69545-39-7

Basic information

• Product Name: 4,4'-(1-BROMOMETHYL) BIS-BENZONITRILE
• Synonyms: 4,4'-(1-BROMOMETHYL) BIS-BENZONITRILE;4,4-Dicyanodiphenylbromomethane;4,4DicyanoDiphenylBromoMethane(ForLetrozole)
• CAS NO: 69545-39-7
• Molecular Formula: C₁₅H₉BrN₂
• Molecular Weight: 297.15
• Mol File: 69545-39-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 447.4 ºC at 760 mmHg
• Flash Point: 224.4ºC
• Appearance: /
• Density: 1.48 g/cm³
• CAS DataBase Reference: 4,4'-(1-BROMOMETHYL) BIS-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-(1-BROMOMETHYL) BIS-BENZONITRILE(69545-39-7)
• EPA Substance Registry System: 4,4'-(1-BROMOMETHYL) BIS-BENZONITRILE(69545-39-7)

Safety Data

• Hazardous Substances Data: 69545-39-7(Hazardous Substances Data)

Usage

General Description

4,4'-(1-Bromomethyl) bis-benzonitrile is a chemical compound with the molecular formula C16H10Br2N2. It is a crystalline solid with a white to pale yellow color. 4,4'-(1-BROMOMETHYL) BIS-BENZONITRILE is commonly used as an intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. It is also used in the production of dyes and other specialty chemicals. 4,4'-(1-Bromomethyl) bis-benzonitrile is a versatile and useful building block for the creation of a wide range of chemical compounds, and its properties make it valuable in various industrial applications.

Upstream product

• 10466-37-2 4,4'-dicyanodiphenylmethane 
• 623-03-0 4-Cyanochlorobenzene 
• 104-85-8 para-methylbenzonitrile 
• 134521-16-7 4,4'-Methanol-bisbenzonitrile 

Downstream Products

• 112809-51-5 letrozol 
• 112809-52-6 4-[α-(4-cyano-phenyl)-1-(1,3,4-triazol-1-yl)-methyl]-benzonitrile 
• 1334667-31-0 1-(4,4'-dicyanodiphenylmethyl)-4-phenyl-1H-1,2,3-triazole 
• 1334667-32-1 1-(4,4'-dicyanodiphenylmethyl)-4-(phenoxymethyl)-1H-1,2,3-triazole 
• 1334667-33-2 1-(4,4'-dicyanodiphenylmethyl)-4-((4-chlorophenoxy)methyl)-1H-1,2,3-triazole 
• 1334667-34-3 1-(4,4'-dicyanodiphenylmethyl)-4-((4-cyanophenoxy)methyl)-1H-1,2,3-triazole 
• 1334667-35-4 1-(4,4'-dicyanodiphenylmethyl)-4-((4-nitrophenoxy)methyl)-1H-1,2,3-triazole 
• 1334667-36-5 1-(4,4'-dicyanodiphenylmethyl)-4-((p-tolyloxy)methyl)-1H-1,2,3-triazole 
• 1334667-37-6 1-(4,4'-dicyanodiphenylmethyl)-4-((4-methoxyphenoxy)methyl)-1H-1,2,3-triazole 
• 1334667-38-7 1-(4,4'-dicyanodiphenylmethyl)-4-((4-phenylphenoxy)methyl)-1H-1,2,3-triazole 
• 1334667-24-1 4,4'-dicyanodiphenylazidomethane 
• 1334667-25-2 1-(4,4'-dicyanodiphenylmethyl)-4-propyl-1H-1,2,3-triazole 
• 1334667-26-3 1-(4,4'-dicyanodiphenylmethyl)-4-hexyl-1H-1,2,3-triazole 
• 1334667-28-5 1-(4,4'-dicyanodiphenylmethyl)-4-heptyl-1H-1,2,3-triazole 

Relevant articles and documents

Preparation method of letrozole

To the method, a continuous flow chemical technology is adopted to prepare the key intermediate, and the temperature of the reaction is accurately controlled. The content of triazole isomeric impurities 4 - [α - (4 - cyanophenyl) -1 - (1, 3, 4 - triazolyl) methyl] - benzonitrile is reduced, so that repeated recrystallization is avoided, the yield is improved, the total yield is 44% more than 67%, and the cost is saved.

Synthesis and structure-activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors

A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole 1. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 μM), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen.

A METHOD OF MANUFACTURE OF LETROZOLE

A novel and convenient method of manufacture of letrozole of formula (I) is described. Letrozole is an aromatase inhibitor drug used in the treatment of postmenopausal breast cancer.