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439606

Diallyl N,N-diisopropylphosphoramidite

Synonym(s):

N,N-Bis(1-methylethyl)phosphoramidous acid di-2-propenyl ester, Diallyloxy(diisopropylamino)phosphine

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About This Item

Linear Formula:
[(CH3)2CH]2NP(OCH2CH=CH2)2
CAS Number:
126429-21-8
Molecular Weight:
245.30
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24867522
MDL number:
MFCD00216647
Beilstein/REAXYS Number:
4383514
Form:
liquid
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form

liquid

Quality Segment

refractive index

n20/D 1.456 (lit.)

bp

130 °C (lit.)

density

0.928 g/mL at 25 °C (lit.)

functional group

amine

storage temp.

2-8°C

SMILES string

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

InChI

1S/C12H24NO2P/c1-7-9-14-16(15-10-8-2)13(11(3)4)12(5)6/h7-8,11-12H,1-2,9-10H2,3-6H3

InChI key

QBLCHHSGJTUNSJ-UHFFFAOYSA-N

Application

Diallyl N,N-diisopropylphosphoramidite may be employed as phophorylating reagent in the following studies:
  • Preparation of peptide substrates.
  • Preparation of rhodamine dyes with phosphorylated CH2OH sites.
  • Synthesis of 3-[4-(bis-allyloxy-phosphoryloxy)-2(R)-hydroxy-3,3-dimethyl-butyrylamino]-thiopropionic acid-S-propylester.
Precursor involved in the synthesis of pharmacologically active molecules including:
  • Selective orally active S1P1 agonists
  • Water-soluble prodrugs of triazole CS-758 with antifungal activity
  • Fostriecin analogs as antitumor agents

Reactant involved in:
  • Phosphitylation of alcohols
  • Deallylation for the synthesis of nucleoside phosphoramidite
  • Posphitylation and stereoselective Pudovik rearrangement

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class

3 - Flammable liquids

WGK

WGK 3

Flash Point (°F)

89.6 °F - closed cup

Flash Point (°C)

32 °C - closed cup

PPE (personal protective equipment)

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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