57933-83-2

Usage

Uses

Used in Pharmaceutical Industry:
Isopropenyl chloroformate is used as a reagent for the preparation of ketones via palladium-catalyzed decarboxylative cross-coupling reaction of benzyl vinyl carbonates. This application is significant in the pharmaceutical industry as it aids in the synthesis of complex organic molecules, which are essential for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
Isopropenyl chloroformate is also employed in organic synthesis as a versatile reagent for the formation of various chemical bonds and functional groups. Its ability to react with a wide range of substrates makes it a valuable tool in the synthesis of complex organic molecules, including those with potential applications in materials science, agrochemicals, and other industries.
Used in Research and Development:
In the field of research and development, Isopropenyl chloroformate is utilized as a key intermediate in the synthesis of novel compounds with potential applications in various industries. Its unique reactivity and versatility make it an attractive candidate for exploring new reaction pathways and developing innovative synthetic methods.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 752, 1978 DOI: 10.1021/jo00398a058

Hazard

Strong irritant to eyes and skin.

InChI:InChI=1/C4H5ClO2/c1-3(2)7-4(5)6/h1H2,2H3

Synthetic route

phosgene (75-44-5) + acetone (67-64-1) → Isopropenyl chloroformate (57933-83-2)

Conditions	Yield
at 20℃;

phosgene (75-44-5) + bis(acetonyl)mercury (6704-33-2) → Isopropenyl chloroformate (57933-83-2)

Conditions	Yield
In dichloromethane

Isopropenyl chloroformate (57933-83-2) + 2-(3,4-dimethoxyphenyl)-2-cyclohexen-1-ol (189363-85-7) → 2-(3,4-dimethoxyphenyl)-3-[(isopropenyloxycarbonyl)oxy]-1-cyclohexene

Conditions	Yield
With pyridine In dichloromethane at 0℃;	100%

Isopropenyl chloroformate (57933-83-2) + 2-(3,4-methylenedioxyphenyl)-2-cyclohexen-1-ol (215609-91-9) → 2-(3,4-methylenedioxyphenyl)-3-[(isopropenyloxycarbonyl)oxy]-1-cyclohexene (335371-06-7)

Conditions	Yield
With pyridine In dichloromethane at 0℃;	100%

ethyl 2-(3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)acetate (897372-42-8) + Isopropenyl chloroformate (57933-83-2) → C21H27N3O4 (897373-29-4)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate at 20℃; for 1h;	100%

(1R)-1-[3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl]-1-(4-fluorophenyl)-2-phenylethan-1-amine (939398-43-3) + Isopropenyl chloroformate (57933-83-2) → (R)-prop-1-en-2-yl 1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethylcarbamate

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 20℃;	100%

Isopropenyl chloroformate (57933-83-2) + 3-(5-amino-4-fluoro-2-methylphenyl)-1-ethyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (1012878-89-5) → prop-1-en-2-yl (5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)carbamate (1442470-95-2)

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 6h;	100%
With sodium hydrogencarbonate In ethyl acetate at 20℃;	100%

Isopropenyl chloroformate (57933-83-2) + 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1012880-11-3) → prop-1-en-2-yl 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (1454682-73-5)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 6h;	100%
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 6h;
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 6h; Schotten-Baumann Reaction;

tert-butyl 5-(5-amino-3-isopropyl-pyrazol-1-yl)-indazole-1-carboxylate (1020173-63-0) + Isopropenyl chloroformate (57933-83-2) → tert-butyl 5-(3-isopropyl-5-((prop-1-en-2-yloxy)carbonylamino)-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (1020173-64-1)

Conditions	Yield
With sodium hydroxide In ethyl acetate at 0 - 20℃;	99%
With sodium hydroxide In water; ethyl acetate at 0 - 20℃;	99%

Isopropenyl chloroformate (57933-83-2) + 3-(3-amino-4-fluorophenyl)-N-(4-methoxybenzyl)-N,2-dimethyl-1,6-naphthyridin-7-amine (1455036-08-4) → prop-1-en-2-yl (2-fluoro-5-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)phenyl)carbamate (1455036-62-0)

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 2h; Schotten-Baumann Reaction;	99%
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 2h;	99%

Isopropenyl chloroformate (57933-83-2) + C12H13Cl2NO (1263184-89-9) → C16H17Cl2NO3

