2719-27-9

Basic information

• Product Name: Cyclohexanecarboxylic acid chloride
• Synonyms: Cyclohexanecarboxylic acid chloride for synthesis;HEXAHYDROBENZOYL CHLORIDE;CYCLOHEXANECARBONYL CHLORIDE;CYCLOHEXANECARBOXYLIC ACID CHLORIDE;AKOS BBS-00003918;Chlorocarbonylcyclohexane;Cyclohexanoyl chloride;Cyclohexylcarbonyl chloride
• CAS NO: 2719-27-9
• Molecular Formula: C₇H₁₁ClO
• Molecular Weight: 146.61
• EINECS: 220-322-7
• Product Categories: Pharmaceutical Intermediates;ACIDHALIDE;Halogen compounds;ACID CHLORIDES;pharmacy, pesticide and organic compounds
• Mol File: 2719-27-9.mol
• Article Data: 109

Chemical Properties

• Boiling Point: 184 °C(lit.)
• Flash Point: 152 °F
• Appearance: Clear colorless to straw/Liquid
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.915mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: HYDROLYSES
• Sensitive: Moisture Sensitive
• BRN: 742163
• CAS DataBase Reference: Cyclohexanecarboxylic acid chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid chloride(2719-27-9)
• EPA Substance Registry System: Cyclohexanecarboxylic acid chloride(2719-27-9)

Safety Data

• Hazard Codes: C
• Statements: 34-37-22
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 1
• F: 9-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2719-27-9(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to straw coloured liquid

Uses

Cyclohexanecarbonyl chloride is used in the preparation of five thiourea derivative ligands having anti-bacterial and anti-yeast activity, (N-(diethylcarbamothioyl)cyclohexanecarboxamide, N-(di-n-propylcarbamothioyl)cyclohexanecarboxamide, di-n-butylcarbamothioyl)cyclohexanecarboxamide, N-(diphenylcarbamothioyl)cyclohexanecarboxamide, N-(morpholine-4-carbonothioyl)cyclohexanecarboxamide.

General Description

Electrochemical reduction of cyclohexanecarbonyl chloride at a hanging mercury drop electrode in acetonitrile has been reported.

InChI:InChI=1/C7H11ClO/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2

Synthetic route

Cyclohexanecarboxylic acid (98-89-5) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
With thionyl chloride In dodecane; benzene at 20℃; for 1h; Heating / reflux;	99%
With thionyl chloride In dodecane; hexane; benzene at 20℃; for 1h; Heating / reflux;	99%
With phosphorus trichloride In dodecane; benzene at 20℃; for 1h; Heating / reflux;	99%

N,N-dimethylcyclohexanecarboxamide (17566-51-7) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
With iodine; N,N-dimethyl-formamide; phosphorus trichloride In 1,2-dichloro-ethane at 100℃; for 12h; Schlenk technique; Sealed tube;	96%

benzoic acid (65-85-0) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
With thionyl chloride	81%

methyl cyclohexylcarboxylate (4630-82-4) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
With iodine; phosphorus trichloride at 160℃; for 48h; Schlenk technique; Sealed tube;	41%

phosgene (75-44-5) + cyclohexane (110-82-7) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
at -20℃; Irradiation.UV-Licht;
UV-Licht;
Irradiation;
Irradiation;
at -20℃; Irradiation.UV-Licht;

phosgene (75-44-5) + cyclohexane (110-82-7) → cyclohexyl chloride (542-18-7) + cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
UV-Licht initiierte Reaktion;

oxalyl dichloride (79-37-8) + cyclohexane (110-82-7) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
at 20℃; Irradiation.UV-Licht;
With dibenzoyl peroxide at 180 - 181℃;
at 180 - 181℃; Irradiation.Gluehlampenlicht;

oxalyl dichloride (79-37-8) + cyclohexane (110-82-7) + dibenzoyl peroxide (94-36-0) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
bei Siedetemperatur im Dunkeln;
Mechanism; bei Siedetemperatur im Dunkeln;

cyclohexane (110-82-7) + carbon monoxide (201230-82-2) → cyclohexyl chloride (542-18-7) + cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
With tetrachloromethane; benzophenone at 50℃; under 62057.8 Torr; Rate constant; Mechanism; Irradiation;

