7144-08-3

Basic information

• Product Name: Cholesteryl chloroformate
• Synonyms: carbonochloridate;Cholest-5-en-3-ol(3.beta.)-,carbonochloridate;CHLOROFORMIC ACID CHOLESTEROL ESTER;CHOLESTERYL CHLOROFORMATE;CHOLESTEROL CHLOROFORMATE;5-CHOLESTEN-3-BETA-OL CHLOROFORMATE;Chloroformic acid cholesteryl ester;cholest-5-ene-3-beta-yl chloroformate
• CAS NO: 7144-08-3
• Molecular Formula: C₂₈H₄₅ClO₂
• Molecular Weight: 449.11
• EINECS: 230-447-9
• Product Categories: Cholesteryl Compounds (Liquid Crystals);Functional Materials;Liquid Crystals & Related Compounds;Chiral Building Blocks;CholestericAsymmetric Synthesis;Complex Molecules;Liquid Crystals;Organic Electronics and Photonics;Steroids
• Mol File: 7144-08-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 115-117 °C(lit.)
• Boiling Point: 556.35°C (rough estimate)
• Flash Point: 203.1 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 0.9344 (rough estimate)
• Vapor Pressure: 2.77E-10mmHg at 25°C
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: O-6°C
• Solubility: SLOWLY HYDROLYZED
• Water Solubility: SLOWLY HYDROLYZED
• Sensitive: Moisture Sensitive
• BRN: 3223154
• CAS DataBase Reference: Cholesteryl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: Cholesteryl chloroformate(7144-08-3)
• EPA Substance Registry System: Cholesteryl chloroformate(7144-08-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 7144-08-3(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white crystalline powder

Uses

Cholesteryl chloroformate is used in the preparation of hydrophobized chitosan oligosaccharide, which finds application as an efficient gene carrier. It acts as an initiator in the polymerization of methyl methacrylate.

InChI:InChI=1/C28H45ClO2/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-26(29)30)13-15-27(20,4)25(22)14-16-28(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,27+,28-/m1/s1

Synthetic route

phosgene (75-44-5) + cholesterol (57-88-5) → Cholesteryl chloroformate (7144-08-3)

Conditions	Yield
In benzene Ambient temperature;	90%
	80%

phosgene (75-44-5) + cholesterol (57-88-5) → Cholesteryl chloroformate (7144-08-3)

Conditions	Yield
With diethyl ether
With antipyrine; benzene
With water; calcium carbonate
With hydrogenchloride; water
With water

bis(trichloromethyl) carbonate (32315-10-9) + cholesterol (57-88-5) → Cholesteryl chloroformate (7144-08-3)

Conditions	Yield
With water
With water; calcium carbonate
With hydrogenchloride; water

bis(trichloromethyl) carbonate (32315-10-9) + cholesterol (57-88-5) → Cholesteryl chloroformate (7144-08-3)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 4h;
With triethylamine
With potassium carbonate In toluene at 0℃;

(8R,9R,10S,13S,14R,17S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-10,13-dimethyl-17-((S)-6-methylheptan-2-yl)-1H-cyclopenta[a]phenanthren-3-yl 2-oxo-2-(pyren-1-yl)ethyl carbonate (1449331-30-9) → Cholesteryl chloroformate (7144-08-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / acetonitrile / pH 7.5 / Photolysis; Inert atmosphere 2: sodium carbonate / toluene / 6 h / 0 °C View Scheme

Cholesteryl chloroformate (7144-08-3) → cholesteryl azidoformate

Conditions	Yield
With sodium azide In acetone at 40℃; for 6h; Inert atmosphere;	100%
With sodium azide

Cholesteryl chloroformate (7144-08-3) + ethylenediamine (107-15-3) → 3β-cholest-5-en-3-yl N-(2-aminoethyl)carbamate (123628-75-1)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 24h; Cooling with ice;	99.1%
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;	96%
With triethylamine In tetrahydrofuran; dichloromethane; isopropyl alcohol at 0 - 20℃; for 6h;	95%

(2-(4-aminophenyl)-6-bromo-1H-benzo[df]isoquinoline-1,3(2H)-dione) + Cholesteryl chloroformate (7144-08-3) → C46H55BrN2O4

Conditions	Yield
With triethylamine In tetrahydrofuran for 1h; Cooling with ice;	99%

Cholesteryl chloroformate (7144-08-3) + propan-1-ol-3-amine (156-87-6) → cholesterol-3-(carboxyaminopropan-3-ol) (200337-33-3)

Conditions	Yield
In dichloromethane for 5h;	98%
In dichloromethane Ambient temperature;	93%
With triethylamine In dichloromethane at 20℃; for 2h;

