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112809-51-5

Basic Information
CAS No.: 112809-51-5
Name: Letrozole
Molecular Structure:
Molecular Structure of 112809-51-5 (Letrozole)
Formula: C17H11N5
Molecular Weight: 285.30
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
Solubility:
Appearance: white to off-whitecrystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
Transport Information:
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%
1194-02-1

4-fluorobenzonitrile

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile With potassium tert-butylate In N,N-dimethyl-formamide at -5 - 0℃; for 2h;
Stage #2: 4-fluorobenzonitrile In N,N-dimethyl-formamide at 0 - 10℃; for 0.25h; Product distribution / selectivity;
73%
Stage #1: 4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -30 - -25℃; for 0.666667h;
Stage #2: 4-fluorobenzonitrile In tetrahydrofuran at -20 - -15℃; for 1.25h; Product distribution / selectivity;
290-87-9

1,3,5-Triazine

1280504-38-2

2-(propan-2-ylidine)-1-[di-(4-cyanophenyl)methyl]hydrazine

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 2-(propan-2-ylidine)-1-[di-(4-cyanophenyl)methyl]hydrazine With hydrogenchloride In methanol at 20℃;
Stage #2: 1,3,5-Triazine In methanol Reflux;
70.7%
288-88-0

1,2,4-Triazole

69545-39-7

4,4'-dicyanodiphenylbromomethane

A

112809-52-6

4-[α-(4-cyano-phenyl)-1-(1,3,4-triazol-1-yl)-methyl]-benzonitrile

B

112809-51-5

letrozol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; toluene at 60 - 80℃; for 1.5h; Product distribution / selectivity;A 3.5%
B 70.5%
557-21-1

zinc(II) cyanide

102994-04-7

1--1H-1,2,4-triazole

112809-51-5

letrozol

Conditions
ConditionsYield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 4h; Inert atmosphere; Sealed tube;68%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 4h; Inert atmosphere; Glovebox; Sealed tube;68%
112809-25-3

4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile

595567-05-8

2-(4-fluorobenzene)-1,3,4-oxadiazole

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile With potassium tert-butylate In N,N-dimethyl-formamide at -5℃; Inert atmosphere;
Stage #2: 2-(4-fluorobenzene)-1,3,4-oxadiazole In N,N-dimethyl-formamide at -5℃; for 7.5h; Inert atmosphere;
64%

4-[1-(1,2,4-triazol-1-yl)methyl] benzonitrile

1194-02-1

4-fluorobenzonitrile

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-[1-(1,2,4-triazol-1-yl)methyl] benzonitrile; 4-fluorobenzonitrile With potassium tert-butylate In DMF (N,N-dimethyl-formamide) at -10 - -5℃; for 4h;
Stage #2: With hydrogenchloride In DMF (N,N-dimethyl-formamide); water pH=7.5 - 8.0;
58%
288-88-0

1,2,4-Triazole

51359-78-5

4-(bromomethyl)benzaldehyde

104-88-1

4-chlorobenzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-(bromomethyl)benzaldehyde; 4-chlorobenzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 12h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
43%
288-88-0

1,2,4-Triazole

51359-78-5

4-(bromomethyl)benzaldehyde

1122-91-4

4-bromo-benzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-(bromomethyl)benzaldehyde; 4-bromo-benzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 10h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
35%
288-88-0

1,2,4-Triazole

73291-09-5

4-chloromethylbenzaldehyde

104-88-1

4-chlorobenzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-chloromethylbenzaldehyde; 4-chlorobenzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 10h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
34%
288-88-0

1,2,4-Triazole

73291-09-5

4-chloromethylbenzaldehyde

1122-91-4

4-bromo-benzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-chloromethylbenzaldehyde; 4-bromo-benzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 10h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
33%
288-88-0

1,2,4-Triazole

112812-08-5

4-iodomethylbenzaldehyde

1122-91-4

4-bromo-benzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-iodomethylbenzaldehyde; 4-bromo-benzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 10h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
32%
288-88-0