N-(pyridin-3-yl)cyclohexanecarboxamide (119520-52-4) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) hexamethyldisilazane, 1.6 M n-BuLi, 2.) CS2, 3.) PhSeO2H / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h 2: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme

N-Pyridin-3-yl-cyclohexanecarboximidothioic acid pyridin-2-yl ester (119541-42-3) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 95 percent / water / dioxane / 12 h / Ambient temperature 2: 1.) hexamethyldisilazane, 1.6 M n-BuLi, 2.) CS2, 3.) PhSeO2H / 1.) THF, hexane, -20 deg C, 30 min, 2.) THF, rt, 3.) THF, rt, 5 h 3: oxalyl chloride, DMF / benzene / Ambient temperature View Scheme

cyclohexanecarbaldehyde (2043-61-0) → cyclohexanylcarbonyl chloride (2719-27-9)

Conditions	Yield
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere;
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere;
With trichloroisocyanuric acid In dichloromethane at 20℃; for 4h; Inert atmosphere; Irradiation;

(trichloromethyl)mesitylene (707-74-4) + Cyclohexanecarboxylic acid (98-89-5) → cyclohexanylcarbonyl chloride (2719-27-9) + mesitylene-2-carboxylic acid chloride (938-18-1)

Conditions	Yield
With iron(III) chloride at 100℃; for 4h; Inert atmosphere;	A 9.6 kg B 12.6 kg

phenethylamine (64-04-0) + cyclohexanylcarbonyl chloride (2719-27-9) → cyclohexanecarboxylic acid phenethylamide (53182-00-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 23℃;	100%
With triethylamine In dichloromethane at 0 - 30℃; for 12h;	100%
With sodium hydroxide In dichloromethane for 0.25h;	97%

[3-benzyloxy-1-(hydroxymethyl)cyclobutyl]methanol (20061-24-9) + cyclohexanylcarbonyl chloride (2719-27-9) → 1-benzyloxy-3,3-bis(cyclohexylcarbonyloxymethyl)cyclobutane (132332-84-4)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	100%

O-trimethylsilyl-2-(trimethylsilylmethyl)prop-2-en-1-ol (83378-96-5) + cyclohexanylcarbonyl chloride (2719-27-9) → 2-Cyclohexyl-4-methyl-furan (51080-23-0)

Conditions	Yield
With titanium tetrachloride In tetrachloromethane at -78℃;	100%

5-(4-nitrophenyl)-1H-1,2,3,4-tetrazole (16687-60-8) + cyclohexanylcarbonyl chloride (2719-27-9) → 2-cyclohexyl-5-(4-nitro-phenyl)-[1,3,4]oxadiazole (866358-13-6)

Conditions	Yield
With pyridine at 20 - 100℃; for 3h;	100%

6-methoxy-pyridin-3-ylamine (6628-77-9) + cyclohexanylcarbonyl chloride (2719-27-9) → cyclohexanecarboxylic acid (6-methoxy-pyridin-3-yl)-amide hydrochloride (548763-48-0)

Conditions	Yield
In tetrahydrofuran; diethyl ether	100%

4-Chloro-3-nitroaniline (635-22-3) + cyclohexanylcarbonyl chloride (2719-27-9) → N-(4-chloro-3-nitrophenyl)cyclohexanecarboxamide (458554-50-2)

Conditions	Yield
Stage #1: 4-Chloro-3-nitroaniline; cyclohexanylcarbonyl chloride With pyridine In dichloromethane at 20℃; for 18h; Stage #2: With hydrogenchloride In dichloromethane; water	100%

methyl 3-(4-((2'-aminobiphenyl-3-yl)methyl)piperazin-1-yl)-3-oxopropanoate (1316807-94-9) + cyclohexanylcarbonyl chloride (2719-27-9) → methyl 3-(4-((2'-(cyclohexanecarboxamido)biphenyl-3-yl)methyl)piperazin-1-yl)-3-oxopropanoate (1316808-21-5)

