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5239-82-7

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5239-82-7 Usage

Chemical Properties

colorless liquid

Uses

Cyclopropylacetic Acid is used in the synthesis of many organic compounds. Such compounds include Cyproconazole which is an agricultural fungicide and also in synthesis of potent nicotinic acid receptor agonists used in treatment of Dyslipidemia.

Check Digit Verification of cas no

The CAS Registry Mumber 5239-82-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,2,3 and 9 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5239-82:
(6*5)+(5*2)+(4*3)+(3*9)+(2*8)+(1*2)=97
97 % 10 = 7
So 5239-82-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H20B2N6S/c1-13-5-6-14(2)9(13)11-17-12-10-15(3)7-8-16(10)4/h5-8H2,1-4H3

5239-82-7 Well-known Company Product Price

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  • Alfa Aesar

  • (L09416)  Cyclopropylacetic acid, 97%   

  • 5239-82-7

  • 1g

  • 448.0CNY

  • Detail
  • Alfa Aesar

  • (L09416)  Cyclopropylacetic acid, 97%   

  • 5239-82-7

  • 5g

  • 1901.0CNY

  • Detail

5239-82-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclopropylacetic acid

1.2 Other means of identification

Product number -
Other names 2-cyclopropylacetic 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:5239-82-7 SDS

5239-82-7Synthetic route

cyclopropyl-malonic acid
5617-88-9

cyclopropyl-malonic acid

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
at 160℃;98%
2-cyclopropylacetonitrile
6542-60-5

2-cyclopropylacetonitrile

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With water; potassium hydroxide In ethanol at 90℃; for 18h;96%
With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 48h; Reflux; Inert atmosphere;83%
With dihydrogen peroxide; sodium hydroxide In water Reflux;81%
diiodomethane
75-11-6

diiodomethane

but-3-enoic acid
625-38-7

but-3-enoic acid

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With diethylzinc In toluene Ambient temperature;75%
With hydrogenchloride
carbon dioxide
124-38-9

carbon dioxide

1,3-dioxoisoindolin-2-yl 2-cyclopropylacetate

1,3-dioxoisoindolin-2-yl 2-cyclopropylacetate

A

pent-4-enoic acid
591-80-0

pent-4-enoic acid

B

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); 2.9-dimethyl-1,10-phenanthroline; silver fluoride In N,N-dimethyl acetamide at 20℃; under 5171.62 Torr; for 24h;A 7%
B 21%
cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With diethyl ether Erwaermen des Reaktionsprodukts mit Ag2O in Methanol und mit wss. KOH;
2-cyclopropylacetaldehyde
56105-19-2

2-cyclopropylacetaldehyde

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With silver(l) oxide
-triphenyl-phosphoran
14902-14-8

-triphenyl-phosphoran

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With sodium hydroxide
β-vinyl-β-propiolactone
7379-74-0

β-vinyl-β-propiolactone

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer; sodium methylate 1.) THF, r.t., 6 h; 2.) r.t., 12 h; Yield given. Multistep reaction;
cyclopropylketene
128871-21-6

cyclopropylketene

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With water Rate constant;
carbon dioxide
124-38-9

carbon dioxide

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

A

pent-4-enoic acid
591-80-0

pent-4-enoic acid

B

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at -120 - -30℃; Yield given. Yields of byproduct given;
tetrachloromethane
56-23-5

tetrachloromethane

Bis(cyclopropylacetyl) peroxide
1607-28-9

Bis(cyclopropylacetyl) peroxide

A

carbon dioxide
124-38-9

carbon dioxide

B

cyclopropyl-acetic acid cyclopropylmethyl ester
61919-47-9

cyclopropyl-acetic acid cyclopropylmethyl ester

C

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

1-cyclopropylethanol
2566-44-1

1-cyclopropylethanol

aqueous potassium permanganate solution

aqueous potassium permanganate solution

A

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

B

cyclopropanecarboxylic acid
1759-53-1

cyclopropanecarboxylic acid

diethyl cyclopropylmalonate
42392-68-7

diethyl cyclopropylmalonate

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NaOH
View Scheme
1-cyclopropylethanol
2566-44-1

