7789-69-7

Basic information

• Product Name: PHOSPHORUS PENTABROMIDE
• Synonyms: Pentabromo phosphorus;PHOSPHORIC BROMIDE;PHOSPHORIC (V) BROMIDE;PHOSPHORUS (V) BROMIDE;PHOSPHORUS BROMIDE;PHOSPHOROUS (V) BROMIDE;PHOSPHORUS PENTABROMIDE;PHOSPHORUS PERBROMIDE
• CAS NO: 7789-69-7
• Molecular Formula: Br₅P
• Molecular Weight: 430.49
• EINECS: 232-186-6
• Product Categories: Bromination;C-X Bond Formation (Halogen);Synthetic Reagents
• Mol File: 7789-69-7.mol

Chemical Properties

• Melting Point: 105-107°C (dec.)
• Boiling Point: 105-107°C
• Flash Point: 105-107°C
• Appearance: /yellow orthorhombic crystals
• Density: 3.610
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• Merck: 14,7350
• BRN: 3903332
• CAS DataBase Reference: PHOSPHORUS PENTABROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHOSPHORUS PENTABROMIDE(7789-69-7)
• EPA Substance Registry System: PHOSPHORUS PENTABROMIDE(7789-69-7)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2691 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 7789-69-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
Phosphorus Pentabromide is used as a brominating agent for converting organic acids to acyl bromides. This application is particularly useful in the synthesis of various organic compounds and pharmaceuticals.
Used in Chemical Production:
Phosphorus Pentabromide is utilized in the production of other chemicals, thanks to its brominating properties. It plays a crucial role in the chemical industry for the synthesis of a wide range of products.

Reactivity Profile

PHOSPHORUS PENTABROMIDE is a yellow crystalline compound, toxic and corrosive. Contact with water or steam leads to violent decomposition (hydrolysis) producing toxic and corrosive phosphoryl bromide fumes. When heated to decomposition PHOSPHORUS PENTABROMIDE emits toxic fumes of bromide and oxides of phosphorus [Lewis, 3rd ed., 1993, p. 1033].

Purification Methods

Dissolve it in pure nitrobenzene at 60o, filtering off any insoluble residue on to sintered glass funnel, then allow it to crystallise by cooling. Wash the collected solid with dry Et2O and remove excess ether in a current of dry N2. (All manipulations should be performed in a dry-box.) [Harris & Payne J Chem Soc 3732 1958]. It fumes in moist air because of hydrolysis. HARMFUL VAPOURS (wash burning eyes with aqueous NaHCO3).

InChI:InChI=1/Br5P/c1-6(2,3,4)5

Synthetic route

bromine (7726-95-6) + phosphorus tribromide (7789-60-8) → phosphorus pentabromide (7789-69-7)

Conditions	Yield
In Petroleum ether at 20℃;
In Petroleum ether at 20℃; for 1h;
In n-heptane Cooling with ice;

phosphorus + bromine (7726-95-6) → phosphorus pentabromide (7789-69-7)

Conditions	Yield
with small, harmless explosions;

bromine (7726-95-6) + phosphorus pentoxide → diphosphorus trioxide + hydrogen bromide (10035-10-6, 12258-64-9) + phosphorus pentabromide (7789-69-7)

Conditions	Yield
In water byproducts: PBr3; with concd. aq. HBr; distn.;
In water byproducts: PBr3; with concd. aq. HBr; distn.;

hydrogen bromide (10035-10-6, 12258-64-9) → diphosphorus trioxide + phosphorus pentabromide (7789-69-7)

Conditions	Yield
With phosphorus pentoxide
With P2O5

hydrogen bromide (10035-10-6, 12258-64-9) → P(O)Cl2Br (13455-03-3) + P(O)ClBr2 (13550-31-7) + phosphorus pentabromide (7789-69-7)

Conditions	Yield
With trichlorophosphate byproducts: POBr3; 400 °C over pumice;
With POCl3 byproducts: POBr3; 400 °C over pumice;

phosphorous → phosphorus tribromide (7789-60-8) + phosphorus pentabromide (7789-69-7)

Conditions	Yield
With bromine at room temp.;

hydrogen bromide (10035-10-6, 12258-64-9) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → P(O)Cl2Br (13455-03-3) + P(O)ClBr2 (13550-31-7) + phosphorus pentabromide (7789-69-7) + phosphorus(V) oxybromide (7789-59-5)

Conditions	Yield
In neat (no solvent) passsing gaseous HBr charged with gaseous POCl3 through tube, filled with pumice and heated to 400 to 500°C;;

phosphorus (12185-10-3) + iodine(I) bromide (7789-33-5) → iodine hexabromophosphate + phosphorus pentabromide (7789-69-7)

