Product Name

  • Name

    Cyclopropylacetonitrile

  • EINECS
  • CAS No. 6542-60-5
  • Article Data14
  • CAS DataBase
  • Density 0.963 g/cm3
  • Solubility Miscible with water, methylene chloride and alcohols.
  • Melting Point
  • Formula C5H7N
  • Boiling Point 159.8 °C at 760 mmHg
  • Molecular Weight 81.1173
  • Flash Point 57.4 °C
  • Transport Information UN 1993
  • Appearance
  • Safety 26-36/37/39-45
  • Risk Codes 10
  • Molecular Structure Molecular Structure of 6542-60-5 (Cyclopropylacetonitrile)
  • Hazard Symbols ToxicT
  • Synonyms (Cyanomethyl)cyclopropane;2-Cyclopropylacetonitrile;Cyclopropylacetonitrile;Cyclopropylcarbinylcyanide;Cyclopropylmethyl cyanide;
  • PSA 23.79000
  • LogP 1.31008

Synthetic route

potassium cyanide

potassium cyanide

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 110℃; for 5h; Inert atmosphere;82%
cyclopropylacetaldehyde oxime
530133-49-4

cyclopropylacetaldehyde oxime

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
With acetic anhydride In ethyl acetate at 25℃; for 3.5h; Heating / reflux;76.7%
sodium cyanide
143-33-9

sodium cyanide

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
phase transfer;75%
In dimethyl sulfoxide at 120℃;41%
In dimethyl sulfoxide for 3h;
sodium cyanide
143-33-9

sodium cyanide

chloro(cyclopropyl)methane
5911-08-0

chloro(cyclopropyl)methane

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide Heating;50%
potassium cyanide
151-50-8

potassium cyanide

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
With ethanol
Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

sodium cyanide
143-33-9

sodium cyanide

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
(i) PBr3, (ii) NaCN, aq. EtOH; Multistep reaction;
diazomethane
186581-53-3, 908094-01-9

diazomethane

but-3-enenitrile
109-75-1

but-3-enenitrile

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Conditions
ConditionsYield
With palladium diacetate In diethyl ether for 0.166667h; Yield given;
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

2-(cyclopropyl)ethylamine
62893-54-3

2-(cyclopropyl)ethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; sulfuric acid In diethyl ether for 2h; Heating;99%
With lithium aluminium tetrahydride; sulfuric acid In diethyl ether at 20℃; for 2h; Heating / reflux;70%
With lithium aluminium tetrahydride; sulfuric acid In diethyl ether for 2h; Heating / reflux;70%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

rac-3-bromocyclohexene
1521-51-3

rac-3-bromocyclohexene

N-(cyclohex-2-en-1-yl)-2-cyclopropylacetamide

N-(cyclohex-2-en-1-yl)-2-cyclopropylacetamide

Conditions
ConditionsYield
With water; silver trifluoromethanesulfonate at 0℃; for 1h; Ritter Amidation; chemoselective reaction;97%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With water; potassium hydroxide In ethanol at 90℃; for 18h;96%
With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 48h; Reflux; Inert atmosphere;83%
With dihydrogen peroxide; sodium hydroxide In water Reflux;81%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

4-t-butoxy-3-methyl-2,5-difluoropyridine
169749-84-2

4-t-butoxy-3-methyl-2,5-difluoropyridine

2-(4-tert-butoxy-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetonitrile
169749-85-3

2-(4-tert-butoxy-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetonitrile

Conditions
ConditionsYield
Stage #1: 4-t-butoxy-3-methyl-2,5-difluoropyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -51 - 17℃; Metallation;
Stage #2: 2-cyclopropylacetonitrile In tetrahydrofuran; hexane at -51 - 17℃; Methylation;		93%
With lithium diisopropyl amide 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h; Yield given. Multistep reaction;
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78℃; for 0.5h;
Stage #2: 2-cyclopropylacetonitrile; 4-t-butoxy-3-methyl-2,5-difluoropyridine In tetrahydrofuran; hexanes at -78 - 20℃; for 2h;
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

