4352-30-1

Basic information

• Product Name: CYCLOHEXYL-METHANESULFONYL CHLORIDE
• Synonyms: CYCLOHEXANEMETHANESULFONYL CHLORIDE;CYCLOHEXYL-METHANESULFONYL CHLORIDE;[(Chlorosulphonyl)methyl]cyclohexane;Cyclohexylmethylsulphonyl chloride;Cyclohexylmethylsulfonyl chloride
• CAS NO: 4352-30-1
• Molecular Formula: C₇H₁₃ClO₂S
• Molecular Weight: 196.69
• Mol File: 4352-30-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 114-115℃
• Boiling Point: 280℃
• Flash Point: 123℃
• Appearance: /
• Density: 1.229
• CAS DataBase Reference: CYCLOHEXYL-METHANESULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEXYL-METHANESULFONYL CHLORIDE(4352-30-1)
• EPA Substance Registry System: CYCLOHEXYL-METHANESULFONYL CHLORIDE(4352-30-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• Hazardous Substances Data: 4352-30-1(Hazardous Substances Data)

Synthetic route

S-(cyclohexylmethyl) ethanethioate (107512-01-6) → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
With hydrogenchloride; N-chloro-succinimide In water; acetonitrile at 0 - 20℃; Inert atmosphere;	100%

cyclohexylmethanesulfonic acid (4352-27-6) → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at -20 - 20℃; for 2.5h;	19%

thiourea (17356-08-0) + (bromomethylcyclohexane) (2550-36-9) → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
With ethanol Behandeln des Reaktionsprodukts mit wss.NaOH und anschliessend mit Chlor und wss.Essigsaeure;

cyclohexylmethylsulfonate sodium salt → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 12h; Heating;
With trichlorophosphate
With trichlorophosphate

cyclohexylmethyl chloride (1072-95-3) → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2SO3 / 1,2-dimethoxy-ethane; H2O / 24 h / Heating 2: SOCl2, DMF / 12 h / Heating View Scheme

(S)-5-(cyclohexylmethyl)sulfanylmethyl-5-methylimidazolidine-2,4-dione → (S)-5-methyl-5-trichloromethylimidazolidine-2,4-dione (1206882-48-5) + cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
With water; chlorine In acetic acid Mechanism; Reagent/catalyst;	A 41 mg B n/a

(bromomethylcyclohexane) (2550-36-9) → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogensulfite / water 2: trichlorophosphate View Scheme
Multi-step reaction with 2 steps 1: sodium sulfite / water; acetone / 16 h / 90 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2.5 h / -20 - 20 °C View Scheme

cyclohexylmethyl alcohol (100-49-2) → cyclohexylmethylsulfonyl chloride (4352-30-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 5 h / 60 °C / Inert atmosphere 3: hydrogenchloride; N-chloro-succinimide / acetonitrile; water / 0 - 20 °C / Inert atmosphere View Scheme

(bromomethylcyclohexane) (2550-36-9) → cyclohexylmethylsulfonyl chloride (4352-30-1) + C7H13BrO2S

Conditions	Yield
Stage #1: Cyclohexylmethyl bromide With thiourea In ethanol for 36h; Reflux; Stage #2: With hydrogenchloride; N-chloro-succinimide In water; acetonitrile at 10℃; for 0.5h;

cyclohexylmethylsulfonyl chloride (4352-30-1) → 2,3-Dicyclohexylthiiran-1,1-dioxid (125125-38-4, 125125-40-8)

Conditions	Yield
With triethylamine In acetonitrile at -40℃;	91%

1-(3-nitrophenyl)-4-piperidin-4-ylmethylpiperazine tris-trifluoroacetic acid salt + cyclohexylmethylsulfonyl chloride (4352-30-1) → 1-(1-cyclohexylmethanesulfonyl-piperidin-4-ylmethyl)-4-(3-nitrophenyl)piperazine (740873-62-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	90%

4-[4-(3-nitrophenyl)piperazin-1-yl]butylamine tris-trifluoroacetic acid salt + cyclohexylmethylsulfonyl chloride (4352-30-1) → C-cyclohexyl-N-{4-[4-(3-nitrophenyl)piperazin-1-yl]butyl}methanesulfonamide (740873-04-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h;	88%

cyclohexylmethylsulfonyl chloride (4352-30-1) + C15H22BrNO3 → C22H34BrNO5S

Conditions	Yield
With pyridine at 20℃; for 53h;	88%

4-(4-(3-nitrophenyl)piperazin-1-yl)butan-1-amine (740873-02-3) + cyclohexylmethylsulfonyl chloride (4352-30-1) → C-cyclohexyl-N-{4-[4-(3-nitrophenyl)piperazin-1-yl]butyl}methanesulfonamide (740873-04-5)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2 - 3h;	75%

