Diphenylphosphoryl azide supplier

Name
Diphenylphosphoryl azide
EINECS 247-644-0
CAS No. 26386-88-9
Article Data21
CAS DataBase
Density 1.277 g/mL at 25 °C(lit.)
Solubility insoluble in water
Melting Point
Formula C₁₂H₁₀N₃O₃P
Boiling Point 157°C0.17mm Hg(lit.)
Molecular Weight 275.203
Flash Point >230°F
Transport Information UN 3278 6.1/PG 2
Appearance colourless or faintly yellow liquid
Safety 26-36/37/39-45
Risk Codes 23/24/25-36/37/38
Molecular Structure
Hazard Symbols T
Synonyms Azidodiphenoxyoxophosphorane;DPPA;Diphenyl azidophosphate;Diphenyl phosphorazidate;Diphenylphosphorazide;O,O-Diphenylphosphoryl azide;Phosphoric aciddiphenyl ester azide;Diphenylphosphoryl azide;
PSA 95.09000
LogP 4.01556

Synthetic route

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 26386-88-9
diphenyl phosphoryl azide

Conditions

Conditions	Yield
With sodium azide In acetone at 25℃; for 4h;	96%
With alkali metal azide at 60℃; for 0.0166667h; Microwave irradiation; neat (no solvent);	95%
With sodium azide In water; acetone for 3h; Ambient temperature;	90%

: 4712-55-4
diphenyl hydrogen phosphite

: 26386-88-9
diphenyl phosphoryl azide

Conditions

Conditions	Yield
With tetrachloromethane; sodium azide; triethylamine In acetonitrile at 20℃; for 0.5h; Atherton-Todd reaction;	76%

: 108-95-2
phenol

phosphorous oxychloride: phosphorous oxychloride

: 26386-88-9
diphenyl phosphoryl azide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 40 percent / POCl3 / 2 h / 180 °C 2: 90 percent / NaN3 / acetone; H2O / 3 h / Ambient temperature View Scheme

: 108-95-2
phenol

: 26386-88-9
diphenyl phosphoryl azide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / dichloromethane / 5 h / 20 °C 2: sodium azide / acetone / 10 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: magnesium chloride; trichlorophosphate / 24 h / 100 °C / Inert atmosphere 2: sodium azide / acetonitrile / 12 h / 0 - 25 °C / Inert atmosphere View Scheme

: 2015-56-7
diphenylphosphoroamidate

: 26386-88-9
diphenyl phosphoryl azide

Conditions

Conditions	Yield
Stage #1: diphenylphosphoroamidate With sulfuric acid In 1,4-dioxane at -15℃; for 0.0833333h; Stage #2: With sodium nitrite In 1,4-dioxane for 0.5h; Stage #3: With sodium azide In 1,4-dioxane

: 26386-88-9
diphenyl phosphoryl azide

: 362-75-4
2',3'-isopropylidene adenosine

: 78111-39-4
5'-diphenylphosphate-5'-deoxy-2',3'-isopropylidene adenosine

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 20℃; for 3h;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 20℃;

: 313653-11-1
(S)-2-((R)-2-Methyl-pentyl)-succinic Acid 4-tert-butyl Ester

: 26386-88-9
diphenyl phosphoryl azide

: C14H25NO3

Conditions

Conditions	Yield
With triethylamine In tert-butyl methyl ether at 45℃; Curtius rearrangement;	100%

: 26386-88-9
diphenyl phosphoryl azide

: 57719-76-3
ent-11α,15α-Dihydroxykaur-16-en-19-oic acid

: 1391633-67-2
4α-isocyanato-11β,15β-dihydroxykaur-16-ene

Conditions

Conditions	Yield
With triethylamine at 20 - 90℃; for 1.5h; Curtius Rearrangement;	100%

: 937-31-5
(4-Nitrophenyl)acetylene

: 26386-88-9
diphenyl phosphoryl azide

: 108-18-9
diisopropylamine

: N1,N1-diisopropyl-N2-(diphenylphosphoryl)-2-(4-nitrophenyl)acetamidine

Conditions

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at 25℃; for 12h;	99%
With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere;

...Expand

: 5894-65-5
N-t-butylbenzamide

: 26386-88-9
diphenyl phosphoryl azide

: diphenyl (2-(tert-butylcarbamoyl)phenyl)phosphoramidate

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 60℃; under 760.051 Torr; for 24h; Reagent/catalyst;	99%

: 938-16-9
2,2-dimethylpropiophenone

: 26386-88-9
diphenyl phosphoryl azide

: diphenyl (2-pivaloylphenyl)phosphoramidate

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 60℃; under 760.051 Torr; for 24h;	99%

: 26386-88-9
diphenyl phosphoryl azide

: 100-06-1
1-(4-methoxyphenyl)ethanone

: diphenyl (2-acetyl-5-methoxyphenyl)phosphoramidate

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 60℃; under 760.051 Torr; for 24h;	99%

