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Triisopropylborat
TIPB · B（OiPr）3 · ISOPROPYL BORATE · Triisopropyl borat · Triisoproyl borate · BORON ISOPROPOXIDE · TRIISOPROPOXYBORANE · tripropan-2-yl borate
Identifikatoren & physikalische Daten
| CAS No. | 5419-55-6 |
|---|---|
| Summenformel | C9H21BO3 |
| Durchschnittliche Molmasse | 188,07 g/mol |
| Monoisotopische Masse | 188,1583747 g/mol |
| SMILES | CC(C)OB(OC(C)C)OC(C)C |
| InChIKey | NHDIQVFFNDKAQU-UHFFFAOYSA-N |
| PubChem CID | 21531 |
| ChEMBL | CHEMBL1902909 |
| EC No. | 226-529-9 |
| DTXSID | DTXSID7027598 |
| Lokaler Name | Triisopropylborat |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 27,7 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 102 |
| Flammpunkt | 82 °F (NFPA, 2010)62.6 °F |
| Dampfdruck | 8.6 [mmHg]76 mm Hg ( 75 °C) |
| Physical Description | Triisopropyl borate appears as a colorless liquid. Less dense than water and insoluble in water. Vapors heavier than air. Used to make other chemicals.[CAMEO] Colorless liquid with an alcohol-like odor[Alfa Aesar MSDS] |
| Schmelzpunkt | -59 °C |
| Siedepunkt | 139-141 °C (lit.) |
| Dichte | 0.815 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.376(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Miscible with ether, ethanol, isopropanol and benzene.decomposes |
| Aggregatzustand | Liquid |
| Wichte | 0.815 |
| Farbe | Clear colorless |
| BRN | 1701469 |
| InChI | 1S/C9H21BO3/c1-7(2)11-10(12-8(3)4)13-9(5)6/h7-9H,1-6H3 |
| InChIKey | NHDIQVFFNDKAQU-UHFFFAOYSA-N |
| SMILES | CC(C)OB(OC(C)C)OC(C)C |
| CAS Datenbank | 5419-55-6(CAS DataBase Reference) |
| NIST chemische Informationen | Boric acid (h3bo3), tris(1-methylethyl) ester(5419-55-6) |
| EPA chemische Informationen | Triisopropyl orthoborate (5419-55-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225 (93.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]H319 (59.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 154 reports by companies from 13 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 | Boric acid (H3BO3), tris(1-methylethyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Boric acid (H3BO3), tris(1-methylethyl) ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 26-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19978Status: Active Update: 14-02-2011 https://echa.europa.eu/registration-dossier/-/registered-dossier/1764Boric acid, tris(1-methylethyl) ester: 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.) |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids will float on water. (ERG, 2024)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.· Vapors may form explosive mixtures with air.· Vapors may travel to source of ignition and flash back.· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).· Vapor explosion hazard indoors, outdoors or in sewers.· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.· Runoff to sewer may create fire or explosion hazard.· Containers may explode when heated.· Many liquids will float on water. |
| Gesundheitsgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)· May cause toxic effects if inhaled or absorbed through skin.· Inhalation or contact with material may irritate or burn skin and eyes.· Fire will produce irritating, corrosive and/or toxic gases.· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.· Runoff from fire control or dilution water may cause environmental contamination. |
| Gefahrenübersicht | A mild eye irritantCauses somnolence, respiratory depression, and diarrhea in oral lethal-dose studies of ratsOral LD50 (mouse) = 2,500 mg/kg[RTECS] May cause irritation[Alfa Aesar MSDS] See Isopropyl alcohol and Boric acid. See Triethyl borate. |
| DOT-Nummer und Handbuch | 2616 129 |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | Borates, such as TRIISOPROPYL BORATE, behave similarly to esters in that they react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters/borates with alkali metals and hydrides. |
| DOT Hazard Classification | Triisopropyl borateUN2616Class 3 Flammable and combustible liquid (49 eCFR § 173.120)PG II: the degree of danger presented by the material is mediumPG III: the degree of danger presented by the material is minorFor more information about the packing group assignment, please visit 49 eCFR § 173 |
| Air and Water Reactions | Highly flammable. Insoluble in water. |
| Hazard Classes and Categories | Flam. Liq. 2 (93.5%)Eye Irrit. 2 (59.7%)Flammable agents - 3rd degree, Reactive agents - 1st degree |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842).LARGE FIRE: Water spray, fog or alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. 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. For massive fire, use unmanned master stream devices or monitor nozzlesif this is impossible, withdraw from area and let fire burn. (ERG, 2024) |
| 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 or walk through spilled material.· Stop leak if you can do it without risk.· Prevent entry into waterways, sewers, basements or confined areas.· A vapor-suppressing foam may be used to reduce vapors.· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.· Use clean, non-sparking tools to collect absorbed material.Large Spill· Dike far ahead of liquid spill for later disposal.· Water spray may reduce vapor, but may not prevent ignition in closed spaces. |
| Erste Hilfe | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Refer to the "General First Aid" section. Specific First Aid: Wash skin with soap and water. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. (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:· Wash skin with soap and water. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: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 or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024) |
| Isolation and Evacuation | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 50 meters (150 feet) in all directions.LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).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 for at least 50 meters (150 feet) in all directions.· Consider initial downwind evacuation for at least 300 meters (1000 feet).· 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. |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. (ERG, 2024) |
| Emergency Response Planning Guidelines | CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.Small Fire· Dry chemical, CO2, water spray or alcohol-resistant foam.· Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842).Large Fire· Water spray, fog or alcohol-resistant foam.· Avoid aiming straight or solid streams directly onto the product.· If it can be done safely, move undamaged containers away from the area around the fire.Fire Involving Tanks, Rail Tank Cars or Highway Tanks· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.· 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.· For massive fire, use unmanned master stream devices or monitor nozzlesif this is impossible, withdraw from area and let fire burn. |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2616 3/PG II/III (TRIISOPROPYL BORATE) |
| Zollcode | 29209085 |
| RTECS-Nr. | ED5950000 |
| R-Sätze (R) | 11 |
| Gefahrensymbole | F,Xi |
| Sicherheitshinweise (S) | 7-16-23-24/25-33-9 |
| Gefahrenklasse | 3Flam. Liq. 2 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
Triisopropyl borate is used as reagent in Pd-catalyzed coupling reaction with aryl halides such as Suzuki reaction. It is used as a reagent for the preparation of the boronic acids and esters; as a Lewis acid catalyst and involved in the ortho-borylation of 1-substituted naphthalenes. Furthermore, it plays an important role as a catalyst for the production of resins, waxes, paints and varnishes.