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59997-51-2

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  • China Largest factory Manufacturer Supply High Quality Pivaloylacetonitrile CAS 59997-51-2

    Cas No: 59997-51-2

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59997-51-2 Usage

Chemical Properties

white to cream crystals or crystalline powder

Uses

Trimethylacetylacetonitrile is a useful intermediate. 4,4-Dimethyl-3-oxopentanenitrile has been used in the preparation of 4,4-dimethyl-3-oxo-2-benzylpentanenitrile, 4,4-dimethyl-3-oxo-2-(4-hydroxybenzyl)pentanenitrile, 4,4-dimethyl-3-oxo-2-(4-methoxybenzyl)pentanenitrile, 4,4-dimethyl-3-oxo-2-(4-fluorobenzyl)pentanenitrile, 4,4-dimethyl-3-oxo-2-(3,4-methylenedioxybenzyl)pentanenitrile, 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-phenylurea.

Check Digit Verification of cas no

The CAS Registry Mumber 59997-51-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,9,9 and 7 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 59997-51:
(7*5)+(6*9)+(5*9)+(4*9)+(3*7)+(2*5)+(1*1)=202
202 % 10 = 2
So 59997-51-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO/c1-7(2,3)6(9)4-5-8/h4H2,1-3H3

59997-51-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A16309)  Trimethylacetylacetonitrile, 99%   

  • 59997-51-2

  • 25g

  • 607.0CNY

  • Detail
  • Alfa Aesar

  • (A16309)  Trimethylacetylacetonitrile, 99%   

  • 59997-51-2

  • 100g

  • 1933.0CNY

  • Detail
  • Alfa Aesar

  • (A16309)  Trimethylacetylacetonitrile, 99%   

  • 59997-51-2

  • 500g

  • 8144.0CNY

  • Detail

59997-51-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Pivaloylacetonitrile

1.2 Other means of identification

Product number -
Other names 4,4-dimethyl-3-oxopentanenitrile

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:59997-51-2 SDS

59997-51-2Synthetic route

sodium cyanide
773837-37-9

sodium cyanide

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With sodium carbonate; sodium iodide In methanol at 60℃; for 3h;95%
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
In methanol; sodium hydroxide90%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium bicarbonate; chlorine In methanol; water; benzene85%
Multi-step reaction with 2 steps
1: chloroform; SnCl4; bromine / -15 °C
2: alcohol / K-Salz
View Scheme
4,4-dimethyl-3-ketovaleronitrile sodium salt

4,4-dimethyl-3-ketovaleronitrile sodium salt

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With hydrogenchloride In water; dimethyl sulfoxide; toluene at 30℃; pH=2.0; Product distribution / selectivity;78%
With hydrogenchloride In water; toluene at 20 - 30℃; pH=2.0; Product distribution / selectivity;58%
With hydrogenchloride In water at 0℃; pH=7.0 - 7.7; Product distribution / selectivity;57%
N-methoxy-N-methylpivalamide
64214-60-4

N-methoxy-N-methylpivalamide

acetonitrile
75-05-8

acetonitrile

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
Stage #1: acetonitrile With methyllithium; lithium bromide In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; Inert atmosphere;
Stage #2: N-methoxy-N-methylpivalamide In tetrahydrofuran; diethyl ether at -78℃; for 1.5h; Inert atmosphere;
74%
Methyl pivalate
598-98-1

Methyl pivalate

acetonitrile
75-05-8

acetonitrile

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With bromobenzene Ambient temperature; electrolysis;60%
With bromobenzene; tetrabutylammonium tetrafluoroborate electroreduction;60%
Stage #1: acetonitrile With sodium hydride In 1,4-dioxane; paraffin oil (nujol) for 0.75h;
Stage #2: Methyl pivalate In 1,4-dioxane; paraffin oil (nujol) for 3h; Reflux;
51%
pivaloyl chloride
3282-30-2

pivaloyl chloride

acetonitrile
75-05-8

acetonitrile

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: pivaloyl chloride In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
41%
ethanol
64-17-5

ethanol

2-chloromethyl-2-hydroxy-3,3-dimethyl-butyronitrile

2-chloromethyl-2-hydroxy-3,3-dimethyl-butyronitrile

sodium ethanolate
141-52-6

sodium ethanolate

A

2,3-epoxy-2-tert-butyl-propionitrile

2,3-epoxy-2-tert-butyl-propionitrile

B

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

sodium cyanide
143-33-9

sodium cyanide

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With ethanol
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

