4023-34-1

Basic information

• Product Name: Cyclopropanecarbonyl Chloride
• Synonyms: Cyclopropanecarboxyl Chloride;(Chlorocarbonyl)cyclopropane;Cyclopropanecarboxylic acid chloride, 98% 100GR;Cyclopropanecarboxylic acid chloride, 98% 25GR;Cyclopropanecarboxylic acid chloride, 98% 5GR;(Chlorocarbonyl)cyclopropane, (Chloroformyl)cyclopropane;Cyclopropanecarbonyl chloride 98%;Cyclopropanecarbonyl Chloride, 97+%
• CAS NO: 4023-34-1
• Molecular Formula: C₄H₅ClO
• Molecular Weight: 104.53
• EINECS: 223-684-4
• Product Categories: Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Carbazoles;Pharmaceutical Intermediates;Cyclopropanes;Simple 3-Membered Ring Compounds
• Mol File: 4023-34-1.mol
• Article Data: 46

Chemical Properties

• Melting Point: 77.5-78.5 °C(Solv: hexane (110-54-3))
• Boiling Point: 119 °C(lit.)
• Flash Point: 74 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.152 g/mL at 25 °C(lit.)
• Vapor Pressure: 16.3mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: decomposes
• Sensitive: Moisture Sensitive
• BRN: 471286
• CAS DataBase Reference: Cyclopropanecarbonyl Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarbonyl Chloride(4023-34-1)
• EPA Substance Registry System: Cyclopropanecarbonyl Chloride(4023-34-1)

Safety Data

• Hazard Codes: C,F
• Statements: 10-34-29-25-36-38
• Safety Statements: 26-36/37/39-45-8-16
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 4023-34-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

Cyclopropanecarbonyl chloride can be used as an alkylating reagent in the preparation of some chemical building blocks such as formylcyclopropane, cyclopropanecarboxylic acid hydrazide, bis(cyclopropylcarbonyl) peroxide, 1-cyclopropanecarboxamide, 2-cyclopropylcarbonylcyclohexane-1,3-diones and cyclopropyl analog of triazolopiperazine-amides.

Purification Methods

If the IR shows OH bands, then some hydrolysis to the free acid must have occurred. In this case heat with oxalyl chloride at 50o for 2hours or SOCl2 for 30minutes, then evaporate and distil three times using a Dufton column (p 10). Store it in an inert dry atmosphere, preferably in sealed tubes. Strong IRRITANT. If it is free from OH bands, then just distil it in vacuo and store as before. [Jeffrey & Vogel J Chem Soc 1804 1948, Beilstein 9 IV 4.]

InChI:InChI=1/C4H5ClO/c5-4(6)3-1-2-3/h3H,1-2H2

Synthetic route

cyclopropanecarboxylic acid (1759-53-1) → cyclopropanecarboxylic acid chloride (4023-34-1)

Conditions	Yield
With thionyl chloride In toluene Heating;	100%
With thionyl chloride for 3h; Heating;	95%
With thionyl chloride for 4h; Heating;	88%

cyclopropanecarboxylic acid Na-salt (155-22-6) → cyclopropanecarboxylic acid chloride (4023-34-1)

Conditions	Yield
With oxalyl dichloride
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h;

oxalyl dichloride (79-37-8) + cyclopropanecarboxylic acid (1759-53-1) → cyclopropanecarboxylic acid chloride (4023-34-1)

cyclopropanecarboxylic acid (1759-53-1) → 5-cyclopropanepentanoyl chloride (663618-19-7) + cyclopropanecarboxylic acid chloride (4023-34-1)

cyclopropanecarboxylic acid chloride (4023-34-1) → Cyclopropancarbamid (6228-73-5)

Conditions	Yield
With ammonia In dichloromethane at 20℃; for 2h;	100%
With ammonia In dichloromethane; water at 20℃; for 2h;	100%
With diethyl ether; ammonia
With ammonium hydroxide

cyclopropanecarboxylic acid chloride (4023-34-1) → Cyclopropanecarboxaldehyde (1489-69-6)

