26272-90-2

Basic information

• Product Name: Cetyl chloroformate
• Synonyms: carbonochloridicacid,hexadecylester;CETYL CHLOROFORMATE;CHLOROFORMIC ACID CETYL ESTER;CHLOROFORMIC ACID HEXADECYL ESTER;CHLOROFORMIC ACID N-HEXADECYL ESTER;HEXADECYL CHLOROCARBONATE;HEXADECYL CHLOROFORMATE;Chloroformic acid n-hexadeyl ester
• CAS NO: 26272-90-2
• Molecular Formula: C₁₇H₃₃ClO₂
• Molecular Weight: 304.9
• EINECS: 247-578-2
• Mol File: 26272-90-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 14 °C
• Boiling Point: 367.1 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 0.923 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.4E-05mmHg at 25°C
• Refractive Index: n20/D 1.4480(lit.)
• CAS DataBase Reference: Cetyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: Cetyl chloroformate(26272-90-2)
• EPA Substance Registry System: Cetyl chloroformate(26272-90-2)

Safety Data

• Hazard Codes: C
• Statements: 34-43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 6.1/8
• PackingGroup: II
• Hazardous Substances Data: 26272-90-2(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C17H33ClO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-17(18)19/h2-16H2,1H3

Synthetic route

1-Hexadecanol (36653-82-4) + bis(trichloromethyl) carbonate (32315-10-9) → cetyl chloroformate (26272-90-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 48h; Cooling with ice;	74%
Stage #1: bis(trichloromethyl) carbonate With potassium carbonate; N,N-dimethyl-formamide In toluene at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-Hexadecanol In toluene at 0 - 20℃; for 12h; Inert atmosphere;	74%
With pyridine In chloroform for 2h; ice cooling;
Stage #1: 1-Hexadecanol; bis(trichloromethyl) carbonate In dichloromethane at 10℃; for 1h; Large scale; Stage #2: With triethylamine In dichloromethane for 2h; Cooling with ice; Large scale; Stage #3: In dichloromethane at 20℃; for 2h; Large scale;	305 kg
With pyridine In tetrachloromethane at -20 - 20℃;

phosgene (75-44-5) + 1-Hexadecanol (36653-82-4) → cetyl chloroformate (26272-90-2)

Conditions	Yield
With diethyl ether
In tetrahydrofuran; toluene Ambient temperature; Yield given;
cooling;

N-(2-hydroxypropyl-3-hexadecyloxy)ethanolamine + cetyl chloroformate (26272-90-2) → N-(hexadecyloxycarbonyl)-N-(2-hydroxy-3-hexadecyloxypropyl) ethanolamine

Conditions	Yield
With triethylamine In tetrahydrofuran; water	98%

cetyl chloroformate (26272-90-2) → O-hexadecyl carbamate (54850-40-7)

Conditions	Yield
With ammonia In water at 0 - 20℃; Inert atmosphere;	95%

cetyl chloroformate (26272-90-2) + L-ornithine hydrochloride (3184-13-2) → Nα,Nδ-bis(hexadecyloxycarbonyl)-L-ornithine (258875-29-5)

Conditions	Yield
With sodium hydroxide In water; acetone for 48h; Acylation;	93.4%

2-Amino-5-methylbenzoic acid (2941-78-8) + cetyl chloroformate (26272-90-2) → 2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid (890655-08-0)

Conditions	Yield
With pyridine In dichloromethane at 20℃; Solvent; Reagent/catalyst; Cooling with ice;	92.3%
Stage #1: 2-Amino-5-methylbenzoic acid; cetyl chloroformate With pyridine at 20℃; for 2h; Cooling with ice; Stage #2: With trichlorophosphate at 20℃; for 2h; Reagent/catalyst;	91.8%
With pyridine In dichloromethane
Stage #1: 2-Amino-5-methylbenzoic acid With pyridine In tetrahydrofuran at 5℃; Stage #2: cetyl chloroformate In tetrahydrofuran at 10 - 30℃; for 1h; Solvent;

cetyl chloroformate (26272-90-2) → 1-Chlorohexadecan (4860-03-1)

