6092-54-2

Basic information

• Product Name: HEXYL CHLOROFORMATE
• Synonyms: CHLOROFORMIC ACID HEXYL ESTER;CHLOROFORMIC ACID N-HEXYL ESTER;HEXYL CHLOROFORMATE;N-HEXYLCHLOROFOMATE;N-HEXYL CHLOROFORMATE;Carbonochloridic acid, hexyl ester;carbonochloridicacid,hexylester;chloro-formicacihexylester
• CAS NO: 6092-54-2
• Molecular Formula: C₇H₁₃ClO₂
• Molecular Weight: 164.63
• EINECS: 228-036-4
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks;Intermediate of Dabigatran
• Mol File: 6092-54-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 60-61°C 7mm
• Flash Point: 61°C
• Appearance: Clear colorless/Liquid
• Density: 1.007 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.637mmHg at 25°C
• Refractive Index: n20/D 1.424(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: HEXYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: HEXYL CHLOROFORMATE(6092-54-2)
• EPA Substance Registry System: HEXYL CHLOROFORMATE(6092-54-2)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: 2742
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 6092-54-2(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 6092-54-2 differently. You can refer to the following data:
1. Hexyl chloroformate has been used as derivatization reagent in: determination of sarcosine and N-ethylglycine in urine and urinary sediments by solid-phase micro extraction and fast GC-MS analysis determination of benzoylecgonine in urine by GC-quadrupole ion trap mass spectrometry
2. Hexyl chloroformate has been used as derivatization reagent in:determination of sarcosine and N-ethylglycine in urine and urinary sediments by solid-phase micro extraction and fast GC-MS analysisdetermination of benzoylecgonine in urine by GC-quadrupole ion trap mass spectrometry

General Description

Hexyl chloroformate belongs to the class of chloroformates. It is widely used in the derivatization of highly hydrophilic compounds to hexyl esters, carbonates and carbamates.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H13ClO2/c1-2-3-4-5-6-10-7(8)9/h2-6H2,1H3

Synthetic route

bis(trichloromethyl) carbonate (32315-10-9) + hexan-1-ol (111-27-3) → n-hexyl chloroformate (6092-54-2)

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate With potassium carbonate; N,N-dimethyl-formamide In toluene at 0℃; for 0.5h; Inert atmosphere; Stage #2: hexan-1-ol In toluene at 0 - 20℃; for 12h; Inert atmosphere;	83%
With pyridine In dichloromethane for 0.166667h;
With triethylamine In dichloromethane cooling;
With pyridine In dichloromethane at 0 - 20℃; for 2h;
With triethylamine In dichloromethane at 0 - 10℃; for 2h;

phosgene (75-44-5) + hexan-1-ol (111-27-3) → n-hexyl chloroformate (6092-54-2)

hexan-1-ol (111-27-3) + trichloromethyl chloroformate (503-38-8) → n-hexyl chloroformate (6092-54-2)

Conditions	Yield
With pyrographite In tetrahydrofuran at 20℃; for 1h; Condensation;
With dmap In toluene at 20℃; for 24h;

chloroform (67-66-3) + hexan-1-ol (111-27-3) → n-hexyl chloroformate (6092-54-2)

Conditions	Yield
With oxygen at 30℃; for 3h; Irradiation;

n-hexyl chloroformate (6092-54-2) + (R)-Phenylglycinol (56613-80-0) → hexyl (1R)-2-hydroxy-1-phenylethylcarbamate (532986-19-9)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane at 0℃; for 2h;	99%

n-hexyl chloroformate (6092-54-2) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → C28H42O10

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine In dichloromethane at 0℃; for 1h;	99%

1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt (872728-85-3) + n-hexyl chloroformate (6092-54-2) → dabigatran etexilate (211915-06-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 0℃; Reagent/catalyst; Solvent; Temperature;	98.4%
With potassium carbonate In water; acetone at 12 - 25℃; for 1.5h; Solvent; Temperature; Time;	17.5 g

n-hexyl chloroformate (6092-54-2) + benzylamine (100-46-9) → hexyl benzylcarbamate (1239969-89-1)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	98%

n-hexyl chloroformate (6092-54-2) + 4-aminobenzamidine dihydrochloride (2498-50-2) → 4-aminobenzamidine-N-hexylcarbamate hydrochloride (1307233-93-7)

