2198-66-5

Basic information

• Product Name: 2-BROMO-4-TERT-BUTYLPHENOL
• Synonyms: Phenol, 2-bromo-4-(1,1-dimethylethyl)-;2-BROMO-4-TERT-BUTYLPHENOL;AKOS BBB/374;4-TERT-BUTYL-2-BROMOPHENOL;2-broMo-4-(1,1-diMethylethyl)-
• CAS NO: 2198-66-5
• Molecular Formula: C₁₀H₁₃BrO
• Molecular Weight: 229.11
• EINECS: 218-602-9
• Mol File: 2198-66-5.mol
• Article Data: 44

Chemical Properties

• Melting Point: 51°C(lit.)
• Boiling Point: 113°C/9mmHg(lit.)
• Flash Point: 102.5 °C
• Appearance: /
• Density: 1.341 g/cm³
• Vapor Pressure: 0.0179mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.65±0.18(Predicted)
• CAS DataBase Reference: 2-BROMO-4-TERT-BUTYLPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-4-TERT-BUTYLPHENOL(2198-66-5)
• EPA Substance Registry System: 2-BROMO-4-TERT-BUTYLPHENOL(2198-66-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2198-66-5(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline

Uses

2-Bromo-4-tert-butylphenol is useful synthetic compound that can be used to prepare 2-?Mesityl-?4-?tert-?butylphenol.

InChI:InChI=1/C10H13BrO/c1-10(2,3)7-4-5-9(12)8(11)6-7/h4-6,12H,1-3H3

Synthetic route

para-tert-butylphenol (98-54-4) → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
With bromine	100%
With bromine In dichloromethane at 20 - 40℃; for 20h;	100%
With bromine In tetrachloromethane; chloroform at 0℃; Inert atmosphere;	100%

para-tert-butylphenol (98-54-4) → 2,6-dibromo-4-tert-butylphenol (98-22-6) + 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
Stage #1: para-tert-butylphenol With toluene-4-sulfonic acid In methanol for 0.166667h; Stage #2: With N-Bromosuccinimide In methanol for 0.416667h;	A n/a B 90%
With N-Bromosuccinimide In water at 20℃; for 8h;
With hydrogen bromide; dihydrogen peroxide In ethanol; water for 24h; Reagent/catalyst; Solvent; Green chemistry; Overall yield = 88 %; Overall yield = 1.35 g;
With perchloric acid; 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetraphenylporphyrinato oxovanadium(IV); dihydrogen peroxide; potassium bromide In water at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst;

4-tercbutyl-cyclohexanone (98-53-3) → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
With diethyl dibromomalonate at 100℃; for 48h; Bromination; aromatization;	76%

6-Bromo-4-tert-butyl-cyclohexa-2,4-dienone (117615-48-2) → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
In dichloromethane for 0.25h; Irradiation;

p-tert-butyl-phenol sodium → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
With carbon disulfide; bromine

phenol (108-95-2) → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: bei Siedetemperatur 2: tetrachloromethane; bromine / 0 °C View Scheme

aqueous Na2SO3 + para-tert-butylphenol (98-54-4) → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
With bromine; sodium hydrogencarbonate In chloroform

para-tert-butylphenol (98-54-4) + trifluoroacetic acid (76-05-1) → 2-bromo-4-tert-butylphenol (2198-66-5) + C12H13F3O2

Conditions	Yield
With copper(I) bromide at 20℃; for 6h;	A 10 %Chromat. B 35 %Chromat.

para-tert-butylphenol (98-54-4) → 4-(tert-butyl)phenyl acetate (3056-64-2) + 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
With copper(I) bromide In acetic acid at 80℃; for 6h;	A 15 %Chromat. B 47 %Chromat.

2,4-di-tert-Butylphenol (96-76-4) → 2-bromo-4-tert-butylphenol (2198-66-5) + C12H13F3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: copper dichloride / formic acid / 6 h / 80 °C 2: copper(I) bromide / 6 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium chloride / 6 h / 20 °C 2: copper(I) bromide / 6 h / 20 °C View Scheme

2,4-di-tert-Butylphenol (96-76-4) → 4-(tert-butyl)phenyl acetate (3056-64-2) + 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper dichloride / formic acid / 6 h / 80 °C 2: copper(I) bromide / acetic acid / 6 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: sodium chloride / 6 h / 20 °C 2: copper(I) bromide / acetic acid / 6 h / 80 °C View Scheme

2,4-di-tert-Butylphenol (96-76-4) → 2-bromo-4-tert-butylphenol (2198-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper dichloride / formic acid / 6 h / 80 °C 2: copper(I) bromide / acetic acid / 6 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: sodium chloride / 6 h / 20 °C 2: copper(I) bromide / acetic acid / 6 h / 80 °C View Scheme

2-bromo-4-tert-butylphenol (2198-66-5) + methyl iodide (74-88-4) → 2-bromo-4-tert-butylanisole (41280-65-3)

Conditions	Yield
With potassium carbonate In acetone for 22h; Inert atmosphere; Reflux;	100%
With potassium carbonate In acetone Reflux;	97%
With potassium carbonate In acetone at 65℃; for 20h; Inert atmosphere;	16.1 g

