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5500-21-0 Usage

Chemical Properties

clear colorless to faintly yellow liquid

Uses

Different sources of media describe the Uses of 5500-21-0 differently. You can refer to the following data:
1. Cyclopropanecarbonitrile is a cyano substituted cycloalkane. Cyclopropanecarbonitrile is an Impurity of pazufloxacin mesylate (P211000).
2. Cyclopropanecarbonitrile is used to prepare cis and trans crotonitrile and allyl cyanide. Further, it reacts with phenylmagnesium bromide to give cyclopropyl-phenyl ketone-imine.

Check Digit Verification of cas no

The CAS Registry Mumber 5500-21-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,0 and 0 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 5500-21:
(6*5)+(5*5)+(4*0)+(3*0)+(2*2)+(1*1)=60
60 % 10 = 0
So 5500-21-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H5N/c5-3-4-1-2-4/h4H,1-2H2

5500-21-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11125)  Cyclopropanecarbonitrile, 98%   

  • 5500-21-0

  • 10g

  • 355.0CNY

  • Detail
  • Alfa Aesar

  • (A11125)  Cyclopropanecarbonitrile, 98%   

  • 5500-21-0

  • 50g

  • 950.0CNY

  • Detail
  • Alfa Aesar

  • (A11125)  Cyclopropanecarbonitrile, 98%   

  • 5500-21-0

  • 250g

  • 4347.0CNY

  • Detail

5500-21-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclopropanecarbonitrile

1.2 Other means of identification

Product number -
Other names cyclopropancarbonitril

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5500-21-0 SDS

5500-21-0Synthetic route

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

cyclopropropanecarbonitrile
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%
4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

cyclopropropanecarbonitrile
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℃;
4-iodobutyronitrile
6727-73-7

4-iodobutyronitrile

cyclopropropanecarbonitrile
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%
cyclopropyl isocyanide
58644-53-4

cyclopropyl isocyanide

cyclopropropanecarbonitrile
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.
acrylonitrile
107-13-1

acrylonitrile

1,1-dibromomethane
74-95-3

1,1-dibromomethane

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

Cyclopropancarbamid

cyclopropropanecarbonitrile
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;
2,4-dichlorobutanenitrile
77100-86-8

2,4-dichlorobutanenitrile

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

4-bromobutanenitrile

A

4-hydroxy-1-butanitrile
628-22-8

4-hydroxy-1-butanitrile

B

cyclopropropanecarbonitrile
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%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

benzaldehyde
100-52-7

benzaldehyde

A

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

trans-2-Phenyltetrahydrofuran-3-carbonitrile

trans-2-Phenyltetrahydrofuran-3-carbonitrile

cis-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
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

A

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

cis-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
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

3-phenyl-propenal
104-55-2

3-phenyl-propenal

A

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

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

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

Conditions
ConditionsYield
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
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

3-phenyl-propenal
104-55-2

3-phenyl-propenal

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

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

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

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

C

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -30℃;A n/a
B n/a
C 15%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

A

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

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

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

Conditions
ConditionsYield
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
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

sodium ethanolate
141-52-6

sodium ethanolate

A

4-ethoxy-butyronitrile
33563-82-5

4-ethoxy-butyronitrile

B

Cyclopropancarbamid
6228-73-5

Cyclopropancarbamid

C

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

A

cyclopropanecarboxamidine; cyclopropanecarboxamidine hydrobromide
23662-46-6

cyclopropanecarboxamidine; cyclopropanecarboxamidine hydrobromide

B

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With ammonia; sodium amide; ferric nitrate
cyclopropyl trifluoromethanesulfonate
25354-42-1

cyclopropyl trifluoromethanesulfonate

tributylhexadecylphosphonium cyanide
66997-38-4

tributylhexadecylphosphonium cyanide

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
In Cyclopentane 1) 22 h, 50 deg C, 2) 14 h, 70 deg C;98.8 % Turnov.
2-aminobutanenitrile hydrochloride
93554-80-4

2-aminobutanenitrile hydrochloride

A

2-hydroxybutanenitrile
4476-02-2

2-hydroxybutanenitrile

B

3-hydroxybutanenitrile
4368-06-3

3-hydroxybutanenitrile

C

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

(Z)-2-butenenitrile

D

crotononitrile
4786-20-3

crotononitrile

E

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

F

syn-2-(Hydroxyimino)butannitril

syn-2-(Hydroxyimino)butannitril

Conditions
ConditionsYield
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.
C4H5N*C2H3N*H(1+)

