ДИИЗОПРОПИЛФОСФОРАМИДНЫЙ ДИХЛОРИД

Substance identification

Diisopropylphosphoramide dichloride is an organophosphorus compound of the aminodichlorophosphine class: the trivalent phosphorus atom carries a diisopropylamino group and two chlorine atoms. English name Diisopropylphosphoramidous dichloride, CAS 921-26-6, formula C6H14Cl2NP, classifier section “Phosphines”. Synonyms: Diisopropylaminodichlorophosphine, Dichloro(diisopropylamino)phosphine, Bis(isopropyl)aminodichlorophosphine, N,N-diisopropyldichlorophosphinamine.

Basic Attributes

• CAS No.: 921-26-6
• Chemical formula: C6H14Cl2NP
• Molecular weight: 202.06
• Exact weight: 201.024
• DSSTox ID: DTXSID30408696
• PSA: 16.83
• XLogP3: 3.8097

Physico-chemical characteristics

• Density: 1.096 g/ml at 25 °C (lit.)
• Boiling point: 56–58 °C at 15 mm Hg. Art.
• Flash point: 66 °C
• Refractive index: n20/D 1.485 (lit.)
• Storage conditions: hygroscopic, store in a refrigerator, in an inert atmosphere
• Stability: moisture sensitive

Chemistry and application

The tricoordinated phosphorus(III) atom is bonded to a diisopropylamino group and two chlorine atoms. Such aminodichlorophosphines are reagents for the sequential increase in phosphorus-oxygen and phosphorus-nitrogen bonds: chlorine atoms are replaced by alcohols or phenols with the release of HCl, and the diisopropylamino group plays the role of a protective group on phosphorus, which is removed at the next stage by activation with an acid catalyst such as tetrazole. According to this scheme, the substance serves as the starting reagent for the preparation of chlorophosphites and phosphoramidite synthons used in the phosphoramidite synthesis of oligonucleotides, as well as in the preparation of phosphorus-containing ligands for metal complex catalysis. The reactions are carried out in anhydrous aprotic solvents (dichloromethane, tetrahydrofuran) in the presence of a base that binds the released hydrogen chloride.

Safety Information

• Packing level: I
• Hazard category: 4.2
• Transport code: UN 2846
• WGK Germany: 3
• Hazard class code: 1-5-14-34
• Safety instructions: 15-26-27-36/37/39-45
• Tags: E, C
• Hazard statements: H250, H314
• Precautions: P222, P231, P280, P305+P351+P338, P310, P422
• GHS classification: H250 (100%) - spontaneously ignites on contact with air (hazardous pyrophoric liquids, pyrophoric solids); additional measures P210, P222, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P405, P422, P501
• Aggregated GHS information provided by 39 companies from 2 notifications to the C&L ECHA Inventory, each notification may relate to several companies

Storage and transportation

The substance is pyrophoric and hygroscopic: contact with air causes spontaneous combustion, contact with moisture causes hydrolysis with the release of hydrogen chloride. Store in an airtight container under an inert gas (nitrogen, argon), in the refrigerator, separate from water, alcohols and bases. Transportation according to UN code 2846, hazard category 4.2, packing group I. Work should be carried out in a glove box or on a Schlenk line, with full protection of skin, breathing and eyes, away from sources of moisture and open flame.