165534-43-0

Basic information

• Product Name: 3-(Diethoxyphosphoryloxy)-1,2,3-benzotrizin-4(3H)-one
• Synonyms: DEPBT;DIETHYL-(4-OXO-3H-1,2,3-BENZOTRIAZIN-3-YL)PHOSPHATE;DIETHYL 3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN-3-YL PHOSPHATE;3-DIETHOXYPHOSPHORYL-1,2,3-BENZOTRIAZIN-4(3H)-ONE;3-(DIETHOXYPHOSPHORYLOXY)-1,2,3-BENZOTRIAZIN-4(3H)-ONE;3-(Diethoxyphosphoryloxy)-1,2,3-benzotrizin-4(3H)-one;3-(DIETHOXY-PHOSPHORYLOXY)-3H-BENZO[D][1,2,3]TRIAZIN-4-ONE;3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT)
• CAS NO: 165534-43-0
• Molecular Formula: C₁₁H₁₄N₃O₅P
• Molecular Weight: 299.22
• EINECS: 2017-001-1
• Product Categories: Coupling Reagent;Peptide Coupling Reagents;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry;Peptide;Building Blocks;Heterocyclic Building Blocks;Triazines;Antibiotics
• Mol File: 165534-43-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 75-77°C
• Boiling Point: 382.1 °C at 760 mmHg
• Flash Point: 184.9 °C
• Appearance: White/Powder
• Density: 1.42 g/cm³
• Vapor Pressure: 4.83E-06mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: -15°C
• Solubility: almost transparency in Ethylacetate
• CAS DataBase Reference: 3-(Diethoxyphosphoryloxy)-1,2,3-benzotrizin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Diethoxyphosphoryloxy)-1,2,3-benzotrizin-4(3H)-one(165534-43-0)
• EPA Substance Registry System: 3-(Diethoxyphosphoryloxy)-1,2,3-benzotrizin-4(3H)-one(165534-43-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 165534-43-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

DEPBT is a peptide coupling reagent used in peptide synthesis. It shows remarkable resistance to racemization.

General Description

3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) is a coupling reagent that facilitates amide bond formation and also resists racemization. It has been shown to be more effective than phosphonium and uronium coupling reagents.

InChI:InChI=1/C11H14N3O5P/c1-3-17-20(16,18-4-2)19-14-11(15)9-7-5-6-8-10(9)12-13-14/h5-8H,3-4H2,1-2H3

Synthetic route

diethyl chlorophosphate (814-49-3) + 3-hydroxy-3,4-dihydrobenzotriazine-4-one (28230-32-2) → 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0)

Conditions	Yield
With triethylamine In dichloromethane for 3h;	82%
With triethylamine In dichloromethane at 0℃; for 3h;	82%

phosphonic acid diethyl ester (762-04-9) + 3-hydroxy-3,4-dihydrobenzotriazine-4-one (28230-32-2) → 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0)

Conditions	Yield
With triethylamine In dichloromethane; benzene for 4h;	57%

Z-Aib-OH (15030-72-5) + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → 2-benzyloxycarbonylamino-2-methyl-propionic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester (654651-46-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 37℃;

N-benzoyl-(R)-methylpiperazine hydrochloride + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → 1H-indol-1-amine (53406-38-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide

3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → 2-oxo-2-(1H-pyrrolo[3,2-c]pyridin-3-yl)-acetamide (1378780-41-6)

Conditions	Yield
With ammonia; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; N,N-dimethyl-formamide

potassium 2-pyrrolecarboxaldehyde-4-oxoacetate + N-benzoylpiperazine hydrochloride (56227-55-5, 79332-89-1) + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → N-benzoyl-N'-[(2-carboxaldehyde-pyrrole-4-yl)-oxoacetyl]-piperazine

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide
With triethylamine In water; N,N-dimethyl-formamide

(7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-oxo-acetic acid (791053-66-2) + phenyl(piperidin-4-ylidene)acetonitrile (676490-69-0) + N-ethyl-N,N-diisopropylamine (7087-68-5) + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → {1-[2-(7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-2-oxo-acetyl]-piperidin-4-ylidene}-phenyl-acetonitrile (676490-39-4)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide

C42H51N7O10S5Si + C35H47N5O8S2Si + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → C77H96N12O17S7Si2 + C81H105N12O20PS7Si2

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 25h; Overall yield = 14.7 mg;

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 28230-32-2 3-hydroxy-3,4-dihydrobenzotriazine-4-one 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 53406-38-5 1H-indol-1-amine 
• 654651-46-4 2-benzyloxycarbonylamino-2-methyl-propionic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester 

Relevant articles and documents

3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.

[formula: see text] The new crystalline phosphate reagent 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) mediates amide bond formation with a remarkable resistance to racemization. Comparative racemization studies were carried out and DEPBT proved to be superior to typical phosphonium and uronium coupling reagents. DEPBT is easily prepared and is exceedingly stable with a shelf life of months at room temperature. The advantageous properties of DEPBT render it a useful and unique addition to the arsenal of coupling reagents.