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760838

Sigma-Aldrich

Allyl tetraisopropylphosphorodiamidite

95%

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Linear Formula:
[[(CH3)2CH]2N]2POCH2CH=CH2
CAS Number:
108554-72-9
Molecular Weight:
288.41
MDL number:
MFCD00191714
UNSPSC Code:
12352302
PubChem Substance ID:
329766898
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.466 (lit.)
n20/D 1.467

bp

114-117 °C/0.4 mmHg (lit.)

density

0.903 g/mL at 25 °C (lit.)
0.910 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CC(C)N(C(C)C)P(OCC=C)N(C(C)C)C(C)C

InChI

1S/C15H33N2OP/c1-10-11-18-19(16(12(2)3)13(4)5)17(14(6)7)15(8)9/h10,12-15H,1,11H2,2-9H3

InChI key

ZTEGHJIXOZLSOH-UHFFFAOYSA-N

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Application

Allyl tetraisopropylphosphorodiamidite may be used in the total synthesis of (−)-tetrahydrolipstatin, dolabelide C, (-)-salicylihalamides A and B.
Phosphitylation agent used in the preparation of oligonucleotides. Selective deallylation is accomplished by palladium catalysis.

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Description
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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

WGK

WGK 3

Flash Point(F)

188.0 °F

Flash Point(C)

86.67 °C

Regulatory Information

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Total synthesis of dolabelide C: a phosphate-mediated approach.
Hanson PR, et al.
The Journal of Organic Chemistry, 76(11), 4358-4370 (2011)
A concise, phosphate-mediated approach to the total synthesis of (?)-tetrahydrolipstatin.
Venukadasula PK, et al.
Organic Letters, 12(7), 1556-1559 (2010)
Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (?)-Salicylihalamides A and B.
Chegondi R, et al.
The Journal of Organic Chemistry, 76(10), 3909-3916 (2011)

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