24468-13-1

Basic information

• Product Name: 2-Ethylhexyl chloroformate
• Synonyms: OCTYL CHLOROFORMATE;CHLOROFORMIC ACID 2-ETHYLHEXYL ESTER;CHLOROFORMIC ACID OCTYL ESTER;2-EHCF;2-etylhexyl-chlorformiat;2-ETHYLHEXYL CHLOROFORMATE;2-ethvlhexvlchloroformate;2-ETHYLHEXYLCHLOROFORMATE(2-EHCF)
• CAS NO: 24468-13-1
• Molecular Formula: C₉H₁₇ClO₂
• Molecular Weight: 192.68
• EINECS: 246-278-9
• Product Categories: CHLOROFORMATES;API intermediates;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 24468-13-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 106-107 °C30 mm Hg(lit.)
• Flash Point: 179 °F
• Appearance: colorless to light yellow colored liquid
• Density: 0.981 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 0.1 psi ( 20 °C)
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: 2-8°C
• Solubility: soluble in Ether,Benzene,Chloroform
• CAS DataBase Reference: 2-Ethylhexyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylhexyl chloroformate(24468-13-1)
• EPA Substance Registry System: 2-Ethylhexyl chloroformate(24468-13-1)

Safety Data

• Hazard Codes: T,T+
• Statements: 23/24/25-34-43-38-26
• Safety Statements: 26-27-36/37/39-45-36/37-28
• RIDADR: UN 2748 6.1/PG 2
• WGK Germany: 2
• RTECS: FG3660000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 24468-13-1(Hazardous Substances Data)

Usage

General Description

A colorless to light yellow colored liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. Toxic by ingestion, inhalation and/or skin absorption.

Air & Water Reactions

Produces corrosive toxic fumes containing HCl on contact with moist air. Decomposes in water.

Reactivity Profile

2-Ethylhexyl chloroformate is water reactive. Incompatible with strong oxidizing agents, alcohols, bases (including amines). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H17ClO2/c1-3-5-6-8(4-2)7-12-9(10)11/h8H,3-7H2,1-2H3

Synthetic route

phosgene (75-44-5) + 2-Ethylhexyl alcohol (104-76-7) → 2-Ethylhexyl chloroformate (24468-13-1)

Conditions	Yield
With toluene

2-Ethylhexyl alcohol (104-76-7) + bis(trichloromethyl) carbonate (32315-10-9) → 2-Ethylhexyl chloroformate (24468-13-1)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;

2-Ethylhexyl chloroformate (24468-13-1) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → C32H50O10

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

2-Ethylhexyl chloroformate (24468-13-1) → 2-ethylhexanoyl 2-ethylhexyl carbonate (334513-51-8)

Conditions	Yield
	98%

2-Ethylhexyl chloroformate (24468-13-1) + ethanolamine (141-43-5) → 2-N-(2-ethylhexyloxycarbonyl)amino-1-ethanol (176516-34-0)

Conditions	Yield
With sodium hydrogencarbonate	98%

3-Amino-1,2-propanediol (616-30-8, 13552-31-3) + 2-Ethylhexyl chloroformate (24468-13-1) → 3-N-(2-ethylhexyloxycarbonyl)amino-1,2-propanediol (176516-38-4)

Conditions	Yield
With sodium bicarbonate In tetrahydrofuran; water; acetone	97%

N-[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]-N'-1H-indazol-4-ylurea (808756-71-0) + 2-Ethylhexyl chloroformate (24468-13-1) → 2-ethylhexyl 4-(3-((R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl)ureido)-1H-indazole-1-carboxylate

Conditions	Yield
Stage #1: N-[(1R)-5-tert-butyl-2,3-dihydro-1H-inden-1-yl]-N'-1H-indazol-4-ylurea With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide for 0.0833333h; Stage #2: 2-Ethylhexyl chloroformate In tetrahydrofuran; N,N-dimethyl-formamide for 0.333333h;	97%

1-Amino-1-deoxy-D-glucitol (488-43-7) + 2-Ethylhexyl chloroformate (24468-13-1) → N-2-ethylhexyloxycarbonyl-D-glucamine (176516-32-8)

Conditions	Yield
With sodium hydrogencarbonate	95%

tert.-butylhydroperoxide (75-91-2) + 2-Ethylhexyl chloroformate (24468-13-1) → OO-tert-butyl O-(2-ethylhexyl) monoperoxycarbonate (34443-12-4)

Conditions	Yield
In water at 55℃;	95%
With pyridine; sodium hydroxide at 35℃; for 2.2h; Temperature; Reagent/catalyst;

4-HYDROXYPIPERIDINE (5382-16-1) + 2-Ethylhexyl chloroformate (24468-13-1) → 2-ethylhexyl 4-hydroxy-1-piperidinecarboxylate (945842-96-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h;	94%

2-Ethylhexyl chloroformate (24468-13-1) + methyl 2-ethoxy-1-((2′-(N′-hydroxycarbamimidoyl)-biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylate (147403-65-4) → C34H40N4O6

