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161718-81-6

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161718-81-6 Usage

Uses

4-Isobutyloxy-1,3-benzenedicarbonitrile is used in the preparation of febuxostat (F229000), a non-purine xanthine oxidase inhibitor used as a treatment for hyperuricaemia and chronic gout.

Check Digit Verification of cas no

The CAS Registry Mumber 161718-81-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,1,7,1 and 8 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 161718-81:
(8*1)+(7*6)+(6*1)+(5*7)+(4*1)+(3*8)+(2*8)+(1*1)=136
136 % 10 = 6
So 161718-81-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H12N2O/c1-9(2)8-15-12-4-3-10(6-13)5-11(12)7-14/h3-5,9H,8H2,1-2H3

161718-81-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(2-methylpropoxy)benzene-1,3-dicarbonitrile

1.2 Other means of identification

Product number -
Other names 4-(2-METHYLPROPOXY)-1,3-BENZENEDICARBONITRILE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:161718-81-6 SDS

161718-81-6Synthetic route

4-hydroxy-isophthalonitrile
34133-58-9

4-hydroxy-isophthalonitrile

isobutyl halide

isobutyl halide

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide for 6h; Inert atmosphere;88.1%
3-bromo-4-isobutoxybenzonitrile
208665-95-6

3-bromo-4-isobutoxybenzonitrile

potassium ferrocyanide

potassium ferrocyanide

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate In N,N-dimethyl-formamide at 140 - 145℃; for 18h;
Isobutyl bromide
78-77-3

Isobutyl bromide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Stage #1: 4-nitrobenzonitrile With potassium cyanide In dimethyl sulfoxide at 100℃; for 1h; Heating;
Stage #2: Isobutyl bromide With potassium carbonate at 80℃; for 2h;
Isobutyl bromide
78-77-3

Isobutyl bromide

4-hydroxy-isophthalonitrile
34133-58-9

4-hydroxy-isophthalonitrile

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In dimethyl sulfoxide at 70 - 75℃; for 16h; Product distribution / selectivity;
2,4-dibromophenol
615-58-7

2,4-dibromophenol

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium diacetate / dimethyl sulfoxide / 4 h / 40 - 45 °C
2: potassium carbonate; potassium iodide / dimethyl sulfoxide / 16 h / 70 - 75 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
2: potassium carbonate; potassium iodide / dimethyl sulfoxide / 16 h / 70 - 75 °C
View Scheme
4-cyanophenol
767-00-0

4-cyanophenol

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-Bromosuccinimide; trifluorormethanesulfonic acid / acetonitrile / -15 - 30 °C
2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 70 - 75 °C
3: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
View Scheme
3-bromo-4-hydroxybenzonitrile
2315-86-8

3-bromo-4-hydroxybenzonitrile

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 12 h / 70 - 75 °C
2: sodium carbonate / palladium diacetate / N,N-dimethyl-formamide / 18 h / 140 - 145 °C
View Scheme
salicylaldehyde
90-02-8

salicylaldehyde

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride / water / 1 h / 20 °C
1.2: 8 h
2.1: acetic acid; hexamethylenetetramine / water / 1 h / Reflux
3.1: hydroxylamine hydrochloride; sodium formate; formic acid / 1-methyl-pyrrolidin-2-one / 6 h / Reflux
4.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
View Scheme
5-formyl-2-hydroxybenzaldehyde
3328-70-9

5-formyl-2-hydroxybenzaldehyde

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium formate; formic acid / 1-methyl-pyrrolidin-2-one / 6 h / Reflux
2: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
View Scheme
5-(chloromethyl)salicylaldehyde
23731-06-8

5-(chloromethyl)salicylaldehyde

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; hexamethylenetetramine / water / 1 h / Reflux
2: hydroxylamine hydrochloride; sodium formate; formic acid / 1-methyl-pyrrolidin-2-one / 6 h / Reflux
3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / Inert atmosphere
View Scheme
Isobutyl bromide
78-77-3

Isobutyl bromide

potassium cyanide
151-50-8

potassium cyanide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

Conditions
ConditionsYield
With potassium carbonate 1.) DMSO, 100 deg C, 1 h, 2.) 6 h; 70 deg C; Yield given. Multistep reaction;
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

3-cyanoisobutoxybenzothioamide
163597-57-7

3-cyanoisobutoxybenzothioamide

Conditions
ConditionsYield
With hydrogenchloride; thioacetamide In N,N-dimethyl-formamide at 45℃; for 40h;85%
With hydrogenchloride; thioacetamide In isopropyl alcohol at 40 - 45℃; for 14h;
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

febuxostat

febuxostat

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / thioacetamide, HCl / dimethylformamide / 40 h / 45 °C
2: 306 mg / ethanol / 2 h / 100 °C
3: 35 percent / 1N NaOH / tetrahydrofuran; ethanol / 1 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
3: sodium hydroxide; ethanol / tetrahydrofuran / 1 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2.1: ethanol / 2 h / 100 °C
2.2: 1 h / 60 °C
View Scheme
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester
160844-75-7

2-(3-cyano-4-isobutyloxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / thioacetamide, HCl / dimethylformamide / 40 h / 45 °C
2: 306 mg / ethanol / 2 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
View Scheme
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid methylamine
1350352-71-4

