3972-65-4

Basic information

• Product Name: 1-Bromo-4-tert-butylbenzene
• Synonyms: P-BROMO-T-BUTYLBENZENE;P-BROMO-TERT-BUTYLBENZENE;4-TERT-BUTYLBROMOBENZENE;4-BROMO-TERT-BUTYLBENZENE;2-(4'-BROMOPHENYL)-2-METHYLPROPANE;1-BROMO-P-T-BUTYLBENZENE;1-BROMO-4-T-BUTYLBENZENE;1-BROMO-4-TERT-BUTYLBENZENE
• CAS NO: 3972-65-4
• Molecular Formula: C₁₀H₁₃Br
• Molecular Weight: 213.11
• EINECS: 223-599-2
• Product Categories: Halides;Phenyls & Phenyl-Het;Bromine Compounds;Phenyls & Phenyl-Het;Aryl;C9 to C12;Halogenated Hydrocarbons
• Mol File: 3972-65-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 13-16 °C(lit.)
• Boiling Point: 80-81 °C2 mm Hg(lit.)
• Flash Point: 97 °C
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.229 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0916mmHg at 25°C
• Refractive Index: n20/D 1.533(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 1859117
• CAS DataBase Reference: 1-Bromo-4-tert-butylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-tert-butylbenzene(3972-65-4)
• EPA Substance Registry System: 1-Bromo-4-tert-butylbenzene(3972-65-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3972-65-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

1-Bromo-4-tert-butylbenzene was used in the synthesis of 4-tert-butyl-phenylboronic acid1, 1-deoxy analogs of CP-47,497 (n = 0 to 7) and 1-deoxy analogs of CP-55,940 (n = 0 to 7). It undergoes lithium-bromide exchange reactions with n-butyllithium and tert-butyllithium at 0°C in various solvents.

General Description

1-Bromo-4-tert-butylbenzene undergoes lithium-bromide exchange reactions with n-butyllithium and tert-butyllithium at 0°C in various solvents.

Synthetic route

tert-butylbenzene (253185-03-4, 253185-04-5) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With bromine; iodine at 0℃;	100%
With carbon dioxide; bromine at 40℃; under 187519 Torr; for 2h; Supercritical conditions; Green chemistry;	100%
With benzyltrimethylazanium tribroman-2-uide; zinc(II) chloride In acetic acid at 70℃; for 2h;	95%

para-bromoacetophenone (99-90-1) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
	97%

2-(4-tert-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (214360-66-4) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With copper(ll) bromide In methanol Heating;	96%

bromobenzene (108-86-1) + 3,6-di-tert-butylbenzene-1,2-diol (15512-06-8) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With sulfuric acid	90%

p-trifluoromethylphenyl bromide (402-43-7) + trimethylaluminum (75-24-1) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
In hexane; 1,2-dichloro-ethane at 25 - 50℃; Inert atmosphere;	89%

bromobenzene (108-86-1) + pivaloyl chloride (3282-30-2) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 1-(4-bromophenyl)-2,2-dimethylpropan-1-one (30314-45-5)

Conditions	Yield
With iodine for 0.166667h; Ambient temperature; Irradiation;	A 8% B 87%
With iron(III) sulfate In hexane at 20℃; for 0.75h; Friedel-Crafts acylation; Sonication;	A 8% B 72%
With aluminium trichloride In hexane for 0.166667h; Ambient temperature; Irradiation;	A 25% B 50%

4-tert-butylphenyl triflate (154318-75-9) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With [Cp*Ru(CH3CN)3]OTf; lithium bromide at 120℃; for 48h; Inert atmosphere;	87%
Multi-step reaction with 2 steps 1: 86 percent / Et3N / PdCl2(dppf) / dioxane / Heating 2: 96 percent / aq. CuBr2 / methanol / Heating View Scheme

potassium (4-tert-butyl)phenyltrifluoroborate → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	86%
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	86%

