122194-07-4

Basic information

• Product Name: DIMETHYL N,N-DIISOPROPYLPHOSPHORAMIDITE
• Synonyms: DIMETHYL N,N-DIISOPROPYLPHOSPHORAMIDITE;DIMETHYL-N,N-DIISOPROPYLPHOSPHOROAMIDITE;Dimethyl N,N-diisopropylphosphoramidite >=95.0% (GC)
• CAS NO: 122194-07-4
• Molecular Formula: C₈H₂₀NO₂P
• Molecular Weight: 193.22
• Product Categories: Organic Building Blocks;Phosphoramidites;Phosphorus Compounds
• Mol File: 122194-07-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 54 °C10 mm Hg(lit.)
• Flash Point: 100 °C
• Appearance: /
• Density: 0.840 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.420(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Sparingly)
• Stability: Moisture Sensitive
• CAS DataBase Reference: DIMETHYL N,N-DIISOPROPYLPHOSPHORAMIDITE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL N,N-DIISOPROPYLPHOSPHORAMIDITE(122194-07-4)
• EPA Substance Registry System: DIMETHYL N,N-DIISOPROPYLPHOSPHORAMIDITE(122194-07-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 122194-07-4(Hazardous Substances Data)

Usage

Uses

A useful reagent for the efficient phosphorylation of alcohols.

Upstream product

• 67-56-1 methanol 
• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 108-18-9 diisopropylamine 
• 124-41-4 sodium methylate 
• 86030-43-5 N,N-diisopropylmethylphosphonamidic chloride 
• 92611-10-4 bis(N,N-diisopropylamino)methoxyphosphine 
• 96163-52-9 methyl N,N-diisopropylphosphonamidate 

Downstream Products

• 108-18-9 diisopropylamine 
• 154469-89-3 dimethyl-(3-methyl-4-methylthiophenyl)phosphite 
• 868-85-9 Dimethyl phosphite 
• 146578-13-4 Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester 
• 122194-08-5 4-Nitro-benzoic acid (2R,3S,5R)-3-(dimethoxy-phosphanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 302808-96-4 dimethyl 2-(4-methoxyphenyl)-2-propen-1-yl phosphite 
• 868367-88-8 Phosphoric acid (2R,3S,5S)-2,5-bis-(4,5-dimethoxy-2-nitro-benzyloxy)-2-(dimethoxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester dimethyl ester 
• 868367-89-9 Phosphoric acid (2S,3S,5R)-2,5-bis-(4,5-dimethoxy-2-nitro-benzyloxy)-2-(dimethoxy-phosphoryloxymethyl)-tetrahydro-furan-3-yl ester dimethyl ester 
• 1374660-13-5 meso-4,6-Di-O-benzyl-D-myo-inositol-1,3,5-tri(dimethyl phosphate)-2-(didecyl phosphate) 
• 27356-57-6 dimethyl (2-phenylaziridin-1-yl) phosphate 

Relevant articles and documents

Phosphoric acid phaseomannite class compound and its preparation method and application (by machine translation)

The invention discloses a phaseomannite class phosphate compound, phosphoric acid phaseomannite class compound preparation method, and these phosphoric acid phaseomannite class compounds in the preparation of an anti-tumor drug. The use of non-small cell lung cancer cells to the compounds of this invention to inhibit the growth of tumor cells in active testing, that the compounds of this invention have high inhibition of tumor cell growth activity, some of the compound inhibiting activity even with cisplatin active quite, which indicates that the compounds of this invention have good cell penetrability and phosphorus esterase stability, can be used for the development of anti-tumor medicament. (by machine translation)

Kinetics and mechanism of tetrazole-catalyzed phosphoramidite alcoholysis

Kinetics of the tetrazole-catalyzed reaction of diisopropyl N,N-diisopropylphosphoramidite (1b) with tert-butyl alcohol has been studied by 31P NMR spectroscopy in THF, and the results obtained have been compared to those observed for the possible partial reactions involved, viz. the formation of diisopropyl tetrazolylphosphite (2b) and its subsequent alcoholysis. The stoichiometry of the processes was first examined with dimethyl N,N-diisopropylphosphoramidite (1a) in MeCN. The tetrazole-promoted disappearance of 1b is as fast in the absence and in the presence of the alcohol: the alcoholysis of 1b is zero-order in the concentration of alcohol and second-order in the concentration of tetrazole. The reaction of 1b with tetrazole is independent of the concentration of the tetrazolide anion and second-order in that of tetrazole, while the reverse reaction, aminolysis of 2b is first-order in the concentration of the amine The alcoholysis of 2b is, in turn, first-order in the concentration of alcohol and second-order in that of tetrazole, but it also proceeds, although slowly, in the absence of tetrazole. The time-dependent product distribution of the alcoholysis of 1b shows intermediary accumulation of 2b, but at a lower level than could be predicted by applying the rate constants determined independently for the assumed partial reactions. Accordingly, tetrazole-catalyzed alcoholysis of 1b is shown to proceed at least mainly via 2b, but an additional pathway not involving 2b as an intermediate is proposed. Mechanisms of the partial reactions are discussed on the basis of the formal kinetics observed.

Nucleoside 3'-N,N-dialkylphosphonamidates: Novel building blocks for oligonucleotide synthesis

Nucleoside 3'-N,N-diisopropylphosphonamidates reacted with tris(2,4,6-tribromophenoxy)dichlorophosphorane (BDCP) to generate the corresponding aminophosphorochloridites without cleavage of the P-N bond. The reaction was applied to internucleotidic bond formation.