Conditions	Yield
Stage #1: n-hexyl chloroformate; 4-aminobenzamidine dihydrochloride With sodium hydroxide In acetone at 5 - 20℃; for 0.25h; Stage #2: With hydrogenchloride In water	97.2%

n-hexyl chloroformate (6092-54-2) + 4-nitrobenzamidine (25412-75-3) → p-nitrobenzamidine iminocarboxylate

Conditions	Yield
With potassium carbonate In ethyl acetate at 0℃; for 1.5h; Temperature; Time; Reagent/catalyst;	96.7%

n-hexyl chloroformate (6092-54-2) + (1R,2S)-1-amino-1-(3-methoxyphenyl)propan-2-ol hydrochloride → hexyl (1R,2S)-2-hydroxy-1-(3-methoxyphenyl)propylcarbamate (289051-64-5)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 1h;	96%

n-hexyl chloroformate (6092-54-2) + phenethylamine (64-04-0) → hexyl phenethylcarbamate

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	96%

n-hexyl chloroformate (6092-54-2) + 5-[(tert-butyldimethylsilyl)oxy]pyridin-2-amine → hexyl N-[5-[(tert-butyldimethylsilyl)oxy]pyridin-2-yl]carbamate

Conditions	Yield
With pyridine for 2h;	95%

1-methyl-2-[N-[4-(1,2,4-oxadiazol-5-one-3-yl)phenyl]-amino-methyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide (872728-84-2) + n-hexyl chloroformate (6092-54-2) → ethyl 3-(1-{2-[({4-[amino({[(hexyloxy)carbonyl]imino})methyl]phenyl}amino)methyl]-1-methyl-1H-1,3-benzodiazol-5-yl}-N-(pyridin-2-yl)formamido)propanoate (211915-06-9)

Conditions

Yield

Stage #1: 1-methyl-2-[N-[4-(1,2,4-oxadiazol-5-one-3-yl)phenyl]-amino-methyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide With hydrogen; palladium 10% on activated carbon In tetrahydrofuran; water at 40℃; under 3000.3 Torr; for 0.416667h; Stage #2: n-hexyl chloroformate With potassium carbonate In tetrahydrofuran; water at 20 - 45℃; Product distribution / selectivity;

94%

n-hexyl chloroformate (6092-54-2) + 6-Chloro-2-methyl-4-(4-methylsulfanyl-phenyl)-1,4-dihydro-pyrimidine-5-carboxylic acid ethyl ester (97934-95-7) → 4-Chloro-2-methyl-6-(4-methylsulfanyl-phenyl)-3,6-dihydro-1λ5-pyrimidine-1,5-dicarboxylic acid 5-ethyl ester 1-hexyl ester

Conditions	Yield
With sodium hydride In tetrahydrofuran at 80℃; for 2h;	93%

n-hexyl chloroformate (6092-54-2) + benzyl (2S,3R)-3-[(2-aminopyridin-4-yl)methyl]-4-oxo-1-{[(1R)-1-phenylethyl]carbamoyl}azetidine-2-carboxylate → benzyl (2S,3R)-3-[(2-{[(hexyloxy)carbonyl]amino}pyridin-4-yl)methyl]-4-oxo-1-{[(1R)-1-phenylethyl]carbamoyl}azetidine-2-carboxylate

Conditions	Yield
With pyridine In dichloromethane at 0 - 25℃; for 3.5h; Inert atmosphere;	92%

n-hexyl chloroformate (6092-54-2) + 4-bromobenzamidine (22265-36-7) → C14H19BrN2O2