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid methylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
3: sodium hydroxide; ethanol / tetrahydrofuran / 1 h / 60 °C
4: ethyl acetate; cyclohexane; methanol / 3 h
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2.1: ethanol / 2 h / 100 °C
2.2: 1 h / 60 °C
3.1: ethyl acetate; cyclohexane; methanol / 3 h
View Scheme
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid tert-butylamine
1350352-72-5

2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methylthiazole-5-carboxylic acid tert-butylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2: ethyl acetate; N,N-dimethyl-formamide / 22 h / 80 - 85 °C
3: sodium hydroxide; ethanol / tetrahydrofuran / 1 h / 60 °C
4: toluene / 10 h
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride; thioacetamide / isopropyl alcohol / 14 h / 40 - 45 °C
2.1: ethanol / 2 h / 100 °C
2.2: 1 h / 60 °C
3.1: toluene / 10 h
View Scheme
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

3-cyano-4-isobutoxybenzimidamide hydrochloride

3-cyano-4-isobutoxybenzimidamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 20 °C
2: ammonium chloride / 50 °C
View Scheme
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

ethyl 2-(3-cyano-4-isobutoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate

ethyl 2-(3-cyano-4-isobutoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanol / 20 °C
2: ammonium chloride / 50 °C
3: sodium hydride / ethanol / 2 h / 80 °C
View Scheme
4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

2-(3-cyano-4-isobutoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid

2-(3-cyano-4-isobutoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: methanol / 20 °C
2: ammonium chloride / 50 °C
3: sodium hydride / ethanol / 2 h / 80 °C
4: lithium hydroxide / ethanol; water; tetrahydrofuran / 50 °C
View Scheme
sodium methylate
124-41-4

sodium methylate

4-isobutoxyisophthalonitrile
161718-81-6

4-isobutoxyisophthalonitrile

C13H16N2O2

C13H16N2O2

Conditions
ConditionsYield
In methanol at 20℃;

161718-81-6Relevant articles and documents

Preparation method of febuxostat intermediate

-

Paragraph 0032; 0038-0070, (2021/11/10)

The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of an important febuxostat intermediate. The preparation method comprises the following steps of: by taking dimethyl 4-isobutoxy isophthalate as a raw material, carrying out ammonolysis on ester groups under the action of a catalyst to obtain acylamino, and further dehydrating the acylamino to obtain 4-isobutoxybenzene-1, 3-dinitrile. According to the method, cyano groups are introduced in ammonolysis and dehydration modes, cyanide with high toxicity is avoided, a traditional catalyst is replaced with a green catalyst, the reaction is milder, economical and environmentally friendly, the yield is high, and the method is suitable for industrial production.

Design, synthesis and biological evaluation of 2-(4-alkoxy-3-cyano)phenyl-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid derivatives as novel xanthine oxidase inhibitors

Mao, Qing,Dai,Xu, Gaoyang,Su, Yu,Zhang, Bing,Liu, Dan,Wang, Shaojie

, (2019/08/01)

In our previous study, we reported a series of 1-hydroxy-2-phenyl-1H-imidazole-5-carboxylic acid derivatives that presented excellent in vitro xanthine oxidase (XO) inhibitory potency. To further investigate the structure-activity relationships of these compounds, the imidazole ring was transformed to a pyrimidine ring to design 2-(4-alkoxy-3-cyano)phenyl-6-oxo-1,6-dihydropyrimidine-5-carboxylic acids (8a-8j), 2-(4-alkoxy-3-cyano)phenyl-4-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylic acids (9c, 9e, 9j, 9l) and 2-(4-alkoxy-3-cyano)phenyl-6-imino-1,6-dihydropyrimidine-5-carboxylic acids (10c, 10e, 10j, 10l). These compounds exhibited remarkable in vitro XO inhibitory potency with IC50 values ranging from 0.0181 μM to 0.5677 μM. Specifically, compounds 10c and 10e, with IC50 values of 0.0240 μM and 0.0181 μM, respectively, emerged as the most potent XO inhibitors, and their potencies were comparable to that of febuxostat. Structure-activity relationship analysis revealed that the methyl group at 4-position of pyrimidine ring could damage the potency, and the XO inhibitory potency was maintained when carbonyl group was changed to an imino group. Lineweaver-Burk plot analysis revealed that the representative compound 10c acted as a mixed-type inhibitor. A potassium oxonate induced hyperuricemia model in rats was chosen to further confirm the hypouricemic effect of compound 10c, and the results showed that compound 10c (5 mg/kg) was able to significantly lower the serum uric acid level. Furthermore, in acute oral toxicity study, no sign of toxicity was observed when the mice were administered with a single 2000 mg/kg oral dose of compound 10c. These results suggested that compound 10c was a potent and promising uric acid-lowing agent for the treatment of hyperuricemia.

PROCESS FOR THE PREPARATION OF 2-[3-CYANO-4-(2-METHYLPROPOXY)PHENYL]-4-METHYLTHIAZOLE-5-CARBOXYLIC ACID AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

-

, (2011/12/02)

The present invention relates to novel and improved processes for the preparation of 2-[3-cyano-4-(2-methylpropoxy) phenyl]-4-methylthiazole-5-carboxylic acid compound of formula-1 and its pharmaceutically acceptable salts thereof. the present invention also provides the novel process for the preparation of crystalline forms of 2-[3-cyano-4-(2-methylpropoxy) phenyl]-4-methylthiazole-5-carboxylic acid compound of formula-1 and its intermediates.

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