potassium cyanide
151-50-8

potassium cyanide

A

2,3-epoxy-2-tert-butyl-propionitrile

2,3-epoxy-2-tert-butyl-propionitrile

B

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With water
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

potassium cyanide
151-50-8

potassium cyanide

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With ethanol
potassium cyanide
151-50-8

potassium cyanide

1-Bromopinacolon
5469-26-1

1-Bromopinacolon

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With ethanol K-Salz;
3,5-di(tert-butyl )isoxazole
1132-15-6

3,5-di(tert-butyl )isoxazole

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
In methanol Irradiation;
pivaloyl chloride
3282-30-2

pivaloyl chloride

cyanoacetic acid
372-09-8

cyanoacetic acid

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With [2,2]bipyridinyl; n-butyllithium 1.) THF, hexane, -70 deg C --> 0 deg C, 2.) -70 deg C, 1 h; Yield given. Multistep reaction;
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane
2,2-dimethyl-propanoic acid ethyl ester
3938-95-2

2,2-dimethyl-propanoic acid ethyl ester

acetonitrile
75-05-8

acetonitrile

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran
With sodium hydride In 1,4-dioxane
With sodium hydride In tetrahydrofuran at 75℃; for 15h;
With sodium hydride In tetrahydrofuran at 80℃;
With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 16h;
1-chloro-3,3-dimethyl-butan-2-one
13547-70-1

1-chloro-3,3-dimethyl-butan-2-one

potassium cyanide
151-50-8

potassium cyanide

A

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

B

α-tert-butyl-α-cyano-ethylene oxide

α-tert-butyl-α-cyano-ethylene oxide

Conditions
ConditionsYield
With water
Methyl pivalate
598-98-1

Methyl pivalate

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With hydrogenchloride In water; toluene; acetonitrile
With hydrogenchloride; hydrogen In water; toluene; acetonitrile
In tetrahydrofuran; water; acetonitrile
With ammonia; iron(III) chloride In diethyl ether; acetonitrile
acetonitrile
75-05-8

acetonitrile

pivalic acid ester

pivalic acid ester

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With sodium hydride In toluene
pivaloyl chloride
3282-30-2

pivaloyl chloride

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1.5 h / 0 - 20 °C
2.1: sodium hydride / 1,4-dioxane; paraffin oil / 0.75 h
2.2: 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: 1.5 h / 0 - 20 °C
2.1: sodium hydride / 1,4-dioxane; paraffin oil (nujol) / 0.75 h
2.2: Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: 1.5 h / 0 - 20 °C
2.1: sodium hydride / 1,4-dioxane; paraffin oil (nujol) / 0.75 h
2.2: 3 h / Reflux
View Scheme
sodium cyanide
773837-37-9

sodium cyanide

1-Bromopinacolon
5469-26-1

1-Bromopinacolon

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 20℃;
Stage #1: sodium cyanide; 1-Bromopinacolon In ethanol; water for 16h;
Stage #2: With hydrogenchloride In ethanol; water
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(2,4-difluorophenyl)hydrazinium chloride
40594-29-4, 51523-79-6

(2,4-difluorophenyl)hydrazinium chloride

3-tert-butyl-1-(2,4-difluorophenyl)-1H-pyrazol-5-amine
778611-49-7

3-tert-butyl-1-(2,4-difluorophenyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
Stage #1: trimethylacetylacetonitrile; (2,4-difluorophenyl)hydrazinium chloride With hydrogenchloride In ethanol for 12h; Heating / reflux;
Stage #2: With sodium hydroxide In ethanol; water at 20℃; pH=12;
100%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine
227623-26-9

3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
for 18h; Reflux;100%
With hydrogenchloride In ethanol for 48h; Reflux;87%
In ethanol at 80℃;80%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

