Conditions | Yield |
---|---|
In benzene | 93.5% |
In benzene | 93.5% |
In neat (no solvent) heating red P with I2; react. at the transition point of red P;; |
phosphorus pentabromide
butyltriethylammonium iodide
phosphorus tribromide
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% |
Conditions | Yield |
---|---|
beim Erwaermen; |
Conditions | Yield |
---|---|
at 160℃; beim Erhitzen; |
butyl phosphorodibromidite
hydrogen bromide
A
1-bromo-butane
B
phosphorus tribromide
Conditions | Yield |
---|---|
at 22℃; |
butyl phosphorodibromidite
Pyridine hydrobromide
A
1-bromo-butane
B
phosphorus tribromide
Conditions | Yield |
---|---|
at 100℃; beim Erhitzen; |
dibromophosphoric acid isobutyl ester
A
t-butyl bromide
B
Isobutyl bromide
C
phosphorus tribromide
Conditions | Yield |
---|---|
at 160℃; |
dibromophosphoric acid isobutyl ester
Pyridine hydrobromide
A
t-butyl bromide
B
Isobutyl bromide
C
phosphorus tribromide
Conditions | Yield |
---|---|
at 100℃; |
dibromophosphoric acid sec-butyl ester
A
phosphorus tribromide
B
s-butyl bromide
Conditions | Yield |
---|---|
at 118℃; |
dibromophosphoric acid sec-butyl ester
hydrogen bromide
A
phosphorus tribromide
B
s-butyl bromide
dibromophosphoric acid isobutyl ester
phosphorus pentabromide
A
Isobutyl bromide
B
phosphorus tribromide
Conditions | Yield |
---|---|
at 180℃; Equilibrium constant; |
Conditions | Yield |
---|---|
o-bromo-camphor; |
Conditions | Yield |
---|---|
Zerfaellt beim Erhitzen; |
Conditions | Yield |
---|---|
at 180℃; Equilibrium constant; |
phosphonic Acid
bromine
A
phosphoric acid
B
hydrogen bromide
C
phosphorus tribromide
Conditions | Yield |
---|---|
In neat (no solvent) heating an excess of H3PO3 with Br2 in a sealed tube at 100 °C;; | |
In neat (no solvent) heating an excess of H3PO3 with Br2 in a sealed tube at 100 °C;; |
Conditions | Yield |
---|---|
In further solvent(s) in PBr3 soln.; |
Conditions | Yield |
---|---|
In gas by distn. over Hg2Br2; |
Conditions | Yield |
---|---|
In gas by distn. over HgBr2; |
hydrogen bromide
phosphorus tribromide
Conditions | Yield |
---|---|
With phosphorus trichloride | |
With PCl3 |
phosphorus tribromide
Conditions | Yield |
---|---|
With bromine In benzene |
Conditions | Yield |
---|---|
With bromine at room temp.; |
Conditions | Yield |
---|---|
at higher temp. and reduced pressure;; | |
at higher temp. and reduced pressure;; |
Conditions | Yield |
---|---|
In neat (no solvent) formation of small amount PBr3;; | |
In neat (no solvent) formation of small amount PBr3;; |
iodine
phosphorus pentabromide
A
IBr5
B
phosphorus tribromide
Conditions | Yield |
---|---|
In not given |
phosphorus(V) bromide
iodine
A
IBr5
B
phosphorus tribromide
Conditions | Yield |
---|---|
In neat (no solvent) formation of red liquid containing PBr3 and IBr5;; | |
In neat (no solvent) formation of red liquid containing PBr3 and IBr5;; |
Conditions | Yield |
---|---|
In not given | A 0% B n/a |
N(C2H5)4(1+)*PCl(CN)3(1-)=(N(C2H5)4)(PCl(CN)3)
bromine
mer-trichlorotricyanophosphate(1-)
B
phosphorus tribromide
Conditions | Yield |
---|---|
In dichloromethane |
N(C2H5)4(1+)*PCl(CN)3(1-)=(N(C2H5)4)(PCl(CN)3)
tetra-n-propylammonium bromide
bromine
D
phosphorus tribromide
Conditions | Yield |
---|---|
