1,1,4,4-Tetraphenylbutadiene supplier

Name
1,1,4,4-TETRAPHENYL-1,3-BUTADIENE
EINECS 215-914-7
CAS No. 1450-63-1
Article Data92
CAS DataBase
Density 1.079 g/cm³
Solubility
Melting Point 207-209 °C(lit.)
Formula C₂₈H₂₂
Boiling Point 556.133 °C at 760 mmHg
Molecular Weight 358.483
Flash Point 288.97 °C
Transport Information
Appearance White to slightly yellow needle-like crystals
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,3-Butadiene,1,1,4,4-tetraphenyl- (6CI,8CI);1,1,4,4-Tetraphenyl-1,3-butadiene;1,1,4,4-Tetraphenylbutadiene;NSC 12572;TPB;TPB (dopant);Tetraphenylbutadiene;
PSA 0.00000
LogP 7.25020

Synthetic route

: 4541-89-3
2-chloro-1,1-diphenylethene

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With 4-(3'-butyl-1'-imidazolio)-1-butanesulfonic acid hydrogen sulfate; aluminium In carbon dioxide at 45℃; under 116262 Torr; for 12h; Ullmann reaction; Supercritical conditions;	98%
With carbon dioxide; aluminium; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 45℃; under 116262 Torr; for 12h; Ullmann reaction;	97%

: 1483-68-7
tetraphenylbutatriene

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With water; zinc(II) chloride; zinc In tetrahydrofuran for 6h; Heating; other substrate;	95%
With water; zinc(II) chloride; zinc In tetrahydrofuran for 6h; Heating;	95%
With i-Amyl alcohol; acetic acid; zinc
With phosphorus; hydrogen iodide
Multi-step reaction with 2 steps 1: 87 percent / sulfur / dimethylformamide / 125 °C 2: 52 percent / 1,8-diazabicyclo<5,4,0>undec-7-ene, / dimethylformamide / 10 h / Heating View Scheme

: 13249-58-6
1-bromo-2,2-diphenylethylene

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With dibromobis(triphenylphosphine)nickel(II); triphenylphosphine; zinc In N,N-dimethyl-formamide at 20℃; for 8h;	90%
With potassium iodide; nickel dichloride; zinc In N,N,N,N,N,N-hexamethylphosphoric triamide at 40℃; for 7h; oth. solvent, oth. time, oth. temperature, presence of additive;	78%
With potassium iodide; zinc; bis(triethylphosphine)nickel(II) chloride In various solvent(s) at 50℃; for 1h; Product distribution; other temperatrure, other time, other catalyst, other solvent;	97 % Chromat.
With potassium iodide; zinc; bis(triethylphosphine)nickel(II) chloride In various solvent(s) at 50℃; for 1h;	97 % Chromat.

: 530-48-3
1,1-Diphenylethylene

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
Stage #1: 1,1-Diphenylethylene With Hg(II) trifluoroacetate In benzene at 0℃; for 0.25h; Substitution; Stage #2: With triethylamine; palladium dichloride In benzene at 0℃; for 0.25h; Coupling reaction;	88%
With oxygen; copper diacetate; palladium diacetate; benzyl chloride In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 10h;	53%

: 6317-10-8
2,2-diphenyl-1,3-dithiolane

: 123752-05-6
2,2-diphenylcyclopropyl magnesium bromide

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 123751-94-0
C20H22

Conditions

Conditions	Yield
bis(triphenylphosphine)nickel(II) chloride In toluene Heating;	A 87% B 31%

...Expand

: 59856-52-9
trans-1,1,4,4-tetraphenyl-2-butene-1,4-diol

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; titanium(III) chloride In tetrahydrofuran for 3h; Heating;	83%

: 147700-73-0
(4R,5R)-4,5-bis[chloro(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With zinc chloride diethyl ether; phosphan at -196 - 90℃; under 9000.9 - 97509.8 Torr; for 37h; Inert atmosphere; Autoclave;	80%

: 55373-68-7
(1Z,3Z)-1,4-dibromo-1,4-diphenylbuta-1,3-diene

: 98-80-6
phenylboronic acid

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 24h; Inert atmosphere; Reflux;	75%

: 270589-02-1
1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With copper(l) iodide; cesium fluoride In acetonitrile at 20℃; for 3h;	58%

: 118091-25-1
6,7-Dibenzhydrylidene-[1,2,3,4,5]pentathiepane

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 118091-34-2
2-(2,2-Diphenyl-vinyl)-3-phenyl-benzo[b]thiophene

