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1759-53-1 Usage

Description

Cyclopropanecarboxylic acid is a kind of organic acid. It is a clear liquid used as an intermediate for agrochemicals, pharmaceuticals, and other organic synthesis for the applications of electronics, chemicals, polymer additives, coatings, adhesives, surfactants, and other applications1. Moreover, its derivatives of are used against parasites in plants and animals. For example, the alkynyl esters of cyclopropane-carboxylic acid are used as pesticides. Similarly, cyclopropane carboxylic acid esters containing a polyhalogenated substituent are used as fungicides. The ethyl derivative is reagent used in the addition of cyclopropane and can act as annulation reagent for the conversion of aromatics to 2-methylindanones under Friedel-Crafts conditions2.

Uses

Cyclopropanecarboxylic acid is a monocarboxylic acid and a member of cyclopropanes. It is a conjugate acid of a cyclopropanecarboxylate.

Chemical Properties

clear colourless to light yellow liquid

Definition

ChEBI: Cyclopropanecarboxylic acid is a monocarboxylic acid and a member of cyclopropanes. It is a conjugate acid of a cyclopropanecarboxylate.

Preparation

Cyclopropanecarboxylic acid has been prepared by the hydrolysis of cyclopropyl cyanide, although it is unnecessary to isolate the nitrile; by heating cyclopropanedicarboxylic acid; and by the action of alkali on ethyl γ-chlorobutyrate.7 The last two methods do not appear to be of practical importance. The oxidation of cyclopropyl methyl ketone with sodium hypobromite is reported to be an excellent preparative method for this acid.Org. Synth. 1944, 24, 36DOI: 10.15227/orgsyn.024.0036

Check Digit Verification of cas no

The CAS Registry Mumber 1759-53-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,7,5 and 9 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1759-53:
(6*1)+(5*7)+(4*5)+(3*9)+(2*5)+(1*3)=101
101 % 10 = 1
So 1759-53-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6)/p-1

1759-53-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A14215)  Cyclopropanecarboxylic acid, 98%   

  • 1759-53-1

  • 50g

  • 393.0CNY

  • Detail
  • Alfa Aesar

  • (A14215)  Cyclopropanecarboxylic acid, 98%   

  • 1759-53-1

  • 250g

  • 1363.0CNY

  • Detail
  • Alfa Aesar

  • (A14215)  Cyclopropanecarboxylic acid, 98%   

  • 1759-53-1

  • 1000g

  • 3900.0CNY

  • Detail

1759-53-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name cyclopropanecarboxylic acid

1.2 Other means of identification

Product number -
Other names CYCLOPROPANE CARBOYLIC ACID

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:1759-53-1 SDS

1759-53-1Synthetic route

1‐cyclopropyl‐4,4,4‐trifluorobutane‐1,3‐dione
30923-69-4

1‐cyclopropyl‐4,4,4‐trifluorobutane‐1,3‐dione

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;98%
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
1427519-95-6

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

A

((3R,6S)-3-methyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
1427520-28-2

((3R,6S)-3-methyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 97%
B n/a
2,3-dibromopropionic acid
600-05-5

2,3-dibromopropionic acid

acetyl chloride
75-36-5

acetyl chloride

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
Stage #1: 2,3-dibromopropionic acid; acetyl chloride With copper(l) chloride; zinc In diethyl ether at 10 - 20℃; for 11h; Inert atmosphere;
Stage #2: With Methylenetriphenylphosphorane In diethyl ether Temperature; Solvent; Concentration;
96%
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-methyl-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
1427519-96-7

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-methyl-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

A

((3R,6S)-6-isobutyl-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
1427520-27-1

((3R,6S)-6-isobutyl-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 94%
B n/a
3,4-dihydronaphthalen-1-yl cyclopropanecarboxylate

3,4-dihydronaphthalen-1-yl cyclopropanecarboxylate

A

2-fluoro-1-tetralone
71019-06-2

2-fluoro-1-tetralone

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Selectfluor In water; acetonitrile at 20℃;A 93%
B n/a
cyclopropropanecarbonitrile
5500-21-0

cyclopropropanecarbonitrile

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With water; nitrile hydratase SP361 at 30℃; for 24h; in potassium phosphate buffer (pH = 7);92%
With phosphoric acid; phosphorus pentoxide at 140℃;
With sodium hydroxide
With potassium hydroxide
In sodium hydroxide
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