Conditions	Yield
With polystyrene N-methylmorpholine In dichloromethane at 20℃; for 1h;	100%

5-butoxy-2,4-dinitrobenzenamine (220066-76-2) + cyclohexanylcarbonyl chloride (2719-27-9) → 1-(cyclohexanecarboxamido)-5-butoxy-2,4-dinitrobenzene (1448876-42-3)

Conditions	Yield
With pyridine Reflux;	100%
With pyridine at 100℃; for 1.5h; Microwave irradiation;	1.44 g

5-(butylthio)-2,4-dinitrobenzenamine (1448876-48-9) + cyclohexanylcarbonyl chloride (2719-27-9) → 1-(cyclohexanecarboxamido)-5-(butylthio)-2,4-dinitrobenzene (1448876-49-0)

Conditions	Yield
With pyridine Reflux;	100%
With pyridine In acetonitrile at 100℃; for 2h; Microwave irradiation;	1.97 g

2,4-dinitro-5-(phenylthio)benzenamine (53488-26-9) + cyclohexanylcarbonyl chloride (2719-27-9) → 1-(cyclohexanecarboxamido)-5-(phenylthio)-2,4-dinitrobenzene (1448876-52-5)

Conditions	Yield
With pyridine Reflux;	100%
With pyridine at 100℃; for 3h; Microwave irradiation;	79%

2-(4-chlorophenyl)-5-ethyl-6-methylthieno[2,3-d]pyrimidin-4-amine + cyclohexanylcarbonyl chloride (2719-27-9) → N-(2-(4-chlorophenyl)-5-ethyl-6-methylthieno[2,3-d]pyrimidin-4-yl)cyclohexanecarboxamide

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20 - 50℃; for 18h; Inert atmosphere;	100%

(2S,3R,4S,5S)-ethyl 3-(tert-butyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate + cyclohexanylcarbonyl chloride (2719-27-9) → (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-1-(cyclohexanecarbonyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 14h; Temperature;	100%
With triethylamine In dichloromethane at 20℃; Cooling with ice;	91%

(2S,3R,4S,5S)-ethyl 3-(tert-butyl)-4-nitro-5-(o-tolyl)pyrrolidine-2-carboxylate + cyclohexanylcarbonyl chloride (2719-27-9) → ethyl (2S,3R,4S,5S)-3-(tert-butyl)-1-(cyclohexanecarbonyl)-4-nitro-5-(o-tolyl)pyrrolidine-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;	100%

(2R,3R,4S,5R)-ethyl 3-(tert-butyl)-5-(2-(difluoromethoxy)phenyl)-4-nitropyrrolidine-2-carboxylate + cyclohexanylcarbonyl chloride (2719-27-9) → (2S,3R,4S,5S)-ethyl 3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-(2-(difluoromethoxy)phenyl)-4-nitropyrrolidine-2-carboxylate

Conditions	Yield
With N,N-dimethyl-formamide In dichloromethane for 2h; Cooling with ice;	100%

rac-(2R,3S,4R,5R)-ethyl 3-(tert-butyl)-5-(2-methoxyphenyl)-4-nitropyrrolidine-2-carboxylate + cyclohexanylcarbonyl chloride (2719-27-9) → rac-(2R,3S,4R,5R)-ethyl 3-(tert-butyl)-1-(cyclohexanecarbonyl)-5-(2-methoxyphenyl)-4-nitropyrrolidine-2-carboxylate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃; for 1.5h;	100%

cyclohexanylcarbonyl chloride (2719-27-9) + 6β-tropanol → 8-methyl-6β-cyclohexanecarbonyloxy-8-azabicyclo[3.2.1]octane