2-bromo-4-tert-butylphenol (2198-66-5) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → (2-((2-bromo-4-(tert-butyl)phenoxy)methoxy)ethyl)trimethylsilane

Conditions	Yield
With N,N-diethyl-N-isopropylamine In dichloromethane at 0 - 20℃;	98%

2-bromo-4-tert-butylphenol (2198-66-5) → 2-deutero-4-tert-butylphenol (159591-91-0)

Conditions	Yield
Stage #1: 2-bromo-4-tert-butylphenol With n-butyllithium In diethyl ether at -78 - 20℃; Inert atmosphere; Stage #2: With water-d2 In diethyl ether Inert atmosphere;	97%

2-bromo-4-tert-butylphenol (2198-66-5) + benzyl bromide (100-39-0) → 1-benzyloxy-2-bromo-4-tert-butylbenzene (52458-11-4)

Conditions	Yield
With potassium carbonate In acetone for 48h; Heating;	96%
With potassium carbonate In acetone for 3h; Inert atmosphere; Reflux;	94%

2-bromo-4-tert-butylphenol (2198-66-5) + ethyl bromoacetate (105-36-2) → (2-bromo-4-tert-butyl-phenoxy)-acetic acid ethyl ester (953091-05-9)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃;	96%

1-Bromoheptane (629-04-9) + 2-bromo-4-tert-butylphenol (2198-66-5) → 2-bromo-4-tert-butylphenyl heptyl ether (65456-43-1)

Conditions	Yield
With potassium carbonate In acetone	85%

2-bromo-4-tert-butylphenol (2198-66-5) + (1R,8S)-1-(dimethylamino)-2-phenyl-2,7-diaza-1-phosphabicyclo[3.3.0]octane (232618-88-1) → (2R,5S)-2-(2-bromo-4-tert-butylphenoxy)-3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.01,5]octane (887280-31-1)

Conditions	Yield
In toluene for 1h;	85%

Benzyl isocyanide (88333-03-3, 10340-91-7) + 2-bromo-4-tert-butylphenol (2198-66-5) → 8-(tert-butyl)-2,3-diphenylbenzofuro[2,3-b]pyrazine

Conditions	Yield
With potassium phosphate In 1,4-dioxane at 130℃; for 8h; chemoselective reaction;	85%

2-bromo-4-tert-butylphenol (2198-66-5) + phenylboronic acid (98-80-6) → 4-tert-butyl-2-phenylphenol (577-92-4)

Conditions	Yield
With potassium hydrogenphosphate trihydrate; 2C2H3O2(1-)*2C6H7N3O2(2-)*2Na(1+)*Pd(2+) In methanol; water at 70℃; for 2.5h; Suzuki coupling;	84%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water Suzuki Coupling; Reflux;	64%
With 2 mol-% Pd/C; cesium fluoride In water at 80℃; for 2.5h; Suzuki-Miyaura Coupling; Schlenk technique;	36%
With palladium diacetate; diisopropylamine In water at 100℃; Suzuki-Miyaura Coupling;

2-bromo-4-tert-butylphenol (2198-66-5) + prenyl bromide (870-63-3) → 2-bromo-4-(tert-butyl)-1-((3-methylbut-2-en-1-yl)oxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Schlenk technique;	83%

2-bromo-4-tert-butylphenol (2198-66-5) + allyl bromide (106-95-6) → 1-(allyloxy)-2-bromo-4-(tert-butyl)benzene (872195-32-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 23 - 27℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox;	82%
With potassium carbonate In acetone Reflux;

[(2)H6]acetone (666-52-4) + 2-bromo-4-tert-butylphenol (2198-66-5) → 4-(tert-butyl)-2-(2-hydroxypropan-2-yl-1,1,1,3,3,3-d6)phenol

Conditions	Yield
With n-butyllithium In tert-butyl methyl ether Solvent; Inert atmosphere;	82%

2-bromo-4-tert-butylphenol (2198-66-5) → 2-hydroxybromobenzene (95-56-7) + 4-tert-butyltoluene (98-51-1)

Conditions	Yield
With Nafion-H; toluene for 8h; Heating;	A 80% B 83 % Chromat.

2-bromo-4-tert-butylphenol (2198-66-5) + toluene (108-88-3) → 2-hydroxybromobenzene (95-56-7) + 4-tert-butyltoluene (98-51-1)

Conditions	Yield
With Nafion-H for 8h; Heating;	A 80% B 83 % Chromat.