Cyclopropanecarboxaldehyde
1489-69-6

Cyclopropanecarboxaldehyde

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
90%
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-(methylsulfonyl)-1,3-diphenylhex-1-yn-3-yl cyclopropanecarboxylate
1427520-01-1

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-(methylsulfonyl)-1,3-diphenylhex-1-yn-3-yl cyclopropanecarboxylate

A

((3R,6S)-3-methyl-6-(2-(methylsulfonyl)ethyl)-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
1427520-30-6

((3R,6S)-3-methyl-6-(2-(methylsulfonyl)ethyl)-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 87%
B n/a
Cyclopropanecarboxaldehyde
1489-69-6

Cyclopropanecarboxaldehyde

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;80%
With Iron(III) nitrate nonahydrate; oxygen In acetonitrile at 25℃; under 760.051 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Schlenk technique;80%
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water; acetone at 22℃; for 3h; Oxidation;71%
With air at 21℃; for 2h;
tert-butyl(cyclopropylmethoxy)dimethylsilane
85696-55-5

tert-butyl(cyclopropylmethoxy)dimethylsilane

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate78%
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-5-((tertbutyldimethylsilyl)oxy)-1,3-diphenylpent-1-yn-3-yl cyclopropanecarboxylate
1427519-98-9

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-5-((tertbutyldimethylsilyl)oxy)-1,3-diphenylpent-1-yn-3-yl cyclopropanecarboxylate

A

((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
1427520-29-3

((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 52%
B n/a
Methyl 4-bromobutyrate
4897-84-1

Methyl 4-bromobutyrate

propargyl alcohol
107-19-7

propargyl alcohol

A

methyl cyclopropylcarboxylate
2868-37-3

methyl cyclopropylcarboxylate

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With lithium amide In diethyl ether for 4h; Heating;A 20%
B n/a
naphthalene
91-20-3

naphthalene

cyclopropane-1,1-dicarboxylic acid
598-10-7

cyclopropane-1,1-dicarboxylic acid

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide at 100℃; Versetzen des Reaktionsgemisches mit Wasser;
With sodium hydroxide at 100℃; Versetzen des Reaktionsgemisches mit Wasser;
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With potassium hypochlorite
With manganese(II) nitrate; oxygen; cobalt(II) nitrate In acetic acid at 100℃; for 6h;
cyclopropane-1,1-dicarboxylic acid
598-10-7

cyclopropane-1,1-dicarboxylic acid

A

4-butanolide
96-48-0

4-butanolide

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

cyclopropane-1,1-dicarboxylic acid
598-10-7

cyclopropane-1,1-dicarboxylic acid

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

ethenylcyclopropane
693-86-7

ethenylcyclopropane

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With permanganate(VII) ion at 0 - 5℃;
cyclopropanecarboxylic acid phenyl ester
5296-56-0

cyclopropanecarboxylic acid phenyl ester

A

phenol
108-95-2

phenol

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
at 360℃;
cyclopropane-1,1-dicarboxylic acid
598-10-7

cyclopropane-1,1-dicarboxylic acid

nitrobenzene
98-95-3

nitrobenzene

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

cyclopropane
75-19-4

cyclopropane

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With carbon dioxide; n-pentylsodium
cyclopropanecarboxylic anhydride
33993-24-7

cyclopropanecarboxylic anhydride

A

propene
187737-37-7

propene

B

1,2-propanediene
463-49-0

1,2-propanediene

C

butadiene monoxide
50888-73-8

butadiene monoxide

D

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
at 666.9℃;
2-Cyclopropyl-4,4-dimethyl-4,5-dihydro-oxazole
83007-77-6

2-Cyclopropyl-4,4-dimethyl-4,5-dihydro-oxazole

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite; tetra(n-butyl)ammonium hydrogensulfate 1.) ethyl acetate, water, room temp.; 2.) CH3OH, 5 h, room temp.; Yield given. Multistep reaction;
cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

A

1-chlorocyclopropane-1-carboxylic acid
108817-35-2

1-chlorocyclopropane-1-carboxylic acid

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With N-chloro-succinimide; sodium hydrogencarbonate 1.) 135 deg C, 1.5 h, 2.) acetone, 0 deg C; Yield given. Multistep reaction;
Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate; copper(II) sulfate In benzene Yield given;
cyclopropylmethyl methyl ether
1003-13-0

cyclopropylmethyl methyl ether

A

methyl cyclopropylcarboxylate
2868-37-3

methyl cyclopropylcarboxylate

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With ruthenium tetroxide In water; acetone at 30℃;
Cyclopropanoyl propranolol

