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112809-51-5

Basic Information
CAS No.: 112809-51-5
Name: Letrozole
Article Data: 34
Molecular Structure:
Molecular Structure of 112809-51-5 (Letrozole)
Formula: C17H11N5
Molecular Weight: 285.308
Synonyms: 4,4'-(1H-1,2,4-Triazol-1-ylmethylene)bisbenzonitrile
EINECS: 675-034-8
Density: 1.21g/cm3
Melting Point: 100-102 °C
Boiling Point: 374.4 °C at 760 mmHg
Flash Point: 180.3 °C
Appearance: white to off-whitecrystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 78.29000
LogP: 2.65916
Synthetic route
112809-26-4

4-(1H-1,2,4-triazol-1-ylmethyl)benzonitrile hydrochloride

1194-02-1

4-fluorobenzonitrile

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-(1H-1,2,4-triazol-1-ylmethyl)benzonitrile hydrochloride With potassium tert-butylate In N,N-dimethyl-formamide at -25 - -20℃; for 1.08333h; Inert atmosphere;
Stage #2: 4-fluorobenzonitrile In N,N-dimethyl-formamide at -25 - -20℃; for 1.08333h;
98.6%
Stage #1: 4-(1H-1,2,4-triazol-1-ylmethyl)benzonitrile hydrochloride With potassium tert-butylate In N,N-dimethyl-formamide at -25 - -20℃; for 1.08333h;
Stage #2: 4-fluorobenzonitrile In N,N-dimethyl-formamide at -25 - -20℃; for 1.08333h;
Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide at -20 - 0℃; for 0.5h; pH=6.0 - 6.5; Product distribution / selectivity;
55%
288-88-0

1,2,4-Triazole

935477-95-5

toluene-4-sulfonic acid bis-(4-cyano-phenyl)-methyl ester

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 1,2,4-Triazole With tetrabutylammomium bromide; potassium carbonate In water; 4-methyl-2-pentanone for 2h;
Stage #2: toluene-4-sulfonic acid bis-(4-cyano-phenyl)-methyl ester In water; 4-methyl-2-pentanone at 20 - 30℃; for 48h;
Stage #3: With hydrogenchloride In water; 4-methyl-2-pentanone for 1h;
97.42%

potassium cyanide

1-(bis(4-bromophenyl)methyl)-1H-1,2,4-triazole

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: potassium cyanide With acetic acid In ethylene glycol Sealed tube;
Stage #2: 1-(bis(4-bromophenyl)methyl)-1H-1,2,4-triazole With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Concentration; Sealed tube;
97%

4-((4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl)benzamide

112809-51-5

letrozol

Conditions
ConditionsYield
With trifluoroacetic anhydride In 1,4-dioxane at 0 - 20℃; for 1h;90%
584-13-4

4-amino-1,2,4-triazole

69545-39-7

4,4'-dicyanodiphenylbromomethane

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-amino-1,2,4-triazole; 4,4'-dicyanodiphenylbromomethane In acetonitrile for 24h; Reflux;
Stage #2: With hydrogenchloride; sodium nitrite In water; acetonitrile at 0 - 5℃; for 6h; Solvent; Time;
88.7%

potassiumhexacyanoferrate(II) trihydrate

1-(bis(4-bromophenyl)methyl)-1H-1,2,4-triazole

112809-51-5

letrozol

Conditions
ConditionsYield
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 24h;87%

zinc cyanide

1-(bis(4-bromophenyl)methyl)-1H-1,2,4-triazole

112809-51-5

letrozol

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; water; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 120℃; for 15h; Inert atmosphere;86%
1194-02-1