Conditions	Yield
With hexabutylguanidinium chloride at 120℃; for 4h;	92%

cetyl chloroformate (26272-90-2) + 9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine (139301-93-2) → hexadecyl (9-((3aR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl)carbamate (1373396-58-7)

Conditions	Yield
With 1-methyl-1H-imidazole In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	92%

2-Amino-5-methylbenzoic acid (2941-78-8) + cetyl chloroformate (26272-90-2) → C26H40O3

Conditions	Yield
Stage #1: 2-Amino-5-methylbenzoic acid; cetyl chloroformate With 4-methyl-morpholine In ethanol at 5 - 10℃; for 0.5h; Stage #2: In ethanol at 0 - 30℃; for 30h; Stage #3: With sulfuryl dichloride In ethanol at 10 - 25℃; for 1.83333h; Solvent;	92%

cetyl chloroformate (26272-90-2) + 2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate → 2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice;	91%

cetyl chloroformate (26272-90-2) + (R)-benzyl 3-((2-aminoethyl)thio)-2-((tert-butoxycarbonyl)amino)propanoate → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-((2-(((hexadecyloxy)carbonyl)amino)ethyl)thio)propanoate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	90.3%

cetyl chloroformate (26272-90-2) + 2-iodo-5-methylbenzylamine (1261826-59-8) → hexadecyl-2-iodo-5-methylbenzyl-carbamate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	89%

cetyl chloroformate (26272-90-2) + (2-bromo-5-methylphenyl)methanamine (1261776-69-5) → hexadecyl-2-bromo-5-methylbenzyl-carbamate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	88%

cetyl chloroformate (26272-90-2) + (2S)-2-amino-N-dodecyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride → hexadecyl N-[(1S)-1-(dodecylcarbamoyl)-4-[(N-nitrocarbamimidoyl)amino]butyl]carbamate

Conditions	Yield
With triethylamine In tetrahydrofuran at 30℃;	84%

cetyl chloroformate (26272-90-2) + ethyl 3,5-dichloro-4-hydroxybenzoate (17302-82-8) → ethyl 4-hexadecyloxycarbonyloxy-3,5-dichlorobenzoate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h; Temperature; Autoclave; Large scale;	83.5%

cetyl chloroformate (26272-90-2) + 1-iodo-3-phenylpropan (4119-41-9) → Kohlensaeure-di-n-hexadecylester (13784-52-6) + 1.7-Diphenylheptan-4-one (63434-46-8)

Conditions	Yield
With [2,2]bipyridinyl; chloro-trimethyl-silane; nickel(II) bromide 2-methoxyethyl ether complex; zinc In tetrahydrofuran; N,N-dimethyl acetamide at 40℃; for 1h; Sealed tube; Inert atmosphere;	A 73% B 83%

cetyl chloroformate (26272-90-2) + methyl L-isoleucinate hydrochloride (18598-74-8) → N-n-hexadecyloxycarbonyl-L-isoleucine methyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 4h; Cooling with ice;	78%

cetyl chloroformate (26272-90-2) + tert-butyl N-[[[(4S)-4-amino-5-(octylamino)-5-oxo-pentyl]amino]-(tert-butoxycarbonylamino)methylene]carbamate → hexadecyl N-[(1S)-4-[[N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]amino]-1-(octylcarbamoyl)butyl]carbamate

Conditions	Yield
With triethylamine In tetrahydrofuran at 30℃;	76%

cetyl chloroformate (26272-90-2) + N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1) → hexadecyl 3-methyl-2-(quinolin-8-ylcarbamoyl)benzoate

Conditions	Yield
With palladium diacetate; silver carbonate In toluene at 100℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere;	75%

cetyl chloroformate (26272-90-2) + 4-((hydroxyamino)methyl)-2-methoxyphenol (201931-69-3) → hexadecyl-N-hydroxy(4-hydroxy-3-methoxybenzyl)carbamate (1400943-39-6)

