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Merck

677264

APhos

95%, solid

Synonym(s):

(4-(N,N-Dimethylamino)phenyl)di-tert-butyl phosphine, A-taPhos, [4-(Dimethylamino)phenyl]bis(tert-butyl)phosphine

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About This Item

Empirical Formula (Hill Notation):
C16H28NP
CAS Number:
Molecular Weight:
265.37
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

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Product Name

APhos, 95%

Quality Level

Assay

95%

form

solid

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
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: catalyst
reagent type: ligand
reaction type: Cross Couplings

mp

57-61 °C

functional group

phosphine

SMILES string

CN(C)c1ccc(cc1)P(C(C)(C)C)C(C)(C)C

InChI

1S/C16H28NP/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8/h9-12H,1-8H3

InChI key

IQTHEAQKKVAXGV-UHFFFAOYSA-N

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This Item
759171900331253189
assay

95%

assay

98%

assay

95%

assay

97%

reaction suitability

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

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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: Cross Couplings

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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: catalyst
reaction type: Cross Couplings, reagent type: ligand
reaction type: click chemistry

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

form

solid

form

solid

form

solid

form

liquid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

mp

57-61 °C

mp

108-113 °C

mp

113-118 °C

mp

-

Application

Ligand used to prepare a palladium dichloride catalyst (678740) on treatment with PdCl2(COD). The catalyst effectively cross-couples aryl boronic acids with heteroaryl chlorides.[1]

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8B - Non-combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Anil S Guram et al.
Organic letters, 8(9), 1787-1789 (2006-04-21)
[reaction: see text] New air-stable PdCl(2){P(t)Bu(2)(p-R-Ph)}(2) (R = H, NMe(2), CF(3),) complexes represent simple, general, and efficient catalysts for the Suzuki-Miyaura cross-coupling reactions of aryl halides including five-membered heteroaryl halides and heteroatom-substituted six-membered heteroaryl chlorides with a diverse range of

Articles

Ligand used to prepare a palladium dichloride catalyst on treatment with PdCl2(COD). The catalyst effectively cross-couples aryl boronic acids with heteroaryl chlorides.

Related Content

แพลตฟอร์ม Catalexis ช่วยเพิ่มการเร่งปฏิกิริยาด้วยการเพิ่มประสิทธิภาพการเลือกตัวเร่งปฏิกิริยาแบบดิจิทัลเพื่อระบุเอ็น phosphine ที่มีประสิทธิภาพมากที่สุดสำหรับปฏิกิริยาข้ามข้อต่อ

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Explore reliable, premium grade catalysis materials for your pharma or industrial project. Specialty chemicals and formulations are available in bulk quantities and volumes from a few grams to multi-metric tons with complete documentation to simplify your leap from development to commercialization.

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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