Product Name

  • Name

    Cetyl chloroformate

  • EINECS 247-578-2
  • CAS No. 26272-90-2
  • Article Data12
  • CAS DataBase
  • Density 0.923
  • Solubility
  • Melting Point 14 °C
  • Formula C17H33 Cl O2
  • Boiling Point 367.1 °C at 760 mmHg
  • Molecular Weight 304.901
  • Flash Point >110 ºC
  • Transport Information UN 3265
  • Appearance
  • Safety S26;S36/37/39;S45
  • Risk Codes R34;R43   
  • Molecular Structure Molecular Structure of 26272-90-2 (Cetyl chloroformate)
  • Hazard Symbols
  • Synonyms Formicacid, chloro-, hexadecyl ester (6CI); Cetyl chloroformate; Chloroformic acidcetyl ester; Hexadecyl chloroformate; NSC 137911; Palmityloxycarbonyl chloride;n-Hexadecyl chloroformate
  • PSA 26.30000
  • LogP 6.84310

Synthetic route

1-Hexadecanol
36653-82-4

1-Hexadecanol

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

cetyl chloroformate
26272-90-2

cetyl chloroformate

Conditions
ConditionsYield
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

phosgene

1-Hexadecanol
36653-82-4

1-Hexadecanol

cetyl chloroformate
26272-90-2

cetyl chloroformate

Conditions
ConditionsYield
With diethyl ether
In tetrahydrofuran; toluene Ambient temperature; Yield given;
cooling;
N-(2-hydroxypropyl-3-hexadecyloxy)ethanolamine

N-(2-hydroxypropyl-3-hexadecyloxy)ethanolamine

cetyl chloroformate
26272-90-2

cetyl chloroformate

N-(hexadecyloxycarbonyl)-N-(2-hydroxy-3-hexadecyloxypropyl) ethanolamine

N-(hexadecyloxycarbonyl)-N-(2-hydroxy-3-hexadecyloxypropyl) ethanolamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water98%
cetyl chloroformate
26272-90-2

cetyl chloroformate

O-hexadecyl carbamate
54850-40-7

O-hexadecyl carbamate

Conditions
ConditionsYield
With ammonia In water at 0 - 20℃; Inert atmosphere;95%
cetyl chloroformate
26272-90-2

cetyl chloroformate

L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

Nα,Nδ-bis(hexadecyloxycarbonyl)-L-ornithine
258875-29-5

Nα,Nδ-bis(hexadecyloxycarbonyl)-L-ornithine

Conditions
ConditionsYield
With sodium hydroxide In water; acetone for 48h; Acylation;93.4%
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

cetyl chloroformate
26272-90-2

cetyl chloroformate

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid
890655-08-0

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid

Conditions
ConditionsYield
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

cetyl chloroformate

1-Chlorohexadecan
4860-03-1

1-Chlorohexadecan

Conditions
ConditionsYield
With hexabutylguanidinium chloride at 120℃; for 4h;92%
cetyl chloroformate
26272-90-2

cetyl chloroformate

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

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

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

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

Conditions
ConditionsYield
With 1-methyl-1H-imidazole In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;92%
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

cetyl chloroformate
26272-90-2

cetyl chloroformate

C26H40O3

C26H40O3

Conditions
ConditionsYield
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

cetyl chloroformate

2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate

2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice;91%
cetyl chloroformate
26272-90-2

cetyl chloroformate

(R)-benzyl 3-((2-aminoethyl)thio)-2-((tert-butoxycarbonyl)amino)propanoate

(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

(R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-((2-(((hexadecyloxy)carbonyl)amino)ethyl)thio)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;90.3%
cetyl chloroformate
26272-90-2

cetyl chloroformate

2-iodo-5-methylbenzylamine
1261826-59-8

2-iodo-5-methylbenzylamine

hexadecyl-2-iodo-5-methylbenzyl-carbamate

hexadecyl-2-iodo-5-methylbenzyl-carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;89%
cetyl chloroformate
26272-90-2

cetyl chloroformate

(2-bromo-5-methylphenyl)methanamine
1261776-69-5

(2-bromo-5-methylphenyl)methanamine

hexadecyl-2-bromo-5-methylbenzyl-carbamate

hexadecyl-2-bromo-5-methylbenzyl-carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;88%
cetyl chloroformate
26272-90-2

