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

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

Downstream Products

• 7103-46-0 N-(cyclohexanecarbonyl)piperidine 
• 7469-80-9 cyclohexyl 4-methoxyphenyl ketone 
• 5461-52-9 N,N-diethylcyclohexanecarboxamide 
• 17773-63-6 cyclohexyl(cyclopentyl)methanone 
• 2789-44-8 cyclohexyl(p-tolyl)methanone 
• 55106-53-1 1-bromocyclohexanecarboxylic acid 
• 6064-43-3 1-cyclohexylheptan-1-one 
• 14919-06-3 heptyl cyclohexyl ketone 
• 17773-62-5 n-octyl cyclohexyl ketone 
• 3876-37-7 nitrosyl cyclohexanecarboxylate 
• 1122-56-1 cyclohexylcarboxamide 
• 52831-99-9 α-chlorocyclohexylcarbonyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 121074-82-6 O''-cyclohexanecarbonyl-erythromycin 

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