HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxybromide
POBr3 · phosphorus(v) oxybromide · Phosphoryl tribromide · PHOSPHORYL BROMIDE · PHOSPHOROUS OXYBROMIDE · Phosphorus Oxytribromide · phosphoryltribromide · tribromophosphorusoxide
Identifiers & Physical Properties
| CAS No. | 7789-59-5 |
|---|---|
| Molecular formula | Br3OP |
| Average molar mass | 286.69 g/mol |
| Monoisotopic mass | 283.72368755 g/mol |
| SMILES | O=P(Br)(Br)Br |
| InChIKey | UXCDUFKZSUBXGM-UHFFFAOYSA-N |
| PubChem CID | 24613 |
| EC No. | 232-177-7 |
| DTXSID | DTXSID2064868 |
Chemical & Physical Properties
| XLogP | 2.2 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 53 |
| Chemical classes | Other Classes -> Halogens, Inorganic CompoundsCorrosives |
| SpringerMaterials Properties | Gibbs energy |
| Density | greater than 1 (NOAA, 2007)2.8222.82 g/mL at 25 °C(lit.) |
| Color/Form | COLORLESS CRYSTALSTHIN PLATES, FAINT ORANGE TINT |
| Solubility | SOL IN ETHER, BENZENE, CHLOROFORM, CARBON DISULFIDE, CONCENTRATED SULFURIC ACIDreacts with H2Osoluble in benzene, ethyl ether,chloroformdecomposes |
| Boiling point | AT 758 MM HG IT BOILS AT 193 °C WITH DECOMPOSITION192 °C(lit.) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES OF BROMIDES & PO(X). |
| Melting point | 133 °F (NOAA, 2007)56 °C (IN HOT WATER)56 °C(lit.) |
| Physical Description | Phosphorus oxybromide appears as a colorless crystalline solid or liquid if heated above 133 °F with a pungent odor. It is commonly heated and shipped in a molten state. Soluble in water, but, decomposed by water to hydrobromic and phosphoric acid with evolution of heat. Reacts with organic materials to cause fire. Evolves highly toxic and corrosive gases when exposed to fire. Corrosive to metals and tissue. Used to make other chemicals.Colorless solid[Hawley] Light brown solid[MSDSonline] |
| Other Experimental Properties | SLOWLY HYDROLYZES IN WATER FORMING PHOSPHORIC ACID & HYDROGEN BROMIDEAT 758 MM HG IT BOILS AT 193 °C WITH DECOMPOSITIONDECOMPOSES IN COLD WATER |
| Flash point | 189°C |
| Storage conditions | Store below +30°C. |
| Physical state | Lump |
| Specific gravity | 2.822 |
| Color | White to yellow |
| Specific heat capacity | Cp(gas): 0.31 J/(g·K), at 25℃ |
| Sensitivity | Moisture Sensitive |
| Merck | 14,7348 |
| InChI | 1S/Br3OP/c1-5(2,3)4 |
| InChIKey | UXCDUFKZSUBXGM-UHFFFAOYSA-N |
| SMILES | BrP(Br)(Br)=O |
| CAS DataBase Reference | 7789-59-5(CAS DataBase Reference) |
| FDA UNII | H98H8Y87QQ |
| NIST Chemistry Reference | Phosphorus tribromide oxide(7789-59-5) |
| EPA Substance Registry System | Phosphoric tribromide (7789-59-5) |
| UNSPSC Code | 12352307 |
| NACRES | NA.22 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H314 |
| GHS precautionary statements | P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P305+P351+P338-P405-P501 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | C |
| Risk statements (R) | 14-34-37 |
| Safety statements (S) | 26-36/37/39-43-45-7/8-Neverusewater. |
| UN transport number | UN 1939 8/PG II (PHOSPHORUS OXYBROMIDE) |
| Water hazard class (WGK) | 3 |
| F | 10-21 |
| Hazard Note | Corrosive |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Eye Dam. 1Skin Corr. 1B |
| Packing group | II |
| Customs code | 28129090 |
| Storage class | 8A - Combustible corrosive hazardous materials |
| Hazardous substances data | 7789-59-5(Hazardous Substances Data) |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH290 (13%): May be corrosive to metals [Warning Corrosive to Metals]P234, P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Phosphoryl bromideStatus: Active Update: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24309Phosphoryl bromide: 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 label | Corrosive |
| Fire hazards | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:· EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily. |