1-(3-chloro-4-methylphenyl)hydrazine hydrochloride
54812-56-5

1-(3-chloro-4-methylphenyl)hydrazine hydrochloride

3-tert-butyl-1-(3-chloro-4-methylphenyl)-1H-pyrazol-5-amine
926242-93-5

3-tert-butyl-1-(3-chloro-4-methylphenyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 18h; Reflux;100%
With hydrogenchloride In ethanol; water at 90℃; for 24h;45%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

n-propylhydrazine oxalate
6340-91-6

n-propylhydrazine oxalate

3-tert-butyl-1-n-propyl-1H-pyrazol-5-amine
884340-11-8

3-tert-butyl-1-n-propyl-1H-pyrazol-5-amine

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 12h; Reflux;100%
Stage #1: trimethylacetylacetonitrile; n-propylhydrazine oxalate In ethanol at 85℃;
Stage #2: With sodium hydroxide In dichloromethane; water
98%
In ethanol at 85℃; for 4h;96%
In ethanol for 18h; Reflux; Inert atmosphere;
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride

(R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride

(R)-3-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1H-pyrazol-5-amine
1140917-39-0

(R)-3-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
Stage #1: trimethylacetylacetonitrile; (R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride In ethanol at 85℃;
Stage #2: With sodium hydrogencarbonate In dichloromethane at 20℃;
100%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

3,3,3-trifluoropropyl-4-methylbenzene sulphonate
2342-67-8

3,3,3-trifluoropropyl-4-methylbenzene sulphonate

3-tert-butyl-1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-amine
1217419-66-3

3-tert-butyl-1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
Stage #1: 3,3,3-trifluoropropyl-4-methylbenzene sulphonate With hydrazine hydrate In ethanol at 85℃;
Stage #2: trimethylacetylacetonitrile In ethanol at 20 - 85℃; Reflux;
100%
2,4-difluorophenylhydrazine
40594-30-7

2,4-difluorophenylhydrazine

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

3-tert-butyl-1-(2,4-difluorophenyl)-1H-pyrazol-5-amine
778611-49-7

3-tert-butyl-1-(2,4-difluorophenyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
With hydrogenchloride In ethanol Reflux;100%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

benzylhydrazine dihydrochloride
20570-96-1

benzylhydrazine dihydrochloride

1-benzyl-3-tert-butyl-1H-pyrazol-5-amine
866255-96-1

1-benzyl-3-tert-butyl-1H-pyrazol-5-amine

Conditions
ConditionsYield
With hydrogenchloride In ethanol Reflux;100%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

3,4-dimethylphenylhydrazine hydrochloride
60481-51-8, 86746-50-1

3,4-dimethylphenylhydrazine hydrochloride

5-tert-butyl-2-(3,4-dimethyl-phenyl)-2H-pyrazol-3-ylamine
1025893-78-0

5-tert-butyl-2-(3,4-dimethyl-phenyl)-2H-pyrazol-3-ylamine

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 18h; Reflux;100%
In methanol for 0.266667h; Reflux;91.5%
In ethanol for 5h; Reflux;90%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

4-hydrazinobenzoic acid hydrochloride
24589-77-3, 52455-33-1

4-hydrazinobenzoic acid hydrochloride

4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoic acid
869663-56-9

4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoic acid

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 18h; Reflux;100%
Stage #1: trimethylacetylacetonitrile; 4-hydrazinobenzoic acid hydrochloride In ethanol for 69h; Reflux;
Stage #2: With water; lithium hydroxide In tetrahydrofuran at 20℃; for 2h;
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

(E/Z)-2-((dimethylamino)methylene)-4,4-dimethyl-3-oxopentanenitrile

(E/Z)-2-((dimethylamino)methylene)-4,4-dimethyl-3-oxopentanenitrile

Conditions
ConditionsYield
In toluene100%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(3-chloro-4-fluorophenyl)hydrazine hydrochloride

(3-chloro-4-fluorophenyl)hydrazine hydrochloride

5-tert-butyl-2-(3-chloro-4-fluorophenyl)pyrazol-3-amine
1001522-07-1

5-tert-butyl-2-(3-chloro-4-fluorophenyl)pyrazol-3-amine

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 18h; Reflux;100%
In ethanol; water Reflux;
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

p-tolylhydrazine hydrochloride
637-60-5

p-tolylhydrazine hydrochloride

3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine
285984-25-0

3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine

Conditions
ConditionsYield
In methanol99%
With hydrogenchloride In ethanol for 48h; Reflux;86%
With hydrogenchloride In ethanol at 80℃; for 8h;86.4%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

