sodium cyanide
1-chloro-3,3-dimethyl-butan-2-one
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With sodium carbonate; sodium iodide In methanol at 60℃; for 3h; | 95% |
1-chloro-3,3-dimethyl-butan-2-one
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
In methanol; sodium hydroxide | 90% |
3,3-dimethyl-butan-2-one
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium bicarbonate; chlorine In methanol; water; benzene | 85% |
Multi-step reaction with 2 steps 1: chloroform; SnCl4; bromine / -15 °C 2: alcohol / K-Salz View Scheme |
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
1-chloro-3,3-dimethyl-butan-2-one
sodium cyanide
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With ethanol |
1-chloro-3,3-dimethyl-butan-2-one
potassium cyanide
B
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With water |
1-chloro-3,3-dimethyl-butan-2-one
potassium cyanide
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
With ethanol K-Salz; |
3,5-di(tert-butyl )isoxazole
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
In methanol Irradiation; |
Conditions | Yield |
---|---|
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
acetonitrile
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
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
potassium cyanide
A
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With water |
Methyl pivalate
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With sodium hydride In toluene |
pivaloyl chloride
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
(2,4-difluorophenyl)hydrazinium chloride
3-tert-butyl-1-(2,4-difluorophenyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
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
4-methoxyphenylhydrazine hydrochloride
3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
for 18h; Reflux; | 100% |
With hydrogenchloride In ethanol for 48h; Reflux; | 87% |
In ethanol at 80℃; | 80% |
trimethylacetylacetonitrile
1-(3-chloro-4-methylphenyl)hydrazine hydrochloride
3-tert-butyl-1-(3-chloro-4-methylphenyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 18h; Reflux; | 100% |
With hydrogenchloride In ethanol; water at 90℃; for 24h; | 45% |
trimethylacetylacetonitrile
n-propylhydrazine oxalate
3-tert-butyl-1-n-propyl-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
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
(R)-3-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
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
3,3,3-trifluoropropyl-4-methylbenzene sulphonate
3-tert-butyl-1-(3,3,3-trifluoropropyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
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
trimethylacetylacetonitrile
3-tert-butyl-1-(2,4-difluorophenyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Reflux; | 100% |
trimethylacetylacetonitrile
benzylhydrazine dihydrochloride
1-benzyl-3-tert-butyl-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Reflux; | 100% |
trimethylacetylacetonitrile
3,4-dimethylphenylhydrazine hydrochloride
5-tert-butyl-2-(3,4-dimethyl-phenyl)-2H-pyrazol-3-ylamine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 18h; Reflux; | 100% |
In methanol for 0.266667h; Reflux; | 91.5% |
In ethanol for 5h; Reflux; | 90% |
trimethylacetylacetonitrile
4-hydrazinobenzoic acid hydrochloride
4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoic acid
Conditions | Yield |
---|---|
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
N,N-dimethyl-formamide dimethyl acetal
Conditions | Yield |
---|---|
In toluene | 100% |
trimethylacetylacetonitrile
5-tert-butyl-2-(3-chloro-4-fluorophenyl)pyrazol-3-amine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 18h; Reflux; | 100% |
In ethanol; water Reflux; |
trimethylacetylacetonitrile
p-tolylhydrazine hydrochloride
3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
In methanol | 99% |
With hydrogenchloride In ethanol for 48h; Reflux; | 86% |
With hydrogenchloride In ethanol at 80℃; for 8h; | 86.4% |
trimethylacetylacetonitrile
4-Hydrazinobenzoic acid
4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoic acid
Conditions | Yield |
---|---|
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
4-hydrazinobenzonitrile hydrochloride
4-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)benzonitrile
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 18h; Reflux; | 99% |
