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Bis-(triphenylphosphino)-cuprous borohydride

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Bis-(triphenylphosphino)-cuprous borohydride Basic information

Product Name:
Bis-(triphenylphosphino)-cuprous borohydride
Synonyms:
  • Bis(triphenylphosphine)copper Tetrahydroborate, (PPh3)2CuBH4
  • BIS(TRIPHENYLPHOSPHINE)COPPER(I) BOROHYD
  • Copper,[tetrahydroborato(1-)-kH,kH']bis(triphenylphosphine)-,(T-4)-
  • BIS(TRIPHENYLPHOSPHINE)COPPER(I) BOROHYDRIDE
  • BIS(TRIPHENYLPHOSPHINE)COPPER(I) TETRAHYDRIDOBORATE
  • BIS(TRIPHENYLPHOSPHINE)COPPER TETRAHYDROBORATE
  • bis-(triphenylphosphino)-cuprous borohydride
  • Copper bis(trimethylphosphine)(tetrahydroborate)
CAS:
16903-61-0
MF:
2C18H15P.Cu.BH4
MW:
602.97
EINECS:
240-951-0
Product Categories:
  • Cu
  • B (Classes of Boron Compounds)
  • Classes of Metal Compounds
  • Cu (Copper) Compounds
  • Reduction
  • Synthetic Organic Chemistry
  • Tetrahydroborates
  • Transition Metal Compounds
Mol File:
16903-61-0.mol
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Bis-(triphenylphosphino)-cuprous borohydride Chemical Properties

Melting point:
164 °C (dec.)(lit.)
storage temp. 
Store below +30°C.
solubility 
sol THF, CHCl3, CH2Cl2, benzene; slightly sol acetone; insol ether, ethanol, and water.
form 
powder to crystal
color 
White to Almost white
Sensitive 
Moisture Sensitive
Exposure limits
ACGIH: TWA 1 mg/m3
NIOSH: IDLH 100 mg/m3; TWA 1 mg/m3
CAS DataBase Reference
16903-61-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-15
Safety Statements 
26-60-43-37-7/8
RIDADR 
2813
WGK Germany 
3
9-21
HazardClass 
4.3
PackingGroup 
III
HS Code 
29319019

MSDS

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Bis-(triphenylphosphino)-cuprous borohydride Usage And Synthesis

Uses

Bis(triphenylphosphine)copper tetrahydroborate (CAS# 16903-61-0) is an organometallic catalyst used in the enantioseletive radical oxytrifluoromethylation of alkenes with alcohols. Bis(triphenylphosphine)copper tetrahydroborate is also used in the preparation of tungsten, ruthenium and copper cluster complexes.

Preparation

Bis-(triphenylphosphino)-cuprous borohydride is prepared by adding Copper(I) Chloride to a stirring solution of 2 equiv of Triphenylphosphine in  chloroform. Once the copper chloride is dissolved the mixture is treated with a suspension of Sodium  Borohydride (1 equiv) in ethanol for at least 15 min to ensure complete reaction. The solution is washed with  water and dried over anhydrous magnesium sulfate. Diethyl ether is added to precipitate the reagent as fine white  needles (90% yield).

Application

Bis-(triphenylphosphino)-cuprous borohydride selectively reduces acyl chlorides to aldehydes, tosyl and triphenylsulfonyl hydrazones to alkanes, aldehydes and ketones to alcohols, and aromatic azides to anilines.

reaction suitability

reagent type: reductant

storage

Stable to air and water. It should be handled in a well-ventilated hood;  contact with the eyes and skin should be avoided.

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