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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

Quality Level

100

Assay

95%

form

solid

mp

67-74 °C (lit.)

functional group

amine

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT5472
MKCQ8348
MKCF7637
MKBW8230V
MKBH6163V

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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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