1,2,4-Triazole

51359-78-5

4-(bromomethyl)benzaldehyde

459-57-4

4-fluorobenzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-(bromomethyl)benzaldehyde; 4-fluorobenzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 12h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
32%
288-88-0

1,2,4-Triazole

112812-08-5

4-iodomethylbenzaldehyde

104-88-1

4-chlorobenzaldehyde

112809-51-5

letrozol

Conditions
ConditionsYield
Stage #1: 4-iodomethylbenzaldehyde; 4-chlorobenzaldehyde With ammonium hydroxide; copper diacetate In dimethyl sulfoxide at 70℃; for 10h;
Stage #2: 1,2,4-Triazole With potassium carbonate; potassium iodide In dimethyl sulfoxide; acetone at 50℃; for 10h; Inert atmosphere;
21%
288-88-0

1,2,4-Triazole

69545-39-7

4,4'-dicyanodiphenylbromomethane

112809-51-5

letrozol

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In isopropyl alcohol for 8 - 9h; Product distribution / selectivity; Heating / reflux;
With potassium carbonate In isopropyl alcohol for 8 - 9h; Product distribution / selectivity; Heating / reflux;

4-[1-(1,2,4-triazolyl)methyl]-benzonitrile

1194-02-1

4-fluorobenzonitrile

112809-51-5

letrozol

Conditions
ConditionsYield
With potassium tert-butylate In N-methyl-acetamide
1194-02-1

4-fluorobenzonitrile

112809-25-3

4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile

112809-51-5

letrozol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -15℃; for 7 - 8h; Product distribution / selectivity;
With lithium hexamethyldisilazane In tetrahydrofuran at -20 - -5℃; for 2h; Product distribution / selectivity;
Stage #1: 4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile With potassium tert-butylate In N,N-dimethyl-formamide at 0 - 5℃; for 1.5h;
Stage #2: 4-fluorobenzonitrile In N,N-dimethyl-formamide at 0 - 5℃; for 1.5h;
112809-27-5

4-[(1-(1,3,4-triazolyl)-methyl)]benzonitrile

1194-02-1

4-fluorobenzonitrile

112809-25-3

4-((1H-1,2,4-triazole-1-yl)methyl)benzonitrile

A

112809-52-6

4-[α-(4-cyano-phenyl)-1-(1,3,4-triazol-1-yl)-methyl]-benzonitrile

B

112809-51-5

letrozol

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -15℃; for 3h; Product distribution / selectivity;

α-(1H-[1,2,4]triazol-1-yl)-4,4'-diformaldoxime-diphenylmethane

112809-51-5

letrozol

Conditions
ConditionsYield
With acetic anhydride for 8 - 10h; Product distribution / selectivity; Heating / reflux;
With sodium acetate; acetic anhydride; acetic acid at 20℃; for 3 - 4h; Product distribution / selectivity; Heating / reflux;

cobalt(II) chloride hexahydrate

112809-51-5

letrozol

CoCl2(1-[bis(4-cyanophenyl)methyl]-1,2,4-triazole)*H2O

Conditions
ConditionsYield
In ethanol; water High Pressure; mixt. of letrozole, CoCl2, EtOH and H2O sealed in stainless steel reactor, heated to 120°C for 24 h, slowly cooled to room temp.; elem. anal.;97.8%
In ethanol; water CoCl2 and letrozole dissolved in EtOH/H2O; mixt. stirred at room temp. for 1 h; filtered, soln. kept at room temp. for 4 d; elem. anal.;33.5%
112809-51-5

letrozol

4,4′-(1H-1,2,4-triazol-1-yl)methylene-bis(benzoic acid)

