N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem CID
Reaxys RN
4-Benzyloxybenzylidene 4-Fluoroaniline, Ezetimibe intermediate
API & Intermediates
KUMI1F81
70627-52-0
MFCD00017951
791783
8420758
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay
Appearance
Melting Point
Packaging
Storage
N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline
C20H16FNO
305.35
≥99%
White to Slightly Pale-yellow Solid
131-133°C
5g,10g,25g,50g,100g and 500g
Store at 2-8°C
N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline is a pharmaceutical intermediate for the synthesis of Azetidinone-Based Cholesterol Absorption Inhibitors, e.g. Ezetimibe, a drug that lowers plasma cholesterol levels.
Discovery of 1-(4-Fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)- hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235):  A Designed, Potent, Orally Active Inhibitor of Cholesterol Absorption. [1]
A Novel One-Step Diastereo- and Enantioselective Formation of trans-Azetidinones and Its Application to the Total Synthesis of Cholesterol Absorption Inhibitors. [2]
Formal Asymmetric Synthesis of a Cholesterol Absorption Inhibitor Bearing a 2-Azaspiro[3.5]nonan-1-one Moiety. [3]
Synthesis of 3-Arylpropenyl, 3-Arylpropynyl and 3-Arylpropyl 2-Azetidinones as Cholesterol Absorption Inhibitors: Application of the Palladium-Catalyzed Arylation of Alkenes and Alkynes. [4]
Heterocyclic ring scaffolds as small-molecule cholesterol absorption inhibitors. [5]
An Improved and Scalable Process for the Synthesis of Ezetimibe: An Antihypercholesterolemia Drug. [6]
Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe. [7]
References:
[1] S.B.Rosenblum, et al, J. Med. Chem., 1998, 41(6), pp 973-980.
[2] G.Wu. et al, J. Org. Chem., 1999, 64(10), pp 3714-3718.
[3] T.Kambara, et al, J. Org. Chem., 1999, 64(25), pp 9282-9285.
[4] S.B.Rosenblum, et al, Tetrahedron, 2000, 56(31), pp 5735-5742.
[5] T.Ritter, et al, Org. Biomol. Chem., 2005, 3, pp 3514-3523.
[6] C.H.V.A.Sasikala, et al, Org. Process Res. Dev., 2009, 13(5), pp 907-910.
[7] M.Isoda, et al, Beilstein J. Org. Chem., 2016, 12, pp 1608-1615.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Not classified as a dangerous goods



NONH for all modes of transport

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