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120511-73-1

Basic Information
CAS No.: 120511-73-1
Name: 1,3-Benzenediacetonitrile, α1133-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-
Molecular Structure:
Molecular Structure of 120511-73-1 (1,3-Benzenediacetonitrile, α<sup>1</sup>,α<sup>1</sup>,α<sup>3</sup>,α<sup>3</sup>-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-)
Formula: C17H19N5
Molecular Weight: 293.37
Synonyms: 10-Methoxy-5H-dibenz[b,f]azepine-5-carbonylchloride;1,3-Benzenediacetonitrile,a,a,a',a'-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)- (9CI);2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methylpropionitrile);2-[3-(2-Cyano-2-propyl)-5-(1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropiononitrile;Asiolex;Anastrol;Tetramethyl-5-(1H-1,2,4-triazol-1ylmethyl) 1,3-benzenediacetionitrile;
EINECS: 601-715-6
Density: 1.085 g/cm3
Melting Point: 81 - 82 °C
Boiling Point: 469.718 °C at 760 mmHg
Flash Point: 237.877 °C
Solubility:
Appearance: crystalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 78.29000
LogP: 2.92876
Synthetic route
288-88-0

1,2,4-Triazole

120511-84-4

2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile

120511-73-1

anastrozol

Conditions
ConditionsYield
With potassium tert-butylate In toluene at 9 - 21℃; for 4.5h;100%
With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 75 - 80℃; for 2h; Solvent; Temperature; Reagent/catalyst;82%
With tetrabutylammomium bromide; potassium carbonate; potassium hydroxide In toluene at 85 - 90℃; for 5h;47%
288-88-0

1,2,4-Triazole

120511-89-9

3,5-bis(2-cyanopropan-2-yl)benzaldehyde

120511-73-1

anastrozol

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 45 - 55℃; for 7h; Reagent/catalyst; Solvent;90%

4-amino-1-[3,5-bis(1-cyano-1-methylethyl)benzyl]-4H-1,2,4-triazolium bromide

120511-73-1

anastrozol

Conditions
ConditionsYield
With sodium azide; sulfuric acid; copper(II) sulfate In methanol; water for 1h; Solvent; Reflux;82%
With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 9 - 9.5h;81.24%
Stage #1: 4-amino-1-[3,5-bis(1-cyano-1-methylethyl)benzyl]-4H-1,2,4-triazolium bromide With hydrogenchloride; sodium nitrite In water at -5 - 20℃; for 8h;
Stage #2: With urea In water
Stage #3: With ammonia In water; toluene at 0 - 25℃; for 4h;
876514-43-1

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]-di(2-methylpropionitrile) hydrobromide

120511-73-1

anastrozol

Conditions
ConditionsYield
With sodium carbonate In water Product distribution / selectivity;74.7%
290-87-9

1,3,5-Triazine

C15H20N4*ClH

120511-73-1

anastrozol

Conditions
ConditionsYield
In ethanol for 2h; Heating / reflux;72.49%
1015083-81-4

anastrozole mesylate

120511-73-1

anastrozol

Conditions
ConditionsYield
With ammonia In methanol; water at 18 - 22℃; Product distribution / selectivity;71.5%

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]-di(2-methylpropionitrile) hydrochloride

120511-73-1

anastrozol

Conditions
ConditionsYield
With sodium carbonate In water Product distribution / selectivity;69.5%
With sodium hydrogencarbonate In water Product distribution / selectivity;
In water for 48.5h; Product distribution / selectivity;
120511-91-3

α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile

41253-21-8

sodium triazole

120511-73-1

anastrozol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;52%
In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;
120511-84-4

2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile

41253-21-8

sodium triazole

120511-73-1

anastrozol

Conditions
ConditionsYield
Stage #1: 2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile; sodium triazole In N,N-dimethyl-formamide at 45 - 50℃; for 4h;
Stage #2: With hydrogenchloride; water at 50℃; pH=2;
Stage #3: With ammonia In water at 0 - 5℃; pH=8 - 9;
34%
In N,N-dimethyl-formamide at 20℃; for 1h;34%
In N,N-dimethyl-formamide at 20℃; for 1h;34%

4-amino-1-[3,5-bis(1-cyano-1-methylethyl)benzyl]-4H-1,2,4-triazolium bromide

A

2-[3-(1-cyano-1-methylethyl)-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropionamide

B

120512-04-1

2-[3-(1-carbamoyl-1-methylethyl)-5-[1,2,4]triazol-1-ylmethylphenyl]-isobutyramide

