Cyclopropanecarbonitrile supplier

Name
Cyclopropanecarbonitrile
EINECS 226-836-8
CAS No. 5500-21-0
Article Data43
CAS DataBase
Density 0.96 g/cm³
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
Hazard Symbols T, F
Synonyms Cyanocyclopropane;Cyclopropylnitrile;Cyclopropyl cyanide;Cyclopropanenitrile;
PSA 23.79000
LogP 0.91998

Synthetic route

: 628-20-6
4-Chlorobutyronitrile

: 5500-21-0
cyclopropropanecarbonitrile

Conditions

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%

: 5332-06-9
4-bromobutanenitrile

: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium iodide; nickel dibromide; zinc In tetrahydrofuran at 0℃; for 42h;	92%

: 6228-73-5
Cyclopropancarbamid

: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

...Expand

: 628-20-6
4-Chlorobutyronitrile

: 104-55-2
3-phenyl-propenal

A: 5500-21-0
cyclopropropanecarbonitrile

: cis-2-[(E)-2-Phenylethenyl]tetrahydrofuran-3-carbonitrile

: trans-2-[(E)-2-Phenylethenyl]tetrahydrofuran-3-carbonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h; Title compound not separated from byproducts;	A 15% B n/a C n/a

...Expand

: 628-20-6
4-Chlorobutyronitrile

: 104-55-2
3-phenyl-propenal

: (2R,3S)-2-((E)-Styryl)-tetrahydro-furan-3-carbonitrile

: (2R,3R)-2-((E)-Styryl)-tetrahydro-furan-3-carbonitrile

C: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30℃;	A n/a B n/a C 15%

...Expand

: 628-20-6
4-Chlorobutyronitrile

: 104-87-0
4-methyl-benzaldehyde

A: 5500-21-0
cyclopropropanecarbonitrile

: trans-2-(4-Methylphenyl)tetrahydrofuran-3-carbonitrile

: cis-2-(4-Methylphenyl)tetrahydrofuran-3-carbonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30℃; for 0.333333h; Title compound not separated from byproducts;	A 14% B n/a C n/a
With potassium tert-butylate In tetrahydrofuran at -30℃;	A 14% B n/a C n/a

...Expand

: 628-20-6
4-Chlorobutyronitrile

: 141-52-6
sodium ethanolate

A: 33563-82-5
4-ethoxy-butyronitrile

B: 6228-73-5
Cyclopropancarbamid

C: 5500-21-0
cyclopropropanecarbonitrile

...Expand

: 5332-06-9
4-bromobutanenitrile

A: 23662-46-6
cyclopropanecarboxamidine; cyclopropanecarboxamidine hydrobromide

B: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
With ammonia; sodium amide; ferric nitrate

: 25354-42-1
cyclopropyl trifluoromethanesulfonate

: 66997-38-4
tributylhexadecylphosphonium cyanide

: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
In Cyclopentane 1) 22 h, 50 deg C, 2) 14 h, 70 deg C;	98.8 % Turnov.

: 93554-80-4
2-aminobutanenitrile hydrochloride

A: 4476-02-2
2-hydroxybutanenitrile

B: 4368-06-3
3-hydroxybutanenitrile

C: 1190-76-7
(Z)-2-butenenitrile

D: 4786-20-3
crotononitrile

E: 5500-21-0
cyclopropropanecarbonitrile

F: syn-2-(Hydroxyimino)butannitril

Conditions

Conditions	Yield
With perchloric acid; sodium nitrite for 24h; Product distribution; Mechanism; Ambient temperature; pH 3.5 or 1.4, also in HOAc/NaOAc, also (R)-2-aminobutanenitrile*HCl as substrate;	A 48.6 % Chromat. B 4.7 % Chromat. C 14.2 % Chromat. D 12.7 % Chromat. E 4.2 % Chromat. F 5.4 % Chromat.

...Expand

: C4H5N*C2H3N*H(1+)

: 67-64-1
acetone

A: C3H7O(1+)*C2H3N

B: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
at 24.9℃; Thermodynamic data; ΔG0;

...Expand

: C4H5N*H(1+)

: 67-64-1
acetone

A: 17104-38-0, 43022-03-3
1-hydroxy-1-methyl-ethylium

B: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
at 24.9℃; Thermodynamic data; ΔG0;

...Expand

: 7664-41-7
ammonia

: sodium amide

: 5332-06-9
4-bromobutanenitrile

iron (III)-nitrate hydrate: iron (III)-nitrate hydrate

: 5500-21-0
cyclopropropanecarbonitrile

...Expand

: 628-20-6
4-Chlorobutyronitrile

: 7664-41-7
ammonia

: sodium amide

: 5500-21-0
cyclopropropanecarbonitrile

...Expand

: 628-20-6
4-Chlorobutyronitrile

potassium hydroxide: potassium hydroxide

: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
at 85℃;

: 628-20-6
4-Chlorobutyronitrile

: 7664-41-7
ammonia

potassium hydroxide: potassium hydroxide

: 5500-21-0
cyclopropropanecarbonitrile

...Expand

: 58644-53-4
cyclopropyl isocyanide

A: 4786-20-3
but-2-enenitrile

B: 109-75-1
but-3-enenitrile

C: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
at 999.84℃; under 0.0750075 Torr; Gas phase;	A 56 %Spectr. B 16 %Spectr. C 12 %Spectr.