C4H5N*C2H3N*H(1+)

acetone
67-64-1

acetone

A

C3H7O(1+)*C2H3N

C3H7O(1+)*C2H3N

B

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
at 24.9℃; Thermodynamic data; ΔG0;
C4H5N*H(1+)

C4H5N*H(1+)

acetone
67-64-1

acetone

A

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

1-hydroxy-1-methyl-ethylium

B

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
at 24.9℃; Thermodynamic data; ΔG0;
ammonia
7664-41-7

ammonia

sodium amide

sodium amide

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

iron (III)-nitrate hydrate

iron (III)-nitrate hydrate

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

ammonia
7664-41-7

ammonia

sodium amide

sodium amide

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

potassium hydroxide

potassium hydroxide

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
at 85℃;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

ammonia
7664-41-7

ammonia

potassium hydroxide

potassium hydroxide

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropyl isocyanide
58644-53-4

cyclopropyl isocyanide

A

but-2-enenitrile
4786-20-3

but-2-enenitrile

B

but-3-enenitrile
109-75-1

but-3-enenitrile

C

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
at 999.84℃; under 0.0750075 Torr; Gas phase;A 56 %Spectr.
B 16 %Spectr.
C 12 %Spectr.
cyclopropanemethylamine
2516-47-4

cyclopropanemethylamine

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

Conditions
ConditionsYield
With copper(l) iodide; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 6h; Sealed tube;72 %Spectr.
ethanol
64-17-5

ethanol

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropanecarboximidic Acid Ethyl Ester Hydrochloride
63190-44-3

cyclopropanecarboximidic Acid Ethyl Ester Hydrochloride

Conditions
ConditionsYield
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%
antimony pentafluoride
7783-70-2

antimony pentafluoride

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

C4H5N*F5Sb

C4H5N*F5Sb

Conditions
ConditionsYield
at -196 - -64℃; for 0.166667h; Sealed tube;100%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

C4H5N*AsF5

C4H5N*AsF5

Conditions
ConditionsYield
With arsenic pentafluoride at -196 - -64℃; for 0.166667h; Sealed tube;100%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

C20H24ClNO3S
1381757-95-4

C20H24ClNO3S

Conditions
ConditionsYield
With lithium diisopropyl amide99%
1-(2-(methylthio)-4-(trifluoromethyl)phenyl)ethanone
178462-92-5

1-(2-(methylthio)-4-(trifluoromethyl)phenyl)ethanone

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

C14H14F3NOS

C14H14F3NOS

Conditions
ConditionsYield
With sodium t-butanolate In 2-methyltetrahydrofuran at 40℃; for 3h; Temperature; Inert atmosphere;99%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

(aminomethyl)cyclopropane hydrochloride
7252-53-1

(aminomethyl)cyclopropane hydrochloride

Conditions
ConditionsYield
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;
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

phenylboronic acid
98-80-6

phenylboronic acid

cyclopropyl phenyl ketone
3481-02-5

cyclopropyl phenyl ketone

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropanecarboximidic acid methyl ester monohydrochloride
77570-14-0

cyclopropanecarboximidic acid methyl ester monohydrochloride

Conditions
ConditionsYield
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
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropanecarbothioamide
20295-34-5

cyclopropanecarbothioamide

Conditions
ConditionsYield
With sodium hydrogensulfide; diethyl amine hydrochloride In 1,4-dioxane; water at 55℃; for 42h;97%
With tetraphosphorus decasulfide In ethanol at 0 - 60℃;
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

tert-butyl alcohol
75-65-0

tert-butyl alcohol

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

N-(tert-butyl)cyclopropanecarboxamide

Conditions
ConditionsYield
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%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

rac-3-bromocyclohexene
1521-51-3

rac-3-bromocyclohexene

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

1-(cyclohex-2-enyl)cyclopropanecarbonitrile

Conditions
ConditionsYield
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran97%
pinacolborane

pinacolborane

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

C20H39B2N

C20H39B2N

Conditions
ConditionsYield
With sodium triethylborohydride In neat (no solvent) at 80℃; for 24h; Inert atmosphere; Glovebox; Green chemistry;97%
dimethyl 2,2-di(prop-2-ynyl)malonate
63104-44-9

dimethyl 2,2-di(prop-2-ynyl)malonate

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

C15H17NO4
1516760-82-9

C15H17NO4

Conditions
ConditionsYield
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%
isopropylhydrazine hydrochloride
70629-60-6, 73941-11-4, 16726-41-3

isopropylhydrazine hydrochloride

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 120℃; for 15h; Inert atmosphere; Sealed tube;96%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

prenyl bromide
870-63-3

prenyl bromide

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

1-(3-methylbut-2-enyl)cyclopropanecarbonitrile

Conditions
ConditionsYield
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran95%
1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