Conditions	Yield
With sodium tris(tert-butoxo)aluminium hydride In tetrahydrofuran; diethylene glycol dimethyl ether at -78℃; for 3h;	100%
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride
With sodium tetrahydroborate; cadmium(II) chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; acetonitrile at -5℃; for 0.0833333h; Yield given;
With thexyl-s-butoxyborane In tetrahydrofuran at 25℃; for 96h; Yield given;
Stage #1: cyclopropanecarboxylic acid chloride With aluminium hydride In tetrahydrofuran at 20℃; for 1h; Metallation; Stage #2: With pyridinium chlorochromate In tetrahydrofuran; dichloromethane at 20℃; for 6h; Oxidation;	98 % Chromat.

cyclopropanecarboxylic acid chloride (4023-34-1) + normorphine (466-97-7, 13396-02-6, 99295-16-6, 142864-36-6) → 3-O,N-dicyclopropylcarbonylnormorphine (81815-58-9)

Conditions	Yield
With triethylamine In chloroform for 8h; Heating;	100%

cyclopropanecarboxylic acid chloride (4023-34-1) + 10,11-dihydro-4-nitro-5H-dibenzo<1,4>diazepine (162930-74-7) → Cyclopropyl-(4-nitro-5,11-dihydro-dibenzo[b,e][1,4]diazepin-10-yl)-methanone (1026556-44-4)

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	100%

cycl-isopropylidene malonate (2033-24-1) + cyclopropanecarboxylic acid chloride (4023-34-1) → 5-(cyclopropyl(hydroxy)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (146380-13-4)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Acylation;	100%
Stage #1: cycl-isopropylidene malonate With pyridine In dichloromethane at 0℃; for 0.25h; Stage #2: cyclopropanecarboxylic acid chloride In dichloromethane at 0 - 20℃; for 3h;	60%
With pyridine In dichloromethane at 0 - 20℃; for 3h; Acylation;

cyclopropanecarboxylic acid chloride (4023-34-1) + 3,4-dimethoxy-4-[[[2-(3-methoxyphenyl)ethyl]amino]methyl]phenoxy-Merrifield resin; 3,5-dimethoxy-4-[[[2-(2,5-dimethoxyphenyl)ethyl]amino]methyl]phenoxy-Merrifield resin → N-[2-(3-methoxyphenyl)ethyl]cyclopropylformamide; N-[2-(2,5-dimethoxyphenyl)ethyl]cyclopropylformamide; mixture of

Conditions

Yield

Stage #1: cyclopropanecarboxylic acid chloride; 3,4-dimethoxy-4-[[[2-(3-methoxyphenyl)ethyl]amino]methyl]phenoxy-Merrifield resin; 3,5-dimethoxy-4-[[[2-(2,5-dimethoxyphenyl)ethyl]amino]methyl]phenoxy-Merrifield resin With triethylamine In 1,2-dichloro-ethane at 20℃; for 20h; Solid phase reaction; acylation; Stage #2: With dimethylsulfide; water; trifluoroacetic acid In dichloromethane at 20℃; for 15h; Solid phase reaction; cleavage of amide;

100%

cyclopropanecarboxylic acid chloride (4023-34-1) + trinexapac ethyl → 4-cyclopropanecarbonyl-3-cyclopropanecarbonyloxy-5-oxo-cyclohex-3-enecarboxylic acid ethyl ester

Conditions	Yield
With triethylamine In dichloromethane	100%

cyclopropanecarboxylic acid chloride (4023-34-1) + 2-isobutyryl-1,3-cyclohexanedione (101386-00-9) → cyclopropanecarboxylic acid 2-isobutyryl-3-oxo-cyclohex-1-enyl ester

Conditions	Yield
With triethylamine In dichloromethane	100%

CYANAMID (420-04-2) + cyclopropanecarboxylic acid chloride (4023-34-1) → C5H6N2O

Conditions	Yield
With sodium hydroxide In acetone	100%

cyclopropanecarboxylic acid chloride (4023-34-1) + 3-nitro-aniline (99-09-2) → N-(3-nitrophenyl) cyclopropanecarboxamide (101946-39-8)

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 2h;	100%
With triethylamine In N,N-dimethyl-formamide at 25℃; for 3h; Cooling with ice;	71.6%
With triethylamine In dichloromethane	71%
With triethylamine In dichloromethane	71%
With potassium carbonate In dichloromethane at 20℃; for 2h;

