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454494

Sigma-Aldrich

tert-Butyl tetraisopropylphosphorodiamidite

95%

Synonym(s):

1,1-Dimethylethyl N,N,N′,N′-tetrakis(1-methylethyl)phosphorodiamidite

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About This Item

Linear Formula:
[[(CH3)2CH]2N]2POC(CH3)3
CAS Number:
137348-88-0
Molecular Weight:
304.45
MDL number:
MFCD00674022
UNSPSC Code:
12352100
PubChem Substance ID:
24868924
NACRES:
NA.22

Assay

95%

form

solid

mp

67-74 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)N(C(C)C)P(OC(C)(C)C)N(C(C)C)C(C)C

InChI

1S/C16H37N2OP/c1-12(2)17(13(3)4)20(19-16(9,10)11)18(14(5)6)15(7)8/h12-15H,1-11H3

InChI key

PSFUFSJCFKUIIG-UHFFFAOYSA-N

General description

Tert-butyl tetraisopropylphosphorodiamidite is an effective ligand for palladium-catalyzed Buchwald–Hartwig amination of aryl- and heteroaryl chlorides and bromides widely used in the synthesis of industrially significant aryl- and heteroarylamines due to its accessibility and air-stability.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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, 2070-2076 (2014)
Palladium-Catalysed Amination of Aryl-and Heteroaryl Halides Using tert-Butyl Tetraisopropylphosphorodiamidite as an Easily Accessible and Air-Stable Ligand.
Roiban G-D, et al.
European Journal of Organic Chemistry, 10, 2070-2076 (2014)
Stéphane Dumas et al.
Investigative radiology, 45(10), 600-612 (2010-09-03)
The donor atoms that bind to gadolinium in contrast agents influence inner-sphere water exchange and electronic relaxation, both of which determine observed relaxivity. The effect of these molecular parameters on relaxivity is greatest when the contrast agent is protein bound.

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