[bis(benzyloxy)phosphanyl]diethylamine

• ChemBase ID: 149690
• Molecular Formular: C18H24NO2P
• Molecular Mass: 317.362421
• Monoisotopic Mass: 317.15446564
• SMILES: CCN(CC)P(OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: CCN(P(OCc1ccccc1)OCc1ccccc1)CC
• InChI: InChI=1S/C18H24NO2P/c1-3-19(4-2)22(20-15-17-11-7-5-8-12-17)21-16-18-13-9-6-10-14-18/h5-14H,3-4,15-16H2,1-2H3
• InChIKey: NLGUJOVLAXLSMX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [bis(benzyloxy)phosphanyl]diethylamine
• IUPAC Traditional name: [bis(benzyloxy)phosphanyl]diethylamine
• Synonyms: TTC; Dibenzyl N,N-diethylphosphoramidite; DDP; Dibenzyl diethylphosphoramidite; N,N-Diethyl-phosphoramidous Acid Bis(phenylmethyl) Ester; Bis(benzyloxy)(diethylamino)phosphine; Dibenzyl (Diethylamido)phosphite; Dibenzyloxydiethylaminophosphine; Dibenzyl N,N-Diethylphosphoramidite, Technical Grade ≥85%; 二苄基二乙基胺基膦

Database IDs

• CAS Number: 67746-43-4
• MDL Number: MFCD00191987
• Beilstein Number: 4189915
• PubChem SID: 24860473; 162243852; 24862337
• PubChem CID: 5066231

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.2826946
• LogD (pH = 7.4): 4.0207696
• Log P: 4.7406
• Molar Refractivity: 93.5456 cm^3
• Polarizability: 36.606922 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Colourless Liquid
• Flash Point: 34 °C; 73°C(163°F); 93.2 °F
• Density: 1.06 g/mL at 25 °C(lit.); 1.060
• Refractive Index: 1.5450; n20/D 1.545(lit.); n20/D 1.55
• Vapor Pressure: 0.71 psi ( 55 °C)

Safety Information

• Storage Condition: glass bottle, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-36/37/38; 36/37/38
• Safety Statements: 16-26-37/39; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335; H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ~90% (GC); 85%; 90+%
• Grade: technical; technical grade
• Linear Formula: (C2H5)2NP(OCH2C6H5)2

DETAILS

Sigma Aldrich - 362883

Packaging
1, 5 g in ampule

Sigma Aldrich - 33732

Other Notes
Phosphitylating reagent employed to prepare various phosphates1,2,3

Toronto Research Chemicals - D417000

A useful reagent for the efficient phosphorylative conversion of alcohols into their corresponding dibenzylphosphorotriesters as well as dibenzyl glycosyl phosphites, which can easily be converted to glycosyl phosphates or used in glycosylation reagents

REFERENCES

• Perich, J.W., et al.: Synthesis, 142 (1988)
• Wong, C-H., et al.: J. Am. Chem. Soc., 115, 2260 (1993)
• Phosphitylating agent which reacts with an alcohol under mild conditions. Subsequent oxidation, e.g. with hydrogen peroxide, followed by hydrogenolysis of the benzyl groups, affords the alkyl phosphate: Tetrahedron, 47, 2643 (1991); J. Org. Chem., 59, 7182 (1994). This sequence provides a convenient route to glycosyl phosphates via the glycosyl phosphites: J. Am. Chem. Soc.115, 2260 (1993).