HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chloroethyl chloroformate
2-Chloroethyl carbonochloridate · CHLORO ETHYL CHLOROFORMATE · tl207 · TL 207 · Chlorethyl chloromethyl · 2-chloroethyl choroformate · 2-CHLOROETHYL CHLOROFORMATE · b-Chloroethyl chloroformate
Identifiers & Physical Properties
| CAS No. | 627-11-2 |
|---|---|
| Molecular formula | C3H4Cl2O2 |
| Average molar mass | 142.97 g/mol |
| Monoisotopic mass | 141.95883473 g/mol |
| SMILES | O=C(Cl)OCCCl |
| InChIKey | SVDDJQGVOFZBNX-UHFFFAOYSA-N |
| PubChem CID | 12305 |
| EC No. | 210-982-4 |
| DTXSID | DTXSID2060832 |
Chemical & Physical Properties
| XLogP | 1.8 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 3 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 64 |
| Chemical classes | Toxic Gases & Vapors -> Acid Halides |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| Density | 1.3847 (EPA, 1998) - Denser than waterwill sink1.3847 @ 20 °C/4 °C1.3847 @ 20°C1.385 |
| Color/Form | Colorless liquid |
| Solubility | Insol in cold waterSol in alcohol, ether, acetone, benzenesoluble in Ether,Benzene,Acetone |
| Boiling point | 312.3 °F at 760 mmHg (EPA, 1998)155 °C155.7 °C @760 [mm Hg]155-156°C |
| Vapor pressure | 13 mm Hg at 48-49 °C13 [mm Hg]0.23 psi ( 20 °C) |
| Refractive index | Index of refraction: 1.4483 @ 20 °C1.446 |
| Physical Description | Chloroethyl chloroformate is a liquid. (EPA, 1998)Colorless liquid[HSDB] Clear colorless liquid[MSDSonline] |
| Other Experimental Properties | Decomp in alkaline soln and hot waterChloroformates are reactive intermediates that combine acid chloride, and ester functions. They undergo many reactions of acid chlorides, however, the rates are usually slower. Reactions of chloroformates, like other acid chlorides, proceed faster with better yields when alkali hydroxides or tertiary amines are present to react with the HCl as it forms. /Chloroformates/Hydrolyze in water /chloroformates/Conversion factor: 5.84 mg/cu m = 1 ppmFlash point: 158 °F (70 °C) |
| Melting point | <25 °C |
| Flash point | 158°F |
| Storage conditions | Inert atmosphere,2-8°C |
| Physical state | Liquid |
| Color | Colorless to yellow |
| BRN | 506639 |
| Henry's law constant | 9.0×10-3 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChIKey | SVDDJQGVOFZBNX-UHFFFAOYSA-N |
| CAS DataBase Reference | 627-11-2(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 4D32H07Z9I |
| NIST Chemistry Reference | Carbonochloridic acid, 2-chloroethyl ester(627-11-2) |
| EPA Substance Registry System | 2-Chloroethyl chloroformate (627-11-2) |
| GHS pictogram | GHS05,GHS06 |
| Signal word | Danger |
| GHS hazard statements | H314-H331 |
| GHS precautionary statements | P261-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Hazard symbols | T |
| Risk statements (R) | 23-34 |
| Safety statements (S) | 26-36/37/39-45 |
| UN transport number | 3277 |
| Water hazard class (WGK) | 3 |
| RTECS number | LQ5950000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1(a) |
| Packing group | II |
| Customs code | 29159000 |
| Hazardous substances data | 627-11-2(Hazardous Substances Data) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH301 (13.2%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Carbonochloridic acid, 2-chloroethyl esterStatus: Active Update: 27-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/31392 |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| DOT label | Poison Corrosive |
| Fire hazards | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Health hazards | (Non-Specific -- Ethyl Chloroformate) Poisonousmay be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. (EPA, 1998) |
| Hazards summary | A strong skin and eye irritant[HSDB] Slowly decomposed by water forming ethanol, hydrogen chloride, and carbon dioxideEvolves hydrogen chloride in moist airMay cause burns[CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause pulmonary edema and chemical pneumonitisA lachrymator[MSDSonline] See CHLOROFORMATES. |
| Reactive group | Halogenated Organic Compounds |
| Reactivity Alerts | Water-Reactive |
| Reactivity Profile | CHLOROETHYL CHLOROFORMATE is an acid halide. Acid halides are water reactivesome are violently reactive. They are incompatible with strong oxidizing agents, alcohols, amines, alkali. 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]. |
| Air and Water Reactions | Decomposed slowly by water forming ethanol, HCl, and CO2on contact with moist air, it gives off HCl fumesattacks many metals especially in humid atmosphere. REF [Handling Chemicals Safely, 1980. p. 476]. |
| CERCLA reportable quantities | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Chloroethyl chloroformate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs. |
| Hazard Classes and Categories | Acute Tox. 3 (13.2%) |
| Fire fighting | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| First aid | Warning: Respiratory effects may be delayed up to 72 hrs after exposure. Caution is advised. |
| Nonfire spill response | (Non-Specific -- Ethyl Chloroformate) Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire. Shut off ignition sourcesno flares, smoking or flames in hazard area. Do not touch spilled materialstop leak if you can do so without risk. Use water spray to reduce vapors. |
| Disposal methods | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protectionequipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Protective Action Criteria (PAC) | 1.8 [mg/m3]20 [mg/m3]120 [mg/m3] |
| Personal Protective Equipment (PPE) | For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998) |