4-tert-butoxy-2,5-difluoro-3-methoxypyridine
477700-61-1

4-tert-butoxy-2,5-difluoro-3-methoxypyridine

(4-tert-butoxy-5-fluoro-3-methoxypyridin-2-yl)cyclopropylacetonitrile
477700-63-3

(4-tert-butoxy-5-fluoro-3-methoxypyridin-2-yl)cyclopropylacetonitrile

Conditions
ConditionsYield
With lithium diisopropyl amide93%
With lithium diisopropyl amide 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h; Multistep reaction;
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

N-cyclohexenyl-N-(4-methoxybenzyl)furan-2-carboxamide
1350894-64-2

N-cyclohexenyl-N-(4-methoxybenzyl)furan-2-carboxamide

4-(cyclopropylmethyl)-2-(furan-2-yl)-5,6,7,8-tetrahydroquinazoline
1350894-77-7

4-(cyclopropylmethyl)-2-(furan-2-yl)-5,6,7,8-tetrahydroquinazoline

Conditions
ConditionsYield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 25℃; Inert atmosphere;91%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

phenylmagnesium bromide

phenylmagnesium bromide

2-cyclopropyl-1-phenylethanone
6739-22-6

2-cyclopropyl-1-phenylethanone

Conditions
ConditionsYield
90%
(i) Et2O, (ii) H2O; Multistep reaction;
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

C22H22N2O2
1350894-62-0

C22H22N2O2

C19H19N3
1350894-75-5

C19H19N3

Conditions
ConditionsYield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 25℃; Inert atmosphere;90%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

benzoic acid tert-butyl ester
774-65-2

benzoic acid tert-butyl ester

N-(tert-butyl)cyclopropanecarboxamide
15924-91-1

N-(tert-butyl)cyclopropanecarboxamide

Conditions
ConditionsYield
With zinc perchlorate In neat (no solvent) at 50℃; for 5h; Ritter Amidation;90%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-cyclopropyl-1-phenylethanone
6739-22-6

2-cyclopropyl-1-phenylethanone

Conditions
ConditionsYield
Stage #1: 2-cyclopropylacetonitrile; phenylmagnesium bromide In diethyl ether at 0 - 20℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether for 12h;		89%
Stage #1: 2-cyclopropylacetonitrile; phenylmagnesium bromide In diethyl ether at 0℃; for 2h;
Stage #2: With hydrogenchloride In diethyl ether; water for 12h;		70%
Stage #1: 2-cyclopropylacetonitrile; phenylmagnesium bromide In diethyl ether at 0 - 20℃;
Stage #2: With hydrogenchloride In diethyl ether; water for 12h;		70%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

methyl 2-amino-4,5-dimethoxybenzoate
26759-46-6

methyl 2-amino-4,5-dimethoxybenzoate

2-(cyclopropylmethyl)-6,7-dimethoxyquinazolin-4-ol
1448676-62-7

2-(cyclopropylmethyl)-6,7-dimethoxyquinazolin-4-ol

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;85%
bromobenzene
108-86-1

bromobenzene

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

2-cyclopropyl-1-phenylethanone
6739-22-6

2-cyclopropyl-1-phenylethanone

Conditions
ConditionsYield
Stage #1: bromobenzene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux;
Stage #2: 2-cyclopropylacetonitrile In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #3: With sulfuric acid for 2h; Reflux;		85%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