Conditions	Yield
with explosion;

thiophosphoryl(V) bromide (3931-89-3) + phosphorus pentachloride (10026-13-8, 874483-75-7) → trichlorothiophosphine (3982-91-0) + phosphorus pentabromide (7789-69-7)

Conditions	Yield
In not given react. with PCl5;;
In not given react. of PCl5 with PSBr3;;

Br7Cl3P → bromine chloride (13863-41-7) + phosphorus pentabromide (7789-69-7)

Conditions	Yield
In neat (no solvent) decomposition with either air or CS2 or on warming;;
In neat (no solvent) decomposition with either air or CS2 or on warming;;

phosphorus pentabromide (7789-69-7) + acetonitrile (75-05-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → tungsten bis(acetonitrile) tetrabromide (12073-14-2, 40354-91-4)

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; addn. of PBr5 to hexacarbonyl suspn. under Ar; emanation of CO, 10 min; pptn.; stirring, 2h; filtration; twofold washing (CH3CN, Et2O); drying (vac.); elem. anal.;	98%

phosphorus pentabromide (7789-69-7) + acetonitrile (75-05-8) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → MoBr3(CH3CN)3 (14219-64-8, 39194-60-0)

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; addn. of PBr5 to hexacarbonyl suspn. under Ar; emanation of CO for a short period of time; pptn.; refluxing, 2h; cooling to room temp.; filtration; evapn.; filtration; washing (Et2O/CH3CN, 1:1); drying (vac.); elem. anal.;	96%
In acetonitrile byproducts: CO, PBr3; addn. of PBr5 in portions to hexacarbonyl suspn. under Ar, room temp., 1h; stirring, 1h; evapn.; pptn.; filtration; washing (Et2O/CH3CN, 1:1); drying (vac.); elem. anal.;	75%

bis(tricarbonyl(η-cyclopentadienyl)tungsten) + phosphorus pentabromide (7789-69-7) + acetonitrile (75-05-8) → acetonitrile(η5-cyclopentadienyl)tetrabromotungsten(V)

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; under Ar, air and moisture excluded, addn. of PBr5 in small portions to suspension of complex in CH3CN at room temp. (CO evolves under pptn. of CpWBr4CH3CN, 24h); filtered, washed (ether and CH2Cl2), dried (vac.), elem. anal.;	95%

cyclopentadienylmolybdenum tricarbonyl dimer + phosphorus pentabromide (7789-69-7) + acetonitrile (75-05-8) → acetonitrile(η5-cyclopentadienyl)tetrabromomolybdenum(V)

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; under Ar, air and moisture excluded, addn. of PBr5 in small portions to suspension of complex in CH3CN at room temp. (CO evolves under pptn. of CpMoBr4CH3CN, 24h); filtered, washed (ether and CH2Cl2), dried (vac.), elem. anal.;	90%

tungsten hexacarbonyl (14040-11-0) + phosphorus pentabromide (7789-69-7) + acetonitrile (75-05-8) → MoBr4(CH3CN)2 (12073-12-0, 131725-24-1) + MoBr3(CH3CN)3 (14219-64-8, 39194-60-0)

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; addn. of PBr5 to hexacarbonyl suspn. under Ar; emanation of CO, 10 min; pptn.; stirring, 2h; filtration; twofold washing (CH3CN, Et2O); drying (vac.); tribromo.compd.: evapn. of filtrate; pptn.; washing (Et2O/CH3CN, 1:1); drying (vac.); elem. anal.;	A 87% B 9%

di[(pentamethylcyclopentadienyl)molybdenum]hexacarbonyl + phosphorus pentabromide (7789-69-7) → C5(CH3)5MoBr4 (152046-82-7)

Conditions	Yield
In dichloromethane stoichiometric amounts; reflux for 12 h;; solvent concentration; filtration; washing of the precipitate with cold CH2Cl2; elem. anal.;;	87%

(η4-1,1-dihydro-2,5-diphenylsilacyclopentadiene)tricarbonyliron (111801-35-5) + phosphorus pentabromide (7789-69-7) → (η4-exo-1-bromo-endo-1-hydro-2,5-diphenylsilacyclopentadiene)tricarbonyliron (111801-30-0)

Conditions	Yield
In tetrahydrofuran PBr5, THF, -40°C to room temp., 0.5 h;	82%
In tetrahydrofuran solns. allowed to warm from -40°C to room temp., stirred for 0.5h; exclusion of air and moisture; solvent removed (vac.), residue extd. with hexane, filtered, concd., cooled to -20°C;	82%

phosphorus pentabromide (7789-69-7) + sodium cyclopentadienide + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → C5H5MoBr4

