(2S,3S)-4-(Anthracen-9-yl)-3-(tert-butyl)-2-ethyl-2,3-dihydrobenzo[d][1,3]oxaphosphole

Name: (2S,3S)-4-(Anthracen-9-yl)-3-(tert-butyl)-2-ethyl-2,3-dihydrobenzo[d][1,3]oxaphosphole
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CAS No. 1884594-03-9
Cat. No. CS-0091112
Purity≥97%
MDL No.None

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(2S,3S)-4-(Anthracen-9-yl)-3-(tert-butyl)-2-ethyl-2,3-dihydrobenzo[d][1,3]oxaphosphole|CS-0091112

Structure of 1884594-03-9

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General Information

CAS No. 1884594-03-9
Cat. No. CS-0091112
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₇H₂₇OP
Molecular Weight 398.48
Synonym(s) ZJ-0146/(2S,3S)-4-(ANTHRACEN-9-YL)3-(TERT-BUTYL)-2-ETHYL-2,3-DIHYDROBENZO[D][1,3]OXAPHOSPHOLE
SMILES CC[C@@H]1[P@@](C(C)(C)C)C2=C(C3=C(C=CC=C4)C4=CC5=C3C=CC=C5)C=CC=C2O1

Description

This chiral phosphole features a sterically shielded tert-butyl group and an anthracen-9-yl moiety, delivering enhanced stability and defined stereochemistry. The ethyl substituent at the 2-position improves solubility and facilitates handling under standard conditions. Designed for asymmetric synthesis, this bench-stable oxaphosphole integrates readily into catalytic systems requiring precise spatial control.

Application

(2S,3S)-4-(Anthracen-9-yl)-3-(tert-butyl)-2-ethyl-2,3-dihydrobenzo[d][1,3]oxaphosphole serves as a chiral, sterically encumbered phosphole ligand that facilitates asymmetric transition-metal-catalyzed transformations. Its rigid fused oxaphosphole core and bulky tert-butyl group enhance stereocontrol in palladium- and nickel-catalyzed cross-couplings. The anthracenyl moiety contributes π-conjugation and electronic modulation, while the ethyl substituent improves solubility and handling. This ligand demonstrates robust performance in standard Buchwald–Hartwig amination protocols and exhibits high bench stability under ambient conditions.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

TPSA 9.23
LogP 7.6942
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 2

Key Words

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(2S,3S)-4-(Anthracen-9-yl)-3-(tert-butyl)-2-ethyl-2,3-dihydrobenzo[d][1,3]oxaphosphole

CAS No. 1884594-03-9

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