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 0℃; for 0.5h; Cooling with ice;	92.2%
With pyridine In N,N-dimethyl-formamide at 0℃; for 0.5h;
With pyridine In N,N-dimethyl-formamide at 0℃; for 0.5h; Cooling with water-ice;

2-Ethylhexyl chloroformate (24468-13-1) → di-(2-ethylhexyl)-peroxydicarbonate (16111-62-9)

Conditions	Yield
With dihydrogen peroxide In water at 30 - 35℃;	92%
With dihydrogen peroxide; sodium carbonate In water at 0 - 10℃; for 0.0618333h; Temperature; Reagent/catalyst; Flow reactor;	90.4%
With sodium hydroxide; water; dihydrogen peroxide

2-Ethylhexyl chloroformate (24468-13-1) → 2-ethylhexyl carbamate (4248-21-9)

Conditions	Yield
With ammonia In tetrahydrofuran; water at 0 - 20℃; Inert atmosphere;	89%

2-Ethylhexyl chloroformate (24468-13-1) + 4,4'-(1,2-ethanediyl)bis(1-hydroxymethyl-2,6-piperazinedione) (98631-86-8) → 1,2-bis[4-(2-ethylhexyloxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethane (98632-27-0)

Conditions	Yield
With pyridine Ambient temperature;	86%

2-Ethylhexyl chloroformate (24468-13-1) → 3-(chloromethyl)heptane (123-04-6)

Conditions	Yield
With N,N-dimethyl-formamide In chloroform at 72℃;	86%
pyrographite

N-(2-hydroxypropyl-3-hexadecyloxy)ethanolamine + 2-Ethylhexyl chloroformate (24468-13-1) → N-(2-ethylhexyloxycarbonyl)-N-(2-hydroxy-3-hexadecyloxypropyl) ethanolamine

Conditions	Yield
With triethylamine In tetrahydrofuran; water	84%

2-Ethylhexyl chloroformate (24468-13-1) + 2,9-bis(p-methylaminomethylphenyl)-1,10-phenanthroline → {4-[9-(4-{[(2-ethyl-hexyloxycarbonyl)-methyl-amino]-methyl}-phenyl)-[1,10]phenanthrolin-2-yl]-benzyl}-methyl-carbamic acid 2-ethyl-hexyl ester

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	82%

2-Ethylhexyl chloroformate (24468-13-1) + eflornithine hydrochloride → sodium 2-amino-2-difluoromethyl-5-({[(2-ethylhexyl)oxy]carbonyl}amino)pentanoate

Conditions	Yield
With sodium hydroxide In water at 20℃; for 120h; pH=11;	80%

(E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene (940881-02-7) + 2-Ethylhexyl chloroformate (24468-13-1) → 2-ethylhex-1-yl (E)-4,4,4-trifluoro-2-(p-tolylthio)but-2-enoate

Conditions	Yield
Stage #1: (E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; Stage #2: 2-Ethylhexyl chloroformate In tetrahydrofuran; hexane at -78℃; for 0.25h; Further stages.;	76%
Stage #1: (E)-1-(4-tolylthio)-3,3,3-trifluoroprop-1-ene With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #3: 2-Ethylhexyl chloroformate In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere;	76%

3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide (916167-81-2) + 2-Ethylhexyl chloroformate (24468-13-1) → 3-(5-Chloro-2-methoxy-benzenesulfonylamino)-N-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-benzamide

Conditions	Yield
Stage #1: 3-(5-chloro-2-methoxy-benzenesulfonylamino)-N-[4-(N-hydroxycarbamimidoyl)-phenyl]-benzamide; 2-Ethylhexyl chloroformate With pyridine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: In xylene at 100 - 145℃; for 2h;	75%

2-Ethylhexyl chloroformate (24468-13-1) + tert-butyl 4-{5-[(Z)-amino(hydroxyimino)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}piperidine-1-carboxylate (1037839-03-4, 1037834-91-5) → tert-butyl 4-[2-oxo-5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-benzimidazol-1-yl]piperidine-1-carboxylate (1037834-90-4)

Conditions	Yield
With pyridine In o-xylene at 0℃; for 4.25h; Heating / reflux;	74%

2-Ethylhexyl chloroformate (24468-13-1) + phenylhydrazine (100-63-0) → 2-ethylhexyl 2-phenylhydrazinecarboxylate (40887-07-8)

Conditions	Yield
With pyridine at 5 - 20℃; for 2h;	73%
With pyridine

4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [4-(N-hydroxycarbamimidoyl)-phenyl]-amide + 2-Ethylhexyl chloroformate (24468-13-1) → 4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-amide

Conditions	Yield
Stage #1: 4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [4-(N-hydroxycarbamimidoyl)-phenyl]-amide; 2-Ethylhexyl chloroformate With pyridine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: In xylene for 2h; Heating / reflux;	73%

2-Ethylhexyl chloroformate (24468-13-1) + N-(3-hydroxyphenyl)-diphenylamine (107396-23-6) → 4-(1-pyrenyl)butyric acid 1-bromo-2-ethylhexane

