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Merck
CN

301558

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:
13716-10-4
Molecular Weight:
180.66
PubChem Substance ID:
24858196
UNSPSC Code:
12352001
MDL number:
MFCD00008815

Key Documents

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Product Name

Di-tert-butylchlorophosphine, 96%

InChI

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

SMILES string

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

InChI key

MCRSZLVSRGTMIH-UHFFFAOYSA-N

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

Quality Level

100

Related Categories

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
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ5743
MKCX8646
MKCV3993
MKCW5406
MKCW4006

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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

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