Cyclopropanoyl propranolol

A

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

B

propranolol
525-66-6

propranolol

Conditions
ConditionsYield
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis;
cyclopropanecarboxylic acid 2-(2-allyl-phenoxy)-1-(isopropylamino-methyl)-ethyl ester

cyclopropanecarboxylic acid 2-(2-allyl-phenoxy)-1-(isopropylamino-methyl)-ethyl ester

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis;
cyclopropanecarboxylic acid 2-(2-allyloxy-phenoxy)-1-(isopropylamino-methyl)-ethyl ester

cyclopropanecarboxylic acid 2-(2-allyloxy-phenoxy)-1-(isopropylamino-methyl)-ethyl ester

A

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

B

oxprenolol
6452-71-7

oxprenolol

Conditions
ConditionsYield
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis;
cyclopropanecarboxylic acid 2-(2-acetyl-4-butyrylamino-phenoxy)-1-(isopropylamino-methyl)-ethyl ester

cyclopropanecarboxylic acid 2-(2-acetyl-4-butyrylamino-phenoxy)-1-(isopropylamino-methyl)-ethyl ester

A

Acebutolol
37517-30-9

Acebutolol

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis;
cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

Conditions
ConditionsYield
With thionyl chloride In toluene Heating;100%
With thionyl chloride for 3h; Heating;95%
With thionyl chloride for 4h; Heating;88%
4-(hexyn-1-yl)anisole
131558-77-5

4-(hexyn-1-yl)anisole

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

(E)-2-iodo-1-(4-methoxyphenyl)hex-1-en-1-yl cyclopropanecarboxylate
1337541-97-5

(E)-2-iodo-1-(4-methoxyphenyl)hex-1-en-1-yl cyclopropanecarboxylate

Conditions
ConditionsYield
With N-iodo-succinimide In 1,2-dichloro-ethane at 70℃; for 1h; stereoselective reaction;100%
2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-amine 1',1'-dioxide
1448039-40-4

2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-amine 1',1'-dioxide

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

N-{2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1',1'-dioxido-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-yl}cyclopropanecarboxamide
1448041-24-4

N-{2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1',1'-dioxido-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-yl}cyclopropanecarboxamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;100%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

(1H-benzo[d][1,2,3]triazol-1-yl)(cyclopropyl)methanone
354996-72-8

(1H-benzo[d][1,2,3]triazol-1-yl)(cyclopropyl)methanone

Conditions
ConditionsYield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h;
Stage #2: cyclopropanecarboxylic acid In dichloromethane at 20℃; for 4h;
100%
With thionyl chloride at 0 - 20℃; Reagent/catalyst;70%
With thionyl chloride In dichloromethane at 20℃;
6,7-didehydro-4,5alpha-epoxy-3-methoxyindolo[2',3': 6,7]morphinan-14beta-ol

6,7-didehydro-4,5alpha-epoxy-3-methoxyindolo[2',3': 6,7]morphinan-14beta-ol

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

6,7-didehydro-4,5alpha-epoxy-14beta-hydroxy-3-methoxyindolo[2',3':6,7]morphinan-17-yl(cyclopropyl)methanone

6,7-didehydro-4,5alpha-epoxy-14beta-hydroxy-3-methoxyindolo[2',3':6,7]morphinan-17-yl(cyclopropyl)methanone

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h;100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;100%
(piperidin-4-yl)carbamic acid tert-butyl ester
73874-95-0

(piperidin-4-yl)carbamic acid tert-butyl ester

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

tert-butyl (1-(cyclopropanecarbonyl)piperidin-4-yl)carbamate

tert-butyl (1-(cyclopropanecarbonyl)piperidin-4-yl)carbamate

Conditions
ConditionsYield
Stage #1: cyclopropanecarboxylic acid With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: (piperidin-4-yl)carbamic acid tert-butyl ester In dichloromethane at 20℃; Inert atmosphere;
100%
Stage #1: cyclopropanecarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: (piperidin-4-yl)carbamic acid tert-butyl ester In dichloromethane at 20℃; Inert atmosphere;
100%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 12h;
C23H21NO4

C23H21NO4

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

C27H25NO5

C27H25NO5

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;100%
5-isopropylspiro[indoline-2,4'-piperidin]-3-one

5-isopropylspiro[indoline-2,4'-piperidin]-3-one

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

N-(cyclopropanecarbonyl)-5-isopropylspiro[indoline-2,4'-piperidin]-3-one

N-(cyclopropanecarbonyl)-5-isopropylspiro[indoline-2,4'-piperidin]-3-one

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 18h;100%
cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Cyclopropanecarboxaldehyde
1489-69-6