In ethanol for 68h; Reflux; | 95% |
In ethanol at 20℃; for 92h; Reflux; | 95% |
trimethylacetylacetonitrile
benzaldehyde
4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile
Conditions | Yield |
---|---|
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
3-tert-butyl-1-(4-fluorobenzyl)-1H-pyrazol-5-amine
Conditions | Yield |
---|---|
Stage #1: trimethylacetylacetonitrile; (4-fluorobenzyl)hydrazine dihydrochloride In ethanol at 85℃; for 2h; Stage #2: With sodium hydrogencarbonate In ethanol; water; ethyl acetate | 99% |
Conditions | Yield |
---|---|
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
p-tolylhydrazine hydrochloride
Conditions | Yield |
---|---|
In methanol at 120℃; for 1h; microwave irradiation; | 98% |
In methanol Inert atmosphere; Reflux; | 94% |
In methanol for 16h; Reflux; | 86% |
trimethylacetylacetonitrile
5-isothiocyanato-benzo[1,3]dioxole
methyl iodide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 80℃; for 4h; Inert atmosphere; | 98% |
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
In ethanol at 85℃; for 4.5h; | 98% |
In ethanol at 85℃; for 4.5h; | 98% |
trimethylacetylacetonitrile
5-amino-3-tert-butylisoxazole
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; hexane; toluene | 97.5% |
97.5% |
trimethylacetylacetonitrile
3-tert-butyl-1H-pyrazole-5-amine
Conditions | Yield |
---|---|
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
trimethylacetylacetonitrile
2-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)ethanol
Conditions | Yield |
---|---|
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
(R)-3-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1H-pyrazol-5-amine hydrochloride
Conditions | Yield |
---|---|
In ethanol at 90℃; for 6h; | 97% |
In ethanol at 90℃; for 6h; | 97% |
trimethylacetylacetonitrile
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 3.5h; Reflux; | 97% |
With hydrogenchloride In ethanol for 3.5h; Reflux; | 97% |
trimethylacetylacetonitrile
2-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)ethanol
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water for 20h; Reflux; | 97% |
The CAS register number of Pentanenitrile,4,4-dimethyl-3-oxo- is 59997-51-2. It also can be called as 4,4-Dimethyl-3-oxovaleronitrile and the IUPAC name about this chemical is 4,4-dimethyl-3-oxopentanenitrile. The molecular formula about this chemical is C7H11NO and the molecular weight is 125.17. It belongs to the following product categories, such as Building Blocks; Aliphatics; Ketone and so on. If you wan to store this chemical, please keep it in a closed container and store it in a cool, dry place.
Physical properties about Pentanenitrile,4,4-dimethyl-3-oxo- are: (1)ACD/LogP: 0.55; (2)ACD/LogD (pH 5.5): 0.55; (3)ACD/LogD (pH 7.4): 0.55; (4)ACD/BCF (pH 5.5): 1.53; (5)ACD/BCF (pH 7.4): 1.53; (6)ACD/KOC (pH 5.5): 47.26; (7)ACD/KOC (pH 7.4): 47.2; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 40.86Å2; (11)Index of Refraction: 1.424; (12)Molar Refractivity: 34.38 cm3; (13)Molar Volume: 134.6 cm3; (14)Polarizability: 13.63x10-24cm3; (15)Surface Tension: 31.5 dyne/cm; (16)Enthalpy of Vaporization: 47.27 kJ/mol; (17)Boiling Point: 236 °C at 760 mmHg; (18)Vapour Pressure: 0.0486 mmHg at 25°C.
Preparation: this chemical can be prepared by acetonitrile and 2,2-dimethyl-propionic acid methyl ester. This reaction will need reagent bromobenzene at ambient temperature//electrolysis. The yield is about 60%.
Uses of Pentanenitrile,4,4-dimethyl-3-oxo-: it can be used to produce 3-tert-butyl-isoxazol-5-ylamine. This reaction will need reagent sodium acetate, acetic acid and NH2OH+HCl.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
You can still convert the following datas into molecular structure:
(1)SMILES: N#CCC(=O)C(C)(C)C
(2)InChI: InChI=1/C7H11NO/c1-7(2,3)6(9)4-5-8/h4H2,1-3H3
(3)InChIKey: MXZMACXOMZKYHJ-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C7H11NO/c1-7(2,3)6(9)4-5-8/h4H2,1-3H3
(5)Std. InChIKey: MXZMACXOMZKYHJ-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | skin | > 1gm/kg (1000mg/kg) | National Technical Information Service. Vol. OTS0555393, | |
rat | LD50 | oral | 283mg/kg (283mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | National Technical Information Service. Vol. OTS0555393, |
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