N-(1-phenylethyl)cyclopropanecarboxamide

Conditions
ConditionsYield
With silica boron-sulfuric acid nanoparticles at 20℃; for 0.166667h; Ritter reaction; Neat (no solvent);95%
2-amino-5-bromobenzoic acid,ethyl ester
63243-76-5

2-amino-5-bromobenzoic acid,ethyl ester

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane Reflux;95%
With hydrogenchloride In 1,4-dioxane; water Reflux;
t-butyl malonate
541-16-2

t-butyl malonate

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

N-(tert-butyl)cyclopropanecarboxamide

Conditions
ConditionsYield
In neat (no solvent) at 80℃; for 2h; Ritter Amidation;95%
6-bromo-1H-indazole
79762-54-2

6-bromo-1H-indazole

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

Conditions
ConditionsYield
With N-Xantphos Pd G4; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Sealed tube;95%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropylcarboxamidine hydrochloride
57297-29-7

cyclopropylcarboxamidine hydrochloride

Conditions
ConditionsYield
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%
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropanecarboxamide oxime
51285-13-3

cyclopropanecarboxamide oxime

Conditions
ConditionsYield
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%
N-hydroxybenzenecarboximidamide
613-92-3

N-hydroxybenzenecarboximidamide

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

5-cyclopropyl-3-phenyl-1,2,4-oxadiazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid; zinc(II) chloride In N,N-dimethyl-formamide at 80℃; Inert atmosphere;94%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

C12H27NO6P2
1351078-23-3

C12H27NO6P2

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; methyloxirane; zinc In tetrahydrofuran for 20h; Inert atmosphere; Reflux;94%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

N-(diphenylmethyl)cyclopropylcarboxamide
545437-24-9

N-(diphenylmethyl)cyclopropylcarboxamide

Conditions
ConditionsYield
With silica-bonded N-propylsulphamic acid In neat (no solvent) at 80℃; for 0.416667h; Ritter Amidation; Green chemistry;94%
styrene
292638-84-7

styrene

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

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

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

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

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

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; bis(4-methoxyphenyl)selenide In hexane; water at 20℃; for 24h; Sealed tube;94%
Diphenylmethane
101-81-5

Diphenylmethane

cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

N-(diphenylmethyl)cyclopropylcarboxamide
545437-24-9

N-(diphenylmethyl)cyclopropylcarboxamide

Conditions
ConditionsYield
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%

5500-21-0Relevant articles and documents

Direct Evidence for the Hydroxide Extraction Mechanism in the Phase Transfer Catalyzed Cyclopropanation of 4-Halobutyronitrile in a Solid-Liquid System

Cohen, Shlomo,Zoran, Ami,Sasson, Yoel

, p. 9815 - 9818 (1998)

The Hoffman degradation reaction is proposed as an unequivocal proof for the validity of the extraction mechanism in Phase Transfer Catalysis (PTC) in the presence of solid NaOH. 4-Chlorobutyronitrile is found to yield cyclopropyl cyanide via an extraction route while 4-bromobutyronitrile reacts to form the same product by the prevalent interfacial mechanism.

Novel method and technology for synthesizing cyclopropyl ammonia

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Paragraph 0017, (2021/09/21)

The invention discloses a synthesis process route of a cyclopropane synthetic route. In the process route, cyanocyclopropane 1 - formic acid (-1 -) and (1) are subjected to hydrolysis under the action of a strong base to generate 1-cyanocyclopropane 1 - formic acid (-1 -), (2) decarboxylation to generate cyclopropanecarboxamide (2 3), and (4 4 3) subjected to Hoffman rearrangement to obtain the target product cyclopropysite. The process route is longer than the production process in the present stage, the reaction route is long, the use of high-temperature and high-pressure is avoided, the danger is reduced, and the safety is improved. The requirement of the reaction equipment is reduced, the used raw materials are easy to obtain, operation is easy, safety and environmental protection are achieved, and industrial production can be realized.

Synthetic method of cyclopropanecarbonitrile

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Paragraph 0024; 0025; 0026; 0027; 0028; 0029, (2017/08/25)

The invention discloses a synthetic method of cyclopropanecarbonitrile. Cyclopropanecarbonitrile is prepared from a 4-halogenated butyronityile compound under the action of dihydric alcohol and sodium. The method has the advantages of simplicity in operation, fast reaction and high yield, solves the problem of simple and fast synthesis of the cyclopropanecarbonitrile compound, and can be used to prepare cyclopropanecarbonitrile.

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