1-cyclopropylethanol

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: durch Dehydrierung an einem Kupfer-Silber-Katalysator
2: Ag2O
View Scheme
jones reagent

jones reagent

2-cyclopropylacetaldehyde
56105-19-2

2-cyclopropylacetaldehyde

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With sulfuric acid In water; acetone
With sulfuric acid In water; acetone
2-(cyclopropanemethyl)-1,3-dithiane

2-(cyclopropanemethyl)-1,3-dithiane

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran
2: sulfuric acid / water; acetone
View Scheme
Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
Stage #1: Cyclopropylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h;
Stage #3: With oxone In acetone at 50℃; for 12h;
475.6 mg
2-(2-cyclopropylethynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1432491-43-4

2-(2-cyclopropylethynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

Conditions
ConditionsYield
With oxone||potassium monopersulfate triple salt; water In acetone at 50℃; for 12h; Inert atmosphere;475 mg
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan
124435-71-8

7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan

1-(7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-2-cyclopropylethan-1-one

1-(7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-2-cyclopropylethan-1-one

Conditions
ConditionsYield
With trifluoroacetic anhydride at -20 - 20℃;100%
1-(4-chloro-benzyl)-5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1H-benzoimidazole
885232-51-9

1-(4-chloro-benzyl)-5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1H-benzoimidazole

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

1-{4-[3-(4-chloro-benzyl)-6-fluoro-2-phenoxymethyl-3H-benzoimidazol-5-yl]-piperazin-1-yl}-2-cyclopropyl-ethanone

1-{4-[3-(4-chloro-benzyl)-6-fluoro-2-phenoxymethyl-3H-benzoimidazol-5-yl]-piperazin-1-yl}-2-cyclopropyl-ethanone

Conditions
ConditionsYield
Stage #1: cyclopropylacetic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0166667h;
Stage #2: 1-(4-chloro-benzyl)-5-fluoro-2-phenoxymethyl-6-piperazin-1-yl-1H-benzoimidazole In N,N-dimethyl-formamide at 20℃; for 22h;
100%
[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)benzylamino]-acetic acid ethyl ester hydrochloride
1310036-75-9

[3-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)benzylamino]-acetic acid ethyl ester hydrochloride

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

{(2-cyclopropyl-acetyl)-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzyl]-amino}-acetic acid ethyl ester
1310038-17-5

{(2-cyclopropyl-acetyl)-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-benzyl]-amino}-acetic acid ethyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃;100%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

5-amino-2-bromo-benzoic acid methyl ester
6942-37-6

5-amino-2-bromo-benzoic acid methyl ester

methyl 2-bromo-5-(2-cyclopropylacetamido)benzoate

methyl 2-bromo-5-(2-cyclopropylacetamido)benzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃;100%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

cyclopropylacetyl chloride
54322-65-5

cyclopropylacetyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25℃; for 4h;99.6%
With oxalyl dichloride In dichloromethane at 20℃; for 4h;98%
With thionyl chloride In dichloromethane at 60℃; for 2h;90%
methyl (2R,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(5-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
884538-52-7

methyl (2R,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(5-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

methyl (2R,12Z,13aS,14aR,16aS)-6-[(cyclopropylacetyl)amino]-5,16-dioxo-2-[(5-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

methyl (2R,12Z,13aS,14aR,16aS)-6-[(cyclopropylacetyl)amino]-5,16-dioxo-2-[(5-pyridin-2-ylthieno[3,2-b]pyridin-7-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane for 15.5h;99%
C39H49BrN6O9S
1219511-65-5

C39H49BrN6O9S

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

C39H47BrN6O8S
1219511-75-7

C39H47BrN6O8S

Conditions
ConditionsYield
Stage #1: C39H49BrN6O9S With hydrogenchloride In dioxanes at 20℃; for 1h;
Stage #2: cyclopropylacetic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 18h;
99%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

4-bromo-N2-methylbenzene-1,2-diamine
337915-79-4

4-bromo-N2-methylbenzene-1,2-diamine

6-bromo-2-(cyclopropylmethyl)-1-methyl-1H-benzimidazole
1447911-05-8

6-bromo-2-(cyclopropylmethyl)-1-methyl-1H-benzimidazole

Conditions
ConditionsYield
Stage #1: cyclopropylacetic acid; 4-bromo-N2-methylbenzene-1,2-diamine With N-ethyl-N,N-diisopropylamine; 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℃; for 1h;
Stage #2: With acetic acid at 80℃; for 1h;
96%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-ol
1630067-58-1

