{4-[5-(diphenylphosphanyl)-2H-1,3-benzodioxol-4-yl]-2H-1,3-benzodioxol-5-yl}diphenylphosphane

• ChemBase ID: 140882
• Molecular Formular: C38H28O4P2
• Molecular Mass: 610.574042
• Monoisotopic Mass: 610.14628264
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccc2c(c1c1c(ccc3c1OCO3)P(c1ccccc1)c1ccccc1)OCO2
• Canonical SMILES: c1ccc(cc1)P(c1ccc2c(c1c1c3OCOc3ccc1P(c1ccccc1)c1ccccc1)OCO2)c1ccccc1
• InChI: InChI=1S/C38H28O4P2/c1-5-13-27(14-6-1)43(28-15-7-2-8-16-28)33-23-21-31-37(41-25-39-31)35(33)36-34(24-22-32-38(36)42-26-40-32)44(29-17-9-3-10-18-29)30-19-11-4-12-20-30/h1-24H,25-26H2
• InChIKey: RZZDRSHFIVOQAF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {4-[5-(diphenylphosphanyl)-2H-1,3-benzodioxol-4-yl]-2H-1,3-benzodioxol-5-yl}diphenylphosphane
• IUPAC Traditional name: {4-[5-(diphenylphosphanyl)-2H-1,3-benzodioxol-4-yl]-2H-1,3-benzodioxol-5-yl}diphenylphosphane
• Synonyms: (R)-(+)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole; [4(R)-(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[diphenylphosphine]; (R)-SEGPHOS®; (S)-(-)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole; (S)-SEGPHOS®; (R)-(+)-5,5′-双(二苯基膦)-4,4′-二-1,3-苯并二噁茂; [4(R)-(4,4′-二-1,3-苯并二噁茂)-5,5′-二基]双[二苯基膦]; (S)-(-)-5,5′-双(二苯基膦)-4,4′-二-1,3-苯并二噁茂

Database IDs

• CAS Number: 244261-66-3; 210169-54-3
• MDL Number: MFCD09753005
• PubChem SID: 162235120
• PubChem CID: 11017510

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 9.2196
• LogD (pH = 7.4): 9.2196
• Log P: 9.2196
• Molar Refractivity: 173.8578 cm^3
• Polarizability: 70.072 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 168-172 °C; 231-235 °C
• Optical Rotation: [α]20/D +11°, c = 0.5 in chloroform; [α]20/D -11°, c = 0.5 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥94%
• Empirical Formula (Hill Notation): C38H28O4P2

DETAILS

Sigma Aldrich - 692395

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Catalytic ligand used for:
• Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes
• Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
• Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
• Preparation of chiral silylated homoallylic alcohols and diols by asymmetric addition of alcohols and aldehydes to silylbutadienes catalyzed by ruthenium complexes
• Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
• Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes

Sigma Aldrich - 693006

Packaging
50, 100 mg in glass bottle
Legal Information
Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.
Application
Takasago Ligands and Complexes for Asymmetric Reactions
Chiral biaryl bisphosphine catalytic ligand used for:
• Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
• Stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydes
• Regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives
• Diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex
• Preparation of dihydroisoquinolinones via nickel-catalyzed denitrogenative annulation of benzotriazinones with 1,3-dienes and alkenes
• Stereoselective preparation of indanol derivatives via Rh-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes