DIBENZYL DIISOPROPYLPHOSPHORAMIDITE Chemical Properties

Boiling point:

130 °C0.55 mm Hg(lit.)

Density 

1.028 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.535(lit.)

Flash point:

158 °F

storage temp. 

2-8°C

solubility 

Soluble in chloroform.

pka

4.50±0.70(Predicted)

form 

Oil

color 

Clear Colourless

Water Solubility 

THF: soluble(lit.)
acetonitrile: soluble(lit.)
cold water: insoluble(lit.)
dichloromethane: soluble(lit.)

Sensitive 

Moisture Sensitive

BRN 

3616864

InChI

InChI=1S/C20H28NO2P/c1-17(2)21(18(3)4)24(22-15-19-11-7-5-8-12-19)23-16-20-13-9-6-10-14-20/h5-14,17-18H,15-16H2,1-4H3

InChIKey

ANPWLBTUUNFQIO-UHFFFAOYSA-N

SMILES

P(N(C(C)C)C(C)C)(OCC1=CC=CC=C1)OCC1=CC=CC=C1

CAS DataBase Reference

108549-23-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

3-10-21

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DIBENZYL DIISOPROPYLPHOSPHORAMIDITE Usage And Synthesis

Description

Dibenzyl diisopropylphosphoramidite is a versatile phosphitylating agent.

Chemical Properties

Clear Colourless Liquid

Uses

A versatile phosphitylating agent

Uses

Dibenzyl N,N-diisopropylphosphoramidite may be used for the preparation of phosphopeptides. It is used for the synthesis of a GDP (guanosine diphosphate) analog, SML-8-73-1. It is useful for nucleotide coupling.

Synthesis

General procedure for the synthesis of diphenyl N,N'-diisopropylphosphoramidite from dichloro-N,N-diisopropylphosphoramidite and benzyl alcohol: 42 g (207.92 mmol) of dichloro-N,N-diisopropylphosphoramidite was placed in a 500 mL round-bottomed flask, and 300 mL of anhydrous tetrahydrofuran was added, and dissolved by stirring. Subsequently 66 mL (455.44 mmol, 46 g) of anhydrous triethylamine was added. The flask was cooled to 0°C in an ice-salt bath and 45 mL (416.67 mmol, 45 g) of anhydrous benzyl alcohol was added slowly and dropwise under nitrogen protection, keeping the reaction temperature close to 0°C. Upon completion of the reaction, the suspension was added dropwise and the formation of a white solid was observed. The reaction mixture was removed from the ice bath, returned to room temperature and stirring was continued for 3 hours. After stopping stirring, it was allowed to stand for 10 minutes for filtration and the solid was washed with tetrahydrofuran. The filtrate was collected and the solvent was removed by rotary evaporation to give the crude product. Without column chromatographic purification, 54.0 g of the oily product was obtained directly in 75.3% yield.

References

[1] Tetrahedron, 1991, vol. 47, # 26, p. 4709 - 4722
[2] Patent: CN102977145, 2017, B. Location in patent: Paragraph 0196; 0197
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 11, p. 1239 - 1246
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 23, p. 3918 - 3927
[5] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7719 - 7726

DIBENZYL DIISOPROPYLPHOSPHORAMIDITE(108549-23-1)Related Product Information

• N-Isopropylbenzylamine
• N-Methyl-2-pyrrolidone
• Zidovudine
• DIETHYL N,N-DIISOPROPYLPHOSPHORAMIDITE
• BIS[1-(2-NITROPHENYL)ETHYL] N,N-DIISOPROPYLPHOSPHORAMIDITE
• DIBENZYL N,N-DIMETHYLPHOSPHORAMIDITE
• Di-p-Chlorobenzyl N,N-Diisopropylphosphoramidite
• DIBENZYL DIETHYLPHOSPHORAMIDITE
• DIBENZYL DIISOPROPYLPHOSPHORAMIDITE