608-71-9

Basic information

• Product Name: Pentabromophenol
• Synonyms: PENTABROMOHYDROXYBENZENE;PENTABROMOPHENOL;2,3,4,5,6-Pentabromophenol;Flammex 5BP;flammex5bp;Pentabromfenol;pentabromo-pheno;Phenol, pentabromo-
• CAS NO: 608-71-9
• Molecular Formula: C₆HBr₅O
• Molecular Weight: 488.59
• EINECS: 210-167-3
• Product Categories: Organics;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 608-71-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 223-226 °C(lit.)
• Boiling Point: 352.3 °C at 760 mmHg
• Flash Point: 166.9 °C
• Appearance: light brown powder
• Density: 2.894
• Vapor Pressure: 1.91E-05mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.43±0.33(Predicted)
• Water Solubility: Insoluble
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1876757
• CAS DataBase Reference: Pentabromophenol(CAS DataBase Reference)
• NIST Chemistry Reference: Pentabromophenol(608-71-9)
• EPA Substance Registry System: Pentabromophenol(608-71-9)

Safety Data

• Hazard Codes: T,N
• Statements: 23/24/25-36/37/38-50/53-50
• Safety Statements: 26-36/37-45-60-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: SM6125000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 608-71-9(Hazardous Substances Data)

Usage

Chemical Properties

light brown powder

Uses

Flame retardant, molluscicide, and chemical intermediate.

General Description

Light brown powder. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Pentabromophenol reacts as a weak acid. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat may be generated by the acid-base reaction with bases.

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES.

Purification Methods

Purify it by crystallisation pKEst (charcoal) from toluene then from CCl4. Dry it for 2 weeks at ca 75o. The diethylammonium salt has m 191-193o (from MeOH). [Beilstein 6 H 206, 6 I 108, 6 II 197, 6 III 766, 6 IV 1069.]

InChI:InChI=1/C6HBr5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H

Synthetic route

phenol (108-95-2) → Pentabromophenol (608-71-9)

Conditions	Yield
With aluminum tri-bromide; bromine for 3h; Heating;	99%
With bromine; aluminium
With aluminum tri-bromide; bromine

methoxybenzene (100-66-3) → Pentabromophenol (608-71-9)

Conditions	Yield
With aluminum tri-bromide; bromine for 3h; Heating;	98%
With bromine; aluminium bromide at 20℃; for 123h;	90%
With aluminum tri-bromide; bromine

propoxybenzene (622-85-5) → Pentabromophenol (608-71-9)

Conditions	Yield
With aluminum tri-bromide; bromine

para-tert-butylphenol (98-54-4) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine; aluminium

2,4,6-Triiodophenol (609-23-4) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine; aluminium

3,5-dibromophenol (626-41-5) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine

2,3,4,6-tetrabromophenol (14400-94-3) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine at 210 - 220℃; im geschlossenen Rohr;
With bromine; iron(III) chloride at 60℃;
Multi-step reaction with 2 steps 1: diluted KOH-solution; hydrochloric acid; bromine water 2: concentrated sulfuric acid / 150 °C View Scheme

N-(4-hydroxy-2-nitrophenyl)-acetamide (7403-75-0) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine; acetic acid

tetrabromo-p-cresol (37721-75-8) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine

2,3,4,4,6-pentabromo-cyclohexa-2,5-dienone → Pentabromophenol (608-71-9)

Conditions	Yield
With sulfuric acid at 150℃;

3,4,5,6-tetrabromo-2-hydroxybenzoic acid (35754-69-9) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine; acetic acid at 60℃;

2,4,6-Trinitrophenol (88-89-1) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine; iodine at 220 - 250℃; im Rohr;

hexabromo-cyclohexa-2,5-dienone (34946-84-4) + aniline (62-53-3) → Pentabromophenol (608-71-9) + 2,3,4-tribromoaniline (642-95-5)

Phenetole (103-73-1) → Pentabromophenol (608-71-9)

Conditions	Yield
With aluminum tri-bromide; bromine

2,4,6-tribromophenol (118-79-6) → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine at 210 - 220℃; im geschlossenen Rohr;
Multi-step reaction with 2 steps 1: bromine / 170 - 180 °C / im geschlossenen Rohr 2: bromine / 210 - 220 °C / im geschlossenen Rohr View Scheme

hexabromobenzene (87-82-1) → Pentabromophenol (608-71-9)

