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448427

Sigma-Aldrich

(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide

98%

Synonym(s):

(2R,4R)-5,5-Dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide, (R)-(−)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide

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About This Item

Empirical Formula (Hill Notation):
C11H15O4P
CAS Number:
Molecular Weight:
242.21
Beilstein:
4294714
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D −62°, c = 0.5 in methanol

impurities

<5% water

mp

224-227 °C (lit.)

functional group

phenyl
phosphate

storage temp.

2-8°C

SMILES string

CC1(C)COP(O)(=O)O[C@@H]1c2ccccc2

InChI

1S/C11H15O4P/c1-11(2)8-14-16(12,13)15-10(11)9-6-4-3-5-7-9/h3-7,10H,8H2,1-2H3,(H,12,13)/t10-/m1/s1

InChI key

PSZSDCWNBXVDFG-SNVBAGLBSA-N

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Application

(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide can be used:
  • As a reactant in the phosphoalkoxylation of aromatic enones.
  • As a chiral resolving agent in the resolution of amino acids, amines, and amino alcohols.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Enantiomeric impurities in chiral catalysts, auxiliaries and synthons used in enantioselective synthesis
Armstrong DW, et al.
Tetrahedron Asymmetry, 9(12), 2043-2064 (1998)
Four-component α-bromo-β-phosphoalkoxylation of aromatic α, β-unsaturated carbonyl compounds
Sohail M, et al.
Royal Society of Chemistry Advances, 5(22), 17014-17017 (2015)

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