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 10h; Heating;	A 52% B 12%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 10h; Heating;	A 52% B 12%

: 325770-97-6
methyl 2-carbomethoxy-4-benzyl-4-(2,2-diphenylvinyl)-6,6-diphenyl-2,5-hexadienoate

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 1-benzyl-3,3,5,5-tetraphenyl-4-(2,2-dicarbomethoxyvinyl)-1-cyclopentene

: trans-1,1-diphenyl-2-benzyl-2-(2,2-dicarbomethoxyvinyl)-3-(2,2-diphenylvinyl)cyclopropane

: cis-1,1-diphenyl-2-benzyl-2-(2,2-dicarbomethoxyvinyl)-3-(2,2-diphenylvinyl)cyclopropane

Conditions

Conditions	Yield
With acetophenone In benzene for 0.25h; Irradiation; Further byproducts given;	A 12 mg B 43% C n/a D n/a

...Expand

: 2592-73-6
1,1-dibromo-2,2-diphenylethylene

A: 530-48-3
1,1-Diphenylethylene

B: 58-72-0
Triphenylethylene

C: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With dibromobis(triphenylphosphine)nickel(II); tetraethylammonium iodide; zinc In tetrahydrofuran Ambient temperature;	A 29% B 21% C 40%

...Expand

: 1483-68-7
tetraphenylbutatriene

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 118091-31-9
2-(2,2-Diphenyl-vinyl)-3-phenyl-benzo[b]selenophene

Conditions

Conditions	Yield
With selenium; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 10h; Heating;	A 38% B 8%

: 114789-76-3
1,1,3,5,5-pentaphenyl-1,4-pentadien-3-ol

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 57365-26-1
1,2,2,5,5-pentaphenyl-4-penten-1-one

: 114789-83-2
cis-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

: 114789-84-3
trans-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

Conditions

Conditions	Yield
In acetonitrile for 5.2h; Irradiation;	A 1.7% B 1.7% C 36.5% D 14.4%

...Expand

: 36858-84-1
ethyl 2,4,4-triphenyl-2,3-butadienoate

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 3-ethoxy-2,4,4-triphenylcyclobut-2-enone

Conditions

Conditions	Yield
In hexane Ambient temperature; Irradiation;	A n/a B 35%

: 325770-96-5
methyl 2-carbomethoxy-4-methyl-4-(2,2-diphenylvinyl)-6,6-diphenyl-2,5-hexadienoate

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 1-methyl-3,3,5,5-tetraphenyl-4-(2,2-dicarbomethoxyvinyl)-1-cyclopentene

C: cis-1,1-dicarbomethoxy-2-methyl-2,3-bis(2,2-diphenylvinyl)cyclopropane

D: cis-1,1-diphenyl-2-methyl-2-(2,2-diphenylvinyl)-3-(2,2-dicarbomethoxyvinyl)cyclopropane

Conditions

Conditions	Yield
With acetophenone In benzene for 0.25h; Irradiation; Further byproducts given;	A 15 mg B 33% C n/a D n/a

...Expand

: 2592-73-6
1,1-dibromo-2,2-diphenylethylene

A: 530-48-3
1,1-Diphenylethylene

B: 58-72-0
Triphenylethylene

C: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

D: 501-65-5
diphenyl acetylene

Conditions

Conditions	Yield
With dibromobis(triphenylphosphine)nickel(II); zinc In tetrahydrofuran at 50℃;	A 3% B 28% C 29% D 1%

...Expand

: 119-61-9
benzophenone

: 778-66-5
1,1-diphenyl-1-propene

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With hydrogenchloride; n-butyllithium; acetic acid In tetrahydrofuran; hexane Product distribution; other substituted 1,1-diphenylpropenes, other phenones;	25%
Yield given. Multistep reaction;

: 63469-15-8
1,1,4,4-tetraphenyl-1,4-butanediol

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

Conditions

Conditions	Yield
With Lawessons reagent In toluene for 0.5h; Heating;	24%
With chloroform; bromine
With hydrogenchloride; acetic acid

: 114789-83-2
cis-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 57365-26-1
1,2,2,5,5-pentaphenyl-4-penten-1-one

: 114789-84-3
trans-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

Conditions

Conditions	Yield
With 4-(Dimethylamino)benzophenone In acetonitrile for 1.67h; Irradiation;	A 4.9% B 1.5% C 22%
In acetonitrile for 2.3h; Irradiation;	A 3.8% B 1.3% C 14.9%