(4aR,5R,6R,7R)-6-hydroxy-7-methoxy-4a,5,6,7-tetrahydro-1,3,4a,5-tetramethylbenz[f]indol-2(4H)-one (209331-16-8) + cyclopropanecarboxylic acid chloride (4023-34-1) → (4AR,5R,6R,7R)-6-Cyclopropylcarbonyloxy-7-methoxy-4a,5,6,7-tetrahydro-1,3,4a,5-tetramethylbenz[f]indol-2(4H)-one

Conditions	Yield
With pyridine at 20℃;	100%
In pyridine; dichloromethane	100%

N-[2-(6-amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (1000334-09-7) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(3-(2-(acetylamino)ethyl)-4-hydroxy-2,3-dihydro-1H-inden-5-yl)cyclopropanecarboxamide (1000334-17-7)

Conditions	Yield
With pyridine at 0℃; for 3h;	100%
With pyridine at 0℃; for 0.25h;

4-methylthiazol-2-ylamine (1603-91-4) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(4-methylthiazol-2-yl)cyclopropanecarboxamide (354547-70-9)

Conditions	Yield
With pyridine at 20℃; for 2h;	100%
With pyridine at 0 - 20℃;

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + cyclopropanecarboxylic acid chloride (4023-34-1) → cyclopropanecarboxylic acid N-methoxy-N-methylamide (147356-78-3)

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; Stage #2: cyclopropanecarboxylic acid chloride In dichloromethane at 4 - 23℃;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	90%
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	90%

cyclopropanecarboxylic acid chloride (4023-34-1) + (3R,4S)-3-triisopropylsilyloxy-4-(2-methylprop-1-enyl)azetidin-2-one (178250-09-4) → (3R,4S)-1-cyclopropanecarbonyl-3-triisopropylsiloxy-4-(2-methylprop-1-enyl)azetidin-2-one (1031784-15-2)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h;	100%

3-aminobenzoic acid ethyl ester (582-33-2) + cyclopropanecarboxylic acid chloride (4023-34-1) → ethyl 3-((cyclopropylcarbonyl)amino)benzoate (723759-58-8)

Conditions	Yield
In dichloromethane at 20℃;	100%

1-[(2R,6S)-8-amino-9-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (1155856-77-1) + cyclopropanecarboxylic acid chloride (4023-34-1) → cyclopropanecarboxylic acid [(2R,6S)-9-hydroxy-6,11,11-trimethyl-3-(2,2,2-trifluoro-acetyl)-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl]-amide (1155857-31-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%
With triethylamine In dichloromethane at 20℃;

tert-butyl ((6-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)(2-methoxyethyl)carbamate (1123837-34-2) + cyclopropanecarboxylic acid chloride (4023-34-1) → tert-butyl (6-(7-(4-(cyclopropanecarboxamido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl(2-methoxyethyl)carbamate (1187214-01-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	100%

6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)imidazo[1,2-b]pyridazin-2-amine trifluoroacetate + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

Conditions	Yield
Stage #1: 6-(1-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl)imidazo[1,2-b]pyridazin-2-amine trifluoroacetate; cyclopropanecarboxylic acid chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Stage #2: With ammonium hydroxide In methanol at 20℃; for 1h;	100%

(S)-methyl 2-(8-(N-hydroxycarbamimidoyl)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoate (1080641-18-4) + cyclopropanecarboxylic acid chloride (4023-34-1) → (S)-methyl 2-(8-(N-(cyclopropanecarbonyl)-N'-hydroxycarbamimidoyl)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoate (1080641-74-2)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;	100%

cyclopropanecarboxylic acid chloride (4023-34-1) + 2-amino-4-nitropyridine (4487-50-7) → N-(4-nitropyridin-2-yl)-cyclopropanecarboxamide (942076-75-7)

Conditions	Yield
With pyridine at 0 - 20℃;	100%
With pyridine at 0 - 20℃;	100%
With pyridine at 20℃; for 30h;	98%

cyclopropanecarboxylic acid chloride (4023-34-1) + 1,1-dimethylethyl (3S)-3-[2-(ethyloxy)-2-oxoethyl]-1-pyrrolidinecarboxylate → ethyl[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetate (1332333-17-1)