(P(o-tol)3)2Pd2(C6H4tBu-4)2Br2 (176780-03-3, 164927-39-3) + tri-tert-butyl phosphine (13716-12-6) → bis(tri-t-butylphosphine)palladium(0) (53199-31-8) + 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
In benzene-d6 byproducts: P(o-tol)3, biaryl, arene; in C6D6 soln. at 70°C; K(eq) = 3.3(6)E-4;	A n/a B 75%

bromobenzene (108-86-1) + pivaloyl chloride (3282-30-2) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 1-(2-bromophenyl)-2,2-dimethyl-propan-1-one (61593-14-4) + 1-(4-bromophenyl)-2,2-dimethylpropan-1-one (30314-45-5)

Conditions	Yield
With iodine for 6h; Ambient temperature;	A 64% B 6% C 17%
With aluminium trichloride In hexane for 5h; Ambient temperature;	A 42% B 5% C 12%

bromobenzene (108-86-1) + t-butyl bromide (507-19-7) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With o-tetrachloroquinone; C16H21IMoO3 In 1,2-dichloro-ethane at 80℃; for 12h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Green chemistry; regioselective reaction;	21.3%

4-tert-Butylaniline (769-92-6) + allyl bromide (106-95-6) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 1-allyl-4-(tert-butyl)benzene (27798-45-4)

Conditions	Yield
With tert.-butylnitrite In acetonitrile at 45 - 50℃; for 1.33h;	A n/a B 19%

bromobenzene (108-86-1) + tertiary butyl chloride (507-20-0) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With o-tetrachloroquinone; C16H21IMoO3 In 1,2-dichloro-ethane at 80℃; for 12h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Green chemistry; regioselective reaction;	17.2%
(i) AlCl3, MeNO2, (ii) /BRN= 1730872/; Multistep reaction;

bromobenzene (108-86-1) + 2-methyl-propan-1-ol (78-83-1) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With phosphoric acid at 160 - 170℃;

tert-butylbenzene (253185-03-4, 253185-04-5) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 2-tert-butylbromobenzene (7073-99-6)

Conditions	Yield
With thallium (III) oxide; trifluoroacetic acid; potassium bromide at 20℃; for 6h;
With bromine In hexane at 25℃; for 0.0333333h; Darkness;
With bromine; iodine

1,4-di-tert-butylbenzene (1012-72-2) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With tetrachloromethane; bromine; iron

bromobenzene (108-86-1) + isobutyryl chloride (513-36-0) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With aluminium trichloride

bromobenzene (108-86-1) + tert-butyl alcohol (75-65-0) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With chlorosulfonic acid

tert-butylbenzene (253185-03-4, 253185-04-5) + bromine (7726-95-6) + acetic acid (64-19-7) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 1-bromo-3-(tertbutyl)benzene (3972-64-3) + 2-tert-butylbromobenzene (7073-99-6)

Conditions	Yield
at 25℃; Kinetics;

perchloric acid (7601-90-3) + tert-butylbenzene (253185-03-4, 253185-04-5) + hypobromous acid + aqueous dioxane → 1-bromo-4-tert-butylbenzene (3972-65-4) + 1-bromo-3-(tertbutyl)benzene (3972-64-3) + 2-tert-butylbromobenzene (7073-99-6)

Conditions	Yield
at 25℃; Kinetics;

tert-butylbenzene (253185-03-4, 253185-04-5) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 1,3-di-tert-butylbenzene (1014-60-4) + 1-bromo-3-(tertbutyl)benzene (3972-64-3) + 2-tert-butylbromobenzene (7073-99-6) + HBr

