2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite

• CAS: 102691-36-1
• Catalog Number: ACM102691361
• Category: Main Products
• Molecular Weight: 301.41
• Molecular Formula: C₁₅H₃₂N₃OP
• Synonyms: Cetipd, 305995_ALDRICH, CID128153, ZINC02539453, Bis(diisopropylamino)(2-cyanoethoxy)phosphine, 2-Cyanoethyl N,N,N,N-tetraisopropylphosphordiamidite, 2-Cyanoethyl tetrakis(1-methylethyl)phosphorodiamidoate, 2-Cyanoethyl-N,N,N,N-tetraisopropylphosphorodiamidite, 102691-36-1, Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester
• IUPAC Name: 3-bis[di(propan-2-yl)amino]phosphanyloxypropanenitrile
• Canonical SMILES: CC(C)N(C(C)C)P(N(C(C)C)C(C)C)OCCC#N
• InChI Key: RKVHNYJPIXOHRW-UHFFFAOYSA-N
• Boiling Point: 100ºC (0.5 mmHg)
• Flash Point: 141 °F
• Density: 0.949
• Appearance: colorless to yellow clear liquid
• EC Number: 600-337-9
• Exact Mass: 301.22800
• Hazard Statements: Xi:Irritant
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Packing Group: I
• Safety Description: S3-S26-S36
• WGK Germany: 3

Case Study

2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite for the Synthesis of Imidazoquinoline

Bazin H G, et al. Tetrahedron letters, 2016, 57(19), 2063-2066.

A high-yield and scalable phosphoramidite process was developed for the phospholipidation of TLR7/8-active imidazoquinolines. In this method, 2-cyanoethyl N,N,N',N'-tetraisopropylphosphoramidite (11) and various fatty alcohols are used in the critical phosphorylation step for the phospholipidation of TLR7/8- active imidazoquinolines 3 and 4.
Synthesis of phosphotriester via the phosphoramidite method
· The lipid (2.0 eq) and 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite (2.1 eq) were dissolved in anhydrous methylene chloride (0.4 M) at rt. 1H-tetrazole (2.1 eq) was added in four portions over 20 minutes and the reaction mixture stirred at room temperature for 1 hour.
· The reaction mixture was cooled to 0 °C, imidazoquinoline (1.0 eq) and imidazolium triflate (1.5 eq) were added, and the reaction mixture allowed to warm up to room temperature for 1 hour.
· The resulting phosphite 13 can be purified at this stage or subsequently oxidized by addition of t-butyl hydroperoxide (1.5 eq) to the reaction mixture and stirring at rt for 30 min. After completion of the oxidation, the reaction mixture was concentrated under vacuum and purified by chromatography on silica gel to give the desired phosphotriester 14.

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite Used in the Synthesis of Phosphoramidites

Schlegel M K, et al. The Journal of Organic Chemistry, 2009, 74(12), 4615-4618.

The following describes the synthesis routes of several phosphoramidite structural units via 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite. These phosphoramidites can be further used in the synthesis of glycol nucleic acids.
· Synthesis of Phosphoramidite G*:
O6 -benzylguanine (1) was used in the ring-opening of (S)-glycidyl 4,4'-dimethoxytrityl ether 2 in DMF to afford compound 3. The benzyl group was subsequently removed using catalytic hydrogenation to produce compound 4. The N2 -dimethylformamidine derivative was synthesized by heating a mixture of compound 4 and dimethylformamide dimethylacetal in DMF at 60 °C for 1 h, affording compound 5. Conversion to the phosphoramidite G* was then accomplished by the reaction with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite and substoichiometric amounts of 4,5-dicyanoimidazole (DCI)14 in CH2Cl2.
· Synthesis of Phosphoramidite A*:
N6 -dimethylformamidine protection of (S)- 9-(3-(4,4'-dimethoxytrityloxy)-2-hydroxypropyl)adenine (7) was obtained from adenine (6) in one step by the reaction with the tritylated glycidol 2 in the presence of catalytic amounts of NaH. The reaction of compound 7 with dimethylformamide dimethyl acetal in DMF afforded compound 8. The following conversion to phosphoramidite A* using 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite and DCI in CH2Cl2 could be accomplished.

Custom Reviews

August 18, 2023

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Work good in organic synthesis
In the experiment, 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite can efficiently synthesize phosphoramidated nucleotide reagent.

Custom Q&A

What's EC number of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

600-337-9

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite belongs to what category of chemical reagents?

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite is a pharmaceutical intermediate, a phosphoramidite reagent or an organophosphorus reagent.

What's boiling point of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

100 °C0.5 mm Hg

What is the acidity factor of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

6.78±0.70

What is the form of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

colorless liquid

What is the density of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

0.949 g/mL at 25 °C

Is 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite sensitive to the environment?

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite is susceptible to moisture

Is 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite stable when heated?

2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite can explode when heated

What's flash point of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

141 °F

What's LogP of 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphordiamidite?

4.04 at 20℃