Conditions	Yield
In tetrahydrofuran; dichloromethane under N2: reaction of 7.25 mmol Mo(CO)6 and NaC5H5; removing of THF solvent; extraction with CH2Cl2; filtration; slow addn. to a suspension of 18.1 mmol PBr5 in CH2Cl2; pptn.; refluxing for 1.5 h; filtration;; washing with CH2Cl2;;	76%

bis{tricarbonyl(η5-cyclopentadienyl)chromium} + phosphorus pentabromide (7789-69-7) + acetonitrile (75-05-8) → acetonitrile(η5-cyclopentadienyl)dibromochromium(III)

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; under Ar, air and moisture excluded, addn. of PBr5 in three portions to soln. of complex at room temp. (CO evolves), 10h; filtered, concd. in vac., crystn. at 10°C, filtered, washed (ether), dried (vac.), addn. of Et2O to mother liquor further crystals of complex, elem. anal.;	62%

MoBr3(CH3CN)3 (14219-64-8, 39194-60-0) + phosphorus pentabromide (7789-69-7) → MoBr4(CH3CN)2 (12073-12-0, 131725-24-1)

Conditions	Yield
In acetonitrile addn. of PBr5 to Mo complex with stirring under Ar; immediate pptn.; stirring, 1h; filtration; washing (CH3CN, Et2O); drying (vac.);	60%

[(η(5)-C5H5)2(CO)4Mo2(μ-η(2)-P2)] + phosphorus pentabromide (7789-69-7) → C12H10Br6Mo2O2P2

Conditions	Yield
for 1h; Inert atmosphere;	54%

iodine(I) bromide (7789-33-5) + phosphorus pentabromide (7789-69-7) → {PBr4}(1+)*{IBr2}(1-)=PBr6I (17978-65-3)

Conditions	Yield
With tributylmethylammonium bis(trifluoromethanesulfonyl)imide salt at 50℃; for 74h; Inert atmosphere; Schlenk technique; Glovebox;	50%
In tetrachloromethane react. of soln. in CCl4;;
In carbon disulfide mixing satd. soln. in CS2;; impured product;;

phosphorus pentabromide (7789-69-7) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) + acetonitrile (75-05-8) → Cr(3+)*2Br(1-)*Br3(1-)*4CH3CN=CrBr5(CH3CN)4

Conditions	Yield
In acetonitrile byproducts: CO, PBr3; five equiv. of PBr5, boiling for 3 h with great excess of PBr5; pptn. on cooling to room temp.;	50%

uranium(III) 2,6-di-tert-butylphenoxide + phosphorus pentabromide (7789-69-7) → BrU(O(C6H3)(C(CH3)3)2)3 (157765-85-0)

Conditions	Yield
In hexane Ar or He, PBr5 added to a soln. of U-compound under stirring, stirred for 3 h; solvent removed under reduced pressure, redissolved (hexane), filtered through Celite, filtrate concd., cooled (-40°C, 24 h), filtered off; elem. anal.;	48%

phosphorus pentabromide (7789-69-7) + butyltriethylammonium iodide (4186-63-4) → phosphorus tribromide (7789-60-8)

Conditions	Yield
In neat (no solvent) byproducts: Et4NIBr2; argon atmosphere; org. compd. addn. to PBr5 (cooling to -20°C), reaction vessel connecting to vac. line; PBr3 collection (trap cooled with liq. nitrogen);	42%

octaphenylcyclotetrasilane (1065-95-8) + hydrogen bromide (10035-10-6, 12258-64-9) + aluminium bromide (7727-15-3) + phosphorus pentabromide (7789-69-7) → Si4Br10 (81626-34-8)

Conditions	Yield
In further solvent(s) byproducts: PBr3; PBr5 in CBr4 droped opver 12 h under stirring to Si-compound in CBr4, solvent and PBr3 removed, residue dissolved (benzene), AlBr3 added, HBr bubbled through the soln.; solvent removed; sublimed (160°C, 0.5 Torr); elem. anal.;	39.2%

iodine(I) bromide (7789-33-5) + phosphorus pentabromide (7789-69-7) → 2Br4P(1+)*Br7I5(2-)

Conditions	Yield
With tributylmethylammonium bis(trifluoromethanesulfonyl)imide salt at 50℃; for 36h; Inert atmosphere; Schlenk technique; Glovebox;	30%

[(η(5)-C5H5)2(CO)4Mo2(μ-η(2)-P2)] + phosphorus pentabromide (7789-69-7) → C14H10Br4Mo2O4P2

