Anastrozole EP Impurity I

Base Information

• Chemical Name: Anastrozole EP Impurity I
• CAS No.: 120511-91-3
• Molecular Formula: C15H17 Cl N2
• Molecular Weight: 260.766
• UNII: UA6KB3ICZ1
• DSSTox Substance ID: DTXSID50598265
• Wikidata: Q82494002
• Mol file: 120511-91-3.mol

Synonyms:120511-91-3;Anastrozole EP Impurity I;UNII-UA6KB3ICZ1;UA6KB3ICZ1;2-[3-(chloromethyl)-5-(2-cyanopropan-2-yl)phenyl]-2-methylpropanenitrile;Anastrozole impurity I [EP];1,3-Benzenediacetonitrile,5-(chloromethyl)-a1,a1,a3,a3-tetramethyl-;2,2-(5-(Chloromethyl)benzene-1,3-diyl)bis(2-methylpropanenitrile);2-(3-(Chloromethyl)-5-(2-cyanopropan-2-yl)phenyl)-2-methylpropanenitrile;2,2'-(5-(chloromethyl)-1,3-phenylene)bis(2-methylpropanenitrile);1,3-Benzenediacetonitrile, 5-(chloromethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-;5-(Chloromethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-1,3-benzenediacetonitrile;2,2'-[5-(Chloromethyl)-1,3-phenylene]bis(2-methylpropanenitrile);HSNGPKBBTHINTG-UHFFFAOYSA-N;SCHEMBL3173073;DTXSID50598265;2-[3-CHLOROMETHYL-5-(CYANO-DIMETHYL-METHYL)-PHENYL]-2-METHYL-PROPIONITRILE;ANASTROZOLE IMPURITY I [EP IMPURITY];CS-0179352;EN300-26981013;2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile);2,2'-[5-(Chloromethyl)benzene-1,3-diyl]bis(2-methylpropanenitrile);5-(Chloromethyl)-?1,?1,?3,?3-tetramethyl-1,3-benzenediacetonitrile;2,2'-(5-(Chloromethyl)-1,3-phenylene)bis(2-methylpropanenitrile) (Anastrozole Impurity);2-[3-(CHLOROMETHYL)-5-(1-CYANO-1-METHYLETHYL)PHENYL]-2-METHYLPROPANENITRILE;1,3-BENZENEDIACETONITRILE, 5-(CHLOROMETHYL)-.ALPHA.1,.ALPHA.1,.ALPHA.3,.ALPHA.3-TETRAMETHYL-;1,3-Benzenediacetonitrile, 5-(chloromethyl)-?1,?1,?3,?3-tetramethyl-;1,3-Benzenediacetonitrile, 5-(chloromethyl)-?,?,?',?'-tetramethyl- (9CI);5-(CHLOROMETHYL)-.ALPHA.1,.ALPHA.1,.ALPHA.3,.ALPHA.3-TETRAMETHYL-1,3-BENZENEDIACETONITRILE

Chemical Property of Anastrozole EP Impurity I

Chemical Property:

• PSA: 47.58000
• LogP: 4.02776
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 260.1080262
• Heavy Atom Count: 18
• Complexity: 357

Purity/Quality:

99%+, ^*data from raw suppliers

5-(Chloromethyl)-α1,α1,α3,α3-tetramethyl-1,3-benzenediacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C#N)C1=CC(=CC(=C1)CCl)C(C)(C)C#N
• Uses: 5-(Chloromethyl)-α1,α1,α3,α3-tetramethyl-1,3-benzenediacetonitrile (Anastrozole EP Impurity I) is an impurity of Anastrozole (A637425), an aromatase inhibitor which functions as an antineoplastic (1,2). Anastrozole is used i post-menopausal women with advanced breast cancer.

Technology Process of Anastrozole EP Impurity I

There total 1 articles about Anastrozole EP Impurity I which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile (120511-88-8) → α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile (120511-91-3)

Guidance literature:

With thionyl chloride; In N,N-dimethyl acetamide; at 15 - 35 ℃; for 1.75 - 3.25h;

Reference yield: 52.0%

α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile (120511-91-3) + sodium triazole (41253-21-8) → anastrozol (120511-73-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1039/b707768h

Reference yield: 44.8%

α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile (120511-91-3) → 1,2-bis[3,5-bis(2-cyanoisopropyl)phenyl]ethane

Guidance literature:

With iodine; magnesium; In 2-methyltetrahydrofuran; at 75 - 80 ℃; for 3h; Inert atmosphere;

upstream raw materials:

2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile

Downstream raw materials:

anastrozol

α,α,α',α'-tetramethyl-5-(4H-1,2,4-triazol-4ylmethyl)-1,3-benzene-diacetonitrile

Refernces

• 1、 Jackson, Toby,Woo, L. W. Lawrence,Trusselle, Melanie N.,Chander, Surinder K.,Purohit, Atul,Reed, Michael J.,Potter, Barry V. L.. "Dual aromatase-sulfatase inhibitors based on the anastrozole template: Synthesis, in vitro SAR, molecular modelling and in vivo activity". . p. 2940 - 2952. Retrieved 2008/04/02.
• 2、 -. "(SUBSTITUTED ARALKYL) HETEROCYCLIC COMPOUNDS". . . Retrieved 2008/06/13.