: 104860-90-4
2-isopropyl-1-methyl-1,2-dihydro-isoquinoline

: 26386-88-9
diphenyl phosphoryl azide

: [2-Isopropyl-1-methyl-1,4-dihydro-2H-isoquinolin-(3E)-ylidene]-phosphoramidic acid diphenyl ester

Conditions

Conditions	Yield
for 4h; Ambient temperature;	98%

: 104860-92-6
1,2-diethyl-1,2-dihydro-isoquinoline

: 26386-88-9
diphenyl phosphoryl azide

: [1,2-Diethyl-1,4-dihydro-2H-isoquinolin-(3E)-ylidene]-phosphoramidic acid diphenyl ester

Conditions

Conditions	Yield
for 4h; Ambient temperature;	98%

: 26386-88-9
diphenyl phosphoryl azide

: 53772-44-4
benzyloxydiphenylphosphine

: 864298-72-6
benzyl P,P-diphenyl-N-(diphenylphosphoryl)phosphinimidate

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	98%
In 1,2-dichloro-ethane

: 124-38-9
carbon dioxide

: 26386-88-9
diphenyl phosphoryl azide

: 111-92-2
dibutylamine

: 1016549-40-8
dibutylcarbamic (diphenyl phosphoric) anhydride

Conditions

Conditions	Yield
With 1,1,3,3-tetramethyl-2-phenylguanidine In acetonitrile at 0 - 20℃; for 5h;	98%

...Expand

: 165814-41-5
1-carboxy-1'-[(dimethylamino)carbonyl]ferrocene

: 26386-88-9
diphenyl phosphoryl azide

: 165814-42-6
1-azidocarbonyl-1'-[(dimethylamino)carbonyl]ferrocene

Conditions

Conditions	Yield
With triethylamine In dichloromethane; toluene (N2), stirring (room temp., 25 min), addn. of CH2Cl2, washing (HCl, NaHCO3) and drying of the org. layer; evapn. of the solvent;	98%

: 16078-30-1
1-Acetyl-2,3-dihydro-1H-indole

: 26386-88-9
diphenyl phosphoryl azide

: diphenyl (1-acetylindolin-7-yl)phosphoramidate

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 60℃; under 760.051 Torr; for 24h;	98%

: 26386-88-9
diphenyl phosphoryl azide

: 98-86-2
acetophenone

: diphenyl (2-acetylphenyl)phosphoramidate

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 60℃; under 760.051 Torr; for 24h;	98%

: 194091-96-8
6-ethoxy-6Η-dibenz[c,e][1,2]oxaphosphorin

: 26386-88-9
diphenyl phosphoryl azide

: diphenyl (6-ethoxy-6H-6λ5-dibenzo[c,e][1,2]oxaphosphinin-6-ylidene)phosphoramidate

Conditions

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	98%

: 26386-88-9
diphenyl phosphoryl azide

: 190771-48-3
2-amino-5-(2-hydroxyethyl)-3,7-dihydro-7H-pyrrolo[2,3-d]pyrimidin-4-one

: 2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl diphenylphosphate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 16h;	98%

: 104860-89-1
2-ethyl-1-methyl-1,2-dihydro-isoquinoline

: 26386-88-9
diphenyl phosphoryl azide

: [2-Ethyl-1-methyl-1,4-dihydro-2H-isoquinolin-(3E)-ylidene]-phosphoramidic acid diphenyl ester

Conditions

Conditions	Yield
for 4h; Ambient temperature;	97%

: 26386-88-9
diphenyl phosphoryl azide

: 603-35-0
triphenylphosphine

: 2809-29-2
N-(diphenoxyphosphinyl)-P,P,P-triphenylphosphine imide

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	97%
In diethyl ether

: 26386-88-9
diphenyl phosphoryl azide

: 705-31-7
4-trifluoromethylphenylacetylene

: 108-18-9
diisopropylamine

: N1,N1-diisopropyl-N2-(diphenylphosphoryl)-2-(4-trifluoromethylphenyl)acetamidine

Conditions

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at 25℃; for 12h;	97%

...Expand

: 26386-88-9
diphenyl phosphoryl azide

: 1663-45-2
1,2-bis-(diphenylphosphino)ethane

: 1192175-67-9
CH2CH2[P{=NP(=O)(OPh)2}Ph2]2

Conditions

Conditions	Yield
In toluene at 20℃;	97%
In N,N-dimethyl-formamide at 20℃; Solvent; Staudinger Azide Reduction;

: 104860-93-7
1-isopropyl-2-methyl-1,2-dihydroisoquinoline

: 26386-88-9
diphenyl phosphoryl azide

: [1-Isopropyl-2-methyl-1,4-dihydro-2H-isoquinolin-(3E)-ylidene]-phosphoramidic acid diphenyl ester