(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-ol

(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-yl 2-cyclopropylacetate
1630067-83-2

(R,E)-6-(benzyloxy)-1-(methoxymethoxy)hex-3-en-2-yl 2-cyclopropylacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 7.5h; Inert atmosphere;95.4%
methyl (2R,6S,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(2-pyridin-2-ylthieno[2,3-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
884538-66-3

methyl (2R,6S,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(2-pyridin-2-ylthieno[2,3-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

methyl (2R,6S,12Z,13aS,14aR,16aS)-6-[(cyclopropylacetyl)amino]-5,16-dioxo-2-[(2-pyridin-2-ylthieno[2,3-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

methyl (2R,6S,12Z,13aS,14aR,16aS)-6-[(cyclopropylacetyl)amino]-5,16-dioxo-2-[(2-pyridin-2-ylthieno[2,3-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Conditions
ConditionsYield
Stage #1: methyl (2R,6S,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(2-pyridin-2-ylthieno[2,3-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate; cyclopropylacetic acid With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane for 15h;
Stage #2: With citric acid In dichloromethane; ethyl acetate pH=4.5;
95%
2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride
766545-20-4

2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

2-chloro-6-(cyclopropylacetyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

2-chloro-6-(cyclopropylacetyl)-5,6,7,8-tetrahydro-1,6-naphthyridine

Conditions
ConditionsYield
Stage #1: cyclopropylacetic acid With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 2-chloro-5,6,7,8-tetrahydro[1,6]naphthyridine hydrochloride With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;
95%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

(±)-(2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

(±)-(2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

(±)-(2R,3R)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester

(±)-(2R,3R)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Steglich Esterification;95%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

(±)-(2R,3R)-2-azido-3-hydroxy-3-(3-methoxyphenyl)propionic acid methyl ester

(±)-(2R,3R)-2-azido-3-hydroxy-3-(3-methoxyphenyl)propionic acid methyl ester

(±)-(2R,3R)-2-azido-3-(2-cyclopropylacetoxy)-3-(3-methoxyphenyl)propionic acid methyl ester

(±)-(2R,3R)-2-azido-3-(2-cyclopropylacetoxy)-3-(3-methoxyphenyl)propionic acid methyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Steglich Esterification;94%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

2-cyclopropyl-N-methoxy-N-methyl-acetamide
227322-00-1

2-cyclopropyl-N-methoxy-N-methyl-acetamide

Conditions
ConditionsYield
Stage #1: cyclopropylacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 25℃; for 1h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 25℃; for 12h;
93.96%
Stage #1: cyclopropylacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane
89%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;84%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

aniline
62-53-3

aniline

2-cyclopropyl-N-phenylacetamide
5687-69-4

2-cyclopropyl-N-phenylacetamide

Conditions
ConditionsYield
Stage #1: cyclopropylacetic acid; aniline With 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
93%
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate at 96 - 100℃; for 7h; chemoselective reaction;42%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

dimedone
126-81-8

dimedone

2-(2-cyclopropylacetyl)-5,5-dimethylcyclohexane-1,3-dione
908117-02-2

2-(2-cyclopropylacetyl)-5,5-dimethylcyclohexane-1,3-dione

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 16.2h;92%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 14h;85%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃;85%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

(2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester
130517-92-9

(2R,3R)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

(2R,3R)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester

(2R,3R)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Steglich Esterification;92%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

(2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester
133179-94-9

(2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

(2S,3S)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester

(2S,3S)-2-azido-3-(2-cyclopropylacetoxy)-3-phenylpropionic acid methyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Steglich Esterification;92%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

(R)-tert-butyl 3-methylpiperazine-1-carboxylate
163765-44-4

(R)-tert-butyl 3-methylpiperazine-1-carboxylate

(R)-tert-butyl 4-(2-cyclopropylacetyl)-3-methylpiperazine-1-carboxylate

(R)-tert-butyl 4-(2-cyclopropylacetyl)-3-methylpiperazine-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 16h; Inert atmosphere;92%
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 16h;92%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-cyclopropylethan-1-one