Conditions	Yield
With triethylamine In toluene at 25℃; for 2.66667h;	99%

Isopropenyl chloroformate (57933-83-2) + 6-(5-amino-4-fluoro-2-methylphenyl)-N-(4-methoxybenzyl)-N-methylpyrido[2,3-d]pyrimidin-2-amine → C27H26FN5O3

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 2h;	99%

Isopropenyl chloroformate (57933-83-2) + 3-(5-amino-4-fluoro-2-methylphenyl)-N-(4-methoxybenzyl)-N,2-dimethyl-1,6-naphthyridin-7-amine (1455036-17-5) → prop-1-en-2-yl (2-fluoro-5-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)-4-methylphenyl)carbamate (1455036-70-0)

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 4h;	99%

Isopropenyl chloroformate (57933-83-2) + N-hydroxy-5-norbornene-2,3-dicarboximide (21715-90-2) → Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl ester isopropenyl ester (137283-63-7)

Conditions	Yield
With triethylamine In acetone; acetonitrile at 0℃;	98%

Isopropenyl chloroformate (57933-83-2) + 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one (1442470-43-0) → prop-1-en-2-yl (4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)carbamate (1442470-93-0)

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 3h;	98%
In ethyl acetate at 20℃; for 3h;	98%

Isopropenyl chloroformate (57933-83-2) + 5-[(2R,3R)-3-amino-2-methylpiperidin-1-yl]-3-[(1-methyl-1H-pyrazol-4-yl)amino]pyrazine-2-carboxamide → prop-1-en-2-yl N-[(2R,3R)-1-{5-carbamoyl-6-[(1-methyl-1H-pyrazol-4-yl)amino]pyrazin-2-yl}-2-methylpiperidin-3-yl]carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	98%

Isopropenyl chloroformate (57933-83-2) + (2R,4aS,8aS)-4-[(3,5-dimethoxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-amine (1619983-12-8) → prop-1-en-2-yl N-[(2R,3S,4S,4aS,8aS)-4-[(3,5-dimethoxyphenyl)carbonyl]-3,4a,8,8-tetramethyldecahydronaphthalen-2-yl]carbamate (1619984-40-5)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 23h; Inert atmosphere;	97%

4-trifluoromethylphenylamine (455-14-1) + Isopropenyl chloroformate (57933-83-2) → prop-1-en-2-yl (4-(trifluoromethyl)phenyl)carbamate (1622427-09-1)

Conditions	Yield
With 4-methyl-morpholine In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere;	97%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Isopropenyl chloroformate (57933-83-2) → Isopropenyl Succinimido Carbonate (96935-01-2)

Conditions	Yield
With triethylamine In acetone; acetonitrile at 0℃; for 4h;	96%

(1S,4aS,5S,8aR)-2, 8a-dihydroxy-3,8-dimethyl-5-(1-methylethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (745065-96-7) + Isopropenyl chloroformate (57933-83-2) → (1S,2R,4aS,5S,8R,8aR)-8a-hydroxy-3,8-dimethyl-2-({[(1-methylethenyl) oxy] carbonyl} oxy)-5-(1-methylethyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (745063-60-9)

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 2.5h;	96%

Isopropenyl chloroformate (57933-83-2) + 7-amino-3-(5-amino-4-fluoro-2-methylphenyl)-1-ethyl-1,6-naphthyridin-2(1H)-one (1012878-90-8) → prop-1-en-2-yl (5-(7-amino-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)carbamate (1442474-13-6)

Conditions	Yield
In pyridine at 0℃; for 0.5h;	96%
With pyridine at 0℃; for 0.5h;	96%

N-hydroxyphthalimide (524-38-9) + Isopropenyl chloroformate (57933-83-2) → Carbonic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester isopropenyl ester (137283-62-6)

Conditions	Yield
With triethylamine In acetone; acetonitrile at 0℃;	95%

Isopropenyl chloroformate (57933-83-2) + 3-(5-amino-2-methylphenyl)-N-(4-methoxybenzyl)-N,2-dimethyl-1,6-naphthyridin-7-amine (1455036-18-6) → prop-1-en-2-yl (3-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)-4-methylphenyl)carbamate (1455036-73-3)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 1h;	95%