Conditions

Conditions	Yield
for 4h; Ambient temperature;	96%

: 26386-88-9
diphenyl phosphoryl azide

: 1486-28-8
diphenyl(methyl)phosphine

: 225658-22-0
C25H23NO3P2

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	96%
In tetrahydrofuran at 25℃; for 0.5h; Staudinger reaction;	95%
at 0℃; for 2h;

: 26386-88-9
diphenyl phosphoryl azide

: N1,N2-bis(diphenylphosphino)-N1,N2-dimethylethane-1,2-diamine

: N,N'-dimethyl-N,N'-bis(diphenylphosphino)ethylenediamine

Conditions

Conditions	Yield
	96%

: 26386-88-9
diphenyl phosphoryl azide

: 820961-79-3
1,1-dimethyl-3-phenylpropyl diphenylphosphinite

: 913542-28-6
1,1-dimethyl-3-phenylpropyl N-(diphenoxyphosphoryl)diphenylphosphinimidate

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h;	96%

: 12150-46-8
1,1'-bis-(diphenylphosphino)ferrocene

: 26386-88-9
diphenyl phosphoryl azide

: 225658-24-2
[C5H4P(C6H5)2(NPO(OC6H5)2)]2Fe

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: N2; argon atmosphere, stirring at room temperature until N2 evolution ceases; concn. to dryness, washing (ether and pentane); elem. anal.;	96%

: 107-10-8
propylamine

: 26386-88-9
diphenyl phosphoryl azide

: 5756-03-6
diphenyl propylamino phosphate

Conditions

Conditions	Yield
With sodium carbonate; zinc(II) acetylacetonate In 1,4-dioxane at 40℃; for 3.5h; Inert atmosphere;	96%
In N,N-dimethyl-formamide at 120℃; for 12h; Solvent; Temperature; Schlenk technique; Green chemistry;	84%

: 26386-88-9
diphenyl phosphoryl azide

: 109-73-9
N-butylamine

: 5756-05-8
N-butyl-P,P-diphenylphosphinic acid

Conditions

Conditions	Yield
With sodium carbonate; zinc(II) acetylacetonate In 1,4-dioxane at 40℃; for 3.5h; Inert atmosphere;	96%
In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Green chemistry;	81%

: 920-66-1
1,1,1,3',3',3'-hexafluoro-propanol

: 26386-88-9
diphenyl phosphoryl azide

: 22410-38-4
1,1,1,3,3,3-hexafluoropropan-2-yl diphenyl phosphate

Conditions

Conditions	Yield
With sodium carbonate at 80℃; for 24h; Schlenk technique;	96%

: 14990-40-0
N-methyl-1,2,3,4-tetrahydroisoquinoline

: 26386-88-9
diphenyl phosphoryl azide

: [2-Methyl-1,4-dihydro-2H-isoquinolin-(3Z)-ylidene]-phosphoramidic acid diphenyl ester

Conditions

Conditions	Yield
for 4h; Ambient temperature;	95%

Diphenylphosphoryl azide Specification

The Diphenylphosphoryl azide, with the CAS registry number 26386-88-9, is also known as Phosphoric acid diphenyl ester azide; DPPA. It belongs to the product categories of Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry.This chemical's molecular formula is C₁₂H₁₀N₃O₃P and molecular weight is 275.20. Its EINECS number is 247-644-0. What's more,Its systematic name is Diphenyl azidophosphate.It is Colorless to yellow liquid, Stable,Incompatible with acids, strong oxidizing agents. And it is insoluble in the water.

Physical properties about Diphenylphosphoryl azide are:
(1)ACD/LogP: 2.995; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.00; (4)ACD/LogD (pH 7.4): 3.00; (5)ACD/BCF (pH 5.5): 111.29; (6)ACD/BCF (pH 7.4): 111.29; (7)ACD/KOC (pH 5.5): 1015.00; (8)ACD/KOC (pH 7.4): 1015.00; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5.

Safety Information of Diphenylphosphoryl azide:
The Diphenylphosphoryl azide is toxic by inhalation, in contact with skin and if swallowed .It is irritating to eyes, respiratory system and skin.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it,wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .

You can still convert the following datas into molecular structure:
(1)SMILES:c1ccc(cc1)OP(=O)(N=[N+]=[N-])Oc2ccccc2;
(2)Std. InChI:InChI=1S/C12H10N3O3P/c13-14-15-19(16,17-11-7-3-1-4-8-11)18-12-9-5-2-6-10-12/h1-10H;
(3)Std. InChIKey:SORGEQQSQGNZFI-UHFFFAOYSA-N;

Product Name

Diphenylphosphoryl azide

Synthetic route

Diphenylphosphoryl azide Specification

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