1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-cyclopropylethan-1-one

Conditions
ConditionsYield
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: cyclopropylacetic acid for 6h; Inert atmosphere; Cooling with ice;
92%
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h;
Stage #2: cyclopropylacetic acid In dichloromethane at 20℃; for 4h;
91%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

1,1'-carbonyldiimidazole

1,1'-carbonyldiimidazole

2-cyclopropyl-N-methoxy-N-methyl-acetamide
227322-00-1

2-cyclopropyl-N-methoxy-N-methyl-acetamide

Conditions
ConditionsYield
Stage #1: cyclopropylacetic acid; 1,1'-carbonyldiimidazole In dichloromethane at 15 - 25℃; for 2h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20 - 25℃; for 15h;
90.5%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

methyl cyclopropylacetate
34108-21-9

methyl cyclopropylacetate

Conditions
ConditionsYield
With sulfuric acid In methanol90%
Multi-step reaction with 2 steps
1: (COCl)2, DMF / benzene / 3 h / Ambient temperature
2: pyridine / Ambient temperature
View Scheme
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

4-methoxy-phenol
150-76-5

4-methoxy-phenol

4-methoxyphenyl 2-bromo-2-cyclopropylacetate

4-methoxyphenyl 2-bromo-2-cyclopropylacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 5h; Inert atmosphere;90%
methyl (2R,6S,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(2-pyridin-2-ylthieno[3,2-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
884538-80-1

methyl (2R,6S,12Z,13aS,14aR,16aS)-6-amino-5,16-dioxo-2-[(2-pyridin-2-ylthieno[3,2-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

methyl (2R,6S,12Z,13aS,14aR,16aS)-6-[(cyclopropylacetyl)amino]-5,16-dioxo-2-[(2-pyridin-2-ylthieno[3,2-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

methyl (2R,6S,12Z,13aS,14aR,16aS)-6-[(cyclopropylacetyl)amino]-5,16-dioxo-2-[(2-pyridin-2-ylthieno[3,2-d]pyrimidin-4-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate

Conditions
ConditionsYield
With dimethyl amine; triethylamine; HATU at 50℃; for 1.5h;89%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 2-cyclopropylacetate
59698-18-9

benzyl 2-cyclopropylacetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;89%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; Inert atmosphere;
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

8-((3R,4S)-4-methylpyrrolidin-3-yl)-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine dihydrobromide

8-((3R,4S)-4-methylpyrrolidin-3-yl)-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine dihydrobromide

2-cyclopropyl-1-((3S,4R)-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)pyrrolidin-1-yl)ethanone
1428243-48-4

2-cyclopropyl-1-((3S,4R)-3-methyl-4-(3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)pyrrolidin-1-yl)ethanone

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 16h;89%
cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

N-β-Z-L-diaminopropionic acid methyl ester
87768-65-8

N-β-Z-L-diaminopropionic acid methyl ester

C17H22N2O5

C17H22N2O5

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;87%
dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

cyclopropylacetic acid
5239-82-7

cyclopropylacetic acid

3-(2-cyclopropylacetyl)oxazolidin-2-one
1330681-58-7

3-(2-cyclopropylacetyl)oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: dimethylenecyclourethane; cyclopropylacetic acid With lithium chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With pivaloyl chloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 2.33333h; Inert atmosphere;
87%

5239-82-7Relevant articles and documents

Rhodes,Vargas

, p. 4077,4078 (1973)

Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides

Li, Chenchen,Li, Ruoling,Zhang, Bing,Zhao, Pei,Zhao, Wanxiang

supporting information, p. 10913 - 10917 (2020/05/25)

A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.

Preparation method of acid with different substituent groups

-

Paragraph 0033-0037, (2019/10/23)

The invention discloses a preparation method of an acid with different substituent groups. A terminal alkyne is lithiated with n-butyllithium, and then reacts with isopropoxyboronic acid pinacol ester, hydrogen chloride is added to achieve quenching, then the obtained reaction product is oxidized by an oxidizing agent, and the oxidized reaction product is separated and purified to obtain the acid.The method of the invention has the advantages of simplicity in operation, one-pot process preparation, no metal catalysis, nontoxic reagents, greenness, environmental friendliness and high atomic utilization rate, and provides a novel and quick way for preparing the acid with different substituent groups; and the obtained acid is an important fine chemical product, and can be widely used in fields of medicines, pesticides, spices and other industries.

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