C

120511-73-1

anastrozol

Conditions
ConditionsYield
Stage #1: 4-amino-1-[3,5-bis(1-cyano-1-methylethyl)benzyl]-4H-1,2,4-triazolium bromide With hydrogenchloride; sodium nitrite In water at -5 - 20℃;
Stage #2: With ammonia; water at 0 - 25℃; for 4h;
A 0.36%
B 0.05%
C n/a
120511-91-3

α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile

120511-73-1

anastrozol

Conditions
ConditionsYield
Stage #1: 1,2,4-Triazole With sodium methylate In methanol at 20 - 30℃; for 0.25h;
Stage #2: α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile In N,N-dimethyl acetamide at 15 - 55℃; for 3h; Product distribution / selectivity;

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methyl)propionitrile p-toluenesulfonate salt

120511-73-1

anastrozol

Conditions
ConditionsYield
With ammonia In water; toluene for 0.5h; pH=8.5 - 9.0; Product distribution / selectivity;
With ammonia In water; ethyl acetate for 0.5h; pH=8.5 - 9.0; Product distribution / selectivity;
With ammonia In water at 10 - 20℃; for 0.75h; pH=~ 9.00 - 10.00; Product distribution / selectivity;

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methyl)propionitrile fumarate salt

120511-73-1

anastrozol

Conditions
ConditionsYield
With ammonia In water Product distribution / selectivity;

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methyl)propionitrile oxalate

120511-73-1

anastrozol

Conditions
ConditionsYield
With ammonia In water Product distribution / selectivity;

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]-di(2-methylpropionitrile) hydrochloride

2,2'-[5-(4H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]-di(2-methyl-propionitrile) hydrochloride

A

120511-92-4

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

B

120511-73-1

anastrozol

Conditions
ConditionsYield
With sodium carbonate In water; ethyl acetate for 0.333333h; Product distribution / selectivity;
With sodium carbonate In water; ethyl acetate; toluene for 0.25h; Product distribution / selectivity;
120511-84-4

2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile

120511-73-1

anastrozol

Conditions
ConditionsYield
Stage #1: 1,2,4-Triazole With sodium hydroxide In 1-methyl-pyrrolidin-2-one at 20 - 60℃; for 14 - 55h;
Stage #2: 2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile In 1-methyl-pyrrolidin-2-one at -26 - -20℃; for 18 - 26h;
Stage #3: With acetic acid In 1-methyl-pyrrolidin-2-one pH=6.5 - 7; Product distribution / selectivity;
120511-72-0

3,5-bis(2-cyanoprop-2-yl)toluene

41253-21-8

sodium triazole

120511-73-1

anastrozol

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In N-methyl-acetamide; tetrachloromethane; water
Stage #1: 3,5-bis(2-cyanoprop-2-yl)toluene; sodium triazole In N,N-dimethyl-formamide at 45 - 50℃; for 4h;
Stage #2: With hydrogenchloride In water at 50℃; pH=1 - 2;
Stage #3: With ammonia In water at 0 - 5℃; pH=8 - 9;
288-88-0

1,2,4-Triazole

120511-91-3

α,α,α',α'-tetramethyl-5-chloromethyl-1,3-benzene diacetonitrile

A

120511-92-4

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

B

120511-73-1

anastrozol

Conditions
ConditionsYield
In acetonitrile
Reaxys ID: 12539645

Reaxys ID: 12539645

120511-73-1

anastrozol

3,5-bis(2-cyanoisopropyl)benzylbromide

41253-21-8

sodium triazole

A

120511-92-4

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

B

120511-73-1

anastrozol

Conditions
ConditionsYield
In isopropyl alcohol Product distribution / selectivity; Heating / reflux;
In N,N-dimethyl-formamide at 5 - 35℃; for 0.5 - 4h; Product distribution / selectivity;
In n-heptane Product distribution / selectivity; Heating / reflux;
In acetone Product distribution / selectivity; Heating / reflux;
In methanol Product distribution / selectivity; Heating / reflux;
120511-84-4

2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile

41253-21-8

sodium triazole

A

120511-72-0

3,5-bis(2-cyanoprop-2-yl)toluene

B

120511-92-4

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

C

120511-73-1

anastrozol

Conditions
ConditionsYield
In N,N-dimethyl-formamide at -10 - -5℃; for 0.75h; Product distribution / selectivity;
120511-88-8