cetyl chloroformate

(2S)-2-amino-N-dodecyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride

(2S)-2-amino-N-dodecyl-5-[(N-nitrocarbamimidoyl)amino]pentanamide hydrochloride

hexadecyl N-[(1S)-1-(dodecylcarbamoyl)-4-[(N-nitrocarbamimidoyl)amino]butyl]carbamate

hexadecyl N-[(1S)-1-(dodecylcarbamoyl)-4-[(N-nitrocarbamimidoyl)amino]butyl]carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 30℃;84%
cetyl chloroformate
26272-90-2

cetyl chloroformate

ethyl 3,5-dichloro-4-hydroxybenzoate
17302-82-8

ethyl 3,5-dichloro-4-hydroxybenzoate

ethyl 4-hexadecyloxycarbonyloxy-3,5-dichlorobenzoate

ethyl 4-hexadecyloxycarbonyloxy-3,5-dichlorobenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 4h; Temperature; Autoclave; Large scale;83.5%
cetyl chloroformate
26272-90-2

cetyl chloroformate

1-iodo-3-phenylpropan
4119-41-9

1-iodo-3-phenylpropan

A

Kohlensaeure-di-n-hexadecylester
13784-52-6

Kohlensaeure-di-n-hexadecylester

B

1.7-Diphenylheptan-4-one
63434-46-8

1.7-Diphenylheptan-4-one

Conditions
ConditionsYield
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%
...Expand
cetyl chloroformate
26272-90-2

cetyl chloroformate

methyl L-isoleucinate hydrochloride
18598-74-8

methyl L-isoleucinate hydrochloride

N-n-hexadecyloxycarbonyl-L-isoleucine methyl ester

N-n-hexadecyloxycarbonyl-L-isoleucine methyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 4h; Cooling with ice;78%
cetyl chloroformate
26272-90-2

cetyl chloroformate

tert-butyl N-[[[(4S)-4-amino-5-(octylamino)-5-oxo-pentyl]amino]-(tert-butoxycarbonylamino)methylene]carbamate

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

hexadecyl N-[(1S)-4-[[N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]amino]-1-(octylcarbamoyl)butyl]carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 30℃;76%
cetyl chloroformate
26272-90-2

cetyl chloroformate

N-(2-methylbenzoyl)-8-aminoquinoline
1182669-71-1

N-(2-methylbenzoyl)-8-aminoquinoline

hexadecyl 3-methyl-2-(quinolin-8-ylcarbamoyl)benzoate

hexadecyl 3-methyl-2-(quinolin-8-ylcarbamoyl)benzoate

Conditions
ConditionsYield
With palladium diacetate; silver carbonate In toluene at 100℃; for 8h; Schlenk technique; Sealed tube; Inert atmosphere;75%
cetyl chloroformate
26272-90-2

cetyl chloroformate

4-((hydroxyamino)methyl)-2-methoxyphenol
201931-69-3

4-((hydroxyamino)methyl)-2-methoxyphenol

hexadecyl-N-hydroxy(4-hydroxy-3-methoxybenzyl)carbamate
1400943-39-6

hexadecyl-N-hydroxy(4-hydroxy-3-methoxybenzyl)carbamate

Conditions
ConditionsYield
With magnesium oxide In methanol; water at 20℃;74%
cetyl chloroformate
26272-90-2

cetyl chloroformate

(S)-methyl 2-((R)-3-((2-aminoethyl)thio)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(tert-butoxy)propanoate
1446483-30-2

(S)-methyl 2-((R)-3-((2-aminoethyl)thio)-2-((tert-butoxycarbonyl)amino)propanamido)-3-(tert-butoxy)propanoate

(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

(2S,5R)-methyl 5-((tert-butoxycarbonyl)amino)-2-(tert-butoxymethyl)-4,11-dioxo-12-oxa-7-thia-3,10-diazaoctacosan-1-oate