Conditions	Yield
Stage #1: 4-bromobenzamidine With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.25h; Stage #2: n-hexyl chloroformate In tetrahydrofuran; water for 12h;	90.4%

n-hexyl chloroformate (6092-54-2) + 1-benzyl-N-[(4-carbamimidoylphenyl)methyl]pyrazole-4-carboxamide hydrochloride → (Z)-hexyl amino-(4-((1-benzylpyrazole-4-carbonylamino)methyl)phenyl)methylenecarbamate (1312689-18-1)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 20℃; for 1h;	90%

n-hexyl chloroformate (6092-54-2) + N-[(4-carbamimidoylphenyl)methyl]-1-(4-fluorophenyl)-2,5-dimethyl-pyrrole-3-carboxamide hydrochloride → (Z)-hexyl amino-(4-((1-(4-fluorophenyl)-2,5-dimethyl-pyrrole-3-carbonylamino)methyl)phenyl)methylenecarbamate (1312689-19-2)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 20℃; for 1h;	90%

n-hexyl chloroformate (6092-54-2) + p-chlorobenzamidine (19563-04-3) → C14H19ClN2O2

Conditions	Yield
Stage #1: p-chlorobenzamidine With triethylamine In tetrahydrofuran; water at 20℃; for 0.25h; Stage #2: n-hexyl chloroformate In tetrahydrofuran; water for 12h;	89.6%

methanesulfonic acid (75-75-2) + 1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt (872728-85-3) + n-hexyl chloroformate (6092-54-2) → [14C]-Dabigatran etexilate mesylate

Conditions	Yield
Stage #1: 1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt; n-hexyl chloroformate With potassium carbonate In water; acetone at 20 - 50℃; Stage #2: methanesulfonic acid In acetone at 30 - 36℃; for 0.333333h; Product distribution / selectivity;	89%
Stage #1: 1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt; n-hexyl chloroformate With potassium carbonate In methanol at 20℃; for 3h; Stage #2: methanesulfonic acid In water; acetone at 42℃;

n-hexyl chloroformate (6092-54-2) + 1-methyl-2-[N-(4-amidinophenyl)-aminomethyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide hydrochloride → dabigatran etexilate (211915-06-9)

Conditions	Yield
With triethylamine In acetone at 0 - 20℃; for 1.5h; Product distribution / selectivity; Inert atmosphere;	89%
Stage #1: 1-methyl-2-[N-(4-amidinophenyl)-aminomethyl]benzimidazol-5-yl-carboxylicacid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide hydrochloride With hydrogenchloride In 2-methyltetrahydrofuran; water at 25℃; pH=3.5; Stage #2: With potassium carbonate In 2-methyltetrahydrofuran; water at 25℃; for 0.5h; Stage #3: n-hexyl chloroformate In 2-methyltetrahydrofuran; water at 25℃; for 2h;	83%

n-hexyl chloroformate (6092-54-2) + 3-Phenylpropan-1-amine (2038-57-5) → hexyl (3-phenylpropyl)carbamate

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	89%

n-hexyl chloroformate (6092-54-2) + 4-phenyl-1-butylamine (13214-66-9) → hexyl (4-phenylbutyl)carbamate

Conditions	Yield
With triethylamine In dichloromethane at 0℃; Inert atmosphere;	89%

n-hexyl chloroformate (6092-54-2) + 4-(methoxycarbonyloxy)benzhydrol → n-hexyl 4-(methoxycarbonyloxy)benzhydryl carbonate

Conditions	Yield
With pyridine at 0℃; for 1h;	89%

1-methyl-2-[N-(4-amidino-phenyl)-aminomethyl]-benzimidazol-5-yl-carboxylic acid N-(2-pyridyl)-N-2-(ethoxycarbonylethyl)-amide p-toluenesulfonic acid salt (872728-85-3) + n-hexyl chloroformate (6092-54-2) → dabigatran etexilate (211915-06-9)

Conditions	Yield
With triethylamine In dichloromethane at 10 - 20℃; Large scale;	88.94%
With potassium carbonate In water; acetone at 15℃; Product distribution / selectivity;

5-aminomethyl-2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-isoindole-1,3-dione hydrochloride (1010100-25-0) + n-hexyl chloroformate (6092-54-2) → {2-[(3S)-3-methyl-2,6-dioxo-piperidin-3-yl]-1,3-dioxo-2,3-dihydro-1H-isoindol-5-ylmethyl}-carbamic acid hexyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 1h;	88%

n-hexyl chloroformate (6092-54-2) + 3-({2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid ethyl ester → dabigatran etexilate (211915-06-9)