4-Hydrazinobenzoic acid
619-67-0

4-Hydrazinobenzoic acid

4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoic acid
869663-56-9

4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoic acid

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran; ethanol for 16h; Heating / reflux;99%
With acetic acid In tetrahydrofuran; ethanol for 16h; Heating / reflux;99%
Stage #1: trimethylacetylacetonitrile; 4-Hydrazinobenzoic acid In methanol at 20℃; for 0.333333h;
Stage #2: With hydrogenchloride at 94.85℃; for 0.666667h;
80%
In toluene at 20℃; for 12h; Heating / reflux;
In toluene at 20℃; for 12h; Heating / reflux;
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

4-hydrazinobenzonitrile hydrochloride
2863-98-1

4-hydrazinobenzonitrile hydrochloride

4-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)benzonitrile
869663-55-8

4-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)benzonitrile

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 18h; Reflux;99%
In ethanol for 68h; Reflux;95%
In ethanol at 20℃; for 92h; Reflux;95%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

benzaldehyde
100-52-7

benzaldehyde

4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile
1189116-34-4

4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile

Conditions
ConditionsYield
With L-proline In ethanol at 20℃; for 24h; Knoevenagel condensation;99%
With dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate In water at 40℃; for 4h; Knoevenagel Condensation;80%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(4-fluorobenzyl)hydrazine dihydrochloride

(4-fluorobenzyl)hydrazine dihydrochloride

3-tert-butyl-1-(4-fluorobenzyl)-1H-pyrazol-5-amine
1217414-99-7

3-tert-butyl-1-(4-fluorobenzyl)-1H-pyrazol-5-amine

Conditions
ConditionsYield
Stage #1: trimethylacetylacetonitrile; (4-fluorobenzyl)hydrazine dihydrochloride In ethanol at 85℃; for 2h;
Stage #2: With sodium hydrogencarbonate In ethanol; water; ethyl acetate
99%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

benzaldehyde
100-52-7

benzaldehyde

malononitrile
109-77-3

malononitrile

2-amino-6-(tert-butyl)-4-phenyl-4H-pyran-3,5-dicarbonitrile

2-amino-6-(tert-butyl)-4-phenyl-4H-pyran-3,5-dicarbonitrile

Conditions
ConditionsYield
With tris(2,2'-bipyridyl)ruthenium dichloride In ethanol; water at 25℃; for 2h; Schlenk technique; Irradiation; Green chemistry;98.6%
In ethanol; water at 20℃; Irradiation; Green chemistry;88%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

p-tolylhydrazine hydrochloride
637-60-5

p-tolylhydrazine hydrochloride

3-amino-5-tert-butyl-2-(p-tolyl)-2H-pyrazole hydrochloride

3-amino-5-tert-butyl-2-(p-tolyl)-2H-pyrazole hydrochloride

Conditions
ConditionsYield
In methanol at 120℃; for 1h; microwave irradiation;98%
In methanol Inert atmosphere; Reflux;94%
In methanol for 16h; Reflux;86%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

5-isothiocyanato-benzo[1,3]dioxole
113504-93-1

5-isothiocyanato-benzo[1,3]dioxole

methyl iodide
74-88-4

methyl iodide

3-(benzo[1,3]dioxol-5ylamino)-2-(2,2-dimethylpropionyl)-3-methylsulfanyl-2-propenenitrile

3-(benzo[1,3]dioxol-5ylamino)-2-(2,2-dimethylpropionyl)-3-methylsulfanyl-2-propenenitrile

Conditions
ConditionsYield
Stage #1: trimethylacetylacetonitrile; 5-isothiocyanato-benzo[1,3]dioxole With potassium carbonate In acetone at 20℃; for 72h;
Stage #2: methyl iodide In acetone at 20℃; for 0.75h;
98%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

2C6H5O2(1-)*C16H22N2O2S4(2+)

2C6H5O2(1-)*C16H22N2O2S4(2+)

C22H20N2O4S4
1118625-18-5

C22H20N2O4S4

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Inert atmosphere;98%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

2C6H5O2(1-)*C16H22N2O2S4(2+)

2C6H5O2(1-)*C16H22N2O2S4(2+)