Conditions	Yield
With triethylamine In chloroform at 20℃; for 1h;	72%

2-Ethylhexyl chloroformate (24468-13-1) + hydroquinone (123-31-9) → 1,4-bis-(1-(2-ethylhexyl))-phenylene carbonate

Conditions	Yield
With pyridine; dmap In ethyl acetate for 24h; Ambient temperature;	71%

2-Ethylhexyl chloroformate (24468-13-1) + C36H46N2O4 (1218938-62-5) → Ethyl E-8-[2-(4-tert-butylbenzyloxy)phenyl]-6-{2-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)phenyl]ethyl}oct-7-enoate (934753-54-5)

Conditions	Yield
Stage #1: 2-Ethylhexyl chloroformate; C36H46N2O4 With pyridine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: In xylene for 2h; Reflux;	70%

2-Ethylhexyl chloroformate (24468-13-1) + arabinosyl cytosine (147-94-4) → [1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2-ethyl-hexyl ester

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl acetamide Ambient temperature;	65%

3-{[2'-(acetylamino)-4'-methyl-4,5'-bi-1,3-thiazol-2-yl]amino}-N-hydroxybenzenecarboximidic acid + 2-Ethylhexyl chloroformate (24468-13-1) → N-(2-{[3-(5-hydroxy-l-2,4-oxadiazol-3-yl) phenyl]amino}-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl)acetamide

Conditions	Yield
With pyridine In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;	64.7%

2-Ethylhexyl chloroformate (24468-13-1) + hydroquinone (123-31-9) → <1-(2-ethylhexyl)>-(4-oxy-phenylene) carbonate

Conditions	Yield
With pyridine; dmap In ethyl acetate for 24h; Ambient temperature;	62%

Upstream product

• 104-76-7 2-Ethylhexyl alcohol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 

Downstream Products

• 310869-68-2 3-(4-tetradecyloxybenzyl)-4H-1,2,4-oxadiazol-5-one 
• 459842-89-8 N-[4,5-dimethyl-2-[2-methyl-4-(5-oxo-1,2,4-oxadiazol-3-yl)phenylmethyloxy]phenyl]-N-isobutyl-(5-methyl-2-furyl)sulfonylamide 
• 16111-62-9 di-(2-ethylhexyl)-peroxydicarbonate 
• 224626-47-5 (R)-1-[[3-[2-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-2-oxo-ethoxy]-5-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxy]-acetyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 147404-01-1 methyl 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl]-2-propylbenzimidazol-7-carboxylate 
• 123-04-6 3-(chloromethyl)heptane 
• 55922-14-0 [2-(1-Amino-4-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yloxy)-ethyl]-phenyl-carbamic acid 2-ethyl-hexyl ester 
• 53082-92-1 Carbonic acid 2-ethyl-hexyl ester 3-oxo-2-(2,4,6-trimethyl-phenyl)-3H-inden-1-yl ester 
• 67648-17-3 phenyl-carbamic acid-(2-ethyl-hexyl ester) 

Relevant articles and documents

Design and Comparative Evaluation of the Anticonvulsant Profile, Carbonic-Anhydrate Inhibition and Teratogenicity of Novel Carbamate Derivatives of Branched Aliphatic Carboxylic Acids with 4-Aminobenzensulfonamide

Epilepsy is one of the most common neurological diseases, with between 34 and 76 per 100,000 people developing epilepsy annually. Epilepsy therapy for the past 100+ years is based on the use of antiepileptic drugs (AEDs). Despite the availability of more than twenty old and new AEDs, approximately 30% of patients with epilepsy are not seizure-free with the existing medications. In addition, the clinical use of the existing AEDs is restricted by their side-effects, including the teratogenicity associated with valproic acid that restricts its use in women of child-bearing age. Thus, there is an unmet clinical need to develop new, effective AEDs. In the present study, a novel class of carbamates incorporating phenethyl or branched aliphatic chains with 6–9 carbons in their side-chain, and 4-benzenesulfonamide-carbamate moieties were synthesized and evaluated for their anticonvulsant activity, teratogenicity and carbonic anhydrase (CA) inhibition. Three of the ten newly synthesized carbamates showed anticonvulsant activity in the maximal-electroshock (MES) and 6?Hz tests in rodents. In mice, 3-methyl-2-propylpentyl(4-sulfamoylphenyl)carbamate(1), 3-methyl-pentan-2-yl-(4-sulfamoylphenyl)carbamate (9) and 3-methylpentyl, (4-sulfamoylphenyl)carbamate (10) had ED50 values of 136, 31 and 14?mg/kg (MES) and 74, 53, and 80?mg/kg (6?Hz), respectively. Compound (10) had rat-MES-ED50 = 13?mg/kg and ED50 of 59?mg/kg at the mouse-corneal-kindling test. These potent carbamates (1,9,10) induced neural tube defects only at doses markedly exceeding their anticonvuslnat-ED50 values. None of these compounds were potent inhibitors of CA IV, but inhibited CA isoforms I, II and VII. The anticonvulsant properties of these compounds and particularly compound 10 make them potential candidates for further evaluation and development as new AEDs.