Conditions	Yield
(i) PhMgBr, (ii) O2; Multistep reaction;

2,3,4,5-tetrabromoanisole (6161-61-1) → Pentabromophenol (608-71-9)

Conditions	Yield
With hydrogen bromide; acetic acid

bromine (7726-95-6) + iodine (7553-56-2) + 2,4,6-Trinitrophenol (88-89-1) → Pentabromophenol (608-71-9) + hexabromobenzene (87-82-1) + 2,3,4,6-tetrabromophenol (14400-94-3)

Conditions	Yield
at 220 - 250℃;

bromine (7726-95-6) + aluminium bromide (7727-15-3) + methoxybenzene (100-66-3) → Pentabromophenol (608-71-9)

bromine (7726-95-6) + aluminium bromide (7727-15-3) + Phenetole (103-73-1) → Pentabromophenol (608-71-9)

p-cresol (106-44-5) + bromine (7726-95-6) → Pentabromophenol (608-71-9)

Conditions	Yield
unter Zutritt der Luftfeuchtigkeit;

bromine (7726-95-6) + aluminium bromide (7727-15-3) + phenol (108-95-2) → Pentabromophenol (608-71-9)

bromine (7726-95-6) + phenol (108-95-2) + aluminium → Pentabromophenol (608-71-9)

bromine (7726-95-6) + phenol (108-95-2) + iron-powder → Pentabromophenol (608-71-9)

3.5.3'.5'-tetrabromo-4.4'-dioxy-benzophenone → Pentabromophenol (608-71-9)

Conditions	Yield
With bromine at 150 - 160℃;

propoxybenzene (622-85-5) + bromine (7726-95-6) + aluminium bromide (7727-15-3) → Pentabromophenol (608-71-9)

para-tert-butylphenol (98-54-4) + bromine (7726-95-6) + aluminium → Pentabromophenol (608-71-9)

2,4,6-Triiodophenol (609-23-4) + bromine (7726-95-6) + aluminium → Pentabromophenol (608-71-9)

3,5,3',5'-tetrabromo-4,4'-dihydroxy-benzophenone (28818-29-3) + bromine (7726-95-6) → Pentabromophenol (608-71-9)

Conditions	Yield
at 150 - 160℃;

phosgene (75-44-5) + Pentabromophenol (608-71-9) → 2,3,4,5,6-pentabromophenyl carbonochloridate (87035-41-4)

Conditions	Yield
With N,N-dimethyl-aniline In dichloromethane at 0 - 20℃;	95%

Pentabromophenol (608-71-9) + methyl iodide (74-88-4) → 1,2,3,4,5-pentabromo-6-methoxybenzene (1825-26-9)

Conditions	Yield
With potassium carbonate In acetone at 99.84℃;	95%

Pentabromophenol (608-71-9) → 3,5-dibromophenol (626-41-5)

Conditions	Yield
With aluminium trichloride In benzene for 3h; Heating;	88%
With aluminum (III) chloride In benzene for 3h; Reflux; Inert atmosphere;	82%
With aluminum (III) chloride In benzene for 3h; Inert atmosphere; Reflux;	82%

Pentabromophenol (608-71-9) + dimethyl sulfate (77-78-1) → 1,2,3,4,5-pentabromo-6-methoxybenzene (1825-26-9)

Conditions	Yield
	84%
With sodium hydroxide

11-bromoundecanoic acid ethyl ester (6271-23-4) + Pentabromophenol (608-71-9) → 11-pentabromophenyloxy-undecanoic acid ethyl ester

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 10h;	83.3%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide

Pentabromophenol (608-71-9) + (S)-2-(4-bromobutyl)-1-tosylindoline → (S)-2-(4-(perbromophenoxy)butyl)-1-tosylindoline

Conditions	Yield
With potassium carbonate In acetone at 70℃; for 36h; Inert atmosphere; Sealed tube;	81.5%

1-bromo dodecane (112-29-8) + Pentabromophenol (608-71-9) → pentabromophenyl-decyl ether (623572-12-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 86h;	75%

Pentabromophenol (608-71-9) + 1-dodecylbromide (143-15-7) → 1,2,3,4,5-pentabromo-6-dodecyloxybenzene

Conditions	Yield
With potassium carbonate In butanone for 24h; Heating;	60%

Pentabromophenol (608-71-9) + perdeuterodecyl 4-toluenesulphonylate (623572-09-8) → pentabromophenyl-perdeuterodecyl ether (623572-10-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 86h;	58%

