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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)-
Article Data: 34
Cas Database
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: 293.371
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: N/A
Appearance: crystalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information: N/A
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
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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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