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Merck
CN

04907

Sigma-Aldrich

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
MDL number:
MFCD08277032
UNSPSC Code:
12352005
PubChem Substance ID:
329747990
NACRES:
NA.22

Key Documents

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Quality Level

100

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

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-[(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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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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