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Cyclopropanecarbonitrile is a cyano-substituted cycloalkane, characterized as a clear colorless to faintly yellow liquid. It is an impurity found in pazufloxacin mesylate (P211000) and is utilized in the synthesis of various chemicals.

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  • 5500-21-0 Structure
  • Basic information

    1. Product Name: Cyclopropanecarbonitrile
    2. Synonyms: Cyclopropanecarboxylic acid nitrile;Cyclopropanenitrile;CYCLOPROPANECARBONITRILE;CYCLOPROPANE CYANIDE;CYCLOPROPYL CYANIDE;CYCLOPROPYLNITRILE;CYANOCYCLOPROPANE;Cyclopropanecarbonitrile,98%
    3. CAS NO:5500-21-0
    4. Molecular Formula: C4H5N
    5. Molecular Weight: 67.09
    6. EINECS: 226-836-8
    7. Product Categories: Pharmaceutical Intermediates;Cyclopropanes;Simple 3-Membered Ring Compounds;Impurities, Miscellaneous Reagents
    8. Mol File: 5500-21-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 135 °C(lit.)
    3. Flash Point: 91 °F
    4. Appearance: Clear colorless to faintly yellow/Liquid
    5. Density: 0.911 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 7.88mmHg at 25°C
    7. Refractive Index: n20/D 1.421(lit.)
    8. Storage Temp.: Flammables area
    9. Solubility: Chloroform, Methanol (Slightly)
    10. Water Solubility: Miscible with water.
    11. BRN: 635790
    12. CAS DataBase Reference: Cyclopropanecarbonitrile(CAS DataBase Reference)
    13. NIST Chemistry Reference: Cyclopropanecarbonitrile(5500-21-0)
    14. EPA Substance Registry System: Cyclopropanecarbonitrile(5500-21-0)
  • Safety Data

    1. Hazard Codes: T,F
    2. Statements: 10-23/24/25-36/37/38
    3. Safety Statements: 23-26-36/37-45-36/37/39-16-7/9
    4. RIDADR: UN 3275 6.1/PG 2
    5. WGK Germany: 2
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: 6.1
    9. PackingGroup: II
    10. Hazardous Substances Data: 5500-21-0(Hazardous Substances Data)

5500-21-0 Usage

Uses

1. Chemical Synthesis:
Cyclopropanecarbonitrile is used as a chemical intermediate for the preparation of cis and trans crotonitrile, as well as allyl cyanide. These compounds are essential in the production of various chemicals and materials.
2. Pharmaceutical Industry:
In the pharmaceutical industry, Cyclopropanecarbonitrile is used as an impurity in pazufloxacin mesylate (P211000), which is an antibiotic medication. Its presence, although as an impurity, contributes to the overall composition and effectiveness of the drug.
3. Organic Chemistry:
Cyclopropanecarbonitrile is used as a reactant in organic chemistry, particularly in the reaction with phenylmagnesium bromide to produce cyclopropyl-phenyl ketone-imine. This reaction is significant in the synthesis of complex organic molecules and pharmaceutical compounds.

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

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  • 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 for synthesizing cyclopropyl cyanide

-

Paragraph 0003; 0012-0017, (2022/03/27)

The invention discloses a novel method for synthesizing cyclopropyl cyanide, which comprises the following steps: carrying out denitrification cyclization reaction on acrylonitrile serving as a raw material and diazomethane in a solvent under the catalytic action of Pd (oAc) 2 to obtain a cyclopropyl cyanide crude product, and carrying out acid pickling, filtration layering and normal-pressure rectification to obtain a pure product with the content of 99.5% or more and the yield of 95% or more. The synthetic route has the advantages of high yield, few byproducts, high purity and environmental friendliness, and is more suitable for industrial amplification.

Novel method and technology for synthesizing cyclopropyl ammonia

-

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.