1,9-Dibromononane (4549-33-1) + Pentabromophenol (608-71-9) → 1,9-bis(pentabromophenyloxy)nonane

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	56%

1-bromo-butane (109-65-9) + Pentabromophenol (608-71-9) → butyl ether of pentabromophenol (257621-06-0)

Conditions	Yield
With sodium carbonate In acetone for 5h; Heating;	46%
With potassium carbonate; acetone; sodium iodide

Pentabromophenol (608-71-9) + C16H18O2 → perbromophenyl (E)-2-((1R,2R)-2-methyl-3',4'-dihydro-2'H-spiro[cyclobutane-1,1'-naphthalen]-3-ylidene)acetate + C22H17Br5O2

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; Inert atmosphere;	A 46% B n/a

1,11-dibromoundecane (16696-65-4) + Pentabromophenol (608-71-9) → 1,8-bis(pentabromophenyloxy)undecane

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	42%

1,8-dibromooctane (4549-32-0) + Pentabromophenol (608-71-9) → 1,8-bis(pentabromophenyloxy)octane

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	40%

Pentabromophenol (608-71-9) + 1,10-dibromodecane (4101-68-2) → 1,10-bis(pentabromophenyloxy)decane

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	38%

Pentabromophenol (608-71-9) + 1,4-di-(4''-hexyloxybenzoyloxy)-2-(11'-bromoundecyl)benzene (586343-48-8) → 1,4-di-(4''-hexyloxybenzoyloxy)-2-(11'-(pentabromophenoxy)undecyl)benzene

Conditions	Yield
With 4 A molecular sieve; sodium hydride; potassium iodide In N,N-dimethyl-formamide at 80℃; for 15h;	33%

1-undecen-11-ylbromide (7766-50-9) + Pentabromophenol (608-71-9) → 10-undecenylpentabromophenyl ether

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	27%

Pentabromophenol (608-71-9) → C6HBr3N2O5 (1400881-35-7) + 2,3,4,5-tetrabromo-6-nitrophenol (6161-57-5) + 2,3,5,6-tetrabromo-4-nitrophenol (6161-55-3) + 3,4,5-tribromo-2,6-dinitro-phenol

Conditions	Yield
With sodium nitrite In acetic acid at 20℃; for 6h;	A n/a B n/a C 22% D n/a

Pentabromophenol (608-71-9) + diphenyliodonium bromide (1483-73-4) → 2,3,4,5,6-pentrabromodiphenyl ether

Conditions	Yield
With sodium hydroxide In water Substitution;	17%

Pentabromophenol (608-71-9) + 2,2',4,4'-tetrabromodiphenyliodonium chloride → 2,2',3,4,4',5,6-heptabromodiphenylether (189084-67-1)

Conditions	Yield
With sodium hydroxide In water Substitution;	11%

Pentabromophenol (608-71-9) + 4,4'-dibromodiphenyliodonium chloride (53601-22-2) → 2,3,4,4',5,6-hexabromodiphenyl ether

Conditions	Yield
With sodium hydroxide In water Substitution;	10%

3,3'-dibromo-4,4'-difluordiphenyliodonium chloride (863314-94-7) + Pentabromophenol (608-71-9) → 4'-fluoro-2,3,3',4,5,6-hexabromodiphenyl ether

Conditions	Yield
With sodium hydroxide In water for 1.5h; Heating / reflux;	8.7%

Pentabromophenol (608-71-9) + 3,3',4,4'-tetrabromodiphenyliodonium chloride → 2,3,3',4,4',5,6-heptabromodiphenylether (189084-68-2)

Conditions	Yield
With sodium hydroxide In water Substitution;	5%

Pentabromophenol (608-71-9) → tetrabromobenzoquinone (488-48-2)

Conditions	Yield
With nitric acid

Pentabromophenol (608-71-9) → 2,4,5-tribromophenol (14401-61-7)

Conditions	Yield
With acetic acid; zinc

Pentabromophenol (608-71-9) → hexabromo-cyclohexa-2,5-dienone (34946-84-4)

