7078-98-0

Basic information

• Product Name: 2,6-BIS(1,1-DIMETHYLETHYL)-4-(PHENYLMETHYLENE)-2,5-CYCLOHEXADIEN-1-ONE
• Synonyms: 2,6-BIS(1,1-DIMETHYLETHYL)-4-(PHENYLMETHYLENE)-2,5-CYCLOHEXADIEN-1-ONE;PROSTAB6007;2,5-Cyclohexadien-1-one, 2,6-bis(1,1-dimethylethyl)-4-(phenylmethylene)-;2,6-bis(i,i-dimethyethyl)-4-(phenylmethylone)-2,5-cyclohexadiene-i-0ne;2,5-Cyclohexadien-1-one,4-benzylidene-2,6-di-tert-butyl- (7CI,8CI);4-Benzylidene-2,6-di-tert-butyl-2,5-cyclohexadien-1-one;4-benzylidene-2,6-ditert-butylcyclohexa-2,5-dien-1-one;2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone
• CAS NO: 7078-98-0
• Molecular Formula: C₂₁H₂₆O
• Molecular Weight: 294.43
• EINECS: 429-460-4
• Mol File: 7078-98-0.mol
• Article Data: 51

Chemical Properties

• Melting Point: 74-75 °C
• Boiling Point: 426.1°C at 760 mmHg
• Flash Point: 183°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 1.82E-07mmHg at 25°C
• Refractive Index: 1.571
• Water Solubility: 5μg/L at 20℃
• CAS DataBase Reference: 2,6-BIS(1,1-DIMETHYLETHYL)-4-(PHENYLMETHYLENE)-2,5-CYCLOHEXADIEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-BIS(1,1-DIMETHYLETHYL)-4-(PHENYLMETHYLENE)-2,5-CYCLOHEXADIEN-1-ONE(7078-98-0)
• EPA Substance Registry System: 2,6-BIS(1,1-DIMETHYLETHYL)-4-(PHENYLMETHYLENE)-2,5-CYCLOHEXADIEN-1-ONE(7078-98-0)

Safety Data

• Hazardous Substances Data: 7078-98-0(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C21H26O/c1-20(2,3)17-13-16(12-15-10-8-7-9-11-15)14-18(19(17)22)21(4,5)6/h7-14H,1-6H3

Synthetic route

(3,5-di-tert-butyl-4-hydroxyphenyl)phenylcarbinol (20017-39-4) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
With chloro-trimethyl-silane In dichloromethane for 3h;	81%
With acetic anhydride In toluene for 0.25h; Inert atmosphere; Schlenk technique;

2,6-di-tert-butylphenol (128-39-2) + benzaldehyde (100-52-7) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Stage #1: 2,6-di-tert-butylphenol; benzaldehyde With piperidine In toluene for 3h; Reflux; Stage #2: With acetic anhydride In toluene at 110 - 125℃; for 0.5h;	79.1%
Stage #1: 2,6-di-tert-butylphenol; benzaldehyde With piperidine In toluene Reflux; Stage #2: With acetic anhydride In toluene for 0.25h;	78%
With piperidine; zinc(II) chloride In toluene Reagent/catalyst; Reflux; Dean-Stark;	77.39%

2,6-di-tert-butyl-4-(phenyl-piperidin-1-yl-methyl)-phenol (17330-09-5) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
With acetic anhydride at 120℃; for 0.05h; Microwave irradiation; Green chemistry;	70.18%

2,6-di-tert-butylphenol + benzaldehyde (100-52-7) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Stage #1: 2,6-di-tert-butylphenol; benzaldehyde With piperidine In toluene for 12h; Reflux; Inert atmosphere; Stage #2: With acetic anhydride In toluene at 100℃; for 0.5h; Inert atmosphere;	70%

4-benzyl-2,6-di-tert-butylphenol (4973-27-7) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
With potassium hydroxide; potassium hexacyanoferrate(III) In benzene

phenyllithium (591-51-5) + trans-benzylidenacetophenone → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / tetrahydrofuran; diethyl ether; cyclohexane 2: 81 percent / trimethylsilyl chloride / CH2Cl2 / 3 h View Scheme

3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / tetrahydrofuran; diethyl ether; cyclohexane 2: 81 percent / trimethylsilyl chloride / CH2Cl2 / 3 h View Scheme

2,6-di-tert-butyl-4-(di-n-propylamino-phenyl-methyl)-phenol → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
at 114℃; under 10 - 250 Torr; for 4h; Product distribution / selectivity;

2,6-di-tert-butyl-4-(di-n-butylamino-phenyl-methyl)-phenol → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
at 110 - 130℃; under 30 Torr; for 3.5 - 5h; Product distribution / selectivity;

