57933-83-2

Basic information

• Product Name: Isopropenyl chloroformate
• Synonyms: ISOPROPENYL CHLOROFORMATE;Isopropenylchloroformate,97%;Isopropenyl chloroformate, stabilized, 99%;Isopropenyl chloroformate, 97%, stabilized;Chloroformic acid 1-methylethenyl ester;Chloroformic acid isopropenyl ester;Chloroformate isopropenyl;AMMGCGVWJMRTQI-UHFFFAOYSA-N
• CAS NO: 57933-83-2
• Molecular Formula: C₄H₅ClO₂
• Molecular Weight: 120.53
• EINECS: 261-018-4
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks;Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 57933-83-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 93 °C746 mm Hg(lit.)
• Flash Point: 50 °F
• Appearance: Clear colorless/Liquid
• Density: 1.103 g/mL at 25 °C(lit.)
• Vapor Pressure: 37.4mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility: reacts
• Stability: Moisture Sensitive, Light Sensitive
• CAS DataBase Reference: Isopropenyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: Isopropenyl chloroformate(57933-83-2)
• EPA Substance Registry System: Isopropenyl chloroformate(57933-83-2)

Safety Data

• Hazard Codes: F,T,T+
• Statements: 11-23/24/25-34-36/37-29-26-21/22
• Safety Statements: 16-26-27-36/37/39-45-8-28A
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 3
• F: 10-19
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 57933-83-2(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Isopropenyl Chloroformate is a reagent involved in the preparation of ketones via palladium-catalyzed decarboxylative cross-coupling reaction of benzyl vinyl carbonates.

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 
• 6704-33-2 bis(acetonyl)mercury 
• 67-64-1 acetone 

Downstream Products

• 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 
• 865094-47-9 isopropenyl (5-tert-butyl-2-(p-tolyl)-2H-pyrazol-3-yl)carbamate 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 1020173-99-2 C₂₁H₂₅N₅O₃ 
• 1439879-02-3 prop-1-en-2-yl (4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2,5-difluorophenoxy)pyridin-2-yl)carbamate 
• 335371-06-7 2-(3,4-methylenedioxyphenyl)-3-[(isopropenyloxycarbonyl)oxy]-1-cyclohexene 
• 176436-10-5 2-benzyl 1-tert-butyl (2S)-4,6-dioxo-1,2-piperidinedicarboxylate 
• 47307-26-6 (S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester 
• 5545-52-8 Z-D(tBu)-OH 
• 113421-90-2 Carbonic acid chloro-phenyl-methyl ester isopropenyl ester 
• 139608-08-5 isopropenyl 2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl carbonate 

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