2-bromo-4-tert-butylphenol (2198-66-5) + sodium methylate (124-41-4) → 4-t-butyl-2-methoxyphenol (37987-27-2)

Conditions	Yield
With copper dichloride In N,N-dimethyl-formamide for 1.5h; Heating;	80%
With copper dichloride In N,N-dimethyl-formamide for 4.5h; Reflux;	79%

2-bromo-4-tert-butylphenol (2198-66-5) + cesium trifluoromethanethiolate → 5-(tert-butyl)-2,2-difluorobenzo[d][1,3]oxathiole

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; cesium fluoride In acetonitrile at 100℃; for 4h; Inert atmosphere; Glovebox; Sealed tube;	80%

(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)benzene (34091-69-5, 34093-70-4, 104696-00-6) + 2-bromo-4-tert-butylphenol (2198-66-5) → 5-tert-butyl-2-phenyl-3-(trifluoromethyl)benzofuran (1565868-53-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; XPhos In N,N-dimethyl-formamide at 140℃; for 36h; Inert atmosphere; Schlenk technique;	79%

2-bromo-4-tert-butylphenol (2198-66-5) + ethyl 2,4-bis(chloromethyl)-6-iodoquinoline-3-carboxylate → 2,4‑bis((2‑bromo‑4‑(tert‑butyl)phenoxy)methyl)‑6‑iodoquinoline‑3‑carboxylic acid

Conditions	Yield
Stage #1: 2-bromo-4-tert-butylphenol; ethyl 2,4-bis(chloromethyl)-6-iodoquinoline-3-carboxylate With potassium carbonate In acetonitrile for 5h; Reflux; Stage #2: With potassium hydroxide In ethanol; water for 3h; Microbiological reaction;	79%

2-bromo-4-tert-butylphenol (2198-66-5) + methanesulfonic acid 2-(2-methoxyethoxy)ethyl ester (60696-83-5) → 2-bromo-4-tert-butyl-1-[2-(2-methoxyethoxy)ethoxy]benzene (1407968-87-9)

Conditions	Yield
With caesium carbonate In acetonitrile for 48h; Reflux;	76.1%

Upstream product

• 98-54-4 para-tert-butylphenol 
• 96-76-4 2,4-di-tert-Butylphenol 
• 76-05-1 trifluoroacetic acid 
• 108-95-2 phenol 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 117615-48-2 6-Bromo-4-tert-butyl-cyclohexa-2,4-dienone 

Downstream Products

• 35154-03-1 propionic acid-(2-bromo-4-tert-butyl-phenyl ester) 
• 854259-90-8 (2-bromo-4-tert-butyl-phenyl)-(4-chloro-benzyl)-ether 
• 100792-28-7 butyric acid-(2-bromo-4-tert-butyl-phenyl ester) 
• 104132-85-6 3-<3-(4-tert-Butyl-2-bromphenoxy)propyl>pyridin 
• 95-56-7 2-hydroxybromobenzene 
• 98-51-1 4-tert-butyltoluene 
• 52570-06-6 (2-Bromo-4-tert-butyl-phenoxy)-acetic acid hydrazide 
• 6640-46-6 NSC 48881 
• 37987-27-2 4-t-butyl-2-methoxyphenol 
• 1022150-32-8 C₂₈H₄₀OSi₂ 
• 41280-65-3 2-bromo-4-tert-butylanisole 
• 1082945-64-9 C₁₂H₁₅BrO₂ 
• 1379658-50-0 rac-1-(2-bromo-4-(tert-butyl)phenoxy)-4-(2-phenoxyphenyl)but-3-yn-2-ol 
• 1379658-82-8 2-(2-bromo-4-(tert-butyl)phenoxy)ethanol 

Relevant articles and documents

Selective metalation of phenol-type proligands for preparative organometallic chemistry

The selective C-metalation of phenol ester derived proligands is a readily applicable addition to state-of-the-art protocols toward cyclometalated structures, in particular of the base metals. The approach is demonstrated by the ortho-nickelation of a 1,10-phenanthroline based strong-field ligand platform that is a sought-after motif in the field of base-metal photochemistry.

Selective Bromination of β-Positions of Porphyrin by Self-Catalytic Behaviour of VOTPP: Facile Synthesis, Electrochemical Redox Properties and Catalytic Application

Oxidovanadium(IV) complex of β-octabromo-meso-tetraphenylporphyrin, {[VIVO(TPPBr8)], 2} was synthesized by self-catalytic oxidative bromination of meso-tetraphenylporphyrinatooxidovanadium(IV) {[VIVO(TPP), 1} in excellent yield under mild conditions at 25 °C and its structure was confirmed by single crystal X-ray study. UV-Vis and 1H NMR spectra further confirmed that the meso-phenyl rings are not brominated and thus emphasizes on the selectivity as well as synthetic importance of this catalytic method. In the presence of substrates e. g. phenol derivatives, 1 biomimics the vanadium bromoperoxidase (VBPO) enzyme and catalyses the oxidative bromination of substrates in water at 25 °C. Remarkably, 2 also catalyses the oxidative bromination of phenol derivatives under similar reaction conditions with very high turnover frequency (TOF) values (ca. 29 s?1) along with its recyclability. It was found that 2 showed superior catalytic performance as compared to 1 because of its electron deficient nature due to electron withdrawing bromo substituents and robust saddle shaped nonplanar structure (further supported by DFT studies).

Regioselective monobromination of phenols with KBr and ZnAl–BrO3?–layered double hydroxides

The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO3?–layered double hydroxides (abbreviated as ZnAl–BrO3?–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols.