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Cyclopropanecarbonitrile

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Name

Cyclopropanecarbonitrile

EINECS 226-836-8
CAS No. 5500-21-0 Density 0.96 g/cm3
PSA 23.79000 LogP 0.91998
Solubility Miscible with water. Melting Point -25oC
Formula C4H5N Boiling Point 135 °C at 760 mmHg
Molecular Weight 67.0904 Flash Point 32.8 °C
Transport Information UN 3275 6.1/PG 2 Appearance clear colorless to faintly yellow liquid
Safety 23-26-36/37-45-36/37/39-16-7/9 Risk Codes 10-23/24/25-36/37/38
Molecular Structure Molecular Structure of 5500-21-0 (Cyclopropanecarbonitrile) Hazard Symbols ToxicT, FlammableF
Synonyms

Cyanocyclopropane;Cyclopropylnitrile;Cyclopropyl cyanide;Cyclopropanenitrile;

Article Data 43

Cyclopropanecarbonitrile Synthetic route

628-20-6

4-Chlorobutyronitrile

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium chloride In water; dimethyl sulfoxide98%
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%
5332-06-9

4-bromobutanenitrile

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With sodium In ethylene glycol at 20 - 50℃; for 0.25h; Temperature; Solvent; Reagent/catalyst;98%
With ammonia; sodium amide; ferric nitrate
With tetra(n-butyl)ammonium hydroxide In xylene at 40℃;
6727-73-7

4-iodobutyronitrile

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With sodium hydride In ethylene glycol; mineral oil at 20 - 40℃; for 0.166667h; Solvent; Reagent/catalyst;96.5%
58644-53-4

cyclopropyl isocyanide

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
at 520 - 550℃; under 0.01 Torr;92%
With 1,1-Diphenylethylene In various solvent(s) at 210℃; Rate constant; Thermodynamic data; ΔG(excit.) <250 deg C>; ΔH(excit.), ΔS(excit.);98 % Chromat.
107-13-1

acrylonitrile

74-95-3

1,1-dibromomethane

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With sodium iodide; nickel dibromide; zinc In tetrahydrofuran at 0℃; for 42h;92%
6228-73-5

Cyclopropancarbamid

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With thionyl chloride In toluene for 8h; Reflux;91%
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;86%
With phosphorus pentoxide at 235℃; for 1h; Temperature;
77100-86-8

2,4-dichlorobutanenitrile

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With tetraethylammonium tosylate In dimethyl sulfoxide for 10h; electrolysis;83%
5332-06-9

4-bromobutanenitrile

A

628-22-8

4-hydroxy-1-butanitrile

B

5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;A 10%
B 67%
628-20-6

4-Chlorobutyronitrile

100-52-7

benzaldehyde

A

5500-21-0

cyclopropropanecarbonitrile

trans-2-Phenyltetrahydrofuran-3-carbonitrile

cis-2-Phenyltetrahydrofuran-3-carbonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h; Title compound not separated from byproducts;A 21%
B n/a
C n/a
With potassium tert-butylate In tetrahydrofuran at -30℃; Product distribution; Further Variations:; Reagents; Temperatures;A 11%
B n/a
C n/a
628-20-6

4-Chlorobutyronitrile

104-88-1

4-chlorobenzaldehyde

A

5500-21-0

cyclopropropanecarbonitrile

trans-2-(4-Chlorophenyl)tetrahydrofuran-3-carbonitrile

cis-2-(4-Chlorophenyl)tetrahydrofuran-3-carbonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h; Title compound not separated from byproducts;A 16%
B n/a
C n/a

Cyclopropanecarbonitrile Specification

The Cyclopropanecarbonitrile, with the CAS registry number 5500-21-0 and EINECS registry number 226-836-8, is a kind of clear colorless to faintly yellow liquid. And the molecular formula of this chemical is C4H5N. It belongs to the following product categories: Pharmaceutical Intermediates; Cyclopropanes; Simple 3-Membered Ring Compounds.

The physical properties of Cyclopropanecarbonitrile are as following: (1)ACD/LogP: -0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.08; (4)ACD/LogD (pH 7.4): -0.08; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 21.54; (8)ACD/KOC (pH 7.4): 21.54; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 23.79 Å2; (13)Index of Refraction: 1.442; (14)Molar Refractivity: 18.43 cm3; (15)Molar Volume: 69.6 cm3; (16)Polarizability: 7.3×10-24cm3; (17)Surface Tension: 33.8 dyne/cm; (18)Density: 0.96 g/cm3; (19)Flash Point: 32.8 °C; (20)Enthalpy of Vaporization: 35.55 kJ/mol; (21)Boiling Point: 135 °C at 760 mmHg; (22)Vapour Pressure: 7.88 mmHg at 25°C.

Uses of Cyclopropanecarbonitrile: It can react with phenylmagnesium bromide to produce cyclopropyl-phenyl ketone-imine. This reaction will need solvent diethyl ether. The reaction time is 2 hours with ambient temperature, and the yield is about 65%.

Cyclopropanecarbonitrile can react with phenylmagnesium bromide to produce cyclopropyl-phenyl ketone-imine

You should be cautious while dealing with this chemical. It is a flammable chemcial which is toxic by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Keep away from sources of ignition - No smoking; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: N#CC1CC1
(2)InChI: InChI=1/C4H5N/c5-3-4-1-2-4/h4H,1-2H2
(3)InChIKey: AUQDITHEDVOTCU-UHFFFAOYAL

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