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Merck
CN

04907

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

≥99.0%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C28H26NO2P
CAS Number:
500103-26-4
Molecular Weight:
439.49
NACRES:
NA.22
PubChem Substance ID:
329747990
UNSPSC Code:
12352005
MDL number:
MFCD08277032

Key Documents

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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

SMILES string

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

InChI key

JISGHECLGYELKD-UHFFFAOYSA-N

assay

≥99.0%

optical purity

enantiomeric ratio: ≥97.0:3.0

reaction suitability

reaction type: click chemistry

mp

99-102 °C

functional group

amine, phenyl

Quality Level

100

Application

N,N-Bis-[(R)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine can be used:
  • In the asymmetric hydrovinylation of 1,3-diene.
  • In the 1,4-asymmetric conjugate addition of 3-substituted cyclohexenones catalyzed by copper.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

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Asymmetric Sequential Cu-Catalyzed 1, 6/1, 4-Conjugate Additions of Hard Nucleophiles to Cyclic Dienones: Determination of Absolute Configurations and Origins of Enantioselectivity
Blons C, et al.
Chemistry?A European Journal , 23(31), 7515-7525 (2017)
Broadly Applicable Stereoselective Syntheses of Serrulatane, Amphilectane Diterpenes, and Their Diastereoisomeric Congeners Using Asymmetric Hydrovinylation for Absolute Stereochemical Control
Tenneti S, et al.
Journal of the American Chemical Society, 140(31), 9868-9881 (2018)

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