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

13578-51-3

1-(4-toluenesulfonyl)-1H-1,2,4-triazole

120511-73-1

anastrozol

Conditions
ConditionsYield
Stage #1: 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile With sodium hydride In tetrahydrofuran at 70℃; for 0.5h;
Stage #2: 1-(4-toluenesulfonyl)-1H-1,2,4-triazole In ISOPROPYLAMIDE at 20℃; for 0.333333h; Product distribution / selectivity;
Stage #1: 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile With sodium hydride In 1,4-dioxane at 70 - 85℃; for 0.5 - 0.583333h;
Stage #2: 1-(4-toluenesulfonyl)-1H-1,2,4-triazole In 1,4-dioxane at 10 - 125℃; for 3.33333 - 5h; Product distribution / selectivity;
Stage #1: 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile With sodium hydride In 1,2-dimethoxyethane at 70℃; for 0.5h;
Stage #2: 1-(4-toluenesulfonyl)-1H-1,2,4-triazole In 1,2-dimethoxyethane at 10 - 100℃; for 3.33333h; Product distribution / selectivity;
Stage #1: 2-[3-(cyano-dimethyl-methyl)-5-hydroxymethyl-phenyl]-2-methyl-propionitrile With sodium hydride In tetrahydrofuran at 70℃; for 0.5h;
Stage #2: 1-(4-toluenesulfonyl)-1H-1,2,4-triazole In tetrahydrofuran at 10 - 100℃; for 3.33333h; Product distribution / selectivity;
288-88-0

1,2,4-Triazole

120511-84-4

2-[3-bromomethyl-5-(cyanodimethylmethyl)phenyl]-2-methylpropanenitrile

A

120511-92-4

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

B

120511-73-1

anastrozol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Product distribution / selectivity; Reflux;
With potassium carbonate In toluene at 9 - 21℃; for 4.5h; Overall yield = 71.8 %; Overall yield = 42.14 g;
120511-72-0

3,5-bis(2-cyanoprop-2-yl)toluene

120511-73-1

anastrozol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 2,2'-azobis(isobutyronitrile) / cyclohexane / 4 h / 25 - 85 °C
2.1: isopropyl alcohol / 5 h / 80 - 85 °C
3.1: hydrogenchloride; sodium nitrite / water / 8 h / -5 - 20 °C
3.2: 4 h / 5 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: N-Bromosuccinimide; acetic acid; 2,2'-azobis(isobutyronitrile) / acetonitrile / 6.5 h / 65 °C / Reflux; Industrial scale
2.1: 3 h / Reflux; Industrial scale
3.1: hydrogenchloride; sodium nitrite / acetonitrile; water / 4 h / 15 - 22 °C / Industrial scale
3.2: 0.5 h / 20 °C / Industrial scale
3.3: 12 h / 12 °C / Industrial scale
View Scheme
37366-09-9

dichloro(benzene)ruthenium(II) dimer

13826-83-0

ammonium tetrafluroborate

120511-73-1

anastrozol

[Ru(η6-C6H6)(η1-anastrozole)2Cl]BF4

Conditions
ConditionsYield
In ethanol for 6h; Reflux; Inert atmosphere;68%
37366-09-9

dichloro(benzene)ruthenium(II) dimer

143-66-8

sodium tetraphenyl borate

120511-73-1

anastrozol

[Ru(η6-C6H6)(η1-anastrozole)2Cl]BPh4

Conditions
ConditionsYield
In ethanol for 6h; Reflux; Inert atmosphere;60%

C63H94ClCoN16O14PPt(1+)*C2F3O2(1-)

120511-73-1

anastrozol

C80H113CoN21O14PPt(2+)*2C2F3O2(1-)

Conditions
ConditionsYield
In water at 40℃; for 24h;58%
131759-88-1, 61779-28-0

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

120511-73-1

anastrozol

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

Conditions
ConditionsYield
In acetone Inert atmosphere; Schlenk technique;56%

Ru(η6-C6H6)oxalate(H2O)

120511-73-1

anastrozol

Ru(η6-C6H6)oxalate(η1-anastrozole)

Conditions
ConditionsYield
In ethanol for 24h; Inert atmosphere; Reflux;52%
120511-73-1

anastrozol

A

120511-72-0

3,5-bis(2-cyanoprop-2-yl)toluene

B

2-(3-((1H-1,2,4-triazol-1-yl)methyl)-5-isopropylphenyl)-2-methylpropanenitrile

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 9h; Electrolysis; Green chemistry;A 47%
B 26%
14104-20-2

silver tetrafluoroborate

32993-05-8

chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II)

