ChemicalBook > CAS DataBase List > 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite

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
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
305995
Product name
2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite
Purity
97%
Packaging
1g
Price
$90.8
Updated
2024/03/01
Sigma-Aldrich
Product number
305995
Product name
2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite
Purity
97%
Packaging
5g
Price
$190
Updated
2024/03/01
TCI Chemical
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
TCI Chemical
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
Strem Chemicals
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
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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

Preparation Products

Ceftibuten anionic starch
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View Lastest Price from 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
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
Shaanxi Dideu Medichem Co. Ltd
Product
2-Cyanoethyl N,N, N',N'-tetraisopropylphosphorodiamidite 102691-36-1
Price
US $1.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20 Tons
Release date
2020-01-14
Henan Fengda Chemical Co., Ltd
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

102691-36-1, 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamiditeRelated Search:

Bis[3-(triethoxysilyl)propyl]tetrasulfide Bis(triethoxysilylpropyl) disulfide N-[2-(di-1-adamantylphosphino) phenyl]morpholine,98% Mor-DalPhos Diisopropylamine Minoxidil (Chloromethylene)dimethyliminium chloride Lithium diisopropylamide DIETHOXYMETHANE Ethoxymethylenemalononitrile LITHIUM PERIODATE Ethoxyquin BLOCKING REAGENT GE 4-Ethoxyphenol Bis(2-methyl-3-furyl)disulfide (3R,5S)-3,5-DiMethylMorpholine hydrochloride Bis(4-chlorobenzyl) azodicarboxylate Bis(4-tert-butylcyclohexyl) peroxydicarbonate Phosphine

  • P-REAGENT
  • 2-Cyanoethoxybis(N,N-diisopropylaMino)phosphine
  • Bis(diisopropylaMino)(2-cyano
  • N,N,N',N'-Tetrakis(1-Methylethyl)phosphorodiaMidous Acid 2-Cyanoethyl Ester
  • THERAPEUTIC GRADE PHOS REAGENT
  • 2-Cyanoethyl N,N,N',N'-tetra(prop-2-yl)phosphorodiamidoite
  • 2-Cyanoethyl N,N,N',N'-tetrakis(isopropyl)phosphorodiamidite
  • β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodiaMidite
  • 2-CYANOETHYLTETRAISOPROPYLPHOSPHORO-DIA
  • 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite 97%
  • 2-Cyanoethyl N,N,N',N'-tetra(i-propyl)phosphorodiamidite
  • CTPPA 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
  • Phosphorous reagent A
  • Phosphorus reagent B
  • 2-CYANOETHYL TETRAISOPROPYLPHOSPHOR
  • BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE
  • β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodia
  • Bis(diisopropylamino)(2-cyanoethoxy)phosphine P-Reagent
  • 2-Cyanoethyl-N,N',N'-Tetraisopropylphosphordiamidite
  • 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORAMIDITE
  • 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORDIAMIDITE
  • 2-CYANOETHYL N,N,N',N'-TETRAISOPROPYLPHOSPHORODIAMIDITE
  • 2-CYANOETHYL TETRAISOPROPYLPHOSPHORODIAMIDITE
  • Phosphorodiamidous acid, tetrakis(1-methylethyl)-, 2-cyanoethyl ester
  • 2-CYANOETHYL-N,N,N'',N''-TETRAISO-PROPYLPHOSPHORAMIDITE(P-REAGENT)
  • b-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite
  • TETRAISOPROPYLPHOSPHORODIAMIDITE
  • 5) 2-cyanoethyl-N,N,N',N'-tetraisopropylphosphorodiamidite
  • PHOSPHORODIAMIDOUS ACID, N,N,N'',N''-TETRAKIS(1-METHYLETHYL)-, 2-CYANOETHYL ESTER
  • 2-Cyanoethyl-N,N,N',N'-tetraisopropylphosphordiamidite 98%
  • 3-(bis(diisopropylamino)phosphinooxy)propanenitrile
  • 2-Cyanoethyl N,N,N',N'-tetra(i-propyl)phosphorodiamidite, min. 98%
  • 2-Cyanoethyl-N,N,Nzzhlxy,Nzzhlxy-tetraisopropylphosphordiamidite (P-Reagent)
  • 2-Cyanoethyl N,N,N',N'-tetrakis(isopropyl)phosphorodiamidite 95+%
  • 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(CTPPA)
  • 94.0%(GC&amp
  • 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite &gt
  • N,N,N',N'-tetraisopropyL
  • phosphordiamidit
  • 2-O-cyanoethyl-N,N,N’,N’-tetraisopropylphosphordiamidite
  • 3-({bis[bis(propan-2-yl)amino]phosphanyl}oxy)propanenitrile
  • 3-Bis(diisopropylamino)phosphanyloxypropanenitrile
  • 3-((Bis(diisopropylamino)phosphino)oxy), 97%
  • β-Cyanoethyl-N,N,N`,N`-tertraisopropylphosphorodiamidite
  • bis(2-cyano-1,1-dimethylethyl)-N,N-diisopropylphosphoramidite
  • 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
  • 2-Cyanoethyl N,N,N',N'-Tetraisopropylphosphordiamidite
  • CTPPA2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
  • 102691-36-1
  • 102691-30-1
  • 916966-01-5
  • CH32CH2N2POCH2CH2CN
  • C15H38N3OP
  • C15H32N3OP
  • C15H32N3P
  • C15H32N3PO
  • Phosphoramidites
  • Phosphorus Compounds