(E)-2-cyclopropyl-N’-hydroxyacetimidamide

(E)-2-cyclopropyl-N’-hydroxyacetimidamide

Conditions
ConditionsYield
With hydroxylamine In ethanol for 1h; Reflux;85%
With hydroxylamine In ethanol for 1h; Reflux;85%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

diphenyl acetylene
501-65-5

diphenyl acetylene

2-(cyclopropylmethyl)-3,4,5,6-tetraphenylpyridine

2-(cyclopropylmethyl)-3,4,5,6-tetraphenylpyridine

Conditions
ConditionsYield
With 1,4-di(diphenylphosphino)-butane; cobalt(II) iodide; zinc In N,N-dimethyl acetamide at 80℃; for 24h; Inert atmosphere;85%
tert-Butoxybis(dimethylamino)methane
5815-08-7

tert-Butoxybis(dimethylamino)methane

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

(2Z)-2-cyclopropyl-3-(dimethylamino)prop-2-enenitrile

(2Z)-2-cyclopropyl-3-(dimethylamino)prop-2-enenitrile

Conditions
ConditionsYield
at 100℃; for 46h;83.5%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

2-Cyclopropylethylamine hydrochloride

2-Cyclopropylethylamine hydrochloride

Conditions
ConditionsYield
With fac-[(CO)3Mn(iPr2P(CH2)2PiPr2)(triflato)]; potassium tert-butylate; hydrogen In iso-butanol at 110℃; under 5171.62 Torr; for 0.25h; Catalytic behavior; Glovebox; Schlenk technique; Inert atmosphere; Autoclave;83%
Multi-step reaction with 2 steps
1.1: BH3 / tetrahydrofuran / 14 h / Heating
1.2: MeOH / 2 h / Heating
1.3: CH2Cl2 / 14 h / 20 °C
2.1: HCl / dioxane; CH2Cl2 / 14 h / 20 °C
View Scheme
With hydrogenchloride; borane In tetrahydrofuran; 1,4-dioxane; dichloromethane
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

C22H22N2O2
1350894-61-9

C22H22N2O2

C19H19N3
1350894-74-4

C19H19N3

Conditions
ConditionsYield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 25℃; Inert atmosphere;83%
ethanol
64-17-5

ethanol

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

2-cyclopropyl-1-ethoxy-1-ethanimine hydrochloride
21572-78-1

2-cyclopropyl-1-ethoxy-1-ethanimine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0℃; for 24h;82%
With hydrogenchloride at 0℃;
tert-Butoxybis(dimethylamino)methane
5815-08-7

tert-Butoxybis(dimethylamino)methane

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

2-cyclopropyl-3-dimethylaminoacrylonitrile
256376-57-5

2-cyclopropyl-3-dimethylaminoacrylonitrile

Conditions
ConditionsYield
at 100℃; for 46h;81%
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

2-cyclopropyl-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)acetonitrile
1404079-40-8

2-cyclopropyl-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-cyclopropylacetonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical With ferrocenium hexafluorophosphate In tetrahydrofuran; hexane at -78℃; Inert atmosphere;		80%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

C22H25NO3
1350894-60-8

C22H25NO3

C19H22N2O
1350894-73-3

C19H22N2O

Conditions
ConditionsYield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 25℃; Inert atmosphere;79%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

phenylhydroxamoyl chloride
934-16-7

phenylhydroxamoyl chloride

4-cyclopropyl-3-phenylisoxazol-5-amine

4-cyclopropyl-3-phenylisoxazol-5-amine

Conditions
ConditionsYield
With tert.-butyl lithium In tetrahydrofuran; n-heptane at -78℃; for 0.5h;78%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

acetic anhydride
108-24-7

acetic anhydride

2-cyclopropyl-3-oxobutanenitrile
918907-28-5

2-cyclopropyl-3-oxobutanenitrile

Conditions
ConditionsYield
Stage #1: 2-cyclopropylacetonitrile With lithium diisopropyl amide In tetrahydrofuran; cyclohexane for 0.166667h; cooling;
Stage #2: acetic anhydride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h;		78%
Stage #1: 2-cyclopropylacetonitrile With lithium diisopropyl amide In tetrahydrofuran; cyclohexane for 0.166667h; cooling;
Stage #2: acetic anhydride In tetrahydrofuran; cyclohexane at 20℃; for 0.166667h; Further stages.;		78%
Stage #1: 2-cyclopropylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: acetic anhydride In tetrahydrofuran at -78 - 15℃; for 1h;
Stage #1: 2-cyclopropylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: acetic anhydride In tetrahydrofuran at -78℃; for 0.333333h;		0.98 g
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