| Environmental fate | TERRESTRIAL FATE: Chloroformates hydrolyze readily in water(1)therefore, aqueous hydrolysis will be the dominant fate process in moist soils(SRC). The low-boiling chloroformic esters, such as chloroethyl chloroformate, are highly volatile(2)therefore, evaporation from dry surfaces to the atmosphere will occur(SRC). Results of a single biodegradation study (using the Japanese MITI protocol) have classified ethyl chloroformate (a compound similar in structure to chloroethyl chloroformate) as biodegradable(3) but ethyl chloroformate hydrolyzes so fast the the biodegradation rates are probably for the hydrolysis products.AQUATIC FATE: Chloroformates hydrolyze readily in water(1)ethyl chloroformate has an hydrolysis half-life of 31.5 min at 25 °C(1) and chloroethyl chloroformate is predicted to hydrolyze at a faster rate(2) forming the chloroethyl carbonate which can further hydrolyze to 2-chloroethanol and formic acidtherefore, aqueous hydrolysis will be the dominant fate process in the aquatic environment(SRC). Aqueous volatilization, bioconcentration, biodegradation, and adsorption to sediment are not expected to be important fate processes due to rapid hydrolysis(SRC).ATMOSPHERIC FATE: Based upon a vapor pressure of 13 mm Hg at 48-49 °C(1), chloroethyl chloroformate is expected to exist primarily in the vapor-phase in the ambient atmosphere(2,SRC). It will degrade in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 14 days(3,SRC). Since chloroformates hydrolyzes readily in water(4), atmospheric degradation may occur through dissolution into clouds or through contact with rain or other atmospheric water(SRC). |
| Adverse effects | Dermatotoxin - Skin burns. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indexes, the Koc for chloroethyl chloroformate can be estimated to be approximately 15(1,SRC). According to a suggested classification scheme(2), this estimated Koc value suggests that chloroethyl chloroformate has high mobility in soil(SRC). However, chloroformates hydrolyzes readily in water(3)therefore, leaching in soil is not expected to be an important fate process(SRC). |
| Artificial Pollution Sources | Chloroethyl chloroformate's use as a chemical intermediate in the synthesis of other chemicals(1) could release the compound to the environment through various waste streams generated at sites of production and use(SRC). |
| Environmental Biodegradation | Using the Japanese MITI protocol (4 week incubation period with activated sludge inoculum), ethyl chloroformate (a compound similar in structure to chloroethyl chloroformate) was classified as biodegradable with a theoretical BOD of 81-86%(1) but this probably refers to the hydrolysis product(SRC). |
| Environmental Bioconcentration | Chloroformates hydrolyze readily in water(1)therefore, bioconcentration in aquatic organisms will not be an important process(SRC). |
| Volatilization from Water/Soil | The Henry's Law Constant for chloroethyl chloroformate can be estimated to be 1.1X10-3 atm-cu m/mole using a structure estimation method(1,SRC)this value of Henry's Law Constant indicates that volatilization from water is potentially an important fate process(2). However, chloroformates hydrolyze readily in water(3)therefore, volatilization from water is not expected to be important(SRC). The low- boiling chloroformic esters, such as chloroethyl chloroformate, are highly volatile(4)therefore, evaporation from dry surfaces will occur(SRC). |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of chloroethyl chloroformate with photochemically produced hydroxyl radicals has been estimated to be 1.13X10-12 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 14 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Chloroformates hydrolyze readily in pure water(2)although the hydrolysis rate specific to chloroethyl chloroformate was not found, the rate constant for the aqueous hydrolysis of ethyl chloroformate in water at 25 °C has been experimentally determined to be 3.67X10-4/sec which corresponds to a half life of 31.5 min(2)an hydrolysis rate estimation program(3) predicts that chloroethyl chloroformate will hydrolyze as much as three times faster than ethyl chloroformate(SRC). |
| Probable Routes of Human Exposure | ... by ingestion and inhalation.The low-boiling chloroformic esters (such as chloroethyl chloroformate) are highly volatile(1)therefore, occupational exposure can occur through inhalation(SRC). |
| Environmental Water Concentrations | Chloroethyl chloroformate was tentatively identified in water sample collected from the Philadelphia, PA Torresdale water treatment plant in Mar 1975(1). |
| Environmental Fate/Exposure Summary | Chloroethyl chloroformate's use as a chemical intermediate could release the compound to the environment through various waste streams generated at sites of production and use. If released to the atmosphere, it will degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals (estimated half-life of about 14 days). Since chloroformates hydrolyze readily in water, atmospheric degradation may occur through dissolution into clouds or through contact with rain or other atmospheric water. If released to water or moist soil, hydrolysis will be the dominate degradation process. If released to dry surfaces, chloroethyl chloroformate will evaporate into the atmosphere. Occupational exposure is most likely to occur through inhalation. (SRC) |
| Toxicity Data | LCLo (mice) = 200 mg/m3/10min |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | LQ5950000 |
| UN transport number | 3277 |
| Customs code | 29159000 |
| Risk statements (R) | 23-34 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS06 |
| Hazard symbols | T |
| Safety statements (S) | 26-36/37/39-45 |
| Hazard class | 6.1(a) |
| Packing group | II |
| GHS hazard statements | H314-H331 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Hazardous substances data | 627-11-2(Hazardous Substances Data) |
Applications & Uses
Uses
2-Chloroethyl Chloroformate is a reactant used in the preparation of artemisinin-derived dimer carbonates and thiocarbonates with antimalarial activity.
General Description
Liquid.