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Acylation;	99.5%

cyclohexanylcarbonyl chloride (2719-27-9) + (3S, 6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one (270902-68-6) → (3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-(cyclohexanecarbonyl)-oxy-2H-azepin-2-one (270902-69-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	99.5%
With triethylamine In dichloromethane at 5 - 20℃;	99.5%
With dmap In ethyl acetate at 50℃; for 3h; Inert atmosphere;	146 g

cyclohexanylcarbonyl chloride (2719-27-9) + N-t-butyl-(RS)-2-hydroxy-2-((S)-2-pyrrolidinyl)acetamide → N-tert-Butyl-2-((S)-1-cyclohexanecarbonyl-pyrrolidin-2-yl)-2-hydroxy-acetamide

Conditions	Yield
With triethylamine In tetrahydrofuran for 2h; Ambient temperature;	99.2%

piperidine (110-89-4) + cyclohexanylcarbonyl chloride (2719-27-9) → N-(cyclohexanecarbonyl)piperidine (7103-46-0)

Conditions	Yield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h;	99%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	98%
With indium In acetonitrile at 20℃; for 3h;	84%

methylamine (74-89-5) + cyclohexanylcarbonyl chloride (2719-27-9) → N-methylcyclohexanecarboxamide (6830-84-8)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	99%
With triethylamine In diethyl ether	90%
In ethanol at 5 - 20℃; for 2.5h;	77.5%

N-methylaniline (100-61-8) + cyclohexanylcarbonyl chloride (2719-27-9) → cyclohexanecarboxylic acid methylphenylamide (23824-50-2)

Conditions	Yield
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction;	99%
With triethylamine In 1,4-dioxane for 2h; Heating;	87%

cyclohexanylcarbonyl chloride (2719-27-9) + benzene (71-43-2) → Cyclohexyl phenyl ketone (712-50-5)

Conditions	Yield
aluminum (III) chloride at 3℃; for 1h; Friedel Crafts Alkylation; Heating / reflux;	99%
aluminum (III) chloride In hexane at 3℃; for 1.33h; Friedel Crafts Alkylation; Heating / reflux;	99%
aluminum (III) chloride at 3℃; for 1h; Product distribution / selectivity; Friedel Crafts Alkylation; Heating / reflux;	99%

((3aR,4R,5S,7S,7aS)-5-Benzenesulfonyl-5-bromo-2,2,3a,7-tetramethyl-hexahydro-benzo[1,3]dioxol-4-yl)-acetic acid (137384-87-3) + cyclohexanylcarbonyl chloride (2719-27-9) → C26H35BrO7S (137384-88-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 25℃; for 0.166667h;	99%

(2S,4aR,6R,8aS/2R,4aS,6S,8aR)-Decahydro-6-(trans-4-propylcyclohexyl)-2-naphthalinol (85603-77-6) + cyclohexanylcarbonyl chloride (2719-27-9) → Cyclohexanecarboxylic acid (2S,4aR,6R,8aS)-6-(4-propyl-cyclohexyl)-decahydro-naphthalen-2-yl ester (85603-85-6)

Conditions	Yield
With pyridine for 15h;	99%

cyclohexanylcarbonyl chloride (2719-27-9) → cyclohexane (110-82-7)

Conditions	Yield
With tris-(trimethylsilyl)silane; 2,2'-azobis(isobutyronitrile) In toluene at 80℃; for 0.666667h;	99%

4,5-dichloro-2H-pyridazin-3-one (932-22-9) + cyclohexanylcarbonyl chloride (2719-27-9) → 4,5-dichloro-2-cyclohexanecarbonyl-2H-pyridazin-3-one (450408-67-0)

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 0.166667h;	99%

(4-methylsulfanyl-phenyl)-acetic acid methyl ester (70290-37-8) + cyclohexanylcarbonyl chloride (2719-27-9) → methyl 3-cyclohexyl-2-(4-methylthiophenyl)-3-oxo-propanoate (691881-03-5)