Conditions	Yield
With bromine at 25℃; for 20h; Irradiation; Yield given;

para-tert-butylphenol (98-54-4) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C 2: 86 percent / Et3N / PdCl2(dppf) / dioxane / Heating 3: 96 percent / aq. CuBr2 / methanol / Heating View Scheme

benzene (71-43-2) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 2: AlCl3 / 45 °C 3: iron-turnings; tetrachloromethane; bromine View Scheme
Multi-step reaction with 3 steps 1: aqueous H2SO4 2: AlCl3 / 45 °C 3: iron-turnings; tetrachloromethane; bromine View Scheme
Multi-step reaction with 2 steps 1: aqueous H2SO4 2: iron-turnings; tetrachloromethane; bromine View Scheme
Multi-step reaction with 2 steps 1: AlCl3 / 15 - 22 °C 2: iron-turnings; tetrachloromethane; bromine View Scheme
Multi-step reaction with 2 steps 1: HCl; AlCl3 / 60 °C / Einleiten von Isobutylen 2: iron-turnings; tetrachloromethane; bromine View Scheme

3-Formylphenylboronic acid (87199-16-4) → 1-bromo-4-tert-butylbenzene (3972-65-4)

(4-tert-butylphenyl)diazonium tetrafluoroborate (52436-75-6) → tert-butylbenzene (253185-03-4, 253185-04-5) + 1-bromo-4-tert-butylbenzene (3972-65-4) + 1-tert-butyl-4-fluorobenzene (701-30-4)

Conditions	Yield
With trimethylsilyl bromide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃;	A 9 % Chromat. B 31 % Chromat. C 42 % Chromat.

bromobenzene (108-86-1) + t-butyl bromide (507-19-7) → 1-bromo-4-tert-butylbenzene (3972-65-4) + 2-tert-butylbromobenzene (7073-99-6)

Conditions	Yield
With o-tetrachloroquinone; C16H21IMoO3 In 1,2-dichloro-ethane at 80℃; for 12h; Friedel-Crafts Alkylation; Inert atmosphere; Schlenk technique; Green chemistry; Overall yield = 25.1 %; regioselective reaction;

4-tert-Butylaniline (769-92-6) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
Stage #1: 4-tert-Butylaniline With hydrogenchloride; tert.-butylnitrite In methanol; diethyl ether; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: With Bromotrichloromethane; tetrabutylammonium perchlorate In methanol; diethyl ether; N,N-dimethyl-formamide at 20℃; for 3h; Sandmeyer Reaction; Electrochemical reaction;	53 %Chromat.

bis(4-fluorophenyl)methanone O-(4-(tert-butyl)benzoyl) oxime → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions	Yield
With Bromotrichloromethane; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In ethyl acetate for 12h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Irradiation;	74 %Chromat.

4-(1,1-dimethylethyl)benzoic acid (98-73-7) → 1-bromo-4-tert-butylbenzene (3972-65-4)

Conditions

Yield

Multi-step reaction with 2 steps 1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere; Schlenk technique 2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; Bromotrichloromethane / ethyl acetate / 12 h / Schlenk technique; Inert atmosphere; Irradiation View Scheme

1-bromo-4-tert-butylbenzene (3972-65-4) + 2-Methylphenylboronic acid (16419-60-6) → 2-methyl-4'-tert-butylbiphenyl

Conditions	Yield
With potassium phosphate; palladium-incarcerated polystyrene-based copolymer; tris(o-methoxyphenyl)phosphine In water; toluene for 2h; Suzuki-Miyaura coupling; Heating;	100%
With C25H29N3; potassium carbonate; palladium dichloride In water; N,N-dimethyl-formamide at 90℃; for 2h; Suzuki-Miyaura Coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In toluene at 110℃; for 1.5h; Suzuki-Miyaura reaction;	98%

1-bromo-4-tert-butylbenzene (3972-65-4) + phenylboronic acid (98-80-6) → 4-tert-butylbiphenyl (1625-92-9)