2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: piperidine / toluene / Inert atmosphere; Schlenk technique; Reflux 2: acetic anhydride / toluene / 0.25 h / Inert atmosphere; Schlenk technique View Scheme

benzaldehyde (100-52-7) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: piperidine / toluene / Inert atmosphere; Schlenk technique; Reflux 2: acetic anhydride / toluene / 0.25 h / Inert atmosphere; Schlenk technique View Scheme

3,5-di-tert-butyl-4-hydroxybenzaldehyde + phenol (108-95-2) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
With piperidine In toluene for 4h; Dean-Stark; Reflux;

2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + benzaldehyde (100-52-7) → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
Stage #1: 2,6-di-tert-butyl-4-hydroxyphenol; benzaldehyde With piperidine In toluene for 7h; Dean-Stark; Inert atmosphere; Reflux; Stage #2: With acetic anhydride In toluene for 0.5h; Dean-Stark; Inert atmosphere;

C26H37NO → 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0)

Conditions	Yield
With sulfuric acid at 105℃; for 2h; Reagent/catalyst;	46.8 g

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → 4-(azido(phenyl)methyl)-2,6-di(tert-butyl)phenol

Conditions	Yield
With trimethylsilylazide; water; caesium carbonate In neat (no solvent) at 20℃; for 4h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique; Inert atmosphere; Green chemistry;	100%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + C11H12O3S → 1-(benzo[d][1,3]dioxole-5-carbonyl)-5,7-di-tert-butyl-2-phenylspiro[2.5]octa-4,7-dien-6-one

Conditions	Yield
In dichloromethane at 20℃; for 12h; Sealed tube;	99%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + Dimethyl phosphite (868-85-9) → dimethyl ((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)phosphate oxide

Conditions	Yield
With 1,3-bis(2,4,6-trimethylphenyl)imidazolium-2-carboxylate In dimethyl sulfoxide at 20℃; for 0.5h; Time; Inert atmosphere;	99%
With caesium carbonate In acetonitrile at 40℃; for 6h; Schlenk technique; Inert atmosphere;	98%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 40℃; for 4h;	91%

diethyl 2-vinylcyclopropane-1,1-dicarboxylate (7686-78-4) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → diethyl 7,9-di-tert-butyl-8-oxo-1-phenyl-4-vinylspiro[4.5]deca-6,9-diene-2,2-dicarboxylate

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; C29H29N2OPS; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 24h; Sealed tube; diastereoselective reaction;	99%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → 2,6-di-tert-butyl-4-(1-phenylbut-3-en-1-yl)phenol

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In 1,4-dioxane at 20℃; for 16h; Catalytic behavior; Solvent; Reagent/catalyst;	99%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + thiophenol (108-98-5) → 2,6-di-tert-butyl-4-(phenyl(phenylthio)methyl)phenol

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 0.000833333h;	99%

1,4-dithiane-2,5-diol (40018-26-6) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → 2-(((3,5-bis-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)thio)acetaldehyde

Conditions	Yield
With methanol; P(p-C6H4F)3 at 20℃; for 24h;	99%

diphenyl malonate (1969-44-4) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → diphenyl (R)-2-((3,5-ditert-butyl-4-hydroxyphenyl)(phenyl)-methyl)malonate

Conditions	Yield
With (S)-(2-(3,5-bis(trifluoromethyl)benzamido)-2-phenylethyl)triphenylphosphonium bromide; potassium carbonate In toluene at -40℃; for 30h; Catalytic behavior; Reagent/catalyst; Solvent; enantioselective reaction;	98%
With (S,S)-2,6-bis(3,5-bis(trifluoromethyl)phenyl)-3,3’,5,5’-tetrahydro-4,4’-spirobi[dinaphtho[2,1-c:1’,2’-e]azepin]-4-ium bromide; potassium carbonate In toluene at -40℃; for 33h; Temperature; Time; Reagent/catalyst; Solvent; enantioselective reaction;	96%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + 2-phenylethynylaniline (13141-38-3) → 2,6-di-tert-butyl-4-(phenyl(2-phenyl-1H-indol-3-yl)methyl)phenol

Conditions	Yield
With palladium dichloride In 1,2-dichloro-ethane at 70℃; Inert atmosphere;	98%
With Na(1+)*[AuCl4](1-)*99H2O=Na[AuCl4]*99H2O In dichloromethane at 50℃; for 6h; Catalytic behavior; Mechanism; Solvent; chemoselective reaction;	90%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + Diethyl 2-bromomalonate (685-87-0) → diethyl 5,7-di-tert-butyl-6-oxo-2-phenylspiro[2.5]octa-4,7-diene-1,1-dicarboxylate