4-fluorobenzonitrile

41253-21-8

sodium triazole

17201-43-3

4-cyanobenzyl bromide

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: sodium triazole; 4-cyanobenzyl bromide With potassium tert-butylate In N,N-dimethyl-formamide at -5 - 5℃; for 2.5h;
Stage #2: 4-fluorobenzonitrile In N,N-dimethyl-formamide at -5 - 5℃; for 2.5h; Product distribution / selectivity;
85%
Stage #1: sodium triazole; 4-cyanobenzyl bromide In N,N-dimethyl-formamide at -10 - 0℃; for 1h;
Stage #2: 4-fluorobenzonitrile With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at -10 - -5℃; Product distribution / selectivity;
Stage #1: sodium triazole; 4-cyanobenzyl bromide In ISOPROPYLAMIDE at -15 - 0℃; for 2.5h;
Stage #2: 4-fluorobenzonitrile With sodium hexamethyldisilazane In tetrahydrofuran; ISOPROPYLAMIDE at -8 - 0℃; for 1h; Product distribution / selectivity;

C40H28ClN10Ru(1+)*BF4(1-)

603-35-0

triphenylphosphine

A

C41H32ClN5PRu(1+)*BF4(1-)

B

112809-51-5

letrozol

Conditions
ConditionsYield
In dichloromethane at 20℃; for 48h;A 75%
B n/a
288-88-0

1,2,4-Triazole

112809-57-1

4-(alpha-chloro-4'-cyanobenzyl)-benzonitrile

112809-51-5

letrozol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 60 - 80℃; for 4h;74.4%
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Specification

1. Introduction of Letrozole
Letrozole is one kind of white to off-whitecrystalline powder. The IUPAC Name of this chemical is 4-[(4-cyanophenyl)-(1,2,4-triazol-1-yl)methyl]benzonitrile. Letrozole belongs to Anti-Cancer;Pharmaceutical material and intermeidates;Active Pharmaceutical Ingredients;Letrozole;Antineoplastic;All Inhibitors;anti-neoplastic;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API's;APIs;Antibiotics;Aromatics;Heterocycles. 

Besides, its Classification Code is Antineoplastic; Antineoplastic agents; Aromatase Inhibitors; Enzyme inhibitors. In addition, Letrozole is freely soluble in dichloromethane, slightly soluble in ethanol, and practically insoluble in water.

2. Properties of Letrozole
Physical properties about Letrozole are:
(1)Molecular Weight: 285.30274 g/mol; (2)Molecular Formula: C17H11N5; (3)XLogP3-AA: 2.7; (4)H-Bond Donor: 0; (5)H-Bond Acceptor: 4.

3. Structure Descriptors of Letrozole
(1)InChI: InChI=1S/C17H11N5/c18-9-13-1-5-15(6-2-13)17(22-12-20-11-21-22)16-7-3-14(10-19)4-8-16/h1-8,11-12,17H
(2)InChIKey: HPJKCIUCZWXJDR-UHFFFAOYSA-N
(3)Canonical SMILES: C1=CC(=CC=C1C#N)C(C2=CC=C(C=C2)C#N)N3C=NC=N3
(4)Smiles: n1(C(c2ccc(cc2)C#N)c2ccc(cc2)C#N)ncnc1

4. Uses of Letrozole
Letrozole (INN, trade name Femara) is an oral non-steroidal aromatase inhibitor that has been introduced for the adjuvant treatment of hormonally-responsive breast cancer. Letrozole is approved by the United States Food and Drug Administration (FDA) for the treatment of local or metastatic breast cancer that is hormone receptor positive or has an unknown receptor status in postmenopausal women. Side effects include signs and symptoms of hypoestrogenism. There is concern that long term use may lead to osteoporosis, which is why prescriptions of Letrozole are often accompanied by prescriptions of osteoporosis-fighting medications such as bisphosphonates.

Estrogens are produced by the conversion of androgens through the activity of the aromatase enzyme. Letrozole blocks production of estrogens in this way by competitive, reversible binding to the heme of its cytochrome P450 unit. The action is specific, and letrozole does not reduce production of mineralo- or corticosteroids. In contrast, the antiestrogenic action of tamoxifen, the major medical therapy prior to the arrival of aromatase inhibitors, is due to its interfering with the estrogen receptor, rather than inhibiting estrogen production.