N-BOC-IMINO-(TRIPHENYL)PHOSPHORANE Chemical Properties

Melting point:

147.0 to 151.0 °C

Boiling point:

491.8±28.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C23H24NO2P/c1-23(2,3)26-22(25)24-27(19-13-7-4-8-14-19,20-15-9-5-10-16-20)21-17-11-6-12-18-21/h4-18H,1-3H3

InChIKey

KNXPVXCUELYHDM-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

CAS DataBase Reference

68014-21-1(CAS DataBase Reference)

Safety Information

Risk Statements 

23/34/35

Safety Statements 

36/37/39

RIDADR 

1759

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29319090

N-BOC-IMINO-(TRIPHENYL)PHOSPHORANE Usage And Synthesis

Uses

tert-Butyl (Triphenylphosphoranylidene)carbamate is used in the preparation of ketimines.

Synthesis

Step 1: Synthesis of triphenyl (tert-butoxycarbonylimino) orthophosphine 25 g (0.19 mol) of tert-butylhydrazinyl formate was dissolved in a mixed solution of 80 mL of acetic acid and 160 mL of water, and 15 g (0.22 mol) of sodium nitrite was added in batches under ice bath cooling conditions. The reaction solution was continuously stirred under ice bath cooling for 30 minutes and subsequently extracted with 250 mL of diisopropyl ether. The organic layer was washed sequentially with 200 mL of saturated aqueous sodium bicarbonate and 100 mL of saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered to give an ether solution of tert-butyl carbonate. To this ether solution was added 49.6 g (0.189 mol) of triphenylphosphine under cooling in an ice bath, and the reaction mixture was stirred at room temperature for 1 hour. The precipitated solid was collected by filtration and washed with water. 200 mL of hexane was added and dried under reduced pressure to give 67 g of the target product triphenyl(tert-butoxycarbonylimino)orthophosphine in the form of white crystals.

References

[1] Journal of Organic Chemistry, 1993, vol. 58, # 18, p. 4791 - 4793
[2] Chemistry - A European Journal, 1997, vol. 3, # 10, p. 1691 - 1709
[3] Synthesis, 2002, # 1, p. 63 - 66
[4] Patent: US2013/253204, 2013, A1. Location in patent: Paragraph 0196; 0197
[5] Patent: US9212348, 2015, B2. Location in patent: Page/Page column 169

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