In dichloromethane under N2, Br2 added dropwise to soln. of (NEt4)(PCl(CN)3) contg. excessof N(n-C3H7)4Br; monitored by (31)P NMR spectra; |
Conditions | Yield |
---|---|
In neat (no solvent) reaction of Br2 in CO2 (as carrier gas) with dry P;; | |
In tetrachloromethane slowly dropping Br2 to P in CCl4;; | |
In neat (no solvent) reaction in CO2 atmosphere;; |
(4-methoxy-2-(trifluoromethyl)phenyl)methanol
phosphorus tribromide
4-methoxy-2-(trifluoromethyl)benzyl bromide
Conditions | Yield |
---|---|
In hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran | 100% |
phosphorus tribromide
2-(2-bromomethylphenyl)-N-(3-Fluoro-2'-methanesulfonyl-biphenyl-4-yl)acetamide
Conditions | Yield |
---|---|
In dichloromethane | 98% |
tert.-butyl lithium
phosphorus tribromide
1,1-dimethylethyldibromophosphane
Conditions | Yield |
---|---|
In pentane at -80 - 20℃; for 12.5h; Schlenk technique; Inert atmosphere; | 98% |
diboron tetrabromide
phosphorus tribromide
bis(tribromophosphane)-tetrabromodiborane(4)
Conditions | Yield |
---|---|
In neat (no solvent) high vac. or inert atmosphere; condensation of B-compd. and P-compd. into a flask, slow warming of the mixt. to room temp. in the sealed flask with vigorous shaking; elem. anal.; | 97% |
Conditions | Yield |
---|---|
With bromine | 96% |
fluorosulfonyldifluoroacetyl fluoride
bromine
phosphorus tribromide
fluorosulfonyldifluoroacetyl bromide
Conditions | Yield |
---|---|
heating, 80°C, 1 h; | 95% |
heating, 80°C, 1 h; | 95% |
tricarbonyl[C6H4(CH2OH)2]chromium(0)
phosphorus tribromide
[Cr(η6-C6H4(CH2Br)2-1,4)(CO)3]
Conditions | Yield |
---|---|
In diethyl ether a soln. of PBr3 in Et2O was slowly added to a soln. of complex in Et2O cooled to 0°C under N2, the mixt. was stirred at 0°C for 2-2.5 h, then stirred at room temp. for 2.5-18 h; H2O was added, the ether layer was washed with H2O, dried over MgSO4, filtered, the solvent was removed under reduced pressure; | 94% |
phosphorus tribromide
4-ferrocenylbenzylbromide
Conditions | Yield |
---|---|
In dichloromethane soln. of PBr3 in CH2Cl2 added dropwise to soln. of ferrocene deriv. in CH2Cl2 at 0°C, mixt. stirred at 0°C for 30 min; mixt. poured onto ice, neutralised with satd. aq. NaHCO3, org. phase sepd., aq. phase extd. with CH2Cl2, combined org. phases washed with brine,dried over MgSO4, filtrate evapd. under vac.; elem. anal.; | 94% |
Conditions | Yield |
---|---|
In toluene at -152℃; for 4h; Heating / reflux; | 93% |
2,2'-bis(hydroxymethyl)biphenyl
phosphorus tribromide
2,2'-bis-(bromomethyl)-1,1'-biphenyl
Conditions | Yield |
---|---|
In CaCl2; dichloromethane; water | 93% |
Conditions | Yield |
---|---|
In methanol; dichloromethane; ethyl acetate | 92% |
(benzyl alcohol)tricarbonylchromium(0)
phosphorus tribromide
[Cr(η6-C6H5CH2Br)(CO)3]
Conditions | Yield |
---|---|
In diethyl ether a soln. of PBr3 in Et2O was slowly added to a soln. of complex in Et2O cooled to 0°C under N2, the mixt. was stirred at 0°C for 2-2.5 h, then stirred at room temp. for 2.5-18 h; H2O was added, the ether layer was washed with H2O, dried over MgSO4, filtered, the solvent was removed under reduced pressure; elem. anal.; | 92% |
[Cr(η6-C6(CH3)3(CH2OH)3-1,3,5)(CO)3]
phosphorus tribromide
[Cr(η6-C6(CH3)3(CH2Br)3-2,4,6)(CO)3]
Conditions | Yield |