Conditions	Yield
With potassium phosphate; phosphinated polymer incarcerated palladium catalyst In water; toluene for 4h; Suzuki-Miyaura coupling; Heating;	100%
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Catalytic behavior; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium carbonate In water; isopropyl alcohol at 100℃; for 10h; Suzuki-Miyaura Coupling; Inert atmosphere;	99%

1-bromo-4-tert-butylbenzene (3972-65-4) + diphenylamine (122-39-4) → N,N-diphenyl-N-(4-tert-butylphenyl)amine (36809-23-1)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); potassium tert-butylate In toluene at 20℃; for 4h;	100%
With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃;	96%
for 3h;	96%

1-bromo-4-tert-butylbenzene (3972-65-4) + [(4-(2,2'-bithiophenyl-5-yl)phenyl)-p-tolyl]amine → [(4-(2,2'-bithiophenyl-5-yl)phenyl)-(4-tert-butylphenyl)-p-tolyl]amine

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h;	99.7%

1-bromo-4-tert-butylbenzene (3972-65-4) + [(4-(2,2'-bithiophenyl-5-yl)phenyl)-(4-methoxyphenyl)]amine → [(4-(2,2'-bithiophenyl-5-yl)phenyl)-(4-tert-butylphenyl)-(4-methoxyphenyl)]amine

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h;	99.6%

1-bromo-4-tert-butylbenzene (3972-65-4) + [(4-(2,2'-bithiophenyl-5-yl)phenyl)-(4-fluorophenyl)]amine → [(4-(2,2'-bithiophenyl-5-yl)phenyl)-(4-tert-butylphenyl)-(4-fluorophenyl)]amine

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 12h;	99.6%

poly(methacrylic acid) (79-41-4) + 1-bromo-4-tert-butylbenzene (3972-65-4) → C14H17O2(1-)*Na(1+)

Conditions	Yield
Stage #1: poly(methacrylic acid) With sodium carbonate In water Stage #2: With palladium dichloride Stage #3: 1-bromo-4-tert-butylbenzene With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In water at 130 - 135℃; under 9000.9 - 12001.2 Torr; for 2h; Autoclave; Inert atmosphere;	99.6%

1-bromo-4-tert-butylbenzene (3972-65-4) → tert-butylbenzene (253185-03-4, 253185-04-5)

Conditions	Yield
With potassium phosphate In N,N-dimethyl-formamide; cyclohexanol at 110℃; for 12h;	99%
With n-butyllithium; samarium diiodide; dipyrrolidinomethylaminophosphoric acid triamide; tert-butyl alcohol In tetrahydrofuran; hexane at -66 - 21℃;	94%
With triethylamine In acetonitrile at 20℃; for 15h; Irradiation; Inert atmosphere;	84%

1-bromo-4-tert-butylbenzene (3972-65-4) → 4,4'-di-tert-butylbiphenyl (1625-91-8)

Conditions	Yield
With tetraethylammonium tosylate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide Ambient temperature; electrolysis;	99%
With DPEPhos; potassium tert-butylate; palladium diacetate; bis(pinacol)diborane for 12h; Heating;	99%
With potassium carbonate In ethanol; water at 80℃; for 4h; Ullmann Condensation; Schlenk technique; Sealed tube;	88%

1-bromo-4-tert-butylbenzene (3972-65-4) + copper(I) cyanide (544-92-3) → 4-tert-butyl benzonitrile (4210-32-6)

Conditions	Yield
Stage #1: 1-bromo-4-tert-butylbenzene; copper(I) cyanide In N,N-dimethyl-formamide for 8h; Heating; Stage #2: With hydrogenchloride; iron(III) chloride In water; N,N-dimethyl-formamide at 70℃; for 0.5h;	99%
In N,N-dimethyl-formamide for 5h; Heating;	71%

1-bromo-4-tert-butylbenzene (3972-65-4) + phenol (108-95-2) → 1-tert-butyl-4-phenoxybenzene (5331-28-2)