...Expand

: 2516-47-4
cyclopropanemethylamine

: 5500-21-0
cyclopropropanecarbonitrile

Conditions

Conditions	Yield
With copper(l) iodide; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 6h; Sealed tube;	72 %Spectr.

: 64-17-5
ethanol

: 5500-21-0
cyclopropropanecarbonitrile

: 63190-44-3
cyclopropanecarboximidic Acid Ethyl Ester Hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 20℃;	100%
With hydrogenchloride In 1,4-dioxane at 20℃;	100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 12h; Inert atmosphere;	90%

: 7783-70-2
antimony pentafluoride

: 5500-21-0
cyclopropropanecarbonitrile

: C4H5N*F5Sb

Conditions

Conditions	Yield
at -196 - -64℃; for 0.166667h; Sealed tube;	100%

: 5500-21-0
cyclopropropanecarbonitrile

: C4H5N*AsF5

Conditions

Conditions	Yield
With arsenic pentafluoride at -196 - -64℃; for 0.166667h; Sealed tube;	100%

: 5500-21-0
cyclopropropanecarbonitrile

: 209391-72-0
8-[Chloro-(toluene-4-sulfinyl)-methylene]-1,4-dioxa-spiro[4.5]decane

: 1381757-95-4
C20H24ClNO3S

Conditions

Conditions	Yield
With lithium diisopropyl amide	99%

: 178462-92-5
1-(2-(methylthio)-4-(trifluoromethyl)phenyl)ethanone

: 5500-21-0
cyclopropropanecarbonitrile

C14H14F3NOS: C14H14F3NOS

Conditions

Conditions	Yield
With sodium t-butanolate In 2-methyltetrahydrofuran at 40℃; for 3h; Temperature; Inert atmosphere;	99%

: 5500-21-0
cyclopropropanecarbonitrile

: 7252-53-1
(aminomethyl)cyclopropane hydrochloride

Conditions

Conditions	Yield
Stage #1: cyclopropropanecarbonitrile With cobalt pivalate; 1,1,3,3-Tetramethyldisiloxane; tert-butylisonitrile at 80℃; for 24h; Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 0.5h;	98%
With hydrogenchloride; dimethylsulfide borane complex 1.) reflux, 0.25 h, 2.) MeOH, reflux, 4h; Yield given. Multistep reaction;

: 5500-21-0
cyclopropropanecarbonitrile

: 98-80-6
phenylboronic acid

: 3481-02-5
cyclopropyl phenyl ketone

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine In water at 60℃; for 6h;	98%
With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 36h; Schlenk technique; Inert atmosphere;	83%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; water; zinc(II) chloride In 1,4-dioxane at 80℃; for 8h; Inert atmosphere;	82%

: 67-56-1
methanol

: 5500-21-0
cyclopropropanecarbonitrile

: 77570-14-0
cyclopropanecarboximidic acid methyl ester monohydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether at 0℃; for 24h;	97%
With hydrogenchloride at -10℃; for 5h;	97%
With hydrogenchloride In diethyl ether at 0 - 20℃; for 17h;	95.5%
With hydrogenchloride In 1,4-dioxane at 0 - 5℃; for 3h;	783 mg

: 5500-21-0
cyclopropropanecarbonitrile

: 20295-34-5
cyclopropanecarbothioamide

Conditions

Conditions	Yield
With sodium hydrogensulfide; diethyl amine hydrochloride In 1,4-dioxane; water at 55℃; for 42h;	97%
With tetraphosphorus decasulfide In ethanol at 0 - 60℃;

: 5500-21-0
cyclopropropanecarbonitrile

: 75-65-0
tert-butyl alcohol

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

Conditions

Conditions	Yield
With silica boron-sulfuric acid nanoparticles at 20℃; for 0.25h; Ritter reaction; Neat (no solvent);	97%
With silica-bonded N-propylsulphamic acid In neat (no solvent) at 80℃; for 1.33333h; Ritter Amidation; Green chemistry;	96%
With bismuth(lll) trifluoromethanesulfonate; water at 100℃; Ritter reaction;	95%

: 5500-21-0
cyclopropropanecarbonitrile

: 1521-51-3
rac-3-bromocyclohexene

: 1352832-71-3
1-(cyclohex-2-enyl)cyclopropanecarbonitrile

Conditions

Conditions	Yield
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran	97%

: pinacolborane

: 5500-21-0
cyclopropropanecarbonitrile

: C20H39B2N

Conditions

Conditions	Yield
With sodium triethylborohydride In neat (no solvent) at 80℃; for 24h; Inert atmosphere; Glovebox; Green chemistry;	97%