| Health hazards | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:· CORROSIVE and/or TOXICinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. |
| Hazards summary | Highly reactive with organic materialsA strong skin and tissue irritant[Hawley] May cause fire on contact with organic substancesCorrosive to tissue[CAMEO] Corrosive to skin and eyes[eChemPortal: ERMA] Reacts violently with waterA corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis[MSDSonline] |
| DOT ID and guide | 1939 1372576 137 |
| Reactive group | Acyl Halides, Sulfonyl Halides, and Chloroformates |
| Reactivity Alerts | Water-Reactive |
| Reactivity Profile | PHOSPHORUS OXYBROMIDE is incompatible with water, strong oxidizing agents, alcohols, bases, including amines. 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]. |
| DOT Emergency Guidelines | /GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Health: CORROSIVE and/or TOXICinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns, or death. Fire will produce irritating, corrosive and/or toxic gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control or dilution water may cause pollution. /Phosphorus oxybromidePhosphorus oxybromide, moltenPhosphorus oxybromide, solid//GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Fire or Explosion: ... Some of these materials may burn, but none ignite readily. May ignite combustibles (wood, paper, oil, clothing, etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases. Flammable/toxic gases may accumulate in confined areas (basement, tanks, hopper/tank cars etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. Substance may be transported in a molten form. /Phosphorus oxybromide/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number ... . As an 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Phosphorus oxybromide/GUIDE 137: SUBSTANCES - WATER-REACTIVE - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLYit is not effective in spill situations where direct contact with the substance is possible. /Phosphorus oxybromideFor more DOT Emergency Guidelines (Complete) data for PHOSPHORUS OXYBROMIDE (8 total), please visit the HSDB record page. |
| DOT Hazard Classification | Phosphorus oxybromideUN1939Class 8 Corrosive material (49 eCFR § 173.136)PG II: the degree of danger presented by the material is mediumPhosphorus oxybromide, moltenUN2576 |
| Air and Water Reactions | Reacts slowly and exothermically with water to form phosphoric acid and hydrobromic acid [Merck, 11th ed. 1989]. Decomposes exothermically in water to form toxic fumes of hydrobromic and phosphoric acids [Lewis]. |
| Fire fighting | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]: |
| Accidental release measures | · 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.· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. |
| First aid | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:General First Aid: |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Storage conditions | ...SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, &...PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...STORE IN SEALED GLASS AMPULES. |
| Nonfire spill response | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]: |
| Preventive Measures | THE BASIC VENTILATION METHODS ARE LOCAL EXHAUST AND DILUTION OR GENERAL VENTILATION. |
| Isolation and Evacuation | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]: |
| Emergency Response Planning Guidelines | · When material is not involved in fire, do not use water on material itself. |
| Adverse effects | Dermatotoxin - Skin burns. |