---|---|
In diethyl ether a soln. of PBr3 in Et2O was slowly added to a soln. of complex in Et2O cooled to 0°C under N2, the mixt. was stirred at 0°C for 2-2.5 h, then stirred at room temp. for 2.5-18 h; H2O was added, the ether layer was washed with H2O, dried over MgSO4, filtered, the solvent was removed under reduced pressure; elem. anal.; | 91% |
2.6-bis(hydroxymethyl)pyridine
phosphorus tribromide
2,6-bis-(bromomethyl)pyridine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 91% |
3-Phenyl-2-propyn-1-ol
phosphorus tribromide
1-bromo-3-phenylprop-2-yne
Conditions | Yield |
---|---|
With pyridine In diethyl ether | 90% |
With pyridine In diethyl ether | 90% |
potassium hydrogenfluoride
phosphorus tribromide
trifluorophosphane
Conditions | Yield |
---|---|
In acetonitrile byproducts: KBr, HBr; PBr3 in MeCN was slowly added to a boiling suspn. of KHF2 in MeCN;; the gaseous prod. was condensed in trap cooled by liq. N2 and distd. at -100°C; elem. anal.; IR; | 90% |
Conditions | Yield |
---|---|
In carbon disulfide mixed (with stirring at -40°C), stirred (15 min); filtered, solv. removed (in vac. at room temp.); | 90% |
phosphorus tribromide
A
bromobis(2,4,6-trimethylborazinyl)phosphane
B
lithium bromide
Conditions | Yield |
---|---|
In diethyl ether; hexane under inert gas; soln. of borazine (3.26 mmol) in mixt. of hexane (10 ml) and Et2O (10 ml) added to soln. of PBr3 (1.63 mmol) in hexane; stirredovernight; LiBr removed by filtration; evapd. (vac.) by 2/3 of volume; kept (5°C, wk); elem. anal.; | A 80% B 90% |
Conditions | Yield |
---|---|
In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | 87% |
phosphorus tribromide
Conditions | Yield |
---|---|
With sodium carbonate In chloroform; water | 86% |
Conditions | Yield |
---|---|
In tetrahydrofuran; toluene byproducts: LiBr; (N2); soln. of Li compd. in THF was added to soln. of PBr3 in toluene at-40°C; after 5 min mixt. was warmed to room temp.; after 3.5 h filtered; volatiles removed (vac.); hexane added; soln. transferred into Schlenk vessel; solvent removed; elem. anal.; | 86% |
Conditions | Yield |
---|---|
With bis(trimethylsilyl)selenide at 20℃; for 8h; Inert atmosphere; | 86% |
phosphorus tribromide
(E:Z)-3-(2-bromophenyl)prop-2-en-1-ol
(E)-1-bromo-2-(3-bromoprop-1-en-1-yl)benzene
Conditions | Yield |
---|---|
In tetrachloromethane | 85% |
In tetrachloromethane | 85% |
phosphorous
Ag[Al(OtBuF)4]*dichloromethane
phosphorus tribromide
P5Br2(1+)*[Al(OC(CF3)3)4](1-)=P5Br2[Al(OC(CF3)3)4]
Conditions | Yield |
---|---|
In dichloromethane byproducts: AgBr; P4 added to solid Ag(Al(OC(CF3)3)4)*CH2Cl2; then PBr3 added at 77 K; CH2Cl2 condensed onto mixt.; allowed to stir at -78 °C for 8 h; thenstored at -80 °C for 10 d with shaking; soln. filtered; its vol. reduced at 0 °C; cooled to -30 °C; | 85% |
phosphorus tribromide
dibromo(2,4,6-trimethylborazinyl)phosphane
Conditions | Yield |
---|---|
In diethyl ether; hexane byproducts: LiBr; under inert gas; soln. of borazine (1.78 mmol) in mixt. of hexane (10 ml) and Et2O (10 ml) added to soln. of PBr3 (1.78 mmol) in hexane; stirredovernight; LiBr removed by filtration; evapd. (vac.); oil aged for mo; elem. anal.; | 85% |
Conditions | Yield |
---|---|
