reactions (Peptide Synthesis)
  • Peptide Synthesis
  • Synthetic Organic Chemistry
  • Peptide
Mol File:
94790-37-1.mol
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HBTU Chemical Properties

Melting point:
200 °C (dec.)(lit.)
Flash point:
200°C
storage temp. 
Store at +2°C to +8°C.
solubility 
acetonitrile: 0.1 g/mL, clear
form 
Powder
color 
White to Off-White
PH
4.1 (1.6g/l, H2O)
Decomposition 
200 ºC
BRN 
7328329
Stability:
Stable. Incompatible with oxidizing agents.
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)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-20/21/22-42/43
Safety Statements 
26-36/37/39-36-22
WGK Germany 
3
8-10-21
Hazard Note 
Irritant
HS Code 
29339980
Toxicity
LD50 orally in Rabbit: > 2000 mg/kg

MSDS

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HBTU Usage And Synthesis

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.

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]

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.

HBTUSupplier

Suzhou Highfine Biotech Co., Ltd Gold
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0512-69209928 18306209922
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cathyjia@highfine.com
Shanghai Medpep Co., Ltd Gold
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021-65566949 13901795941
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0519-85223897 13766960291
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Lianyungang Guanxin Pharmaceutical Technology Co., Ltd Gold
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15351860687
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Wuxi Asia Peptide Biotechnology Limited Company Gold
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0510-83583050 13771062561
Email
willsun@peptide-search.com