: 63104-44-9
dimethyl 2,2-di(prop-2-ynyl)malonate

: 5500-21-0
cyclopropropanecarbonitrile

: 1516760-82-9
C15H17NO4

Conditions

Conditions	Yield
With η6-(naphtalene)(η5-cyclopentadienyl)-iron(II) hexafluorophosphate; tris(2,4,6-trimethoxyphenyl)phosphine In toluene at 120℃; Inert atmosphere; Schlenk technique; Microwave irradiation;	96%

: 70629-60-6, 73941-11-4, 16726-41-3
isopropylhydrazine hydrochloride

: 5500-21-0
cyclopropropanecarbonitrile

: 3,5-dicyclopropyl-1-isopropyl-1H-1,2,4-triazole

Conditions

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 120℃; for 15h; Inert atmosphere; Sealed tube;	96%

: 5500-21-0
cyclopropropanecarbonitrile

: 870-63-3
prenyl bromide

: 95647-30-6
1-(3-methylbut-2-enyl)cyclopropanecarbonitrile

Conditions

Conditions	Yield
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran	95%

: 98-85-1, 13323-81-4
1-Phenylethanol

: 5500-21-0
cyclopropropanecarbonitrile

: 78172-92-6
N-(1-phenylethyl)cyclopropanecarboxamide

Conditions

Conditions	Yield
With silica boron-sulfuric acid nanoparticles at 20℃; for 0.166667h; Ritter reaction; Neat (no solvent);	95%

: 63243-76-5
2-amino-5-bromobenzoic acid,ethyl ester

: 5500-21-0
cyclopropropanecarbonitrile

: 6-bromo-2-cyclopropyl-quinazolin-4-ol

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane Reflux;	95%
With hydrogenchloride In 1,4-dioxane; water Reflux;

: 541-16-2
t-butyl malonate

: 5500-21-0
cyclopropropanecarbonitrile

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

Conditions

Conditions	Yield
In neat (no solvent) at 80℃; for 2h; Ritter Amidation;	95%

: 79762-54-2
6-bromo-1H-indazole

: 5500-21-0
cyclopropropanecarbonitrile

: 1-(1H-indazol-6-yl)cyclopropane-1-carbonitrile

Conditions

Conditions	Yield
With N-Xantphos Pd G4; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Sealed tube;	95%

: 5500-21-0
cyclopropropanecarbonitrile

: 57297-29-7
cyclopropylcarboxamidine hydrochloride

Conditions

Conditions	Yield
Stage #1: cyclopropropanecarbonitrile With hydrogenchloride; methanol In toluene at 15 - 23℃; for 18h; Stage #2: With ammonia In methanol; toluene at 5 - 25℃; for 1.16667h;	94%
Stage #1: cyclopropropanecarbonitrile With hydrogenchloride In ethanol at 20℃; for 24h; Stage #2: With ammonia In ethanol at 23℃; Cooling with ice;	79.5%
Stage #1: cyclopropropanecarbonitrile With hydrogenchloride; methanol In diethyl ether at 0℃; for 2h; Stage #2: With ammonia In methanol for 1h; Cooling with ice;	67%

: 5500-21-0
cyclopropropanecarbonitrile

: 51285-13-3
cyclopropanecarboxamide oxime

Conditions

Conditions	Yield
With hydroxylamine In ethanol; water at 80℃;	94%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In isopropyl alcohol at 80 - 85℃;	70%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux;	52%

: 613-92-3
N-hydroxybenzenecarboximidamide

: 5500-21-0
cyclopropropanecarbonitrile

: 884637-65-4
5-cyclopropyl-3-phenyl-1,2,4-oxadiazole

Conditions

Conditions	Yield
With toluene-4-sulfonic acid; zinc(II) chloride In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	94%

: 762-04-9
phosphonic acid diethyl ester

: 5500-21-0
cyclopropropanecarbonitrile

: 1351078-23-3
C12H27NO6P2

Conditions

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; methyloxirane; zinc In tetrahydrofuran for 20h; Inert atmosphere; Reflux;	94%

: 91-01-0
1,1-Diphenylmethanol

: 5500-21-0
cyclopropropanecarbonitrile

: 545437-24-9
N-(diphenylmethyl)cyclopropylcarboxamide

Conditions

Conditions	Yield
With silica-bonded N-propylsulphamic acid In neat (no solvent) at 80℃; for 0.416667h; Ritter Amidation; Green chemistry;	94%

: 292638-84-7
styrene

: 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

: 5500-21-0
cyclopropropanecarbonitrile

: N-(1-phenyl-2-((trifluoromethyl)thio)ethyl)cyclopropanecarboxamide

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; bis(4-methoxyphenyl)selenide In hexane; water at 20℃; for 24h; Sealed tube;	94%

...Expand

: 101-81-5
Diphenylmethane

: 5500-21-0
cyclopropropanecarbonitrile

: 545437-24-9
N-(diphenylmethyl)cyclopropylcarboxamide

Conditions

Conditions	Yield
With manganese(II) acetate dihydrate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 90℃; for 12h; Inert atmosphere;	94%
With manganese(III) triacetate dihydrate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 90℃; for 12h; Schlenk technique; Inert atmosphere;	90%

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

Product Name

Cyclopropanecarbonitrile

Synthetic route

Cyclopropanecarbonitrile Specification

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