Conditions	Yield
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; sodium hydride; bis(dibenzylideneacetone)-palladium(0) In o-xylene at 110℃; for 18h; Inert atmosphere;	99%
With caesium carbonate; copper(l) iodide In 1-methyl-pyrrolidin-2-one at 195℃; for 2h; microwave irradiation;	89%
With potassium phosphate; copper(l) iodide; N,N′-bis(2-phenylphenyl)oxalamide In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	88%
With copper(I) trifluoromethanesulfonate benzene; 1-naphthalenecarboxylic acid; caesium carbonate; ethyl acetate In toluene at 110℃;	81%

morpholine (110-91-8) + 1-bromo-4-tert-butylbenzene (3972-65-4) → 4-(4-(tert-butyl)phenyl)morpholine (84736-47-0)

Conditions	Yield
With sodium t-butanolate; 1-(2-di-isopropylphosphinophenyl)-3,5-diphenyl-1H-pyrazole; tris(dibenzylideneacetone)dipalladium (0) In toluene at 85℃;	99%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃; for 5h;	99%
With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃;	99%

1-bromo-4-tert-butylbenzene (3972-65-4) + aniline (62-53-3) → 4-tert-butyldiphenylamine (4496-49-5)

Conditions	Yield
With palladium diacetate; P(i-BuNCH2CH2)3N; sodium t-butanolate In toluene at 80℃;	99%
With potassium tert-butylate; (ϖ-allyl)(diphosphinecyclobutene)palladium at 20℃; for 12h;	97%
With tris-(dibenzylideneacetone)dipalladium(0); (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); sodium t-butanolate In toluene at 80℃; for 21h; Schlenk technique; Inert atmosphere;	95%

1-bromo-4-tert-butylbenzene (3972-65-4) → 1-Bromo-4-tert-butyl-2-nitro-benzene (70729-05-4)

Conditions	Yield
With sulfuric acid; nitric acid at 20℃; for 12h;	99%
With sulfuric acid; nitric acid	95%
With sulfuric acid; nitric acid Inert atmosphere;	95%

1-bromo-4-tert-butylbenzene (3972-65-4) → 4-tert-Butylaniline (769-92-6)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); lithium hexamethyldisilazane; CyJohnPhos In tetrahydrofuran at 65℃; for 15h;	99%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;	90%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 6h; Inert atmosphere;	88%

hexan-1-amine (111-26-2) + 1-bromo-4-tert-butylbenzene (3972-65-4) → N,N-di(4-tert-butylphenyl)-n-hexylamine

Conditions	Yield
With monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; palladium compound; sodium t-butanolate In toluene at 100℃; for 4h;	99%
With sodium t-butanolate; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; palladium diacetate In toluene	99%

1-bromo-4-tert-butylbenzene (3972-65-4) + phenethylamine (64-04-0) → N-(4-tert-butylphenyl)-N-(2-phenylethyl)amine

Conditions	Yield
With sodium t-butanolate; 1-(di-2-tert-butylphosphinophenyl)-2,5-diphenyl-1H-pyrrole; tris(dibenzylideneacetone)dipalladium (0) In toluene at 85℃;	99%
With 5-(di-t-butylphosphanyl)-1-naphthalen-1-yl-1H-pyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃;	90%

1-bromo-4-tert-butylbenzene (3972-65-4) + 2,6-dimethylaniline (87-62-7) → N-(4-(tert-butyl)phenyl)-2,6-dimethylaniline

Conditions	Yield
With sodium t-butanolate; 1-(2-di-tert-butylphosphinophenyl)-3,5-diphenyl-1H-pyrazole; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol at 85℃;	99%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃; for 5h;	99%
With sodium t-butanolate; dicyclohexyl[2-(1-phenylvinyl)phenyl]phosphane; palladium diacetate In toluene at 100℃;	72%