Conditions	Yield
With potassium carbonate In water; acetone at 10 - 25℃;	88%
Stage #1: 3-({2-[(4-carbamimidoylphenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-yl-amino)propionic acid ethyl ester With potassium carbonate In tetrahydrofuran; water at 20℃; for 0.5h; Stage #2: n-hexyl chloroformate In tetrahydrofuran; water at 10℃; for 2h;	78%

n-hexyl chloroformate (6092-54-2) + ethyl 2-{[(4-{carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-carboxylate (1408238-41-4) → ethyl 2-[[4-[(n-hexyloxycarbonyl)aminoiminomethyl]phenylamino]methyl]-1-methyl-1H-benzimidazole-5-carboxylate (1408238-36-7)

Conditions	Yield
With sodium hydroxide In water; acetone at 10 - 25℃;	87%

n-hexyl chloroformate (6092-54-2) + 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazole-5-ylcarboxylic acid N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide hydrochloride salt → dabigatran etexilate (211915-06-9)

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; for 1h; Reagent/catalyst;	86.4%
Stage #1: 3-({2-[(4-carbamimidoyl-phenylamino)methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}pyridin-2-ylamino)propionic acid ethyl ester hydrochloride With potassium carbonate In tetrahydrofuran; water at 0 - 5℃; for 0.5h; Stage #2: n-hexyl chloroformate In tetrahydrofuran; water at 0 - 5℃;	72.7%
With triethylamine In water; acetonitrile at 15℃;

n-hexyl chloroformate (6092-54-2) + p-aminobenzamidine (3858-83-1) → hexyl ((4-aminophenyl)(imino)methyl)carbamate

Conditions	Yield
With sodium hydroxide In acetone at 0 - 10℃;	85.9%

n-hexyl chloroformate (6092-54-2) + methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate (52263-88-4) → hexyl 6-chloro-2-(1-methoxy-1-oxoprop-2-yl)-9H-carbazole-9-carboxylate

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 100℃; for 3h; Microwave irradiation;	85%

n-hexyl chloroformate (6092-54-2) + ethyl N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-yl)carbonyl]-N-(pyridine-2-yl)-β-alaninate bis(p-toluenesulfonic acid salt) → dabigatran etexilate (211915-06-9)

Conditions	Yield
With potassium carbonate In ethanol; water; acetone at 28 - 32℃; for 0.333333h;	85%
With potassium carbonate In ethanol; water; acetone at 28 - 32℃; for 0.333333h;	85%

n-hexyl chloroformate (6092-54-2) + 4-nitrobenzamide (619-80-7) → 4-[[[(hexyloxy)carbonyl]amino]carbonyl]nitrobenzene

Conditions	Yield
With sodium hydride In tetrahydrofuran for 2h;	85%

Upstream product

• 111-27-3 hexan-1-ol 
• 503-38-8 trichloromethyl chloroformate 
• 67-66-3 chloroform 
• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 20633-11-8 n-hexyl nitrate 
• 15719-64-9 methylammonium carbonate 
• 321358-92-3 hexyl N-[2-[3-chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]carbamate 
• 881381-67-5 C₃₅H₅₂ClN₇O₄SSi 
• 675850-43-8 (3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid hexyl ester 
• 1381757-44-3 2-(N-(3-ethoxy-3-oxopropyl)-2-((4-(N'-(hexyloxycarbonyl)carbamimidoyl)phenylamino)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxamido)pyridine-1-oxide 
• 872728-81-9 N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl]phenyl] amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-β-alanine ethyl ester methanesulfonate 
• 211915-06-9 dabigatran etexilate 
• 1239969-89-1 hexyl benzylcarbamate 
• 872728-81-9 dabigatran etexilate mesylate 
• 1408238-36-7 ethyl 2-[[4-[(n-hexyloxycarbonyl)aminoiminomethyl]phenylamino]methyl]-1-methyl-1H-benzimidazole-5-carboxylate 
• 112406-26-5 hexyl phenyl carbonate 
• 67987-31-9 carbonic acid benzyl ester hexyl ester 
• 110247-97-7 [2-(2-piperidino-ethoxy)-phenyl]-carbamic acid hexyl ester 

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