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Key Documents

638072

Sigma-Aldrich

SPhos

greener alternative

98%

동의어(들):

SPhos, 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos

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About This Item

실험식(Hill 표기법):
C26H35O2P
CAS Number:
Molecular Weight:
410.53
MDL number:
UNSPSC 코드:
12352128
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

98%

반응 적합성

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Kumada Coupling

reagent type: ligand
reaction type: Negishi Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

환경친화적 대안 제품 점수

old score: 10
new score: 1
Find out more about DOZN™ Scoring

환경친화적 대안 제품 특성

Waste Prevention
Less Hazardous Chemical Syntheses
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

164-166 °C (lit.)

작용기

phosphine

환경친화적 대안 카테고리

SMILES string

COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI

1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3

InChI key

VNFWTIYUKDMAOP-UHFFFAOYSA-N

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일반 설명

SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Less Hazardous Chemical Syntheses” and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

애플리케이션

Learn more about Buchwald Phosphine Ligands

For small scale and high throughput uses, product is also available as ChemBeads (932191)
SPhos may be used as a ligand in the following processes:
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
  • Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation.
Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

법적 정보

Usage subject to Patents: US 6307087; EP 1097158; JP 5758844; CA 2336691

관련 제품

제품 번호
설명
가격

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


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시험 성적서(COA)

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이 제품을 이미 가지고 계십니까?

문서 라이브러리에서 최근에 구매한 제품에 대한 문서를 찾아보세요.

문서 라이브러리 방문

Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRa agonists.
Hioki H, et al.
Bioorganic & Medicinal Chemistry Letters, 19(3), 738-741 (2009)
Seel S, et al.
Journal of the American Chemical Society, 133(13), 4774-4777 (2011)
Sustainable Fe?ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water
Handa, Sachin, et al.
Science, 349.6252, 1087-1091 (2015)
Pd-catalyzed Suzuki?Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
Altman, Ryan A., and Stephen L. Buchwald
Nature Protocols, 2.12 (2007)
A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates
Knapp, David M., Eric P. Gillis, and Martin D. Burke
Journal of the American Chemical Society, 131.20, 6961-6963 (2009)

문서

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

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