1-bromo-4-tert-butylbenzene (3972-65-4) + tri-n-butyl(vinyl)tin (7486-35-3) → 4-tert-Butylstyrene (1746-23-2)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); 2,8,9-tribenzyl-2,3,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane; cesium fluoride In tetrahydrofuran at 20℃; for 10h; Stille cross-coupling;	99%
With cesium fluoride; palladium diacetate In 1,4-dioxane at 100℃; for 3h; Stille cross-coupling;	99%
With bis(tri-t-butylphosphine)palladium(0) In water at 20℃; for 4h; Stille Cross Coupling; Inert atmosphere;	92%

1-bromo-4-tert-butylbenzene (3972-65-4) + rac-methylbenzylamine (618-36-0) → 4-(tert-butyl)-N-(1-phenylethyl)aniline

Conditions	Yield
With 5-(di-t-butylphosphanyl)-1-naphthalen-1-yl-1H-pyrazole; potassium hydroxide; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol; water at 90℃;	99%

1-bromo-4-tert-butylbenzene (3972-65-4) + di-4-methoxyphenylzinc (97302-05-1) → 4-tert-butyl-4'-methoxylbiphenyl

Conditions	Yield
With catalyst 1 (aliphatic, phosphine based pincer complex of palladium) In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 100℃; for 0.25h; Negishi cross-coupling reaction;	99%

4-benzyl pyridine (2116-65-6) + 1-bromo-4-tert-butylbenzene (3972-65-4) → (4-tert-butylphenyl)(4-pyridyl)phenylmethane (1393444-74-0)

Conditions	Yield
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	99%
With BF4(1-)*C20H25N2O2(1+); palladium diacetate; sodium hexamethyldisilazane In toluene at 60℃; for 12h; Reagent/catalyst; Inert atmosphere;	96%
With BF4(1-)*C20H25N2O2(1+); palladium diacetate; sodium hexamethyldisilazane In toluene at 60℃; for 16h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	95%
With C25H21N2O(1+)*Cl(1-); palladium diacetate; sodium hexamethyldisilazane In toluene at 60℃; for 12h; Reagent/catalyst; Inert atmosphere;	89%
With bis(1,5-cyclooctadiene)nickel (0); sodium hexamethyldisilazane; nixantphos at 110℃; for 16h;	80%

2-Benzylpyridine (101-82-6) + 1-bromo-4-tert-butylbenzene (3972-65-4) → (4-tert-butylphenyl)(2-pyridyl)phenylmethane (1393444-73-9)

Conditions	Yield
With diethylene glycol dimethyl ether; NiXantphos; palladium diacetate; sodium hexamethyldisilazane at 23℃; for 12h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	99%
With bis(1,5-cyclooctadiene)nickel (0); sodium hexamethyldisilazane; nixantphos at 20℃; for 16h; Catalytic behavior; Temperature; Concentration; Time;	99%
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	96%

xanthene (92-83-1) + 1-bromo-4-tert-butylbenzene (3972-65-4) → 9-(4-tert-butylphenyl)xanthene (1393444-71-7)

Conditions	Yield
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	99%
With bis(1,5-cyclooctadiene)nickel (0); sodium hexamethyldisilazane; nixantphos at 110℃; for 16h;	81%

9H-fluorene (86-73-7) + 1-bromo-4-tert-butylbenzene (3972-65-4) → 9-(4-tert-butylphenyl)fluorene

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); sodium hexamethyldisilazane; nixantphos at 50℃; for 16h;	99%
With KN(SiMe3)2; palladium diacetate; nixantphos In tetrahydrofuran at 85℃; for 12h; Inert atmosphere;	87%

1-bromo-4-tert-butylbenzene (3972-65-4) + Diphenylmethane (101-81-5) → ((4-(tert-butyl)phenyl)methylene)dibenzene (26167-26-0)

