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393835

Sigma-Aldrich

o-Xylylene N,N-diethylphosphoramidite

technical grade

Synonym(s):

3-(Diethylamino)-1,5-dihydro-2,4,3-benzodioxaphosphepine

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About This Item

Empirical Formula (Hill Notation):
C12H18NO2P
CAS Number:
82372-35-8
Molecular Weight:
239.25
Beilstein:
3590087
MDL number:
MFCD00192025
UNSPSC Code:
12352100
PubChem Substance ID:
24864545
NACRES:
NA.22

grade

technical grade

form

liquid

refractive index

n20/D 1.541 (lit.)

bp

95-96 °C/0.1 mmHg (lit.)

solubility

THF: soluble
acetonitrile: soluble
cold water: insoluble
dichloromethane: soluble

density

1.109 g/mL at 25 °C (lit.)

SMILES string

CCN(CC)P1OCc2ccccc2CO1

InChI

1S/C12H18NO2P/c1-3-13(4-2)16-14-9-11-7-5-6-8-12(11)10-15-16/h5-8H,3-4,9-10H2,1-2H3

InChI key

JDAKPBBWYIWXJF-UHFFFAOYSA-N

Related Categories

Application

o-Xylylene N,N-diethylphosphoramidite (N,N-diethyl-1,5-dihydro-2,4,3-benzodioxaphosphepin-3-amine) may be used in the synthesis of the following:
  • bicyclic glycosyl phosphite
  • pentakis(o-xylylene phosphate)
  • o-xylylene alkyl phosphites

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °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’.

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Utilization of O-xylylene N,N-diethylphosphoramidite for the synthesis of phosphoric diesters.
Watanabe Y, et al
Tetrahedron Letters, 33(10), 1313-1316 (1992)
Honglu Zhang et al.
Organic letters, 11(7), 1551-1554 (2009-03-04)
The phosphorylated inositol diphosphates, including the diphosphoinositol pentakisphosphate regioisomers, play critical roles in signal transduction and cellular regulation. In particular, the IP(7) isomer 5-PP-Ins(1,2,3,4,6)P(5) is implicated in a nonenzymatic phosphate transfer converting a protein serine phosphate residue to a serine
Synergistic inhibition of human Synergistic inhibition of human α-1, 3-fucosyltransferase V.
Qiao L, et al
Journal of the American Chemical Society, 118(33), 7653-7662 (1996)

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