Corresponding amine nitrile and method of manufacturing thereof

-

Paragraph 0143-0147; 0158; 0180; 0191; 0213; 0224, (2017/10/22)

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

A cyclopropyl armor cyanogen method for preparing derivatives of

-

Paragraph 0035; 0036, (2016/12/22)

The invention relates to a preparation method of a cyclopropyl methyl cyanide derivative with a general formula I. The preparation method is as below: first synthesizing cyclopropyl formonitrile by using cyclopropanecarboxamide as raw material, then synthesizing a halogenated butyronitrile derivative, and finally synthesizing the target product cyclopropyl methyl cyanide derivative. The invention provides a complete process route, and carefully investigates and researches raw materials and process conditions in each step, so that the method provided by the invention is more efficient and secure, and low in energy consumption and cost, and applicable to large-scale industrialized production.

Synthetic method of cyclopropanecarbonitrile

-

Paragraph 0011; 0012; 0013; 0014; 0015; 0016; 0017, (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.

Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion

Xu, Boran,Hartigan, Elizabeth M.,Feula, Giancarlo,Huang, Zheng,Lumb, Jean-Philip,Arndtsen, Bruce A.

supporting information, p. 15802 - 15806 (2016/12/16)

We describe the use of simple copper-salt catalysts in the selective aerobic oxidation of amines to nitriles or imines. These catalysts are marked by their exceptional efficiency, operate at ambient temperature and pressure, and allow the oxidation of amines without expensive ligands or additives. This study highlights the significant role counterions can play in controlling selectivity in catalytic aerobic oxidations.

SUBSTITUTED NAPHTHYRIDINES AND THEIR USE AS SYK KINASE INHIBITORS

-

Page/Page column 45, (2011/08/21)

The invention relates to new substituted naphthyridines of formula (1), as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein R1 is selected from among -O-R3 or -NR3R4, R3 is C1-6-alkyl which is substituted by R5 and R6 R5 is selected from hydrogen, branched or linear C1-6-alkyl, C2-6-alkenyl, -C1-6-alkylen-O-C1-3-alkyl, C1-3-haloalkyl, R6 is ring X wherein n is either 0 or 1, and Formula (I) is a either a single or a double bond and wherein A, B, D and E are each independently from one another selected from CH2, CH, C, N, NH, O or S and wherein ring X is attached to the molecule either via position A, B, D or E, wherein said ring X may optionally be further substituted by one, two or three residues each selected individually from the group consisting of -oxo, hydroxy, -C1-3-alkyl, -C1-3-haloalkyl, -O-C1-3-alkyl, -C1-3-alkanol and halogen, and wherein R4, R2, R7, R8, R9, R10, R11 and Q may have the meanings as given in claim 1, as well as pharmaceutical compositions containing these compounds.

COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES

-

, (2012/04/23)

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Looking for heteroaromatic rings and related isomers as interstellar candidates

Lattelais,Ellinger,Matrane,Guillemin

experimental part, p. 4165 - 4171 (2011/08/02)

Finding complex organic molecules in the interstellar medium (ISM) is a major concern for understanding the possible role of interstellar organic chemistry in the synthesis of prebiotic species. The present interdisciplinary report is a prospective study aimed at helping detection of heteroaromatic compounds or at least of some of their isomers in the ISM. The thermodynamic stabilities of the C4H5N, C4H4O, C4H4S families were calculated using density functional theory (DFT). It was found that pyrrole, furan and thiophene are unambiguously the most stable isomers at the 10-50 K temperatures of the ISM. Several of the less stable isomers were synthesized and flash vacuum thermolysis experiments were performed on these species. Although the detection of pyrrole in the pyrolysis of many compounds has been reported in the literature, we observed that none of its isomers led to pyrrole in these conditions, which suggests that other formation routes are to be considered. On the other hand, these three aromatic compounds present a very high stability, few % been decomposed at 1500 K by flash vacuum thermolysis; these experiments also show a great stability of crotonitrile that is the most stable compound that can be formed in these conditions. The rotational constants, dipole moments and IR frequencies of the low-lying isomers are given to encourage laboratory experiments on these prototype molecules.

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