| Human Toxicity Excerpts | SYMPTOMATOLOGY (...INGESTION OR SKIN CONTACT): 1. CORROSION OF MUCOUS MEMBRANES OF MOUTH, THROAT...ESOPHAGUS, WITH...PAIN & DYSPHAGIA. NECROTIC AREAS...GRAYISH WHITE BUT SOON...BLACKISH DISCOLORATION (YELLOW IN CASE OF NITRIC ACID) & SOMETIMES SHRUNK OR WRINKLED TEXTURE. 2. EPIGASTRIC PAIN...MAY BE ASSOC WITH NAUSEA & VOMITING...INTENSE THIRST. 3. CIRCULATORY COLLAPSE...CLAMMY SKIN, WEAK & RAPID PULSE, SHALLOW RESP...SCANTY URINE. ...SHOCK IS OFTEN...CAUSE OF DEATH. 4. ASPHYXIAL DEATH DUE TO GLOTTIC EDEMA. /ACIDS/SYMPTOMATOLOGY.../INGESTION/: 5. ULCERATION OF ALL MEMBRANES & TISSUES WITH WHICH ACID COMES IN CONTACT. ULCERATED AREAS OFTEN PERFORATE, LEADING TO MEDIASTINITIS & PERITONITIS. 6. LATE ESOPHAGEAL, GASTRIC & PYLORIC STRUCTURES & STENOSIS...MAY REQUIRE...SURGICAL REPAIR, SHOULD BE ANTICIPATED. PERMANENT SCARS MAY...APPEAR IN CORNEA, SKIN & OROPHARYNX. 7. UNCORRECTED CIRCULATORY COLLAPSE OF SEVERAL HR...MAY LEAD TO RENAL FAILURE & ISCHEMIC LESIONS IN LIVER & HEART. /ACIDS/ |
| F | 10-21 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 2576 8/PG II (PHOSPHORUS OXYBROMIDE, MOLTEN) |
| Customs code | 28129090 |
| Risk statements (R) | 14-34-37 |
| Signal word | Danger |
| GHS pictogram | GHS05 |
| Hazard symbols | C |
| hazard_note | Corrosive |
| Safety statements (S) | 26-36/37/39-43-45-7/8-Neverusewater. |
| Hazard class | 8Eye Dam. 1Skin Corr. 1B |
| Storage class | 8A - Combustible corrosive hazardous materials |
| Packing group | II |
| GHS hazard statements | H314 |
| Limited quantities | 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P305+P351+P338-P405-P501 |
| Hazardous substances data | 7789-59-5(Hazardous Substances Data) |
Applications & Uses
Uses
Phosphorus(V) Oxybromide is a reagent used in the preparation of phosphoryl halide for N-protection of amino acids using group assisted purification (GAP). Phosphorus(V) Oxybromide is a brominating agent.
Uses
Phosphorus(V) oxybromide may be used as brominating reagent in the synthesis of 2,4,6-tribromopyrimidine. It may be used in the preparation of bromoheterocyclic compounds.
General Description
A colorless crystalline solid or liquid if heated above 133° F with a pungent odor. Phosphorus oxybromide is commonly heated and shipped in a molten state. Soluble in water, but, decomposed by water to hydrobromic and phosphoric acid with evolution of heat. Reacts with organic materials to cause fire. Evolves highly toxic and corrosive gases when exposed to fire. Corrosive to metals and tissue. Used to make other chemicals.
Preparation & Synthesis
Preparation
Phosphorus oxychloride method: take phosphorus oxychloride as raw material and aluminum trichloride as the catalyst, upon heating at about 80 ℃, introduce hydrogen bromide gas for reaction, generating tribromo phosphorus. The reaction is: POC13 + 3HBr → POBr3 + 3HCl ↑ The produced hydrogen chloride gas during the reaction, after being absorbed by water, can produce dilute hydrochloric acid. Phosphorus tribromide method: to a round bottom flask equipped with a reflow condenser, add the mixture of phosphorus pentabromide and phosphorus pentoxide (250 g of PBr5/about 30 g of P2O5) and heat slowly to 150 ° C. Phosphorus pentoxide is a bit more than the phosphorus pentabromide in stoichiometry. At this time, one the one hand, pay attention to expel the bromine out; on the other hand, make sure that the reaction is completed within 5h. Then, 10 g of bromine and equivalent amount of phosphorus pentoxide were added to the melt and refluxed at 150 ° C for several hours. This is because it takes time for the intermediate product, phosphorus tribromide, to be oxidized to phosphorus pentabromide and transited to tribromonic phosphorus. The resultant was subjected to vacuum distillation under reduced pressure. After removing the initial distillate and the phosphorus tribromide contained therein, the trapping was carried out. The receiver is cooled with ice brine to generate tribromo phosphorus. Its reaction is: 3PBr5 + P2O5 → 5POBr3