dibromamine-T
21849-40-1

dibromamine-T

N-(tert-butyl)-2-cyclopropyl-N'-tosylacetimidamide

N-(tert-butyl)-2-cyclopropyl-N'-tosylacetimidamide

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 0.5h;78%
...Expand
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 2-cyano-2-cyclopropylacetate
42392-67-6

ethyl 2-cyano-2-cyclopropylacetate

Conditions
ConditionsYield
With sodium hydride In toluene for 2h; Heating;77%
With sodium hydride In toluene; mineral oil for 2.67h; Reflux;50 g
With sodium hydride In toluene for 2.5h; Inert atmosphere; Reflux;
With potassium tert-butylate In N,N-dimethyl-formamide at 50℃;130 g
Stage #1: 2-cyclopropylacetonitrile; Diethyl carbonate With sodium hydride In toluene for 2.5h; Inert atmosphere; Reflux;
Stage #2: With acetic acid In toluene at 0℃;
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

C22H25NO3
1350894-59-5

C22H25NO3

C19H22N2O
1350894-72-2

C19H22N2O

Conditions
ConditionsYield
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 25℃; Inert atmosphere;77%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

(Z)-2-cyclopropyl-N-hydroxyacetimidamide

(Z)-2-cyclopropyl-N-hydroxyacetimidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 80℃; for 12h;77%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

zirconacarborane methyl

zirconacarborane methyl

C22H45B9N2Zr

C22H45B9N2Zr

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;76%

Cyclopropylacetonitrile Specification

This chemical is called Cyclopropaneacetonitrile, and its CAS registry number is 6542-60-5. With the molecular formula of C5H7N, its molecular weight is 81.12. Additionally, its product categories are C1 to C5; Cyanides / Nitriles; Nitrogen Compounds.

Other characteristics of the Cyclopropaneacetonitrile can be summarised as followings: (1)ACD/LogP: 0.45; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.45; (4)ACD/LogD (pH 7.4): 0.45; (5)ACD/BCF (pH 5.5): 1.3; (6)ACD/BCF (pH 7.4): 1.3; (7)ACD/KOC (pH 5.5): 41.91; (8)ACD/KOC (pH 7.4): 41.91; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 23.79 Å2; (13)Index of Refraction: 1.46; (14)Molar Refractivity: 23.07 cm3; (15)Molar Volume: 84.1 cm3; (16)Polarizability: 9.14×10-24cm3; (17)Surface Tension: 40.6 dyne/cm; (18)Density: 0.963 g/cm3; (19)Flash Point: 57.4 °C; (20)Enthalpy of Vaporization: 39.64 kJ/mol; (21)Boiling Point: 159.8 °C at 760 mmHg; (22)Vapour Pressure: 2.46 mmHg at 25°C.

Production method of this chemical: The Cyclopropaneacetonitrile could be obtained by the reactants of bromomethyl-cyclopropane and hydrocyanic acid; sodium salt. The yield is 75 %.

Uses of this chemical: The could react with phenylmagnesium bromide, and obtain the cyclopropyl-2 acetophenone. The yield is 90 %.

When you are using this chemical, please be cautious about it as the following: This chemical is flammable. Keep it away from the sources of ignition. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1.SMILES: N#CCC1CC1
2.InChI: InChI=1/C5H7N/c6-4-3-5-1-2-5/h5H,1-3H2
3.InChIKey: FAUQRRGKJKMEIW-UHFFFAOYAZ

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