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Phenylchlorformiat
Phenyl carbonochloridate · CARBONOCHLORIDIC ACID · chlorocarbonic acid · PHENYL CHLOROFORMAT · Phenyl choroformate · PHENYL CHLOROCARBONATE · CHLOROFORMIC ACID PHENYL ESTER · carbonochloridic acid phenyl ester
Identifikatoren & physikalische Daten
| CAS No. | 1885-14-9 |
|---|---|
| Summenformel | C7H5ClO2 |
| Durchschnittliche Molmasse | 156,56 g/mol |
| Monoisotopische Masse | 155,9978071 g/mol |
| SMILES | O=C(Cl)Oc1ccccc1 |
| InChIKey | AHWALFGBDFAJAI-UHFFFAOYSA-N |
| PubChem CID | 15891 |
| EC No. | 217-547-8 |
| DTXSID | DTXSID9044403 |
| Lokaler Name | Phenylchlorformiat |
Chemische & physikalische Eigenschaften
| XLogP | 2,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 119 |
| Dichte | Density (at 20 °C): 1.2 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001.244 @25 °C1.248 g/mL at 25 °C (lit.) |
| Löslichkeit | Solubility in water: reactionMiscible with N,N-dimethylformamide.hydrolysis |
| Flammpunkt | 69 °C c.c.168 °F |
| Siedepunkt | 188-189 °C74-75 °C/13 mmHg (lit.) |
| Schmelzpunkt | -28 °C |
| Dampfdichte | Relative vapor density (air = 1): 5.411 (vs air) |
| Dampfdruck | 0.67 [mmHg]Vapor pressure, Pa at 20 °C: 9063.074 [mm Hg] @20 °C1.22 psi ( 20 °C) |
| Physical Description | Phenyl chloroformate appears as a colorless liquid with a strong odor. Toxic by ingestion, inhalation and skin absorption. Very irritating to skin and eyes. Used to make other chemicals.Colorless liquid with a pungent odor[ICSC]COLOURLESS-TO-LIGHT-YELLOW LIQUID WITH PUNGENT ODOUR. |
| Selbstentzündungstemperatur | 540 °C |
| Brechungsindex | n20/D 1.511(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear |
| BRN | 606778 |
| InChI | 1S/C7H5ClO2/c8-7(9)10-6-4-2-1-3-5-6/h1-5H |
| InChIKey | AHWALFGBDFAJAI-UHFFFAOYSA-N |
| SMILES | ClC(=O)Oc1ccccc1 |
| CAS Datenbank | 1885-14-9(CAS DataBase Reference) |
| NIST chemische Informationen | Carbonochloridic acid, phenyl ester(1885-14-9) |
| EPA chemische Informationen | Carbonochloridic acid, phenyl ester (1885-14-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH290 (60.1%): May be corrosive to metals [Warning Corrosive to Metals]H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H314 (93.1%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H317 (10.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (31.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H330 (96.8%): Fatal if inhaled [Danger Acute toxicity, inhalation]H335 (67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H412 (23.4%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P234, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P362+P364, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 188 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Carbonochloridic acid, phenyl esterStatus: Active Update: 08-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/5352Phenyl chloroformate: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health |
| DOT-Kennzeichnung | Poison Corrosive |
| Brandgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]: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 the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapors may travel to source of ignition and flash back. Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2024)· 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 the ground and collect in low or confined areas (sewers, basements, tanks, etc.).· Vapors may travel to source of ignition and flash back.· Corrosives in contact with metals may evolve flammable hydrogen gas.· Containers may explode when heated or if contaminated with water.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 69 °C explosive vapour/air mixtures may be formed. |
| Gesundheitsgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:TOXIC and/or CORROSIVEinhalation, 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 may 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 environmental contamination. (ERG, 2024)· TOXIC and/or CORROSIVEinhalation, 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 may 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 environmental contamination. |
| Gefahrenübersicht | Decomposed by water producing hydrogen chloride and phenolA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause pulmonary edema[ICSC] Reacts with water evolving hydrogen chlorideFumes in moist air releasing hydrogen chlorideA strong skin and eye irritant[CAMEO] A skin irritantCorrosive to eyes[eChemPortal: ERMA] Reacts with waterInhalation may cause chemical pneumonitis[MSDSonline] See CHLOROFORMATES. |
| DOT-Nummer und Handbuch | 2746 156 |
| Reaktive Gruppe | Acyl Halides, Sulfonyl Halides, and Chloroformates |
| UN-Einstufung | UN Hazard Class: 6.1UN Subsidiary Risks: 8UN Pack Group: II |
| Reactivity Alerts | Water-Reactive |
| Reactivity Profile | PHENYL CHLOROFORMATE is 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]. |
| Chemical Dangers | Decomposes on heating and on contact with water and moisture. This produces toxic and corrosive fumes including hydrogen chloride and phenol. Reacts violently with acids, alcohols, amines, bases, oxidants and metals. |
