692980

Sigma-Aldrich

(S)-DTBM-SEGPHOS®

≥94%

Synonym(s):
(S)-(+)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole
Empirical Formula (Hill Notation):
C74H100O8P2
CAS Number:
Molecular Weight:
1179.53
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥94%

SMILES string

COc1c(cc(cc1C(C)(C)C)P(c2cc(c(OC)c(c2)C(C)(C)C)C(C)(C)C)c3ccc4OCOc4c3-c5c6OCOc6ccc5P(c7cc(c(OC)c(c7)C(C)(C)C)C(C)(C)C)c8cc(c(OC)c(c8)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI

1S/C74H100O8P2/c1-67(2,3)47-33-43(34-48(61(47)75-25)68(4,5)6)83(44-35-49(69(7,8)9)62(76-26)50(36-44)70(10,11)12)57-31-29-55-65(81-41-79-55)59(57)60-58(32-30-56-66(60)82-42-80-56)84(45-37-51(71(13,14)15)63(77-27)52(38-45)72(16,17)18)46-39-53(73(19,20)21)64(78-28)54(40-46)74(22,23)24/h29-40H,41-42H2,1-28H3

InChI key

ZNORAFJUESSLTM-UHFFFAOYSA-N

Related Categories

Application

Catalytic ligand for:
  • Enantioselective synthesis of secondary allylic alcohols via enantioselective reductions of α,β-unsaturated ketones
  • Stereoselective preparation of cyclohexanone derivatives via rhodium-catalyzed rearrangement of allyl or allenic cyclobutanols
  • Cu-catalyzed asymmetric conjugate reduction of beta-substituted unsaturated phosphonates to give optically active beta-stereogenic alkylphosphonates
  • Asymmetric synthesis of cyclohexenones via Rh-catalyzed desymmetrization through enantioselective C-C bond activation and ring expansion of allenyl cyclobutanols
  • Enantioselective synthesis and crystal structure of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition

Packaging

1 g in glass bottle
50, 100 mg in glass insert

Legal Information

Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Articles
Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.