Cholesteryl chloroformate (7144-08-3) + 1,1-dibromo-1-fluoro-4-phenyl-2-butanol (171503-39-2) → C38H55Br2FO3 (1354974-33-6)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	98%

Cholesteryl chloroformate (7144-08-3) + 2-bromoethylamine hydrobromide (2576-47-8) → C30H50BrNO2 (378229-48-2)

Conditions	Yield
With triethylamine In dichloromethane at -4 - 20℃; for 16h; Cooling with ice;	97.4%
With triethylamine In dichloromethane at 20℃; for 16h; Cooling with ice;	97.4%

Cholesteryl chloroformate (7144-08-3) → 6-(Cholesteryloxycarbonylamino)hexanoic acid (112538-31-5)

Conditions	Yield
Stage #1: 6-aminohexanoic acid With pyridine; chloro-trimethyl-silane at 0℃; for 1h; Stage #2: Cholesteryl chloroformate at 0 - 20℃; for 4h; Stage #3: With hydrogenchloride; water at 0℃; Product distribution / selectivity;	97%

Cholesteryl chloroformate (7144-08-3) + Trimethylenediamine (109-76-2) → 3β-cholest-5-en-3-yl N-(2-aminopropyl)carbamate

Conditions	Yield
In dichloromethane at 20℃;	97%
In dichloromethane at 20℃; for 4h;	92%
In dichloromethane at 0℃;	70%

Cholesteryl chloroformate (7144-08-3) + 4-nitro-4'-ethoxyazobenzene (147118-56-7) → cholesteryl 4-nitro-4'-ethoxyazophenyl carbonate

Conditions	Yield
With pyridine In benzene for 1h; Heating;	96%
With pyridine In toluene Acylation;

4-aminopyridine (504-24-5) + Cholesteryl chloroformate (7144-08-3) → Pyridin-4-yl-carbamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 24h;	96%
With triethylamine

Cholesteryl chloroformate (7144-08-3) + 3-butoxy-4-(6-hydroxy-1-methyl-1H-quinolin-2-ylidenemethyl)-cyclobut-3-ene-1,2-dione → carbonic acid 2-(2-butoxy-3,4-dioxo-cyclobut-1-enylmethylene)-1-methyl-1,2-dihydro-quinolin-6-yl ester 17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (874949-71-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 25℃; for 6h;	95%

Cholesteryl chloroformate (7144-08-3) → 3β-[N-(hydrazino)carbamoyl]cholesterol (539792-23-9)

Conditions	Yield
With hydrazine hydrate In tetrahydrofuran; dichloromethane; water at 20℃; for 2h;	95%
With triethylamine; hydrazine In dichloromethane at 0 - 20℃;	65%
With hydrazine hydrate In dichloromethane at 0℃; for 1h;
With hydrazine

N-BOC-1,2-diaminoethane (57260-73-8) + Cholesteryl chloroformate (7144-08-3) → C35H60N2O4 (1018466-45-9)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	94.2%
Stage #1: N-BOC-1,2-diaminoethane With triethylamine In dichloromethane at 0℃; Stage #2: Cholesteryl chloroformate In dichloromethane for 18h;

Cholesteryl chloroformate (7144-08-3) + trans-4-hydroxy-4′-butyl diazobenzene (103939-81-7) → cholesteryl 4-butylazophenyl carbonate

Conditions	Yield
With pyridine In benzene for 1h; Heating;	94%
With pyridine In toluene Acylation;

Cholesteryl chloroformate (7144-08-3) + 1-bromo-3-propanol (627-18-9) → 3-bromopropyl cholesterylformate

Conditions	Yield
With pyridine In dichloromethane at 20℃;	94%

phenylphosphinic acid (1779-48-2) + Cholesteryl chloroformate (7144-08-3) → cholestyl phenylphosphinate

Conditions	Yield
Stage #1: phenylphosphinic acid; Cholesteryl chloroformate With pyridine In dichloromethane at 20℃; Stage #2: for 0.25h; Heating;	93%

Tetraethylene glycol (112-60-7) + Cholesteryl chloroformate (7144-08-3) → bis(cholesteryloxycarbonyl)tetraethylene glycol (139136-57-5)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 24h;	93%

N-(2-pyridinyl)piperazine (20980-22-7) + Cholesteryl chloroformate (7144-08-3) → cholest-5-en-3-yl 4-(2-pyrimidinyl)-1-piperazinecarboxylate (1120327-16-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	93%
In dichloromethane at 0 - 20℃;

Cholesteryl chloroformate (7144-08-3) + (E)-4-(pyridin-4-yldiazenyl)phenol (253333-13-0) → cholest-5-en-3β-yl 4-(pyridin-4-ylazo)phenyl carbonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	93%