| Brandbekämpfung | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Note: Most foams will react with the material and release corrosive/toxic gases. CAUTION: For Acetyl bromide (UN1716), use CO2 or dry chemical only.SMALL FIRE: CO2, dry chemical, dry sand, alcohol-resistant foam.LARGE FIRE: Water spray, fog or alcohol-resistant foam. FOR CHLOROSILANES, DO NOT USE WATERuse alcohol-resistant foam. If it can be done safely, move undamaged containers away from the area around the fire. Avoid aiming straight or solid streams directly onto the product.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)NO water. Use dry powder, carbon dioxide, alcohol-resistant foam. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer immediately for medical attention.Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer immediately for medical attention. |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· Keep unauthorized personnel away.· Stay upwind, uphill and/or upstream.· Ventilate closed spaces before entering, but only if properly trained and equipped.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.· All equipment used when handling the product must be grounded.· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.· Stop leak if you can do it without risk.· A vapor-suppressing foam may be used to reduce vapors.· FOR CHLOROSILANES, use alcohol-resistant foam to reduce vapors.· DO NOT GET WATER on spilled substance or inside containers.· Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material.· Prevent entry into waterways, sewers, basements or confined areas.Small Spill· Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain.· Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. |
| Erste Hilfe | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Refer to the "General First Aid" section. Specific First Aid: For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required. Removal of solidified molten material from skin requires medical assistance. (ERG, 2024)General First Aid:· Call 911 or emergency medical service.· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.· Move victim to fresh air if it can be done safely.· Administer oxygen if breathing is difficult.· If victim is not breathing:-- DO NOT perform mouth-to-mouth resuscitationthe victim may have ingested or inhaled the substance.-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.· Remove and isolate contaminated clothing and shoes.· For minor skin contact, avoid spreading material on unaffected skin.· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.· For severe burns, immediate medical attention is required.· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.· Keep victim calm and warm.· Keep victim under observation.· For further assistance, contact your local Poison Control Center.· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.Specific First Aid:· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required. |
| Sichere Lagerung | Dry. Well closed. Ventilation along the floor. Separated from acids, alcohols, amines, bases, oxidants and food and feedstuffs. Store in an area without drain or sewer access. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. |
| Freisetung ohne Brand | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use alcohol-resistant foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas.SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2024) |
| Verschüttetes entsorgen | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable plastic containers. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)Immediate precautionary measure· Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. |
| Eye Prevention | Wear face shield or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. Above 69 °C use a closed system and ventilation. |
| Inhalation Risk | A harmful contamination of the air will be reached quickly on evaporation of this substance at 20 °C. |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour and by ingestion. Serious local effects on contact with eyes and skin. |
| Signs and Symptoms | Sore throat. Burning sensation. Cough. Laboured breathing. Shortness of breath. Symptoms may be delayed.Redness. Pain. Skin burns.Redness. Pain. Severe burns.Burning sensation in the mouth and in the throat and chest. Sore throat. Abdominal pain. Diarrhoea. Shock or collapse. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Toxicity Data | LCLo (rat) = 44 ppm/4h |
| F | 10-19-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2746 |
| Zollcode | 29159020 |
| RTECS-Nr. | FG3850000 |
| R-Sätze (R) | 22-26-34-41-38-29-37 |
| Toxizität | LD50 orally in Rabbit: 1730 mg/kg LD50 dermal Rabbit 4880 mg/kg |
| Gefahrensymbole | T+ |
| Sicherheitshinweise (S) | 26-28-36/37/39-45-28A |
| Gefahrenklasse | 6.1Acute Tox. 1 InhalationAcute Tox. 4 OralMet. Corr. 1Skin Corr. 1BSTOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Selbstentzündungstemperatur | 540 °C |
Anwendungen & Verwendung
Verwenden
Phenyl chloroformate is used in the synthesis of poly(2-(phenoxycarbonyloxy)ethyl methacrylate) and phenyl-(4-vinylphenyl) carbonate. It acts as a precursor of phenyl mixed anhydrides which are used in peptide coupling reactions. It serves as a dehydrating reagent for the conversion of primary amides to nitriles and an intermediate in the synthesis of pharmaceuticals and carbamates.
Herstellung & Synthese
synthetische
Phenyl chloroformate is synthesized by the reaction of phenol with phosgene. Phenol was dissolved in chloroform, phosgene was introduced under cooling, and the absorbed phosgene was in an equal molar ratio to phenol, and equimolar N,N-dimethylaniline was added dropwise under stirring at 5-10 °C. Then add cold water to dilute, separate the oil layer, wash with dilute hydrochloric acid and water successively. After drying with anhydrous calcium chloride, chloroform is evaporated, and then distilled under reduced pressure to collect 74-75°C (1.73kPa) fraction, which is phenyl chloroformate. The yield is about 90%.