[bis(prop-2-en-1-yloxy)phosphanyl]bis(propan-2-yl)amine

• ChemBase ID: 145949
• Molecular Formular: C12H24NO2P
• Molecular Mass: 245.298221
• Monoisotopic Mass: 245.15446564
• SMILES: CC(C)N(C(C)C)P(OCC=C)OCC=C
• Canonical SMILES: C=CCOP(N(C(C)C)C(C)C)OCC=C
• InChI: InChI=1S/C12H24NO2P/c1-7-9-14-16(15-10-8-2)13(11(3)4)12(5)6/h7-8,11-12H,1-2,9-10H2,3-6H3
• InChIKey: QBLCHHSGJTUNSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [bis(prop-2-en-1-yloxy)phosphanyl]bis(propan-2-yl)amine
• IUPAC Traditional name: [bis(prop-2-en-1-yloxy)phosphanyl]diisopropylamine
• Synonyms: N,N-Bis(1-methylethyl)phosphoramidous acid di-2-propenyl ester; Diallyloxy(diisopropylamino)phosphine; Diallyl N,N-diisopropylphosphoramidite; 己二烯 N,N-二异丙基亚磷酰胺

Database IDs

• CAS Number: 126429-21-8
• MDL Number: MFCD00216647
• Beilstein Number: 4383514
• PubChem SID: 24867522; 162240149
• PubChem CID: 4686855

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.4419499
• LogD (pH = 7.4): 1.923369
• Log P: 3.4948
• Molar Refractivity: 71.4834 cm^3
• Polarizability: 27.978455 Å^3
• Polar Surface Area: 21.7 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 130 °C(lit.)
• Flash Point: 32 °C; 89.6 °F
• Density: 0.928 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)

Safety Information

• 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
• Safety Statements: 26-36
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: 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

• Linear Formula: [(CH3)2CH]2NP(OCH2CH=CH2)2

DETAILS

Sigma Aldrich - 439606

Packaging
1 g in glass bottle
Application
Precursor involved in the synthesis of pharmacologically active molecules including:
• Selective orally active S1P1 agonists1
• Water-soluble prodrugs of triazole CS-758 with antifungal activity2
• Fostriecin analogs as antitumor agents3Reactant involved in:
• Phosphitylation of alcohols4
• Deallylation for the synthesis of nucleoside phosphoramidite5
• Posphitylation and stereoselective Pudovik rearrangement6