tris(propan-2-yl) phosphite

• ChemBase ID: 89799
• Molecular Formular: C9H21O3P
• Molecular Mass: 208.235001
• Monoisotopic Mass: 208.12283116
• SMILES: P(OC(C)C)(OC(C)C)OC(C)C
• Canonical SMILES: CC(OP(OC(C)C)OC(C)C)C
• InChI: InChI=1S/C9H21O3P/c1-7(2)10-13(11-8(3)4)12-9(5)6/h7-9H,1-6H3
• InChIKey: SJHCUXCOGGKFAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(propan-2-yl) phosphite
• IUPAC Traditional name: triisopropyl phosphite
• Synonyms: Triisopropyl phosphite; TRIISOPROPYL PHOSPHITE; Triisopropyl phosphite tech. 90%; Phosphorous acid triisopropyl ester; 亚磷酸三异丙酯

Database IDs

• CAS Number: 116-17-6
• EC Number: 204-130-0
• MDL Number: MFCD00008874
• Beilstein Number: 1701528
• PubChem SID: 162076655; 24900404
• PubChem CID: 8304

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.1726868
• LogD (pH = 7.4): 3.1727
• Log P: 3.1727
• Molar Refractivity: 55.4789 cm^3
• Polarizability: 22.123232 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 63°C; 63-64 °C/11 mmHg(lit.); 63-64°C/11mm; 63-64°C/11mm
• Flash Point: 154.4 °F; 46°C(114°F); 67°C; 68 °C
• Density: 0.844; 0.844 g/ml; 0.844 g/mL at 25 °C(lit.); 0.908
• Refractive Index: 1.411; 1.4110; n20/D 1.411; n20/D 1.411(lit.)
• Vapor Pressure: <2 mmHg ( 20 °C)

Safety Information

• Storage Warning: Air & Moisture Sensitive; Toxic/Flammable/Moisture Sensitive/
• RTECS: TH2800000
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: 3278; UN1993
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 3; III
• Risk Statements: 10-36/37/38-68; 25-38; R:25-27
• Safety Statements: 26-36/37; 37-46; S:28-29-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H341-H315-H319-H335; H301-H315
• GHS Precautionary statements: P280H-P305+P351+P338; P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3278 6.1/PG 3

Product Information

• Purity: ≥90% (GC); 90+%; 95%
• Grade: technical
• Linear Formula: [(CH3)2CHO]3P

DETAILS

MP Biomedicals - 05219422

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T67806

Packaging
100, 500 mL in glass bottle

REFERENCES

• Reagent for the preparation of phosphonate esters by the Arbuzov reaction; cf Triethyl phosphite, L00339. Has the advantage over primary phosphites that the bulky alkyl groups minimize the product of self-alkylation. For an example (diisopropyl methanephosphonate), see: Org. Synth. Coll., 4, 325 (1963).
• Convenient means of introduction of an isopropyl group into an aromatic ring by Friedel-Crafts alkylation. Using nitromethane as solvent, rearrangement of existing groups can be avoided: Synthesis, 423 (1972).
• The complex with CuCl, the "Moser" catalyst, promotes the cyclopropanation of alkenes by diazoalkanes: J. Am. Chem. Soc., 91, 1135 (1969). For comparison with other catalysts, see: Synthesis, 787 (1981).
• The combination with Pd(OAc)₂ is reported to be an efficient catalyst system for cross-coupling of arylboronic acids with both aryl bromides and chlorides: Chem. Eur. J., 6, 1830 (2000).