4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With aluminum oxide; calcium hydroxide; 2-hydroxynitrobenzene In cyclohexane at 77 - 97℃; for 5.5h; Temperature; Reflux; | 92% |
Conditions | Yield |
---|---|
With formaldehyd; formic acid; acetonitrile for 12h; Heating; | 87% |
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With N-chloro-succinimide; potassium acetate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 1h; Irradiation; Sealed tube; Inert atmosphere; | 59% |
Conditions | Yield |
---|---|
With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite at 20℃; nitrosative cleavage; | 57% |
Conditions | Yield |
---|---|
With chlorine Irradiation.mit UV-Licht; | |
With sodium persulfate; copper dichloride In water at 85 - 90℃; for 10h; Yield given. Yields of byproduct given; | |
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; Product distribution; Rate constant; Irradiation; relative rate constants, position selectivity, substrate selectivity; |
Conditions | Yield |
---|---|
With thionyl chloride; benzene | |
With trichlorophosphate; benzene | |
With phosphorus trichloride |
ethanol
sodium cyanide
1,3-chlorobromopropane
A
4-Chlorobutyronitrile
B
4-bromobutanenitrile
ethanol
potassium cyanide
1,3-chlorobromopropane
A
4-Chlorobutyronitrile
B
Glutaronitrile
sodium cyanide
1,3-chlorobromopropane
A
4-Chlorobutyronitrile
B
Glutaronitrile
Conditions | Yield |
---|---|
With methanol |
Conditions | Yield |
---|---|
With ethanol | |
With ethanol; water Alkohol abdestillieren,Wasser zum Rueckstand geben,abgeschiedene Oelschicht abheben und fraktionieren; |
Conditions | Yield |
---|---|
(i) liq. NH3, (ii) SOCl2; Multistep reaction; |
Conditions | Yield |
---|---|
In dichloromethane |
2,4-dichlorobutanenitrile
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With acetic acid; zinc for 2h; Yield given; |
propyl cyanide
chlorine
A
3-chlorobutyronitrile
B
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
mit UV-Licht in der Dampfphase.Irradiation; |
propyl cyanide
chlorine
A
3-chlorobutyronitrile
B
4-Chlorobutyronitrile
C
2-chlorobutyronitrile
Conditions | Yield |
---|---|
at 450℃; Dampfphase; |
Conditions | Yield |
---|---|
With chlorine at 450℃; |
4-Chlorobutyronitrile
sodium thiomethoxide
4-(methylthio)butyronitrile
Conditions | Yield |
---|---|
In ethanol at 20℃; for 25h; Inert atmosphere; Cooling with ice; | 100% |
In ethanol | |
In ethanol at 25℃; for 15h; |
4-Chlorobutyronitrile
tert-butyl N-(benzyloxy)carbamate
4-[N-(tert-butyloxycarbonyl)benzyloxyamino]butyronitrile
Conditions | Yield |
---|---|
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 80℃; for 6h; | 100% |
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 70℃; for 18h; Inert atmosphere; | 98% |
With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 60 - 70℃; for 5h; | 80% |
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: 4-Chlorobutyronitrile In N,N-dimethyl-formamide at 85℃; Inert atmosphere; | 70% |
With sodium hydride; potassium iodide In N,N-dimethyl-formamide |
4-Chlorobutyronitrile
(S)-(-)-[1-phenylethyl]-1H-imidazole
3-(3-cyanopropyl)-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium chloride
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 72h; | 99% |
In toluene for 7h; Reflux; | 65% |
at 20℃; | 63% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium chloride In water; dimethyl sulfoxide | 98% |
With sodium hydride In ethylene glycol; mineral oil at 20 - 80℃; for 0.5h; Solvent; Reagent/catalyst; | 97.2% |
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h; | 89% |
4-Chlorobutyronitrile
methyl N-tosylanthranilate
methyl 2-{(3-cyanopropyl)[(4-methylphenyl)sulfonyl]amino}benzoate
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In butanone for 12h; Heating; | 98% |
With potassium carbonate; potassium iodide In acetone for 168h; Heating; | 95% |
With potassium carbonate; potassium iodide In butanone for 12h; Reflux; | 80.1% |
4-Chlorobutyronitrile
[1(R)-methyl-3-[(phenylmethyl)amino]propyl]carbamic acid, 1,1-dimethylethyl ester
3-[(3-cyanopropyl)(phenylmethyl)amino-1(R)-methylpropyl]carbamic acid, 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In butan-1-ol for 20h; Alkylation; Heating; | 98% |