Conditions	Yield
With magnesium oxide In methanol; water at 20℃;	74%

cetyl chloroformate (26272-90-2) + (S)-methyl 2-((R)-3-((2-aminoethyl)thio)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(tert-butoxy)propanoate (1446483-30-2) → (2S,5R)-methyl 5-((tert-butoxycarbonyl)amino)-2-(tert-butoxymethyl)-4,11-dioxo-12-oxa-7-thia-3,10-diazaoctacosan-1-oate (1446483-47-1)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	74%
With triethylamine In dichloromethane at 20℃; for 0.5h;	74%

cetyl chloroformate (26272-90-2) + agmatine sulphate (2482-00-0) → hexadecyl N-(4-guanidinobutyl)carbamate hydrochloride

Conditions	Yield
Stage #1: agmatine sulphate With sodium hydroxide In water; isopropyl alcohol at 10 - 20℃; pH=12 - 13; Stage #2: cetyl chloroformate With hydrogenchloride In ethyl acetate at 20℃; for 0.5h;	72%

cetyl chloroformate (26272-90-2) + L-phenylalanine (63-91-2) → 2-Hexadecyloxycarbonylamino-3-phenyl-propionic acid (133230-94-1)

Conditions	Yield
	70%

cetyl chloroformate (26272-90-2) + (4-hydroxyphenyl)methanol (623-05-2) → hexadecyl (4-(hydroxymethyl)phenyl) carbonate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	68%

cetyl chloroformate (26272-90-2) + naltrexone Hydrochloride (16676-29-2) → (4aS,7aR,12bs)-3-(cyclopropylmethyl)-4a-hydroxy-7-oxo-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl hexadecyl carbonate

Conditions	Yield
With triethylamine In dichloromethane at -10 - 25℃; for 5h; Inert atmosphere;	65.06%

cetyl chloroformate (26272-90-2) + C26H32N4O3 → C38H56N4O3

Conditions	Yield
Stage #1: C26H32N4O3 With trifluoroacetic acid In dichloromethane at 0℃; for 6h; Stage #2: cetyl chloroformate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;	62.8%

cetyl chloroformate (26272-90-2) + N1,N3-bis(hydroxymethyl)-5-fluorouracil (74179-14-9) → (5-fluoro-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)methyl hexadecyl carbonate + Carbonic acid 5-fluoro-3-hexadecyloxycarbonyloxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester hexadecyl ester

Conditions	Yield
With triethylamine In acetonitrile Ambient temperature;	A 62% B 16%

cetyl chloroformate (26272-90-2) + L-Lysine hydrochloride (657-27-2, 10098-89-2) → Nα,Nε-bis(hexadecyloxycarbonyl)-L-lysine (258875-26-2)

Conditions	Yield
With sodium hydroxide In water; acetone for 48h; Acylation;	62%

3-aminopropyltriethoxysilane (919-30-2) + cetyl chloroformate (26272-90-2) → 3-(triethoxysilyl)propyl-cetylcarbamate

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 5h;	58%

L-arginine (74-79-3) + cetyl chloroformate (26272-90-2) → Nα-hexadecyloxycarbonyl-L-arginine

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water; acetone	58%

Upstream product

• 75-44-5 phosgene 
• 36653-82-4 1-Hexadecanol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 133230-94-1 2-Hexadecyloxycarbonylamino-3-phenyl-propionic acid 
• 258875-41-1 N^α,N^γ-bis(hexadecyloxycarbonyl)-L-2,4-diaminobutyric acid benzyl ester 
• 26322-14-5 di-cetyl peroxydicarbonate 
• 4860-03-1 1-Chlorohexadecan 
• 258875-35-3 N^α,N^δ-bis(hexadecyloxycarbonyl)-N-[2-(benzyloxycarbonyl)ethyl]-L-ornithinamide 
• 258875-34-2 N^α,N^ε-bis(hexadecyloxycarbonyl)-N-[2-(benzyloxycarbonyl)ethyl]-L-lysinamide 
• 133231-00-2 S₁₆-L-Phe-L-His-OMe 
• 133231-06-8 S₁₆-L-Phe-L-His-OH 
• 54850-40-7 n-hexadecyl carbamate 
• 1400943-39-6 hexadecyl-N-hydroxy(4-hydroxy-3-methoxybenzyl)carbamate 
• 890655-08-0 2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid 
• 282526-98-1 2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one 
• 115895-09-5 ethyl 4-hexadecyloxycarbonyloxy-3,5-dichlorobenzoate 

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