Conditions
ConditionsYield
Stage #1: letrozol With sodium hydroxide In water for 6h; Reflux;
Stage #2: With hydrogenchloride In water
94.9%
Stage #1: letrozol With potassium hydroxide In ethanol; water for 36h; Reflux;
Stage #2: With hydrogenchloride In water pH=2;
86.1%
Stage #1: letrozol With sodium hydroxide In N,N-dimethyl-formamide at 120℃; for 12h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=1;
77%
With [Rh(6,7-dihydrotribenzo-[e,i,m][1,4,7,12]-ioxadiazacyclotetradecine)]Cl; water; sodium hydroxide at 70℃; for 0.25h; Reagent/catalyst; Time;97.43 %Spectr.
Alkaline conditions;

nickel(II) chloride hexahydrate

112809-51-5

letrozol

NiCl2(1-[bis(4-cyanophenyl)methyl]-1,2,4-triazole)*H2O

Conditions
ConditionsYield
In ethanol; water High Pressure; mixt. of letrozole, NiCl2, EtOH and H2O sealed in stainless steel reactor, heated to 120°C for 24 h, slowly cooled to room temp.; elem. anal.;94.8%
In ethanol; water NiCl2 and letrozole dissolved in EtOH/H2O; mixt. stirred at room temp. for 1 h; filtered, soln. kept at room temp. for 4 d; elem. anal.;45.3%
19046-92-5, 55176-74-4

trans-Cl2Pd(H2NCH2C6H5)2

silver nitrate

112809-51-5

letrozol

[Pd(PhCH2NH2)2(4,4'-((1H-1,2,4-triazol-1-yl)methylene)dibenzonitrile)2](NO3)2

Conditions
ConditionsYield
Stage #1: trans-Cl2Pd(H2NCH2C6H5)2; silver nitrate In acetone at 25℃; for 2h; Darkness;
Stage #2: letrozol In acetone
78.5%
37366-09-9

dichloro(benzene)ruthenium(II) dimer

ammonium tetrafluoroborate

112809-51-5

letrozol

C40H28ClN10Ru(1+)*BF4(1-)

Conditions
ConditionsYield
In ethanol for 1h; Reflux;73%
112809-51-5

letrozol

C17H15N5S2

Conditions
ConditionsYield
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate; sodiumsulfide nonahydrate In neat (no solvent) at 20℃; for 2h; Green chemistry;73%
64-17-5

ethanol

112809-51-5

letrozol

diethyl 4,4′-(1H-1,2,4-triazol-1-ylmethanediyl)dibenzenecarboximidate

Conditions
ConditionsYield
With acetyl chloride at 20℃; Cooling with ice;72%
131759-88-1, 61779-28-0

Sodium trans-Bis(dimethhyl sulfoxide) tetrachlororuthenate(III)

112809-51-5

letrozol

Na[trans-RuCl4(letrozole)(dimethyl sulfoxide)]

Conditions
ConditionsYield
In acetone Inert atmosphere; Schlenk technique;66%
112809-51-5

letrozol

C17H13N5S

Conditions
ConditionsYield
With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate; sodiumsulfide nonahydrate In neat (no solvent) at 20℃; for 2h; Green chemistry;64%
112809-51-5

letrozol

10466-37-2

4,4'-dicyanodiphenylmethane

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 6h; Electrolysis; Green chemistry;55%

copper(II) choride dihydrate

112809-51-5

letrozol

[Cu(1-[bis(4-cyano-phenyl)methyl]-1,2,4-triazole)3Cl2]

Conditions
ConditionsYield
In ethanol; water at 120℃; for 72h;47%

tetrakis(acetonitrile)copper(I)tetrafluoroborate

67-66-3

chloroform

112809-51-5

letrozol

364594-74-1

Cu(I)(1-[bis(4-cyanophenyl)methyl]-1,2,4-triazole)BF4*CHCl3

Conditions
ConditionsYield
In chloroform; benzene solvothermal treatment of Cu-complex with ligand in benzene and CHCl3 for 3 ds at 100°C; elem. anal.;40%
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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.