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439606

Sigma-Aldrich

Diallyl N,N-diisopropylphosphoramidite

Synonym(s):
N,N-Bis(1-methylethyl)phosphoramidous acid di-2-propenyl ester, Diallyloxy(diisopropylamino)phosphine
Linear Formula:
[(CH3)2CH]2NP(OCH2CH=CH2)2
CAS Number:
Molecular Weight:
245.30
Beilstein:
4383514
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

refractive index

n20/D 1.456 (lit.)

bp

130 °C (lit.)

density

0.928 g/mL at 25 °C (lit.)

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

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Application

Diallyl N,N-diisopropylphosphoramidite may be employed as phophorylating reagent in the following studies:
  • Preparation of peptide substrates.[1]
  • Preparation of rhodamine dyes with phosphorylated CH2OH sites.[2]
  • Synthesis of 3-[4-(bis-allyloxy-phosphoryloxy)-2(R)-hydroxy-3,3-dimethyl-butyrylamino]-thiopropionic acid-S-propylester.[3]
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

Packaging

1 g in glass bottle

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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