Skip to Content
Merck
All Photos(1)

Documents

439606

Sigma-Aldrich

Diallyl N,N-diisopropylphosphoramidite

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

form

liquid

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

Looking for similar products? Visit Product Comparison Guide

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 Statements

H226,H315,H319,H335

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Lutz Tautz et al.
European journal of organic chemistry, 2010(9), 1728-1735 (2010-03-01)
Co-translational myristoylation of the N-terminal glycine residue of diverse signaling proteins is required for membrane attachment and proper function of these molecules. The transfer of myristate from myristoyl-coenzyme A (myr-CoA) is catalyzed by the enzyme N-myristoyltransferase (Nmt). Nmt has been
Solid-phase synthesis of adenosine phosphopeptides as potential bisubstrate inhibitors of protein kinases.
Medzihradszky D, et al.
Journal of the American Chemical Society, 116(21), 9413-9419 (1994)
Kirill Kolmakov et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(41), 12986-12998 (2012-09-13)
Fluorescent dyes emitting red light are frequently used in conventional and super-resolution microscopy of biological samples, although the variety of the useful dyes is limited. We describe the synthesis of rhodamine-based fluorescent dyes with absorption and emission maxima in the

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service