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07033

Sigma-Aldrich

N,N-Bis-((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine

≥99.0%

Synonym(s):

(S,S)-N-(5,7-Diox-6-phosphadibenzo[a,c]cyclohepten-6-yl)bis(1-phenylethyl)amine, O,O′-(2,2′-Biphenyldiyl) N,N-bis[(S)-1-phenylethyl]phosphoramidite, BIPOL-A1(S)

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About This Item

Empirical Formula (Hill Notation):
C28H26NO2P
CAS Number:
376355-58-7
Molecular Weight:
439.49
MDL number:
MFCD08277033
UNSPSC Code:
12352005
PubChem Substance ID:
329748328
NACRES:
NA.22

Quality Level

100

assay

≥99.0%

form

powder

optical activity

[α]/D -250±10°, c = 1 in toluene

reaction suitability

reaction type: click chemistry

mp

99-102 °C

SMILES string

C[C@H](N([C@@H](C)c1ccccc1)P2Oc3ccccc3-c4ccccc4O2)c5ccccc5

InChI

1S/C28H26NO2P/c1-21(23-13-5-3-6-14-23)29(22(2)24-15-7-4-8-16-24)32-30-27-19-11-9-17-25(27)26-18-10-12-20-28(26)31-32/h3-22H,1-2H3

InChI key

JISGHECLGYELKD-UHFFFAOYSA-N

Application

N,N-Bis-((S)-1-phenylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine can be used:
  • In the iridium catalyzed allylic arylation.
  • To prepare a copper complex (Cu2X2L3), which is used to detect the transmetalation intermediates in asymmetric addition reactions using ZnEt2.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
1206180V
1206180

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Elusive Transmetalation Intermediate in Copper-Catalyzed Conjugate Additions: Direct NMR Detection of an Ethyl Group Attached to a Binuclear Phosphoramidite Copper Complex
von Rekowski F, et al.
Journal of the American Chemical Society, 136(32), 11389-11395 (2014)
Enantioselective Iridium-Catalyzed Allylic Arylation
Polet D, et al.
Chemistry?A European Journal , 15(5), 1205-1216 (2009)

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