Cholesteryl chloroformate (7144-08-3) + propargyl alcohol (107-19-7) → cholesteryl 2-propyn-1-yl carbonate (33985-07-8)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 12h;	92.7%
With triethylamine In dichloromethane at -15 - 20℃; for 48h; Inert atmosphere;	79%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	64%

Cholesteryl chloroformate (7144-08-3) → 3-cholesterylfluoroformate (65928-85-0)

Conditions	Yield
With tetrabutyl ammonium fluoride In dichloromethane Ambient temperature;	92%
With thallium(I) fluoride In 1,2-dimethoxyethane

2-aminophenyl β-D-glucopyranoside (7265-01-2) + Cholesteryl chloroformate (7144-08-3) → 3β-cholest-5-en-3-yl N-[2-(β-D-glucopyranosyl)phenyl]carbamate

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃; for 4h;	92%

Cholesteryl chloroformate (7144-08-3) + 4-aminophenyl β-D-glucopyranoside (20818-25-1) → 3β-cholest-5-en-3-yl N-[4-(β-D-glucopyranosyl)phenyl]carbamate

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃; for 4h;	92%

[4-((E)-2-{4-[(E)-2-(2,5-Bis-hexyloxy-4-hydroxymethyl-phenyl)-vinyl]-2,5-bis-hexyloxy-phenyl}-vinyl)-2,5-bis-hexyloxy-phenyl]-methanol + Cholesteryl chloroformate (7144-08-3) → C116H182O12

Conditions	Yield
With pyridine In benzene for 12h; Heating;	92%

3-[(6-amino-hexanoyl)-ethoxycarbonylmethyl-amino]-propionic acid ethyl ester hydrochloride + Cholesteryl chloroformate (7144-08-3) → 3-({6-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-hexanoyl}ethoxycarbonylmethyl-amino)-propionic acid ethyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	92%

3-[(6-amino-hexanoyl)-ethoxycarbonylmethyl-amino]-propionic acid ethyl ester hydrochloride (786681-43-4) + Cholesteryl chloroformate (7144-08-3) → 3-({6-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-hexanoyl}ethoxycarbonylmethyl-amino)-propionic acid ethyl ester (786681-44-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	92%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	92%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	92%

3-[(6-amino-hexanoyl)-ethoxycarbonylmethyl-amino]-propionic acid ethyl ester hydrochloride (786681-43-4) + Cholesteryl chloroformate (7144-08-3) → 3-({6-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-hexanoyl}ethoxycarbonylmethyl-amino)-propionic acid ethyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;	92%

Cholesteryl chloroformate (7144-08-3) + 1-amino-3-(dimethylamino)propane (109-55-7) → 3α[N-(N',N'-dimethylaminopropane)carbamoyl]cholesterol (184582-91-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	92%
With triethylamine In dichloromethane at 20℃;

Cholesteryl chloroformate (7144-08-3) + 1-(o-fluorophenyl)piperazine (1011-15-0) → cholest-5-en-3-yl 4-(2-fluorophenyl)-1-piperazinecarboxylate (1120327-20-9)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	92%
In dichloromethane at 0 - 20℃;

Upstream product

• 1449331-30-9 (8R,9R,10S,13S,14R,17S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-10,13-dimethyl-17-((S)-6-methylheptan-2-yl)-1H-cyclopenta[a]phenanthren-3-yl 2-oxo-2-(pyren-1-yl)ethyl carbonate 
• 75-44-5 phosgene 
• 57-88-5 cholesterol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 57-88-5 cholesterol 

Downstream Products

• 79824-89-8 (3-nitro-phenyl)-cholesteryl carbonate 
• 116046-78-7 3β-cholesteryl-(4-formylphenyl)-carbonate 
• 57228-72-5 3β-(4-methoxy-phenylcarbamoyloxy)-cholestene-(5) 
• 57228-74-7 3β-(4-nitro-phenylcarbamoyloxy)-cholestene-(5) 
• 29678-79-3 trans-cholesteryl azophenyl carbonate 
• 38168-83-1 cholesteryl 2-ethoxyethyl-carbonate 
• 79824-84-3 Carbonic acid 2-cyano-phenyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 79824-91-2 Carbonic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 4-fluoro-phenyl ester 
• 79824-94-5 Carbonic acid 4-bromo-phenyl ester (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 79824-87-6 3-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-benzoic acid ethyl ester 
• 79824-83-2 cholesteryl nitrophenyl carbonate 
• 79862-59-2 2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-benzoic acid ethyl ester 
• 187279-53-4 {2-[2-(2-Benzylsulfanyl-ethoxy)-ethoxy]-ethyl}-carbamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 194425-24-6 C₄₇H₇₇NO₇S 

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