4-nitro-phenol (100-02-7) + Isopropenyl chloroformate (57933-83-2) → 4-nitrophenyl prop-1-en-2-yl carbonate (96916-42-6)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 1.5h;	94%
With pyridine; sodium hydroxide In chloroform	84%
With pyridine; sodium hydroxide In hydrogenchloride; chloroform
With pyridine In chloroform at 20℃; Cooling with ice;

Isopropenyl chloroformate (57933-83-2) + 3-(5-amino-2-chloro-4-fluorophenyl)-7-chloro-1-ethyl-1,6-naphthyridin-2(1H)-one (1012878-91-9) → prop-1-en-2-yl (4-chloro-5-(7-chloro-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)carbamate (1442474-41-0)

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 2h;	94%
With sodium hydrogencarbonate In ethyl acetate at 20℃; for 2h;	94%

Isopropenyl chloroformate (57933-83-2) + N-((5-((2-aminopyridin-4-yl)oxy)-6-methylpyridin-2-yl)carbamoyl)pivalamide → prop-1-en-2-yl (4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)carbamate

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

Isopropenyl chloroformate (57933-83-2) + 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one (43200-81-3) → 6-(5-chloropyridin-2-yl)-7-oxo-5-(2-propenyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine (862210-86-4)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 6h;	93%

Isopropenyl chloroformate (57933-83-2) + (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]-phenyl}prop-2-enol (1332523-83-7) → 1-methylethenyl (Z)-3-{3,4,5-trimethoxy-2-[2-(trifluoroacetylamino)ethyl]phenyl}prop-2-enyl carbonate (1332523-88-2)

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 3h; Inert atmosphere;	91%

Isopropenyl chloroformate (57933-83-2) + diethylamine (109-89-7) → prop-1-en-2-yl diethylcarbamate (130032-69-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	91%

Isopropenyl chloroformate (57933-83-2) + sodium 2,4,6-trichlorophenolate (3784-03-0) → Carbonic acid isopropenyl ester 2,4,6-trichloro-phenyl ester (96916-44-8)

Conditions	Yield
In acetonitrile Ambient temperature;	90%

Isopropenyl chloroformate (57933-83-2) + sodium salt of N-hydroxysuccinimide (72719-82-5) → Isopropenyl Succinimido Carbonate (96935-01-2)

Conditions	Yield
In acetonitrile Ambient temperature;	90%

Isopropenyl chloroformate (57933-83-2) + tert-butyl (3-(4-fluoro-2-methyl-5-(3-phenylureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)carbamate (1442474-50-1) → prop-1-en-2-yl (3-(4-fluoro-2-methyl-5-(3-phenylureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)carbamate (1442474-52-3)

Conditions	Yield
Stage #1: tert-butyl (3-(4-fluoro-2-methyl-5-(3-phenylureido)phenyl)-1-isopropyl-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl)carbamate With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 16h; Stage #2: Isopropenyl chloroformate With pyridine at 20℃; for 1h;	90%
With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 16h;	175 mg

Upstream product

• 75-44-5 phosgene 
• 67-64-1 acetone 
• 6704-33-2 bis(acetonyl)mercury 

Downstream Products

• 64294-81-1 Isoprenyl-N-cyclohexylcarbamat 
• 3479-47-8 Z-Asp(OBzl)-OH 
• 4779-31-1 Z-Asp-OBn 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 5672-83-3 Z-L-GluOMe 
• 3160-47-2 N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester 
• 4668-42-2 (S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester 
• 139608-02-9 isopropenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl carbonate 
• 139608-01-8 isopropenyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl carbonate 
• 112700-30-8 Z-Glu(Ocetyl)-OH 
• 112700-29-5 Z-Asp(OH)-Ocetyl 
• 83206-74-0 percarbonate de O,O-α-cumyle et O-isopropenyle 
• 124-38-9 carbon dioxide 
• 10144-64-6 Z-L-Ala 4-nitrobenzyl ester 

Relevant academic research and scientific papers

Qunoline intermediates useful therein for synthesizing antibacterial compounds

A novel process and intermediates used therein for linking a cephalosporin compound to a quinolone are disclosed. According to the disclosed process, the 2-carboxylic acid moiety of the cephalosporin compound is treated with an organic base. The resulting salt is then reacted with a quinolone compound which has been activated using a haloformate. The reaction is run in a non-aqueous organic solvent. 4-Dimethylaminopyridine is used to promote the reaction between the cephalosporin salt and the activated quinolone.