2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
- Product Name
- 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
- CAS No.
- 102691-36-1
- Chemical Name
- 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
- Synonyms
- P-REAGENT;2-CYANOETHYL TETRAISOPROPYLPHOSPHORODIAMIDITE;3-Bis(diisopropylamino)phosphanyloxypropanenitrile;3-(bis(diisopropylamino)phosphinooxy)propanenitrile;THERAPEUTIC GRADE PHOS REAGENT;BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE;94.0%(GC&phosphordiamidit;Phosphorus reagent B;Phosphorous reagent A
- CBNumber
- CB1231672
- Molecular Formula
- C15H32N3OP
- Formula Weight
- 301.41
- MOL File
- 102691-36-1.mol
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Property
- Boiling point:
- 100 °C0.5 mm Hg(lit.)
- Density
- 0.949 g/mL at 25 °C(lit.)
- refractive index
- n20/D 1.470(lit.)
- Flash point:
- 141 °F
- storage temp.
- -20°C
- solubility
- Acetonitrile (Slightly), Benzene, Chloroform (Sparingly), Methanol (Slightly)
- form
- liquid
- pka
- 6.78±0.70(Predicted)
- color
- colorless
- Sensitive
- moisture sensitive, store cold
- BRN
- 3590103
- Stability:
- Explodes When Heated
- InChIKey
- RKVHNYJPIXOHRW-UHFFFAOYSA-N
- LogP
- 4.04 at 20℃
- CAS DataBase Reference
- 102691-36-1(CAS DataBase Reference)
- EPA Substance Registry System
- Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester (102691-36-1)
Safety
- Hazard Codes
- Xi,Xn
- Risk Statements
- 5-36/37/38-42/43-36/38
- Safety Statements
- 3-26-36-24/25-23-45-36/37
- RIDADR
- UN 1993 3/PG 3
- WGK Germany
- 3
- F
- 10-21-34
- Hazard Note
- Irritant/May Explode on Heating
- HazardClass
- 8
- PackingGroup
- I
- HS Code
- 29299000
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H226Flammable liquid and vapour
H302Harmful if swallowed
H317May cause an allergic skin reaction
H412Harmful to aquatic life with long lasting effects
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233Keep container tightly closed.
P273Avoid release to the environment.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
N-Bromosuccinimide Price
- Product number
- 305995
- Product name
- 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite
- Purity
- 97%
- Packaging
- 1g
- Price
- $90.8
- Updated
- 2024/03/01
- Product number
- 305995
- Product name
- 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite
- Purity
- 97%
- Packaging
- 5g
- Price
- $190
- Updated
- 2024/03/01
- Product number
- C2228
- Product name
- 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite
- Purity
- >95.0%(GC)(T)
- Packaging
- 1g
- Price
- $63
- Updated
- 2024/03/01
- Product number
- C2228
- Product name
- 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite
- Purity
- >95.0%(GC)(T)
- Packaging
- 5g
- Price
- $189
- Updated
- 2024/03/01
- Product number
- 15-0695
- Product name
- 2-Cyanoethyl N,N,N',N'-tetra(i-propyl)phosphorodiamidite, min. 98%
- Packaging
- 1g
- Price
- $60
- Updated
- 2024/03/01
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Chemical Properties,Usage,Production
Description
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is a colorless viscous liquid, which is soluble in most organic solvents. It is a widely used phosphitylating reagent for the preparation of various phosphorylated biomolecules, such as nucleoside carbohydrate conjugates, phospholipids and glycopeptides. In particular, this reagent is highly effective for automated solid-phase DNA/RNA oligonucleotide synthesis. It has shown great utility in the coupling of nucleobases or carbohydrates via their phosphotriesters in the presence of activators such as 1H-tetrazole, in moderate yields under mild conditions.This compound is cheaper and more stable than 2-cyanoethyl N,N-diisopropylchlorophosphorodiamidite (the other commonly used phosphinylating reagent)[1].
Chemical Properties
Clear to Cloudy Colourless Liquid
Uses
Reagent for synthesizing phosphitylated nucleotides.1
Uses
2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:
- in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotide
- as phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserine
- in situ preparation of deoxyribonucleoside phosphoramidites
- in preparation of 2′-deoxy-2′-fluoro-3′-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-5′-O-(4-methoxytrityl)-4′-thio-β-D-arabinouridine and 1-(3-O-(β-cyanoethyl-N,N-diisopropylphosphoramidic)-2-deoxy-2-fluoro-5-O-(4,4′-dimethoxytrityl)-4-thio-β-D-arabinofuranosyl)-thymine
- as reagent for synthesizing phosphitylated nucleotides
Application
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite is an important organic reagent widely used in the preparation of modified and unmodified nucleoside phosphoramidites. Nucleoside phosphoramidites are ideal reagents for polymer-supported synthesis of oligonucleotides. The diisopropylamino leaving group is readily cleaved upon contact with the azole catalyst, resulting in an efficient coupling reaction with the free hydroxyl group on the protected nucleoside.
Synthesis
3-((dichlorophosphaneyl)oxy)propanenitrile could synthesize 2-Cyanoethyl N, N, N', N'-tetraisopropylphosphorodiamidite with diisopropylamine. This method is inexpensive manner using a two-step, one-pot procedure and purified by vacuum distillation[2].
References
[1] Hada N, et al. Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi. Carbohydrate Research, 2008; 343: 343, 2221.
[2] Ching S, et al. Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting
diguanylate cyclase. Bioorganic & Medicinal Chemistry, 2010; 18: 6657-6665.
2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite Preparation Products And Raw materials
Raw materials
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View Lastest Price from 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite manufacturers
- Product
- 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 102691-36-1
- Price
- US $8.00-0.80/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-09
- Product
- 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 102691-36-1
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%min PNMR
- Supply Ability
- 10KG
- Release date
- 2021-06-08
- Product
- Bis(diisopropylamino)(2-cyanoethoxy) phosphine 102691-36-1
- Price
- US $100.00/kg
- Min. Order
- 0.01kg
- Purity
- 99%
- Supply Ability
- 20tons
- Release date
- 2023-03-17