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Diphenylphosphoryl azide

  • Name Diphenylphosphoryl azide
  • EINECS247-644-0
  • CAS No. 26386-88-9
  • Density1.277 g/mL at 25 °C(lit.)
  • PSA95.09000
  • LogP4.01556
  • Solubilityinsoluble in water
  • Melting PointN/A
  • FormulaC12H10N3O3P
  • Boiling Point157°C0.17mm Hg(lit.)
  • Molecular Weight275.203
  • Flash Point>230°F
  • Transport InformationUN 3278 6.1/PG 2
  • Appearancecolourless or faintly yellow liquid
  • Safety26-36/37/39-45
  • Risk Codes23/24/25-36/37/38
  • Molecular Structure
    Molecular Structure of 26386-88-9 (Diphenylphosphoryl azide)
  • Hazard SymbolsToxicT
  • SynonymsToxicT
  • Article Data21

Diphenylphosphoryl azide Synthetic route

2524-64-3

chlorophosphoric acid diphenyl ester

26386-88-9

diphenyl phosphoryl azide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With copper(l) iodide In tetrahydrofuran at 25℃; for 12h;99%
With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere;
5894-65-5

N-t-butylbenzamide

26386-88-9

diphenyl phosphoryl azide

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

Conditions
ConditionsYield
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%

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;

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