120511-73-1

anastrozol

Ru(cyclopentadienyl)(PPh3)2(anastrozole)BF4

Conditions
ConditionsYield
In acetone for 2h; Inert atmosphere; Schlenk technique; Reflux;36%

(η4-1,5-cyclooctadiene)dichlororuthenium(II)

120511-73-1

anastrozol

Ru(cyclooctadienyl)(anastrozole)2Cl2

Conditions
ConditionsYield
In acetonitrile at 80℃; under 775.743 Torr; for 48h; Microwave irradiation; Inert atmosphere; Schlenk technique;22%
75-75-2

methanesulfonic acid

120511-73-1

anastrozol

1015083-81-4

anastrozole mesylate

Conditions
ConditionsYield
In ethyl acetate Product distribution / selectivity; Acidic conditions;
104-15-4

toluene-4-sulfonic acid

120511-73-1

anastrozol

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methyl)propionitrile p-toluenesulfonate salt

Conditions
ConditionsYield
In acetone at 20 - 25℃; for 13h;
In acetone for 1h;
In toluene for 0.5h; Heating / reflux;
120511-73-1

anastrozol

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]-di(2-methylpropionitrile) hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol; acetone
With hydrogenchloride In water at 20 - 42℃; for 0.5h; Product distribution / selectivity;
110-17-8

(2E)-but-2-enedioic acid

120511-73-1

anastrozol

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methyl)propionitrile fumarate salt

Conditions
ConditionsYield
In acetone at 20℃; for 5h; Heating / reflux;
144-62-7

oxalic acid

120511-73-1

anastrozol

2,2'-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-phenylene]di(2-methyl)propionitrile oxalate

Conditions
ConditionsYield
In isopropyl alcohol at 20℃; for 4h;
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Specification

The Anastrozole, with the CAS registry number 120511-73-1, is also known as 2-[3-(2-Cyano-2-propyl)-5-(1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropiononitrile. It belongs to the product categories of Active Pharmaceutical Ingredients; Antineoplastic; All Inhibitors; Anti-neoplastic; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Anastrozole. This chemical's molecular formula is C17H19N5 and molecular weight is 293.37. What's more, its systematic name is 2,2'-[5-(1H-1,2,4-Triazol-1-ylmethyl)-1,3-phenylene]bis(2-methylpropanenitrile). Its classification codes are: (1)Antineoplastic; (2)Antineoplastic Agents; (3)Antineoplastic agents, hormonal; (4)Aromatase Inhibitors; (5)Drug / Therapeutic Agent; (6)Enzyme inhibitors. This chemical is an aromatase-inhibiting drug approved for treatment of breast cancer after surgery, as well as for metastasis in both pre and post-menopausal women. It is an aromatase inhibitor and it is ued as an antineoplastic. 

Physical properties of Anastrozole are: (1)ACD/LogP: 0.291; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.29; (4)ACD/LogD (pH 7.4): 0.29; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 34.24; (8)ACD/KOC (pH 7.4): 34.31; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 78.29 Å2; (13)Index of Refraction: 1.58; (14)Molar Refractivity: 90.013 cm3; (15)Molar Volume: 270.287 cm3; (16)Polarizability: 35.684×10-24cm3; (17)Surface Tension: 42.2 dyne/cm; (18)Density: 1.085 g/cm3; (19)Flash Point: 237.877 °C; (20)Enthalpy of Vaporization: 73.213 kJ/mol; (21)Boiling Point: 469.718 °C at 760 mmHg ; (22) Vapour Pressure: 0 mmHg at 25°C.

Chemical synthesis: the synthesis begins with nucleophilic substitution of two benzylic bromides in α,α'-dibromomesitylene (prepared by radical bromination of mesitylene, not shown on the scheme) with cyanide by treatment with potassium cyanide under phase transfer conditions, affording the dinitrile. Exhaustive methylation with methyl iodide and sodium hydride leads to the replacement of the more acidic side chain hydrogen atoms by methyl groups. The treatment with bromine in the presence of benzoyl peroxide leads to the formation of the corresponding benzyl bromide. Reaction of that product with 1,2,4-triazole in the presence of a base completes the synthesis of the aromatase inhibitor.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C#N)c1cc(cc(c1)C(C)(C)C#N)Cn2cncn2
(2)Std. InChI: InChI=1S/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3
(3)Std. InChIKey: YBBLVLTVTVSKRW-UHFFFAOYSA-N

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