Conditions	Yield
Stage #1: 1,1-dimethylethyl (3S)-3-[2-(ethyloxy)-2-oxoethyl]-1-pyrrolidinecarboxylate With hydrogenchloride In 1,4-dioxane at 20℃; for 1h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Stage #3: cyclopropanecarboxylic acid chloride at 0 - 20℃; for 1h;	100%

4-bromo-7-(5-fluoro-2-methylphenyl)isoquinolin-3-amine (1382848-69-2) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(4-bromo-7-(5-fluoro-2-methylphenyl)isoquinolin-3-yl)cyclopropanecarboxamide (1382841-06-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 1h;	100%

cyclopropanecarboxylic acid chloride (4023-34-1) + N-desmethylthebaine hydrochloride (7679-18-7) → 17-cyclopropylcarbonylnorthebaine (25098-38-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Cooling with ice;	100%
With triethylamine In dichloromethane at 0 - 20℃;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 10h;	99%
With triethylamine In dichloromethane at 0 - 20℃;	91%

C23H23N7O4S (1429324-16-2) + cyclopropanecarboxylic acid chloride (4023-34-1) → C27H27N7O5S (1429324-17-3)

Conditions	Yield
With triethylamine In dichloromethane for 1h; Inert atmosphere;	100%

(2SS,3RS)-2-(4-methylthiophen-2-yl)-4-oxo-1,2,3,4-tetrahydropyridin-3-yl methyl(phenyl)carbamate + cyclopropanecarboxylic acid chloride (4023-34-1) → (2SR,3RS)-1-(cyclopropanecarbonyl)-2-(4-methylthiophen-2-yl)-4-oxo-1,2,3,4-tetrahydropyridin-3-yl methyl(phenyl)-carbamate

Conditions	Yield
With dmap In tetrahydrofuran	100%

(1RS,2RS)-ethyl 2-(4-amino-3-bromophenyl)-3-phenylcyclopropanecarboxylate + cyclopropanecarboxylic acid chloride (4023-34-1) → (1RS,2RS,3RS)-ethyl 2-(3-bromo-4-(cyclopropanecarboxamido)phenyl)-3-phenylcyclopropanecarboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;	100%

2-amino-4-bromopyridine (84249-14-9) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(4-bromopyridin-2-yl)cyclopropanecarboxamide (1529768-99-7)

Conditions	Yield
Stage #1: 2-amino-4-bromopyridine With pyridine In dichloromethane at 20℃; for 0.0833333h; Stage #2: cyclopropanecarboxylic acid chloride In dichloromethane at 20℃; for 2h;	100%
With triethylamine In dichloromethane at 0 - 20℃;	93%
With pyridine In tetrahydrofuran at 0℃; for 4h;	90%

p-nitrobenzenesulfonamide (6325-93-5) + cyclopropanecarboxylic acid chloride (4023-34-1) → N-(4-nitrophenylsulfonyl)cyclopropanecarboxamide

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%

Upstream product

• 155-22-6 cyclopropanecarboxylic acid Na-salt 
• 1759-53-1 cyclopropanecarboxylic acid 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 2868-37-3 methyl cyclopropylcarboxylate 
• 60128-01-0 cyclopropanecarboxylic acid propyl ester 
• 4606-07-9 ethyl cyclopropylcarboxylate 
• 64969-79-5 cyclopropanecarboxylic acid isobutyl ester 
• 60128-02-1 cyclopropanecarboxylic acid pentyl ester 
• 10528-56-0 bis-cyclopropanecarbonyl-amine 
• 57235-50-4 2-amino-5-cyclopropyl-1,3,4-thiadiazole 
• 7152-03-6 p-methoxyphenyl cyclopropyl ketone 
• 2759-52-6 N-phenylcyclopropanecarboxamide 
• 1453-50-5 N-cyclopropylcyclopropanecarboxamide 
• 54947-39-6 cyclopropanecarboxylic acid n-butyl ester 
• 3481-02-5 cyclopropyl phenyl ketone 
• 5296-56-0 cyclopropanecarboxylic acid phenyl ester 
• 50438-01-2 cyclopropyl-mesityl ketone 

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