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911402

(CyPAd-DalPhos)NiCl(otol)

Name: (CyPAd-DalPhos)NiCl(otol)
Brand: ALDRICH

≥95%, powder

Synonym(s):

8-(2-(Dicyclohexylphosphaneyl)phenyl)-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantane nickel(II) o-tolyl chloride

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About This Item

Empirical Formula (Hill Notation):

C₃₅H₄₉ClNiO₃P₂

CAS Number:

2115838-60-1

Molecular Weight:

673.86

MDL number:

MFCD32205518

NACRES:

NA.22

UNSPSC Code:

12352200

Assay:

≥95%

Form:

powder

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Properties

Product Name

(CyPAd-DalPhos)NiCl(otol), ≥95%

assay

≥95%

form

powder

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

mp

193-197 °C

Description

Application

(CyPAd-DalPhos)NiCl(otol) is an air stable precatalyst developed in the Stradiotto lab used for C(sp²)-O coupling and N-arylation reactions.

Other Notes

Technology Spotlight: DalPhos ligands

Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C–O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols

Nickel-Catalyzed N-Arylation of Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl (Pseudo)halides at Room Temperature

pictograms

GHS08,GHS07,GHS09

signalword

Danger

hcodes

H302 + H312 + H332,H341,H351,H372,H410

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 Inhalation - Muta. 2 - STOT RE 1 Inhalation

target_organs

Respiratory Tract,Skin

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable

pcodes

P273 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313

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Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols.

Preston M MacQueen et al.

Journal of the American Chemical Society, 140(15), 5023-5027 (2018-03-31)

The use of (L)Ni( o-tolyl)Cl precatalysts (L = PAd-DalPhos or CyPAd-DalPhos) enables the C( sp2)-O cross-coupling of primary, secondary, or tertiary aliphatic alcohols with (hetero)aryl electrophiles, including unprecedented examples of such nickel-catalyzed transformations employing (hetero)aryl chlorides, sulfonates, and pivalates. In

Nickel-Catalyzed N-Arylation of Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl (Pseudo)halides at Room Temperature

Tassone J P, et al.

ACS Catalysis, 7(9), 6048-6059 (2017)