Conditions	Yield
In dichloromethane for 1h; Inert atmosphere;	29%

iodine trichloride (865-44-1) + phosphorus pentabromide (7789-69-7) + tributylmethylammonium bis(trifluoromethanesulfonyl)imide salt → 2Cl4P(1+)*Cl2I(1-)*Cl4I(1-)

Conditions	Yield
at 50℃; for 12h; Schlenk technique; Inert atmosphere; Glovebox;	20%

2,3-dimethyl-glutaric acid-anhydride (138500-84-2) + bromine (7726-95-6) + phosphorus pentabromide (7789-69-7) → α'-bromo-α.β-dimethyl-glutaric acid diethyl ester

Conditions	Yield
Behandeln des Reaktionsproduktes mit absol. Alkohol;

bromine (7726-95-6) + phosphorus pentabromide (7789-69-7) + 2-isopentyl-3-methyl-succinic acid-anhydride → α-bromo-α-methyl-α'-isopentyl-succinic acid diethyl ester

Conditions	Yield
Behandeln des Reaktionsproduktes mit Alkohol; anhydride of/the/ low-melting α-methyl-α'-isopentyl-succinic acid;

4,4-dimethyl-tetrahydro-pyran-2-one (22791-80-6) + phosphorus pentabromide (7789-69-7) → δ-bromo-β.β-dimethyl-n-valeric acid ethyl ester

Conditions	Yield
Behandeln des Reaktionsprodukts mit absol. Alkohol;

4,4-dimethyl-tetrahydro-pyran-2-one (22791-80-6) + phosphorus pentabromide (7789-69-7) → δ-bromo-β.β-dimethyl-n-valeric acid

Conditions	Yield
Behandeln des Reaktionsprodukts mit Wasser;

(+/-)-4-isopropyltetrahydropyran-2-one (56947-55-8) + phosphorus pentabromide (7789-69-7) → δ-bromo-β-isopropyl-n-valeric acid ethyl ester

Conditions	Yield
Behandeln des Reaktionsproduktes mit absol. Alkohol;

3,3'-dimethylbutyrolactone (3709-08-8) + phosphorus pentabromide (7789-69-7) → γ-bromo-α.α-dimethyl-butyric acid

Conditions	Yield
Behandeln des Reaktionsproduktes mit Wasser;

dihydro-5,5-dimethyl-2(3H)-furanone (3123-97-5) + phosphorus pentabromide (7789-69-7) → γ-bromo-isocaproic acid ethyl ester

Conditions	Yield
Behandeln des Reaktionsprodukts mit absol. Alkohol;

1,3-dimethyluric acid (944-73-0) + phosphorus pentabromide (7789-69-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → 1.3-dimethyl-8-bromo-xanthine + 1.3-dimethyl-8-chloro-xanthine

1-methyl-2-pyridone (694-85-9) + phosphorus pentabromide (7789-69-7) + phosphorus oxybromide → 2-bromo-pyridine (109-04-6)

Conditions	Yield
at 120 - 130℃;

Upstream product

• 7726-95-6 bromine 
• 7789-60-8 phosphorus tribromide 
• 10035-10-6 hydrogen bromide 
• 7789-33-5 iodine(I) bromide 
• 10294-28-7 gold bromide 
• 12185-10-3 phosphorous 
• 10025-87-3 trichlorophosphate 
• 12185-10-3 phosphorus 
• 3931-89-3 thiophosphoryl(V) bromide 
• 10026-13-8 phosphorus pentachloride 
• 7783-55-3 trifluorophosphane 
• 7789-59-5 phosphorus(V) oxybromide 
• 12440-00-5 phosphorus(III) oxide 
• 80937-33-3 oxygen 

Downstream Products

• 109-04-6 2-bromo-pyridine 
• 626-05-1 2,6-Dibromopyridine 
• 624-28-2 2,5-dibromopyridine 
• 77514-31-9 2,6-di-bromoquinoline 
• 120258-64-2 2,5-dibromo-quinoline 
• 2766-64-5 2,3,5,6-tetrabromopyridine 
• 2402-92-8 2,3,6-tribromopyridine 
• 5427-93-0 4-bromo-2-phenylquinoline 
• 5428-22-8 3,4-Dibrom-2-phenyl-chinolin 
• 5315-25-3 2-bromo-6-methylpyridine 
• 91733-25-4 3,4-dibromo-2,5-bis-(4-bromo-phenyl)-furan 
• 521-74-4 broxyquinoline 
• 110-52-1 1,4-dibromo-butane 
• 100-47-0 benzonitrile 

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