Cyclopropanecarboxaldehyde

Conditions
ConditionsYield
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h;99%
With nonane; 9-borabicyclo; lithium 9-boratabicyclo In tetrahydrofuran for 1h; Ambient temperature;85%
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 1 h; Yield given. Multistep reaction;
With ThxBHO-s-Bu In tetrahydrofuran at 25℃; for 96h; Yield given;
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

1-O-(cyclopropanecarbonyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

1-O-(cyclopropanecarbonyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions
ConditionsYield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;99%
5-bromoindoline
22190-33-6

5-bromoindoline

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

(5-bromoindolin-1-yl)(cyclopropyl)methanone

(5-bromoindolin-1-yl)(cyclopropyl)methanone

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h;99%
cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

4-iodobutanoic acid
7425-27-6

4-iodobutanoic acid

Conditions
ConditionsYield
With trimethylsilyl iodide for 96h;98%
2-benzyloxy-1-methylpyridinium triflate

2-benzyloxy-1-methylpyridinium triflate

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

cyclopropanecarboxylic acid benzyl ester
20121-75-9

cyclopropanecarboxylic acid benzyl ester

Conditions
ConditionsYield
With triethylamine In various solvent(s) at 83℃; for 24h;98%
cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

ethyl cyclopropylcarboxylate
4606-07-9

ethyl cyclopropylcarboxylate

Conditions
ConditionsYield
With sulfuric acid In ethanol98%
styrene
292638-84-7

styrene

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

2-iodo-1-phenylethyl cyclopropanecarboxylate

2-iodo-1-phenylethyl cyclopropanecarboxylate

Conditions
ConditionsYield
With N-iodo-succinimide In dichloromethane at 20 - 22℃; for 0.25h; regioselective reaction;98%
tert-butyl 1,4-diazepine-1-carboxylate
112275-50-0

tert-butyl 1,4-diazepine-1-carboxylate

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

tert-butyl 4-(cyclopropylaminocarbamoyl)-1,4-N-cycloheptane-1-carboxylate
1363838-32-7

tert-butyl 4-(cyclopropylaminocarbamoyl)-1,4-N-cycloheptane-1-carboxylate

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere;98%
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h;98%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Cyclopropanecarbothioic acid S-cyclohexyl ester
75839-77-9

Cyclopropanecarbothioic acid S-cyclohexyl ester

Conditions
ConditionsYield
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature;97%
1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

1-cyclopropcarbonylimidazole
204803-26-9

1-cyclopropcarbonylimidazole

Conditions
ConditionsYield
at 20℃; for 20h;96%
at 20℃; for 20h;96%
In tetrahydrofuran Heating;
ethyl 2-(2-hydroxyphenyl)acetate
41873-65-8

ethyl 2-(2-hydroxyphenyl)acetate

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

ethyl (2-cyclopropanecarbonyloxy)phenylacetate

ethyl (2-cyclopropanecarbonyloxy)phenylacetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Steglich Esterification; Inert atmosphere;96%
tri-p-fluorophenylstibine
33756-42-2

tri-p-fluorophenylstibine

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

tris(4-fluorophenyl)antimonybis(cyclopropanecarboxylate)

tris(4-fluorophenyl)antimonybis(cyclopropanecarboxylate)

Conditions
ConditionsYield
With tert.-butylhydroperoxide In diethyl ether at 20℃; for 24h;96%
N-tert-butyl-N'-phenyl-S-phenylisothiourea

N-tert-butyl-N'-phenyl-S-phenylisothiourea

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

N-phenylcyclopropanecarboxamide
2759-52-6

N-phenylcyclopropanecarboxamide

Conditions
ConditionsYield
With iron(III)-acetylacetonate In isopropyl alcohol at 83℃; for 24h; Microwave irradiation;96%
2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester

2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

tert-butyl 7-(cyclopropanecarbonyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

tert-butyl 7-(cyclopropanecarbonyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere;96%
levonorgestrel
797-63-7

levonorgestrel

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

D-(-)-norgestrel 17β-cyclopropanecarboxylate
86679-35-8

D-(-)-norgestrel 17β-cyclopropanecarboxylate

Conditions
ConditionsYield
With sodium carbonate; trifluoroacetic anhydride In benzene for 1h; Ambient temperature;95.9%
cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

