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341347

Sigma-Aldrich

Bis(diisopropylamino)chlorophosphine

≥95.0%

Synonym(s):

Chlorobis(N,N-diisopropyl)phosphoramidite, Chlorobis(N,N-diisopropylamino)phosphine, Tetraisopropylphosphorodiamidous chloride

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About This Item

Linear Formula:
[[(CH3)2CH]2N]2PCl
CAS Number:
56183-63-2
Molecular Weight:
266.79
MDL number:
MFCD00061482
UNSPSC Code:
12352001
PubChem Substance ID:
24860930
NACRES:
NA.22

assay

≥95.0%

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

mp

100-104 °C (lit.)

functional group

phosphine

SMILES string

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

InChI

1S/C12H28ClN2P/c1-9(2)14(10(3)4)16(13)15(11(5)6)12(7)8/h9-12H,1-8H3

InChI key

FEHUTHGOLLQBNW-UHFFFAOYSA-N

Application

Bis(diisopropylamino)chlorophosphine has been used in the synthesis of tert-butyl tetraisopropylphosphorodiamidite ligand for palladium-catalyzed Buchwald–Hartwig amination reaction.

It is also can be used to synthesize:
  • acyclic N-phosphonio imine catalyst for selective epoxidations
  • boryl-substituted methylenephosphonium derivatives

Other Notes

Contains varying amounts of diisopropylamine hydrochloride

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Borylated methylenephosphonium salts: precursors of elusive boryl (phosphino) carbenes
Lavigne F, et al.
Journal of the American Chemical Society, 132(26), 8864-8865 (2010)
Novel N-phosphonio imine-catalyzed epoxidation reactions
Prieur D, et al.
Organic Letters, 10(11), 2291-2294 (2008)
Palladium?Catalysed Amination of Aryl?and Heteroaryl Halides Using tert?Butyl Tetraisopropylphosphorodiamidite as an Easily Accessible and Air?Stable Ligand
Roiban GD , et al.
European Journal of Organic Chemistry, 2014(10), 2070-2076 (2014)
Shiyue Fang et al.
Current protocols in nucleic acid chemistry, 82(1), e111-e111 (2020-07-07)
This protocol provides details for the preparation of nucleoside phosphoramidites with 1,3-dithian-2-yl-methyl (Dim) and 1,3-dithian-2-yl-methoxycarbonyl (Dmoc) as protecting groups, and a linker with Dmoc as the cleavable function, then using them for solid phase synthesis of sensitive oligodeoxynucleotides (ODNs). Using

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