Diphenylphosphoryl azide (HCID 123414)

Overview

reagent for racemization-free peptide synthesis; structure

Names & identifiers

Preferred name: Diphenylphosphoryl azide
IUPAC: [azido(phenoxy)phosphoryl]oxybenzene
English name: Diphenylphosphoryl azide
Molecular formula: C12H10N3O3P
Molecular weight: 275.2

Names & synonyms

Diphenylphosphoryl azide26386-88-9Diphenyl azidophosphateDiphenylphosphorazidatediphenyl phosphorazidatePhosphorazidic acid, diphenyl esterPhosphoric acid diphenyl ester azideGXM91165AVDTXSID10949274RefChem:588944DTXCID10909772247-644-0

Show more names

DPPADiphenyl azide phosphatePS-DPPAdiphenylphophoryl azideDiphenylphosphorazindate（DPPA）(PHO)2PO-N3Diphenylazidophosphat

Diphenyl phosphoryl azideDiphenylphosphonic azide{[azido(phenoxy)phosphoryl]oxy}benzene[azido(phenoxy)phosphoryl]oxybenzeneMFCD00001987diphenyl phosphoryl azide (dppa)phosphorazidic acid diphenyl esterDiphenyl phosphonyl azide

Database identifiers

CAS: 26386-88-9
PubChem CID: 123414
DTXSID: DTXSID10949274
UNII: GXM91165AV
EC Number: 247-644-0
Nikkaji: J87.297K

Properties

Computed structural properties

XLogP: 4.4
Topological polar surface area: 49.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 5
Heavy atoms: 19
Formal charge: 0
Complexity: 348

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Biochemical Research

Physical DescriptionColorless odorless liquid; [Alfa Aesar MSDS]

Physicochemical properties

Boiling point: 157 °C/0.17 · 157 °C/0.17 mmHg (lit.)
Density: 1.277 g/mL · 1.277 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.551(lit.)
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly)
form: Liquid
Specific Gravity: 1.277 · 1.277
color: slightly yellow
Water Solubility: insoluble
Hydrolytic Sensitivity: 7 · 7: reacts slowly with moisture/water
BRN: 2058967 · 2058967
Stability: Stable. Incompatible with acids, strong oxidizing agents.
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
InChIKey: SORGEQQSQGNZFI-UHFFFAOYSA-N
SMILES: [N-]=[N+]=NP(=O)(Oc1ccccc1)Oc2ccccc2
CAS DataBase Reference: 26386 · 26386-88-9(CAS DataBase Reference)
FDA UNII: 91165 AV · GXM91165AV
NIST Chemistry Reference: Diphenylphosphoryl azide(26386-88-9)
UNSPSC Code: 12352302 · 12352302
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301+H311+H331-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: T
Risk Statements: 23 · 23/24/25-36/37/38
Safety Statements: 26 · 26-36/37/39-45
RIDADR: 3278 · UN 3278 6.1/PG 2
WGK Germany: 3 · 3
F: 3 · 3-10
Hazard Note: Toxic/Keep Cold
TSCA: No
HazardClass: 6.1 · 6.1
PackingGroup: III
HS Code: 29299000 · 29299000
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active
Limited Quantities: 100 ml · 100ml (liquid) or 0.5 Kg (solid)
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 81 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 11-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/20608

Diphenyl azidophosphate: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA skin and strong eye irritant; Toxic by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS]

Hazard Classes and CategoriesAcute Tox. 3 (97.5%)

Safety & protection

Exposure Control and Personal Protection · 1 item

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Safety data

F: 3-10
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: No
ridadr: UN 3278 6.1/PG 2
hs_code: 29299000
risk_code: 23/24/25-36/37/38
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T
hazard_note: Toxic/Keep Cold
safety_code: 26-36/37/39-45
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: III
target organs: Respiratory system
Hazard statements: H301+H311+H331-H315-H319-H335
Limited Quantities: 100ml (liquid) or 0.5 Kg (solid)
Excepted Quantities: Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338

Chemistry & industry

Uses & manufacturing

UsesReagent for racemization-free peptide synthesis. [ChemIDplus]

Applications · 1 item

UsesDiphenylphosphoryl azide (DPPA or diphenyl phosphorazidate, (PhO)2P(O)N3) is a very toxic and potentially explosive organic compound. DPPA has been found to be effective for a variety of organic reactions as a versatile synthetic reagent. It is widely used in synthesis of other organic compounds especially as a reagent for the synthesis of peptides by virtue of its reactions with carboxylic acids leading to either the urethane or the amide.

Preparation methods · 1 item

PreparationDiphenylphosphoryl azide (DPPA) is easily prepared in high yield by the reaction of the corresponding chloride with sodium azide in acetone. Combination of sodium azide and 18-crown-6 in the same reaction was reported, and the use of a quaternary ammonium salt as a phase-transfer catalyst in a biphasic phase of water and an organic solvent was also reported to be effective, as shown in Scheme 3.Diphenyl Phosphorazidate (DPPA) - More Than Three Decades LaterTakayuki ShioiriGraduate School of Environmental and Human Sciences, Meijo University

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

南京一化生物科技有限公司13429882898; 13429882898

INTATRADE GmbH+49 3493/605464 · [email protected]

Related reactions

271 records

New reaction record

HRID 36780As reactantuspto-grants-1995_05

HRID 46293As reactantuspto-grants-2013_09

HRID 59875As reactantuspto-grants-2016_09

HRID 59881As reactantuspto-grants-2016_09

HRID 75002As reactantuspto-grants-2014_09

HRID 75050As reactantuspto-grants-2014_09

HRID 85762As reactantuspto-grants-2014_09

HRID 174912As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)

Linked notes

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Diphenylphosphoryl azide

Basic information