4-Chlorobutyronitrile
N-(2,4,6-trimethylphenyl)imidazole
1-(2,4,6-trimethylphenyl)-3-(butylnitrile)imidazolium chloride
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane for 72h; Reflux; Inert atmosphere; | 98% |
In 1,2-dimethoxyethane Inert atmosphere; Heating; | 98% |
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With triphenyl phosphite; bromine at 80℃; for 4h; Reagent/catalyst; | 98% |
4-Chlorobutyronitrile
dimethylsilicon dichloride
(3-cyanopropyl)dimethylsilyl chloride
Conditions | Yield |
---|---|
With magnesium; ethylene dibromide; manganese(ll) chloride In tetrahydrofuran at 65℃; for 2h; Inert atmosphere; | 96.1% |
Stage #1: 4-Chlorobutyronitrile With sodium In toluene at 108 - 110℃; for 3h; Stage #2: dimethylsilicon dichloride In toluene at 40 - 45℃; for 4h; Temperature; |
4-Chlorobutyronitrile
1-(2-Methoxyphenyl)piperazine
4‐[4‐(2‐methoxyphenyl)piperazin‐1‐yl]butannitrile
Conditions | Yield |
---|---|
With cesium hydroxide; sodium iodide at 60℃; for 1.33333h; Microwave irradiation; Neat (no solvent); chemoselective reaction; | 96% |
4-Chlorobutyronitrile
N-p-toluenesulfonyl-4-chloro-anthranilic acid methyl ester
methyl 4-chloro-2-(N-tosyl-3-cyanopropylamino)benzoate
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone for 168h; Heating; | 95% |
4-Chlorobutyronitrile
N-[N-(tert-Butyloxycarbonyl)-3-aminopropyl]benzylamine
N-[N-(tert-Butoxycarbonyl)-3-aminopropyl]-N-(3-cyanopropyl)benzylamine
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In butan-1-ol for 48h; Heating; | 95% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 48h; Inert atmosphere; | 95% |
With triethylamine In N,N-dimethyl-formamide at 25℃; | |
With sodium methylate; sodium iodide 1.) methanol, 1 h, 2.) reflux, 12 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 4h; Heating; | 95% |
4-Chlorobutyronitrile
1,2,3,4-tetrahydro-4-methylspiro
N-(γ-cyanopropyl)-3,4-dihydro-4-methylspiro[quinoline-2,1'-cyclohexane]
Conditions | Yield |
---|---|
With sodium carbonate; potassium iodide In butan-1-ol Heating; | 95% |
Conditions | Yield |
---|---|
at 80℃; for 24h; | 95% |
at 70℃; for 48h; Neat (no solvent); Sealed vial; | 92% |
at 80℃; for 24h; | 82% |
Heating; | 78% |
at 79.84℃; for 48h; |
4-Chlorobutyronitrile
trans-hydridochloro-di-{1,2-bis(diphenylphosphino)ethane}iron(II)
trans-[FeH(4-chlorobutyronitrile)(dppe)2]Cl
Conditions | Yield |
---|---|
In further solvent(s) Ar-atmosphere; stirring in ClCH2CH2CH2CN for 1 h; filtration, solvent removal (vac.), washing (Et2O); elem. anal.; | 95% |
methanol
4-Chlorobutyronitrile
methyl 3-chloropropanimidate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 20℃; for 4h; | 94% |
With hydrogenchloride In diethyl ether at -20℃; for 24h; | 90% |
With hydrogenchloride In diethyl ether at 0℃; for 24h; | 70% |
With hydrogenchloride In diethyl ether at -20 - 0℃; for 28h; |
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With aluminum oxide; calcium hydroxide; 2-hydroxynitrobenzene In cyclohexane at 77 - 97℃; for 5.5h; Temperature; Reflux; | 92% |
Conditions | Yield |
---|---|
With formaldehyd; formic acid; acetonitrile for 12h; Heating; | 87% |
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With N-chloro-succinimide; potassium acetate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 1h; Irradiation; Sealed tube; Inert atmosphere; | 59% |
Conditions | Yield |
---|---|
With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite at 20℃; nitrosative cleavage; | 57% |
Conditions | Yield |
---|---|
With chlorine Irradiation.mit UV-Licht; | |
With sodium persulfate; copper dichloride In water at 85 - 90℃; for 10h; Yield given. Yields of byproduct given; | |
With N-chloropiperidine; 2,2'-azobis(isobutyronitrile) In trifluoroacetic acid at 30℃; Product distribution; Rate constant; Irradiation; relative rate constants, position selectivity, substrate selectivity; |
Conditions | Yield |
---|---|
With thionyl chloride; benzene | |
With trichlorophosphate; benzene | |
With phosphorus trichloride |
ethanol
sodium cyanide
1,3-chlorobromopropane
A
4-Chlorobutyronitrile
B
4-bromobutanenitrile
ethanol
potassium cyanide
1,3-chlorobromopropane
A
4-Chlorobutyronitrile
B
Glutaronitrile
sodium cyanide
1,3-chlorobromopropane