1-phenylcyclopropylmethylamine (23459-38-3) + cyclohexylmethylsulfonyl chloride (4352-30-1) → C17H25NO2S (1376394-94-3)

Conditions	Yield
Stage #1: 1-phenylcyclopropylmethylamine; cyclohexylmethylsulfonyl chloride With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	69%

1-(4-amino-2-chlorophenyl)methanamine (400721-75-7) + cyclohexylmethylsulfonyl chloride (4352-30-1) → C14H21ClN2O2S (1581308-31-7)

Conditions	Yield
Stage #1: 1-(4-amino-2-chlorophenyl)methanamine; cyclohexylmethylsulfonyl chloride With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	60%

2-chloro-4-{(cyclobutylmethyl)[(3S)-3-pyrrolidinyl]amino}benzonitrile (940865-94-1) + cyclohexylmethylsulfonyl chloride (4352-30-1) → 2-chloro-4-((cyclobutylmethyl) {(3S)-1-[(cyclohexylmethyl)sulfonyl]-3-pyrrolidinyl}amino)benzonitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18h;	54%

cyclohexylmethylsulfonyl chloride (4352-30-1) + 2-methyl-1-phenyl-propylamine (6668-27-5, 23844-66-8, 42070-94-0, 68906-26-3) → C17H27NO2S (1376394-90-9)

Conditions	Yield
Stage #1: cyclohexylmethylsulfonyl chloride; 2-methyl-1-phenyl-propylamine With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	54%

2-methyl-6-[3-(piperidin-4-ylidene)prop-1-yn-1-yl]pyridine (1107616-82-9) + cyclohexylmethylsulfonyl chloride (4352-30-1) → 2-(3-{1-[(cyclohexylmethyl)sulfonyl]piperidin-4-ylidene}prop-1-yn-1-yl)-6-methylpyridine (1107617-81-1)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 1h;	51%

cyclohexylmethylsulfonyl chloride (4352-30-1) + 8-(2-chlorophenyl)-9-(4-chlorophenyl)-6-(piperazin-1-yl)-9H-purine → 8-(2-chlorophenyl)-9-(4-chlorophenyl)-6-{4-[(cyclohexylmethyl)sulfonyl]piperazin-1-yl}-9H-purine

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	46%

4-(4-(6-fluoropyridin-2-yl)piperazin-1-yl)butan-1-amine (1351411-81-8) + cyclohexylmethylsulfonyl chloride (4352-30-1) → 1-cyclohexyl-N-(4-(4-(6-fluoropyridin-2-yl)piperazin-1-yl)butyl)methane-sulfonamide (1351411-09-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	44%

4-(4-(6-nitropyridin-2-yl)piperazin-1-yl)butan-1-amine (1351412-10-6) + cyclohexylmethylsulfonyl chloride (4352-30-1) → 1-cyclohexyl-N-(4-(4-(6-nitropyridin-2-yl)piperazin-1-yl)butyl)methane-sulfonamide (1351412-08-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	44%

cyclohexylmethylsulfonyl chloride (4352-30-1) + 1-(4-bromophenyl)-cyclopropylamine (345965-54-0) → N-[1-(4-bromophenyl)cyclopropyl]-C-cyclohexylmethanesulfonamide (1376395-22-0)

Conditions	Yield
Stage #1: cyclohexylmethylsulfonyl chloride; 1-(4-bromophenyl)-cyclopropylamine With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	42%

(1-(4-fluorophenyl)cyclopropyl)methanamine (75180-46-0) + cyclohexylmethylsulfonyl chloride (4352-30-1) → C17H24FNO2S (1376323-02-2)

Conditions	Yield
Stage #1: (1-(4-fluorophenyl)cyclopropyl)methanamine; cyclohexylmethylsulfonyl chloride With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	37%

m-aminobenzylamine (4403-70-7) + cyclohexylmethylsulfonyl chloride (4352-30-1) → C14H22N2O2S (1270882-91-1)

Conditions	Yield
Stage #1: m-aminobenzylamine; cyclohexylmethylsulfonyl chloride With triethylamine In acetonitrile at 20℃; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Stage #2: In acetonitrile at 80℃; for 2h; Combinatorial reaction / High throughput screening (HTS); Sealed tube; Sonication;	30%

[2-(4-Chloro-phenyl)-2H-indazol-3-yl]cyclohexyl-amine (1218938-02-3) + cyclohexylmethylsulfonyl chloride (4352-30-1) → N-[2-(4-chloro-phenyl)-2H-indazol-3-yl]-C-dicyclohexyl-methanesulfonamide (1218937-79-1)

Conditions	Yield
Stage #1: [2-(4-Chloro-phenyl)-2H-indazol-3-yl]cyclohexyl-amine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1.16667h; Cooling with ice; Inert atmosphere; Stage #2: cyclohexylmethylsulfonyl chloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	28%

cyclohexylmethylsulfonyl chloride (4352-30-1) → cyclohexylmethanesulfonohydrazide

Conditions	Yield
With hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 1h;	27%

1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-piperidin-4-amine (1408075-34-2) + cyclohexylmethylsulfonyl chloride (4352-30-1) → C29H32Cl2N6O2S

Conditions	Yield
With dmap; triethylamine at 20℃; for 16h; Inert atmosphere;	26%

cyclohexylmethylsulfonyl chloride (4352-30-1) + tert-butyl (3S)-3-[[4-[2-(4-amino-2,3-difluoro-phenoxy)-3-pyridyl]pyrimidin-2-yl]amino]piperidine-1-carboxylate → tert-butyl (3S)-3-((4-(2-(4-(cyclohexylmethylsulfonylamino)-2,3-difluoro-phenoxy)-3-pyridyl)pyrimidin-2-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With 4-methyl-morpholine In chloroform at 20℃; for 72h; Inert atmosphere;	24.6%

methyl 4-{2-[2-(2-aminoethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]ethoxy}benzoate amine (540522-69-8) + cyclohexylmethylsulfonyl chloride (4352-30-1) → methyl 4-{2-[5-chloro-2-(2-{[(cyclohexylmethyl)sulfonyl]amino}ethyl)-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoate (683813-37-8)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 20℃; Schotten-Baumann reaction;	20%

cyclohexylmethylsulfonyl chloride (4352-30-1) + 4-(4-aminobutyl)piperazine-1-carboxylic acid tert-butyl ester (745048-07-1) → tert-butyl 4-(4-(cyclohexylmethylsulfonamido)butyl)piperazine-1-carboxylate (1351412-06-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	18%

cyclohexylmethylsulfonyl chloride (4352-30-1) → 1,2-Dicyclohexylethen (58372-36-4)

Conditions	Yield
With triethylamine 1) acetonitrile, -40 deg C, 2) reflux; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 91 percent / Et3N / acetonitrile / -40 °C 2: 57 percent / 80 - 100 °C View Scheme

cyclohexylmethylsulfonyl chloride (4352-30-1) → cyclohexylmethanesulfonic acid (4352-27-6)

Conditions	Yield
With water at 25℃; Rate constant; 0.1 M KCl;
With potassium chloride at 25℃; Rate constant;

cyclohexylmethylsulfonyl chloride (4352-30-1) → C7H12O2S

Conditions	Yield
With sodium hydroxide at 25℃; Rate constant; 0.1 M KCl;

Upstream product

• 17356-08-0 thiourea 
• 2550-36-9 Cyclohexylmethyl bromide 
• 4352-27-6 cyclohexylmethanesulfonic acid 
• 100-49-2 cyclohexylmethyl alcohol 
• 107512-01-6 S-(cyclohexylmethyl) ethanethioate 
• 1072-95-3 cyclohexylmethyl chloride 

Downstream Products

• 740873-04-5 C-cyclohexyl-N-{4-[4-(3-nitrophenyl)piperazin-1-yl]butyl}methanesulfonamide 
• 740873-62-5 1-(1-cyclohexylmethanesulfonyl-piperidin-4-ylmethyl)-4-(3-nitrophenyl)piperazine 
• 1107617-81-1 2-(3-{1-[(cyclohexylmethyl)sulfonyl]piperidin-4-ylidene}prop-1-yn-1-yl)-6-methylpyridine 
• 1376323-02-2 C₁₇H₂₄FNO₂S 
• 1376395-22-0 N-[1-(4-bromophenyl)cyclopropyl]-C-cyclohexylmethanesulfonamide 

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