Conditions	Yield
With caesium carbonate In dichloromethane at 20℃; for 12h; Reagent/catalyst; Sealed tube;	98%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + 3-phenyloxindole (3456-79-9, 123742-97-2) → C35H37NO2

Conditions	Yield
With Bis-QN-SQA; sodium carbonate In tetrahydrofuran at -40℃; for 18h; Catalytic behavior; Temperature; Inert atmosphere; stereoselective reaction;	98%

3-Methylindole (83-34-1) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → 2,6-di-tert-butyl-4-((3-methyl-1H-indol-2-yl)(phenyl)methyl)phenol

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;	98%
With phosphoric acid In water at 100℃; for 6h; Temperature; Inert atmosphere; Schlenk technique;	93%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + methyl indolizine-1-carboxylate (316375-85-6) → methyl 3-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)indolizine-1-carboxylate

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;	98%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + dicyclohexylzinc(II) (15658-08-9) → 2,6-di-tert-butyl-4-(cyclohexyl(phenyl)methyl)phenol

Conditions	Yield
In diethyl ether; toluene at 25℃; for 0.166667h; Flow reactor; regiospecific reaction;	98%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + 4-((1,3-diphenyl-1,3,2-diazaphospholidin-2-yl)oxy)-N-phenylbutanethioamide → 2-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-1,3-diphenyl-1,3,2-diazaphospholidine 2-oxide

Conditions	Yield
In chloroform at 20℃; for 16h; Solvent; Concentration; Inert atmosphere;	98%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + 1-(4-((1,3-diphenyl-1,3,2-diazaphospholidin-2-yl)oxy)butyl)-3-phenylthiourea → (E)-N-phenylthiazolidin-2-imine + 2-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-1,3-diphenyl-1,3,2-diazaphospholidine 2-oxide

Conditions	Yield
In chloroform at 20℃; for 16h; Inert atmosphere;	A 96% B 98%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + Br(1-)*C27H38N3O3(1+) (1342295-82-2) → C27H37NO2

Conditions	Yield
With caesium carbonate In dichloromethane for 96h; Inert atmosphere; Schlenk technique; Reflux;	98%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + C27H34BrNO3Si → tert-butyl (E)-3-(1-(3-bromophenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-phenylpropylidene)-2-oxoindoline-1-carboxylate

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at -78℃; for 12h; Inert atmosphere; diastereoselective reaction;	98%

ethyl 2,3-butadienoate (14369-81-4) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → ethyl 2-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)buta-2,3-dienoate

Conditions	Yield
With dmap In dichloromethane at 25℃; for 12h; Reagent/catalyst; Solvent; Time; Inert atmosphere;	98%
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetone at 25℃; for 0.0833333h;	89%

2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) + para-thiocresol (106-45-6) → 2,6-di-tert-butyl-4-[(phenyl)(p-tolylthio)methyl]phenol

Conditions	Yield
With BiCl6(3-)*2C4H10N2*Cl(1-)*4H(1+)*H2O In dichloromethane at 25 - 35℃; Green chemistry;	98%
With (C4H12N2)2[BiCl6]Cl*H2O In dichloromethane at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent;	98%

4-methyl-3-phenylisoxazole-5(4H)-one (23244-37-3) + 2,6-di-tert-butyl-4-benzylidene-cyclohexa-2,5-dienone (7078-98-0) → (S)-2-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)-4-methyl-3-phenylisoxazol-5(2H)-one

Conditions	Yield
With C31H29F3N4O3 In 1,2-dichloro-ethane at 45℃; for 12h; enantioselective reaction;	98%

Upstream product

• 17330-09-5 2,6-di-tert-butyl-4-(phenyl-piperidin-1-yl-methyl)-phenol 
• 2444-28-2 2,6-di-tert-butyl-4-hydroxyphenol 
• 100-52-7 benzaldehyde 
• 108-95-2 phenol 
• 128-39-2 2,6-di-tert-butylphenol 
• 1620-98-0 3,5-di-t-butyl-4-hydroxybenzaldehyde 
• 591-51-5 phenyllithium 
• 20017-39-4 (3,5-di-tert-butyl-4-hydroxyphenyl)phenylcarbinol 
• 4973-27-7 4-benzyl-2,6-di-tert-butylphenol 

Downstream Products

• 96275-07-9 4-((benzyloxy)(phenyl)methyl)-2,6-di-tert-butylphenol 
• 1350327-40-0 5-(tert-butyl)-3-((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)benzene-1,2-diol 

Relevant articles and documents

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