C22H20N2O4S4
1118625-18-5

C22H20N2O4S4

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Inert atmosphere;98%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(2-methoxyethyl)hydrazine oxalic acid

(2-methoxyethyl)hydrazine oxalic acid

5-tert-butyl-2-(2-methoxyethyl)-2H-pyrazol-3-ylamine

5-tert-butyl-2-(2-methoxyethyl)-2H-pyrazol-3-ylamine

Conditions
ConditionsYield
In ethanol at 85℃; for 4.5h;98%
In ethanol at 85℃; for 4.5h;98%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

5-amino-3-tert-butylisoxazole
59669-59-9

5-amino-3-tert-butylisoxazole

Conditions
ConditionsYield
With sodium hydroxide; hydroxyammonium sulfate at 100℃; for 2.5h;97.6%
With hydroxylamine hydrochloride; sodium hydroxide In water at 100℃; for 2.5h;97%
With hydroxylamine hydrochloride; sodium hydroxide In water at 60℃; for 3h;88%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

methyl 4,4-dimethyl-3-oxopentanimidate hydrochloride

methyl 4,4-dimethyl-3-oxopentanimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; hexane; toluene97.5%
97.5%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

3-tert-butyl-1H-pyrazole-5-amine
82560-12-1

3-tert-butyl-1H-pyrazole-5-amine

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 120℃; for 0.666667h; microwave irradiation;97%
With hydrazine hydrate In ethanol at 110℃; for 7h; Inert atmosphere;97%
With hydrazine hydrate In ethanol for 3h; Reflux;89%
2-hydroxyethylhydrazine
109-84-2

2-hydroxyethylhydrazine

trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

2-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)ethanol
908267-36-7

2-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)ethanol

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 20h; Reflux;97%
With hydrogenchloride In ethanol for 20h; Reflux;97%
With hydrogenchloride In ethanol; water for 20h; Reflux;97%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride

(R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride

(R)-3-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1H-pyrazol-5-amine hydrochloride
1140917-98-1

(R)-3-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1H-pyrazol-5-amine hydrochloride

Conditions
ConditionsYield
In ethanol at 90℃; for 6h;97%
In ethanol at 90℃; for 6h;97%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

(2-chloro-5-hydrazino-phenyl)-methanol

(2-chloro-5-hydrazino-phenyl)-methanol

[5-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-chloro-phenyl]-methanol hydrochloride

[5-(5-amino-3-tert-butyl-pyrazol-1-yl)-2-chloro-phenyl]-methanol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 3.5h; Reflux;97%
With hydrogenchloride In ethanol for 3.5h; Reflux;97%
trimethylacetylacetonitrile
59997-51-2

trimethylacetylacetonitrile

2-hydrazinoethanol

2-hydrazinoethanol

2-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)ethanol
908267-36-7

2-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)ethanol

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 20h; Reflux;97%

59997-51-2Relevant articles and documents

A simplified method for the efficient preparation of pivaloylacetonitrile

Zelinka, Karel,Simbera, Jan,Pazdera, Pavel

, p. 386 - 389 (2014)

-

Identification of TRD-35 as Potent and Selective DRAK2 Inhibitor

Ali, Imran,Park, Sangjun,Jung, Myoung Eun,Lee, Nari,Bibi, Maimoona,Chae, Chong Hak,Yang, Kyung-Min,Kim, Seong-Jin,Choi, Gildon,Lee, Kwangho

, p. 567 - 569 (2020/03/23)

-

Microwave synthesis of 1-aryl-1H-pyrazole-5-amines

Everson, Nikalet,Yniguez, Kenya,Loop, Lauren,Lazaro, Horacio,Belanger, Briana,Koch, Grant,Bach, Jordan,Manjunath, Aashrita,Schioldager, Ryan,Law, Jarvis,Grabenauer, Megan,Eagon, Scott

supporting information, p. 72 - 74 (2018/11/30)

A microwave-mediated synthesis of 1H-pyrazole-5-amines utilizing 1 M HCl at 150 °C was developed in order to provide products in a matter of minutes with minimal purification. Most reactions are complete in only 10 min and can be isolated via a simple filtration without the need for further purification by column chromatography or recrystallization. This method tolerates a range of functional groups and can be performed on milligram to gram scales.

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