In dichloromethane (inert atm.); addn. of 1 equiv. of phosphorus tribromide to aluminium compd. in CH2Cl2 at -78°C, keeping at -80°C overnight; filtration, concg., keeping at -30°C for few d, isolation of crystals, NMR and IR; | 84.1% |
In dichloromethane-d2 (inert atm.); addn. of 1 equiv. of phosphorus tribromide to aluminium compd. in CD2Cl2 at -78°C, keeping at -80°C overnight; not isolated, NMR; |
boron tribromide
phosphorus tribromide
phosphorus tribromide-boron tribromide
Conditions | Yield |
---|---|
In carbon disulfide mixed (with stirring at -40°C), stirred (15 min); filtered, solv. removed (in vac. at room temp.); | 83% |
2,3-dichlorobenzyl alcohol
phosphorus tribromide
1-(bromomethyl)-2,3-dichlorobenzene
Conditions | Yield |
---|---|
In toluene | 83% |
potassium hexafluorophosphate
phosphorus tribromide
Conditions | Yield |
---|---|
Stage #1: C26H32N4O2(2+)*2Br(1-); phosphorus tribromide In N,N-dimethyl-formamide at 50℃; for 12h; Stage #2: potassium hexafluorophosphate In water | 82% |
Molecular Structure:
Molecular Formula: H8Br3P
Molecular Weight: 278.7493
IUPAC Name: Tribromophosphane
Synonyms of Phosphorus tribromide (CAS NO.7789-60-8): EINECS 232-178-2 ; HSDB 1217 ; Phosphorous bromide ; Phosphorus bromide (PBr3) ; Phosphorus tribromide ; Tribromophosphine ; Phosphorus tribromide [UN1808] [Corrosive] ; UN1808
CAS NO: 7789-60-8
Product Categories: Inorganics ; BrominationMicro/Nanoelectronics ; C-X Bond Formation (Halogen) ; Electronic Chemicals ; Others ; Synthetic Reagents
Melting point: -40 °C
SMILES: [PH6+3].[Br-].[Br-].[Br-]
InChI: InChI=1/3BrH.P/h3*1H;/q;;;+3/p-3
InChIKey: BEXNWOOMHDDWHU-DFZHHIFOAC
Std. InChI: InChI=1S/3BrH.P/h3*1H;/q;;;+3/p-3
Std. InChIKey: BEXNWOOMHDDWHU-UHFFFAOYSA-K
Phosphorus tribromide (CAS NO.7789-60-8) is used in organic synthesis, used as a brominating agent and reducing agent, etc.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LDLo | oral | 50mg/kg (50mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Technical Information Service. Vol. OTS0555394, |
Reported in EPA TSCA Inventory.
Probably highly toxic. A corrosive irritant to the eyes, skin, and mucous membranes. Will react with water, steam, or acids to produce heat, toxic and corrosive fumes. Violent reaction or ignition with calcium hydroxide + sodium carbonate, phenylpropanol, sulfuric acid, oleum, fluorosulfuric acid, chlorosulfuric acid, 1,1,1-tris(hydroxymethyl)methane, water, potassium, sodium, RuO4. When heated to decomposition it emits very toxic fumes of Br− and POx. See also PHOSPHIDES and BROMIDES.
Hazard Codes of Phosphorus tribromide (CAS NO.7789-60-8): C
Risk Statements: 34-37-40-14
R34: Causes burns.
R37: Irritating to respiratory system
R40: Limited evidence of a carcinogenic effect.
R14: Reacts violently with water.
Safety Statements: 26-45-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 3264 8/PG 2
WGK Germany: 2
RTECS: TH4460000
F: 21
HazardClass: 8
PackingGroup: II
DOT Classification: 8; Label: Corrosive
Chemical Stability: Moisture sensitive.
Conditions to Avoid: Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Carbon monoxide, oxides of phosphorus, carbon dioxide, hydrogen bromide.
Hazardous Polymerization Has not been reported.
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