Conditions	Yield
Stage #1: (4-methylsulfanyl-phenyl)-acetic acid methyl ester With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 1.16667h; Stage #2: cyclohexanylcarbonyl chloride In tetrahydrofuran at -78 - 0℃; for 2h;	99%

2-iodophenylamine (615-43-0) + cyclohexanylcarbonyl chloride (2719-27-9) → N-(2-iodophenyl)cyclohexanecarboxamide (378786-44-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;	99%
With triethylamine at 0 - 20℃; for 0.5h;	75%
With triethylamine In tetrahydrofuran at 0 - 20℃;	74%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.666667h;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 0.5h;

Upstream product

• 79-37-8 oxalyl dichloride 
• 110-82-7 cyclohexane 
• 201230-82-2 carbon monoxide 
• 65-85-0 benzoic acid 
• 2043-61-0 cyclohexanecarbaldehyde 
• 707-74-4 (trichloromethyl)mesitylene 
• 98-89-5 Cyclohexanecarboxylic acid 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 17566-51-7 N,N-dimethylcyclohexanecarboxamide 
• 119541-42-3 N-Pyridin-3-yl-cyclohexanecarboximidothioic acid pyridin-2-yl ester 
• 119520-52-4 N-(pyridin-3-yl)cyclohexanecarboxamide 
• 94-36-0 dibenzoyl peroxide 
• 75-44-5 phosgene 

Downstream Products

• 7103-46-0 N-(cyclohexanecarbonyl)piperidine 
• 79852-25-8 cyclohexyl(thiophen-2-yl)methanone 
• 16386-45-1 benzo[d][1,3]dioxol-5-yl cyclohexanecarboxylate 
• 56882-77-0 2-amino-5-cyclohexyl-1,3,4-thiadiazole 
• 7469-80-9 cyclohexyl 4-methoxyphenyl ketone 
• 53182-00-6 cyclohexanecarboxylic acid phenethylamide 
• 5814-04-0 1,2-bis-(cyclohexanecarbonyl)hydrazine 
• 4350-76-9 N-cyclohexanecarbonyl-sulfanilic acid amide 
• 17566-51-7 N,N-dimethylcyclohexanecarboxamide 
• 5461-52-9 N,N-diethylcyclohexanecarboxamide 
• 16491-63-7 cyclohexanecarboxylic acid allyl ester 
• 2719-26-8 N-phenylcyclohexanamide 
• 6553-80-6 isopropyl cyclohexylmethanoate 
• 17773-63-6 cyclohexyl(cyclopentyl)methanone 

Relevant articles and documents

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Synthesis, characterization, antimicrobial, antioxidant and computational evaluation of N-acyl-morpholine-4-carbothioamides

Abstract: The present research paper reports the convenient synthesis, successful characterization, in vitro antibacterial, antifungal, antioxidant potency and biocompatibility of N-acyl-morpholine-4-carbothioamides (5a–5j). The biocompatible derivatives were found to be highly active against the tested bacterial and fungal strains. Moreover, some of the screened N-acyl-morpholine-4-carbothioamides exhibited excellent antioxidant potential. Docking simulation provided additional information about possibilities of their inhibitory potential against RNA. It has been predicted by in silico investigation of the binding pattern that compounds 5a and 5j can serve as the potential surrogate for design of novel and potent antibacterial agents. The results for the in vitro bioassays were promising with the identification of compounds 5a and 5j as the lead and selective candidate for RNA inhibition. Results of the docking computations further ascertained the inhibitory potential of compound 5a. Based on the in silico studies, it can be suggested that compounds 5a and 5j can serve as a structural model for the design of antibacterial agents with better inhibitory potential. Graphic abstract: Binding mode of compound 5j inside the active site of RNA in 3D space. 5j displayed highest antibacterial potential than the reference drug ampicillin with ZOI 10.50?mm against Staphylococcus aureus. 5j also displayed highest antifungal potential than the reference drug amphotericin B with ZOI 18.20?mm against Fusarium solani.[Figure not available: see fulltext.].

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