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)

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

F 

8-10-21

Hazard Note 

Irritant

HS Code 

29339980

Toxicity

LD50 orally in Rabbit: > 2000 mg/kg

MSDS

• Language:English Provider:2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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.

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.

HBTU(94790-37-1)Related Product Information

• 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate
• HOAt
• 1-Hydroxybenzotriazole
• HATU
• Hexafluorophosphoric acid
• Potassium hexafluorophosphate
• 5-Methyl-1H-benzotriazole
• Tolyltriazole
• Lithium hexafluorophosphate
• Sodium hexafluorophosphate
• 1H-Benzotriazole
• 2-(7-Azabenzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate
• 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one
• 1-Hydroxybenzotriazole hydrate
• Ammonium hexafluorophosphate
• 5-Chloro-1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide hexafluorophosphate
• (Benzotriazol-1-yloxy)dipyrrolidinocarbenium hexafluorophosphate
• HBTU