A
4-Chlorobutyronitrile
B
Glutaronitrile
Conditions | Yield |
---|---|
With methanol |
Conditions | Yield |
---|---|
With ethanol | |
With ethanol; water Alkohol abdestillieren,Wasser zum Rueckstand geben,abgeschiedene Oelschicht abheben und fraktionieren; |
Conditions | Yield |
---|---|
(i) liq. NH3, (ii) SOCl2; Multistep reaction; |
Conditions | Yield |
---|---|
In dichloromethane |
2,4-dichlorobutanenitrile
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
With acetic acid; zinc for 2h; Yield given; |
propyl cyanide
chlorine
A
3-chlorobutyronitrile
B
4-Chlorobutyronitrile
Conditions | Yield |
---|---|
mit UV-Licht in der Dampfphase.Irradiation; |
propyl cyanide
chlorine
A
3-chlorobutyronitrile
B
4-Chlorobutyronitrile
C
2-chlorobutyronitrile
Conditions | Yield |
---|---|
at 450℃; Dampfphase; |
Conditions | Yield |
---|---|
With chlorine at 450℃; |
4-Chlorobutyronitrile
sodium thiomethoxide
4-(methylthio)butyronitrile
Conditions | Yield |
---|---|
In ethanol at 20℃; for 25h; Inert atmosphere; Cooling with ice; | 100% |
In ethanol | |
In ethanol at 25℃; for 15h; |
4-Chlorobutyronitrile
tert-butyl N-(benzyloxy)carbamate
4-[N-(tert-butyloxycarbonyl)benzyloxyamino]butyronitrile
Conditions | Yield |
---|---|
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 80℃; for 6h; | 100% |
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4-Chlorobutyronitrile With sodium iodide In N,N-dimethyl-formamide at 70℃; for 18h; Inert atmosphere; | 98% |
With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 60 - 70℃; for 5h; | 80% |
Stage #1: tert-butyl N-(benzyloxy)carbamate With sodium hydride; sodium iodide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #2: 4-Chlorobutyronitrile In N,N-dimethyl-formamide at 85℃; Inert atmosphere; | 70% |
With sodium hydride; potassium iodide In N,N-dimethyl-formamide |
4-Chlorobutyronitrile
(S)-(-)-[1-phenylethyl]-1H-imidazole
3-(3-cyanopropyl)-1-((1S)-1-phenylethyl)-1H-imidazol-3-ium chloride
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 72h; | 99% |
In toluene for 7h; Reflux; | 65% |
at 20℃; | 63% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; sodium chloride In water; dimethyl sulfoxide | 98% |
With sodium hydride In ethylene glycol; mineral oil at 20 - 80℃; for 0.5h; Solvent; Reagent/catalyst; | 97.2% |
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h; | 89% |
1.Introduction of 4-Chlorobutyronitrile
The 4-Chlorobutanenitrile, with the CAS registry number 628-20-6, is also known as 1-Chloro-3-cyanopropane. It belongs to the product categories of Halogen compounds; Miscellaneous; Aliphatics; C1 to C5; Cyanides/Nitriles; Nitrogen Compounds. It should be stored in shady and cool warehouse and mainly used as Intermediate for Buflomedil.
2.Physical properties of 4-Chlorobutanenitrile
(1)ACD/LogP: 0.56; (2)ACD/LogD (pH 5.5): 0.56; (3)ACD/LogD (pH 7.4): 0.56; (4)ACD/BCF (pH 5.5): 1.57; (5)ACD/BCF (pH 7.4): 1.57; (6)ACD/KOC (pH 5.5): 48.04; (7)ACD/KOC (pH 7.4): 48.04; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.423; (11)Molar Refractivity: 25.34 cm3; (12)Molar Volume: 99.3 cm3; (13)Surface Tension: 32.9 dyne/cm; (14)Density: 1.042 g/cm3; (15)Flash Point: 85 °C; (16)Enthalpy of Vaporization: 42.72 kJ/mol; (17)Boiling Point: 191 °C at 760 mmHg; (18)Vapour Pressure: 0.525 mmHg at 25°C.
3.Structure descriptors of 4-Chlorobutyronitrile
(1)Canonical SMILES: C(CC#N)CCl
(2)InChI: InChI=1S/C4H6ClN/c5-3-1-2-4-6/h1-3H2
(3)InChIKey: ZFCFBWSVQWGOJJ-UHFFFAOYSA-N
4. Preparation of 4-Chlorobutyronitrile
The 4-Chlorobutyronitrile can be prepared by 1-chloro-3-bromopropane and potassium cyanide.
BrCH2CH2CH2Cl+KCN→ClCH2CH2CH2CN+KBr
5. Uses of 4-Chlorobutanenitrile
The 4-Chlorobutyronitrile can be used to produce 4-chloro-butyric acid at temperature of 240 °C. This reaction will need reagent CuSO4•H2O with reaction time of 1 hour. The yield is about 65%.
6.Safety information of 4-Chlorobutyronitrile
This chemical that at low levels can cause damage to health. It may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.
7.The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 53380ug/kg (53.38mg/kg) | Archives of Toxicology. Vol. 55, Pg. 47, 1984. |
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