Conditions	Yield
With 15-crown-5; NiXantphos; palladium diacetate; sodium hexamethyldisilazane at 23℃; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Concentration; Glovebox; Inert atmosphere; Sealed tube;	99%
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	95%
Stage #1: 1-bromo-4-tert-butylbenzene; Diphenylmethane With palladium diacetate; potassium hexamethylsilazane; nixantphos at 24℃; for 12h; Inert atmosphere; Glovebox; Stage #2: With depe at 24℃; for 0.666667h;	91%

1-bromo-4-tert-butylbenzene (3972-65-4) + 1-Benzyl-naphthalene (611-45-0) → (4-tert-butylphenyl)(1-naphthyl)phenylmethane (1393444-66-0)

Conditions	Yield
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	99%

1-bromo-4-tert-butylbenzene (3972-65-4) + 4-fluorodiphenylmethane (587-79-1) → (4-tert-butylphenyl)(4-fluorophenyl)phenylmethane (1393444-68-2)

Conditions	Yield
With 1,1,4,7,10,10-hexamethyltriethylenetetramine; NiXantphos; palladium diacetate; sodium hexamethyldisilazane at 23℃; for 12h; Catalytic behavior; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube;	99%
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	96%

1-bromo-4-tert-butylbenzene (3972-65-4) + 2-benzylthiophene (13132-15-5) → (4-tert-butylphenyl)(2-thienyl)phenylmethane (1393444-77-3)

Conditions	Yield
With KN(SiMe3)2; palladium diacetate; nixantphos In cyclopentyl methyl ether at 24℃; for 12h; Inert atmosphere;	99%

Upstream product

• 108-86-1 bromobenzene 
• 78-83-1 2-methyl-propan-1-ol 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 15512-06-8 3,6-di-tert-butylbenzene-1,2-diol 
• 3282-30-2 pivaloyl chloride 
• 253185-03-4 tert-butylbenzene 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 7601-90-3 perchloric acid 
• 98-54-4 para-tert-butylphenol 
• 99-90-1 para-bromoacetophenone 
• 52436-75-6 (4-tert-butylphenyl)diazonium tetrafluoroborate 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 769-92-6 4-tert-Butylaniline 

Downstream Products

• 65276-29-1 4-Brom-3-chlormethyl-tert.-butyl-benzol 
• 17595-96-9 2-<4-(1,1-Dimethylethyl)phenyl>thiophene 
• 121443-25-2 (4-Anisyl)(4-tert-butylphenyl)phenylmethanol 
• 106910-88-7 1,4-dihydro-3,6-diphenyl-1-(p-t-butylphenyl)-s-tetrazine 
• 125016-84-4 4-chlorophenylbis(4-t-butylphenyl)methanol 
• 79653-82-0 9-(4-(tert-butyl)phenyl)-9H-fluoren-9-ol 
• 93741-49-2 1-tert-Butyl-4-(3,7-dimethyl-oct-6-enyl)-benzene 
• 121443-13-8 (4-Biphenylyl)(4-tert-butylphenyl)phenylmethanol 
• 154710-48-2 di(1-adamantyl)-p-(tert-butyl)phenylmethanol 
• 128881-98-1 1-tert-Butyl-4-((E)-5,9-dimethyl-deca-4,8-dienyl)-benzene 
• 6934-33-4 tris(4-(tert-butyl)phenyl)methanol 
• 121443-23-0 (4-tert-Butylphenyl)(4-phenoxyphenyl)phenylmethanol 
• 125016-83-3 bis(p-tert-butylphenyl)(p-methoxyphenyl)methanol 
• 125952-12-7 4-tert-butyl-1-(1-ethoxyvinyl)benzene 

Relevant articles and documents

Photochemical Sandmeyer-type Halogenation of Arenediazonium Salts

Trihalide salts were found to efficiently promote photochemical dediazotizing halogenations of diazonium salts. In contrast to classical Sandmeyer reactions, no metal catalysts are required to achieve high yields and outstanding selectivities for halogena

Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions

Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.