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301558

Sigma-Aldrich

Di-tert-butylchlorophosphine

96%, liquid

Synonym(s):

P, P-bis(1 1-dimethylethyl), Phosphinous chloride

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About This Item

Linear Formula:
[(CH3)3C]2PCl
CAS Number:
Molecular Weight:
180.66
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:

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Product Name

Di-tert-butylchlorophosphine, 96%

Quality Level

assay

96%

form

liquid

reaction suitability

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

refractive index

n20/D 1.482 (lit.)

bp

48 °C/3 mmHg (lit.)

density

0.951 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CC(C)(C)P(Cl)C(C)(C)C

InChI

1S/C8H18ClP/c1-7(2,3)10(9)8(4,5)6/h1-6H3

InChI key

MCRSZLVSRGTMIH-UHFFFAOYSA-N

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This Item
381020707230631493
reaction suitability

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

reaction suitability

-

reaction suitability

-

assay

96%

assay

98%

assay

-

assay

97%

form

liquid

form

-

form

liquid

form

solid

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

bp

48 °C/3 mmHg (lit.)

bp

-

bp

-

bp

-

General description

Di-tert-butylchlorophosphine belongs to the class of phosphine ligands. It is used for cross-coupling reactions because of the flexibility of its electronic and steric properties. It plays a key role in stabilizing and activating the central metal atom and is used in reactions such as transition metal-catalyzed C-O, C-N, and C-C bond-forming reactions.

Application

Di-tert-butylchlorophosphine can be used as a ligand in:      
  • The Pd-catalyzed amination reaction with aryl halides.      
  • The Pd-catalyzed Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides and chlorides.

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Jesudoss V Kingston et al.
The Journal of organic chemistry, 72(8), 2816-2822 (2007-03-24)
Pro-azaphosphatrane 1a [P(iBuNCH2CH2)3N] reacts with iodine under mild conditions to give [IP(iBuNCH2CH2)3N]I in excellent yield, which on subsequent reaction with ammonia followed by deprotonation with KOtBu provided HN=P(iBuNCH2CH2)3N (3a) in quantitative yield. Reaction of 3a with R'2PCl afforded sterically bulky

Related Content

Phosphine Ligand Application Guide

Questions

1–2 of 2 Questions  
  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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