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Cetyl chloroformate
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Name

Cetyl chloroformate

 EINECS 247-578-2
CAS No. 26272-90-2 Density 0.923
PSA 26.30000 LogP 6.84310
Solubility N/A 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 N/A
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

Article Data 12

Cetyl chloroformate Synthetic route

36653-82-4

1-Hexadecanol

32315-10-9

bis(trichloromethyl) carbonate

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℃;
75-44-5

phosgene

36653-82-4

1-Hexadecanol

26272-90-2

cetyl chloroformate

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

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

26272-90-2

cetyl chloroformate

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

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

cetyl chloroformate

54850-40-7

O-hexadecyl carbamate

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

cetyl chloroformate

3184-13-2

L-ornithine hydrochloride

258875-29-5

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

Conditions
ConditionsYield
With sodium hydroxide In water; acetone for 48h; Acylation;93.4%
2941-78-8

2-Amino-5-methylbenzoic acid

26272-90-2

cetyl chloroformate

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;
26272-90-2

cetyl chloroformate

4860-03-1

1-Chlorohexadecan

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

cetyl chloroformate

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

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%
2941-78-8

2-Amino-5-methylbenzoic acid

26272-90-2

cetyl chloroformate

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%
26272-90-2

cetyl chloroformate

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

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 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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