102691-36-1

Basic information

• Product Name: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite
• Synonyms: P-REAGENT;BIS(DIISOPROPYLAMINO)(2-CYANOETHOXY)PHOSPHINE;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)
• CAS NO: 102691-36-1
• Molecular Formula: C₁₅H₃₂N₃OP
• Molecular Weight: 301.41
• EINECS: 2017-001-1
• Product Categories: Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Regant series;Nucleic acids;Phosphorylating and Phosphitylating Agents;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphoramidites;Phosphorus Compounds;OLED materials,pharm chemical,electronic
• Mol File: 102691-36-1.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 100 °C0.5 mm Hg(lit.)
• Flash Point: 141 °F
• Appearance: colorless/liquid
• Density: 0.949 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.470(lit.)
• Storage Temp.: 2-8°C
• PKA: 6.78±0.70(Predicted)
• Sensitive: moisture sensitive, store cold
• Stability: Explodes When Heated
• BRN: 3590103
• CAS DataBase Reference: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(102691-36-1)
• EPA Substance Registry System: 2-Cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite(102691-36-1)

Safety Data

• Hazard Codes: Xi,Xn
• 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
• HazardClass: 8
• PackingGroup: I
• Hazardous Substances Data: 102691-36-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear to Cloudy Colourless Liquid

Uses

Different sources of media describe the Uses of 102691-36-1 differently. You can refer to the following data:
1. Reagent for synthesizing phosphitylated nucleotides.1
2. 2-Cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite was used:in preparation of prosphoramidite reagent, required for synthesis of 12-mer oligodeoxynucleotideas phosphorylating agent in synthesis of 1,2-diacyl-sn-glycerophosphatidylserinein situ preparation of deoxyribonucleoside phosphoramiditesin 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)-thymineas reagent for synthesizing phosphitylated nucleotides

Upstream product

• 108-18-9 diisopropylamine 
• 109-78-4 3-Hydroxypropionitrile 
• 7719-12-2 phosphorus trichloride 
• 56183-63-2 bis(diisopropylamino)chlorophosphine 
• 76101-30-9 2-cyanoethyl phosphorodichloridite 
• 25152-20-9 5'-amino-5'-deoxythymidine 

Downstream Products

• 102690-88-0 bis(2-cyanoethyl) diisopropylamidophosphite 
• 108549-22-0 (p-chlorobenzyloxy)(2-cyanoethyl)(diisopropylamino)phosphine 
• 171285-25-9 (2-cyanoethyl) <2,2-bis(ethoxycarbonyl)-3-(4,4'-dimethoxytrityloxy)propyl-1> N,N-diisopropylphosphoramidite 
• 155831-90-6 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 

Relevant articles and documents

83. Nucleotide Coupling in Reverse Micelles

Nucleotide coupling was investigated in reverse micelles formed by (cetyl)trimethylammonium bromide (CTAB), in hexane/pentan-1-ol.In particular, the coupling of 2'-deoxy-5'-O-methylcytidine 3'-O-phosphate, prepared by phosphoramidite chemistry, with 5'-amino-5'-deoxythymidine was studied in the presence of a H2O-soluble carbodiimide at w0 = 11 and 22 (w0 = /).The effect of w0 on the reaction rate was investigated.A solid-phase strategy was developed for the synthesis of 2'-deoxy-5'-O-methyl-cytidyl-(3'-5')-5'-amino-5'-deoxythymidine.The nucleotide coupling yielding the expected product occurred readily in reverse micelles, and this is discussed in connection with the micelle self-replication program.

Voriconazole phosphorylcholine ester inner salt intermediates, preparation method and method for preparing voriconazole phosphorylcholine ester inner salt

The invention relates to the field of pharmaceutical chemicals, and discloses a plurality of voriconazole phosphorylcholine ester inner salt intermediates, voriconazole phosphorylcholine ester inner salts and a preparation method thereof, and the preparation method specifically comprises the following steps: carrying out oxidation reaction on a compound as shown in a formula II to prepare a compound as shown in a formula IV; dissolving the intermediate shown in the formula IV in a reaction solvent, and controlling the temperature to react for a certain time; then adding a hydrolytic agent, and purifying to obtain a voriconazole phosphorylcholine ester inner salt intermediate V shown as a formula V; and preparing the voriconazole phosphorylcholine ester inner salt as shown in the formula I from the intermediate as shown in the formula V under the action of an acid-binding agent. The obtained intermediates are good in purity and high in yield; the finally prepared voriconazole phosphorylcholine ester inner salt finished product is high in yield, and the purity is up to 99.5% or above; the preparation method of the intermediate is simple and convenient to operate, mature, reliable, short in reaction route, easily available in raw materials and suitable for large-scale industrial production.

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.