Conditions
ConditionsYield
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

cetyl chloroformate

agmatine sulphate
2482-00-0

agmatine sulphate

hexadecyl N-(4-guanidinobutyl)carbamate hydrochloride

hexadecyl N-(4-guanidinobutyl)carbamate hydrochloride

Conditions
ConditionsYield
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

cetyl chloroformate

L-phenylalanine
63-91-2

L-phenylalanine

2-Hexadecyloxycarbonylamino-3-phenyl-propionic acid
133230-94-1

2-Hexadecyloxycarbonylamino-3-phenyl-propionic acid

Conditions
ConditionsYield
70%
cetyl chloroformate
26272-90-2

cetyl chloroformate

(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

hexadecyl (4-(hydroxymethyl)phenyl) carbonate

hexadecyl (4-(hydroxymethyl)phenyl) carbonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;68%
cetyl chloroformate
26272-90-2

cetyl chloroformate

naltrexone Hydrochloride
16676-29-2

naltrexone Hydrochloride

(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

(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
ConditionsYield
With triethylamine In dichloromethane at -10 - 25℃; for 5h; Inert atmosphere;65.06%
cetyl chloroformate
26272-90-2

cetyl chloroformate

C26H32N4O3

C26H32N4O3

C38H56N4O3

C38H56N4O3

Conditions
ConditionsYield
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

cetyl chloroformate

N1,N3-bis(hydroxymethyl)-5-fluorouracil
74179-14-9

N1,N3-bis(hydroxymethyl)-5-fluorouracil

A

(5-fluoro-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)methyl hexadecyl carbonate

(5-fluoro-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-yl)methyl hexadecyl carbonate

B

Carbonic acid 5-fluoro-3-hexadecyloxycarbonyloxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester hexadecyl ester

Carbonic acid 5-fluoro-3-hexadecyloxycarbonyloxymethyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ylmethyl ester hexadecyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature;A 62%
B 16%
...Expand
cetyl chloroformate
26272-90-2

cetyl chloroformate

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

Nα,Nε-bis(hexadecyloxycarbonyl)-L-lysine
258875-26-2

Nα,Nε-bis(hexadecyloxycarbonyl)-L-lysine

Conditions
ConditionsYield
With sodium hydroxide In water; acetone for 48h; Acylation;62%
3-aminopropyltriethoxysilane
919-30-2

3-aminopropyltriethoxysilane

cetyl chloroformate
26272-90-2

cetyl chloroformate

3-(triethoxysilyl)propyl-cetylcarbamate

3-(triethoxysilyl)propyl-cetylcarbamate

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 5h;58%
L-arginine
74-79-3

L-arginine

cetyl chloroformate
26272-90-2

cetyl chloroformate

Nα-hexadecyloxycarbonyl-L-arginine

Nα-hexadecyloxycarbonyl-L-arginine

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water; acetone58%

Cetyl chloroformate Chemical Properties

IUPAC Name: Hexadecyl carbonochloridate
CAS: 26272-90-2
Formula: C17H33ClO2
Molecular Weight: 304.9
Molecular Structure of Hexadecyl carbonochloridate (CAS NO.26272-90-2):

Density: 0.94 g/cm3 
Flash Point: 125 °C
Boiling Point: 367.1 °C at 760 mmHg 
Index of Refraction: 1.452 
Molar Refractivity: 87.43 cm3 
Molar Volume: 324 cm3 
Polarizability: 34.66×10-24cm3 
Surface Tension: 32.1 dyne/cm 
Enthalpy of Vaporization: 61.36 kJ/mol 
Vapour Pressure: 1.4E-05 mmHg at 25°C 
Water Solubility: 0.004501 (mg/L) at 25°C

Cetyl chloroformate Safety Profile

Safety Information about  Hexadecyl carbonochloridate (CAS NO.26272-90-2):
Hazard Codes:
C: 
Risk Statements  about  Hexadecyl carbonochloridate (CAS NO.26272-90-2):
R34: Causes burns.
R43: May cause sensitization by skin contact.
Safety Statements  about  Hexadecyl carbonochloridate (CAS NO.26272-90-2): 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
RIDADR: UN 3265 8/PG 2
WGK Germany: 3

Cetyl chloroformate Specification

  The chemical synonyms of  Hexadecyl carbonochloridate (CAS NO.26272-90-2) are 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 .
 

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