Conditions	Yield
With bromine

Upstream product

• 622-85-5 propoxybenzene 
• 98-54-4 para-tert-butylphenol 
• 14400-94-3 2,3,4,6-tetrabromophenol 
• 88-89-1 2,4,6-Trinitrophenol 
• 87-82-1 hexabromobenzene 
• 7726-95-6 bromine 
• 7727-15-3 aluminium bromide 
• 100-66-3 methoxybenzene 
• 103-73-1 Phenetole 
• 106-44-5 p-cresol 
• 108-95-2 phenol 
• 28818-29-3 3,5,3',5'-tetrabromo-4,4'-dihydroxy-benzophenone 
• 7403-75-0 N-(4-hydroxy-2-nitrophenyl)-acetamide 
• 64-19-7 acetic acid 

Downstream Products

• 488-48-2 tetrabromobenzoquinone 
• 626-41-5 3,5-dibromophenol 
• 14401-61-7 2,4,5-tribromophenol 
• 34946-84-4 hexabromo-cyclohexa-2,5-dienone 
• 99980-11-7 2,3,4,5,6-pentabromo-6-chloro-cyclohexa-2,4-dienone 
• 5435-58-5 pentabromophenyl acetate 
• 38949-27-8 3-pentabromophenoxy-benzo[d]isothiazole 1,1-dioxide 
• 14666-17-2 Iminokohlensaeure-bis-<2,3,4,5,6-pentabromphenylester> 
• 95624-39-8 (1,3,5-Tri-tert-butyl-4-oxo-cyclohexa-2,5-dienyl)-pentabromphenyl-ether 
• 22849-41-8 Z-Phenylalanin-pentabrom-phenylester 
• 17199-05-2 Tris(pentabromphenoxy)silan 
• 17363-73-4 Tetrakis(pentabromphenoxy)silan 
• 17209-89-1 Bis-pentabromphenoxy-dimethyl-silan 
• 87-82-1 hexabromobenzene 

Relevant articles and documents

Preparation method of tris(pentabromophenoxy)isocyanurate

The invention relates to a preparation method of tris(pentabromophenoxy)isocyanurate. The preparation method is capable of solving technical problems in the prior art that the synthesis method is complex, the cost is high, and it is not beneficial for industrialized production. The preparation method comprises following steps: 1, preparation of a sodium pentabromophenol aqueous solution, wherein phenol is added into an organic solvent, a catalyst I is added, reaction temperature is controlled to be 0 to 5 DEG C, a brominating agent is added dropwise, thermal insulation reaction is carried outso as to obtain the sodium pentabromophenol aqueous solution; 2, preparation of tris(pentabromophenoxy)isocyanurate, wherein water and a catalyst II are introduced into a reaction container, the watertemperature is controlled to be 0 to 5 DEG C, cyanuric chloride is added, the sodium pentabromophenol aqueous solution prepared in step 1 is added dropwise, heating backflow reaction is carried out,cooling to room temperature is carried out so as to obtain tris(pentabromophenoxy)isocyanurate white powder. The preparation method is widely used in the field of fire retardant synthesis.

Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH

The reaction of 2,3,5,6-tetrabromo-4-hydroxybenzoic acid with a 10-fold excess of NaNO2 in the glacial acetic acid at 20°C affords tetrabromonitrosophenols whose further transformations under the reaction conditions leads to the formation of a mixture of 2,4,5,6-tetrabromo-p-quinone diazide and tetrabromo-p- and -o-nitrophenols in the molar ratio 37 : 2 : 1. Under similar conditions the 3,4,5,6-tetrabromo-2-hydroxybenzoic acid is converted into a mixture of 3,4,5,6-tetrabromo-o-quinone diazide with the same nitrophenols in the ratio 13 : 1 : 3. The reaction of sodium 2,3,5,6-tetrabromo-4-hydroxy-benzoate with NaNO2 in dilute acetic acid resulted in a quantitative yield of tetrabromo-p-quinone monooxime. Pleiades Publishing, Ltd., 2012.

Dichloro (acetic or propionic) acid aryl ester flame retardants

The present disclosure relates to novel compounds of the formula: STR1 where Y is a hydrogen atom or a metal group and p=1 or 2, and when p=1, STR2 n=2, 3, 4 or 5 and n+r≤5 and when p=2, STR3 m=2, 3 or 4 and m+s≤4 and q=0 or 1, where R represents a lower alkyl group containing 1 to 3 carbon atoms, and when q=1, A has the meaning of a substituted or unsubstituted alkylidene group containing 1 to 3 carbon atoms, SO2, S or O; fire retardant polymer compositions in which these compounds are incorporated, and shaped articles that are entirely or partly made up of such fire retardant polymer compositions.