Cyclopropylmethanol
2516-33-8

Cyclopropylmethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In tert-butyl methyl ether at 0 - 50℃; for 24h;95%
With lithium aluminium tetrahydride83%
With lithium aluminium tetrahydride67%
benzyl alcohol
100-51-6

benzyl alcohol

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

cyclopropanecarboxylic acid benzyl ester
20121-75-9

cyclopropanecarboxylic acid benzyl ester

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 17h; Heating;95%
With 2,5-dimethylpyridine; 4,5-dichloro-1,2,3-dithiazolium chloride In dichloromethane 1) -78 deg C, 2 h, 2) to room temperature, 12 h;76%
With tributyl-amine; 2-chloro-1-ethylpyridinium tetrafluoroborate In dichloromethane Ambient temperature;
6-methoxy-9-(propa-1,2-dien-1-yl)-9H-purine
1538583-91-3

6-methoxy-9-(propa-1,2-dien-1-yl)-9H-purine

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

(E)-3-(6-methoxy-9H-purin-9-yl)allyl cyclopropanecarboxylate
1538584-21-2

(E)-3-(6-methoxy-9H-purin-9-yl)allyl cyclopropanecarboxylate

Conditions
ConditionsYield
With silver carbonate In acetonitrile at 80℃; for 8h; chemoselective reaction;95%
3-bromoaniline
591-19-5

3-bromoaniline

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

N-(3-bromophenyl)cyclopropanecarboxamide
14372-07-7

N-(3-bromophenyl)cyclopropanecarboxamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;95%

1759-53-1Relevant articles and documents

-

Lanpher et al.

, p. 1370 (1958)

-

ALKYLATION REACTIONS OF PROPARGYL ALCOHOL; IMPROVED ROUTES TO PROSTAGLANDIN α-SIDE CHAIN PRECURSORS

Casy, Guy,Furber, Mark,Richardson, Kevan A.,Stephenson, Richard G.,Taylor, Richard J.K.

, p. 5849 - 5856 (1986)

Alkylation reactions of the dilithio derivative of propargyl alcohol and the lithio derivative of tetrahydropyranyl protected propargyl alcohol have been explored in order to develop improved synthetic routes to the key prostaglandin α-side chain precursor methyl 7-hydroxyhept-5-ynoate (5).The use of methyl 4-bromobutanoate or the lithium salt of 4-bromobutanoic acid in these reactions did not produce the required products whereas alkylation using trimethyl ortho-4-bromobutanoate (15) gave methyl 7-hydroxyhept-5-ynoate (5) or the corresponding THP ether (4) in good yield after orthoester hydrolysis.Procedures are also described for the transformation of alcohol (5) and THP (4) into methyl 7-bromohept-5-ynoate (1).Alcohol (5) can also be converted into methyl (Z)-7-bromohept-5-enoate (2) using literature procedures.

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun

supporting information, p. 2020 - 2024 (2022/03/31)

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

CONDENSED HETEROCYCLIC COMPOUND HAVING CYCLOALKYLPYRIDYL GROUP OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE

-

, (2018/09/24)

An object of the present invention is to provide and develop novel agricultural and horticultural insecticides in view of the still immense damage caused by insect pests etc. and the emergence of insect pests resistant to existing insecticides in crop production in the fields of agriculture, horticulture and the like. Provided are a condensed heterocyclic compound represented by the general formula (1): {wherein R1 represents an ethyl group, R2 represents a cycloalkyl group, R3 represents a haloalkyl group, A, A2 and A3 each represent a nitrogen atom or a CH group, A1 represents N-Me, m represents 0 or 2, and n represents 1} or a salt thereof; an agricultural and horticultural insecticide comprising the compound or a salt thereof as an active ingredient; and a method for using the insecticide.

Iron-Catalyzed Aerobic Oxidation of Aldehydes: Single Component Catalyst and Mechanistic Studies

Jiang, Xingguo,Zhai, Yizhan,Chen, Junyu,Han, Yulin,Yang, Zheng,Ma, Shengming

supporting information, p. 15 - 19 (2017/11/23)

An aerobic oxidation of aldehydes towards carboxylic acids in MeCN using 1 atm of pure oxygen or oxygen in air as the oxidant and a catalytic amount of single component catalyst, Fe(NO3)3·9H2O, has been developed. Carboxylic acids with different synthetically useful functional groups were obtained at room temperature. Two mechanistic pathways have been proposed based on isotopic labeling, NMR monitoring, and control experiments. The practicality of this reaction has been demonstrated by conducting several 50 mmol-scale reactions using pure oxygen or an air-flow of ~30 mL/min.

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