...Expand

: 52217-17-1
2-(2,2-diphenylvinylidene)-4-butanolide

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 3-(2,2-diphenylvinyl)dihydrofuran-2(3H)-one

C: 2-(1-ethoxyethyl)-2-(2,2-diphenylvinyl)-4-butanolide

Conditions

Conditions	Yield
In diethyl ether; hexane for 30h; Ambient temperature; Irradiation;	A 3% B 18% C 21%

...Expand

: 57365-26-1
1,2,2,5,5-pentaphenyl-4-penten-1-one

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 114789-83-2
cis-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

: 114789-84-3
trans-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

Conditions

Conditions	Yield
In acetonitrile at 94℃; for 1.56667h; Irradiation;	A 9.65% B 21% C 16.8%
In acetonitrile for 1.56667h; Irradiation;	A 9.65% B 21% C 16.8%
In acetonitrile for 1.56667h; Irradiation;	A 9.65% B 21% C 16.8%

...Expand

: 114789-76-3
1,1,3,5,5-pentaphenyl-1,4-pentadien-3-ol

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 114789-83-2
cis-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

: 114789-84-3
trans-1-hydroxy-1,2,2-triphenyl-3-(2,2-diphenylvinyl)cyclopropane

Conditions

Conditions	Yield
With 4-(Dimethylamino)benzophenone In acetonitrile for 0.666667h; Irradiation;	A 4.65% B 17.9% C 1.56%

...Expand

: 886-66-8
1,4-diphenyl-1,3-butadiyne

: 143-66-8
sodium tetraphenyl borate

A: 1005197-76-1
C28H22

B: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

C: 1608-11-3
(1Z,3Z)-1,2,3,4-tetraphenylbuta-1,3-diene

Conditions

Conditions	Yield
With water; acetic acid; bis-triphenylphosphine-palladium(II) chloride at 20℃; for 6h;	A n/a B n/a C 15%

...Expand

: 5717-43-1
α-methyl-γ,γ-diphenylallenecarboxylic acid ethyl ester

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: ethyl 1-methyl-3-phenylindene-1-carboxylate

Conditions

Conditions	Yield
With dicobalt octacarbonyl In hexane for 16h; Ambient temperature; Irradiation;	A 12% B 4%

: 70582-44-4
methyl 2-methyl-4,4-diphenyl-2,3-butadienoate

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 3-Methoxy-2-methyl-4,4-diphenyl-cyclobut-2-enone

Conditions

Conditions	Yield
In hexane Ambient temperature; Irradiation;	A n/a B 5%

: 5717-43-1
α-methyl-γ,γ-diphenylallenecarboxylic acid ethyl ester

A: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

B: 3-Ethoxy-2-methyl-4,4-diphenyl-cyclobut-2-enone

Conditions

Conditions	Yield
In hexane Ambient temperature; Irradiation;	A n/a B 5%

: 91-22-5
quinoline

: 858807-12-2
(α-acetoxy-benzhydryl)-benzhydrylidene-succinic acid

: 142-71-2
copper diacetate

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

...Expand

: 75-11-6
diiodomethane

: 1,1,4,4-tetraphenyl-but-2-enediyl dipotassium

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 60-29-7
diethyl ether

: 3531-24-6
3,3-diphenylacrylonitrile

: 2,2-diphenyl-vinyl magnesium (1+); bromide

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

...Expand

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 696-33-3
iodoxybenzene

: 119-61-9
benzophenone

Conditions

Conditions	Yield
With obj. of study: similarity in reactions to ozone, other olefins In nitrobenzene at 170℃; for 5h;	78.5%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 98760-59-9
2,2-diphenyl-3-(2,2-diphenylvinyl)oxirane

Conditions

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 26h;	77%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 119-61-9
benzophenone

Conditions

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation;	68%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: (E)-1,1,4,4-tetraphenylbut-2-ene-1,4-d2

Conditions

Conditions	Yield
With ethyl [2]alcohol; sodium In diethyl ether; mineral oil at 20℃; for 0.166667h; Inert atmosphere;	62%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 2923-28-6
silver trifluoromethanesulfonate

: [Ag2(1,1,4,4-tetraphenyl-1,3-butadiene)(CF3SO3)2]

Conditions

Conditions	Yield
In 1,3,5-trimethyl-benzene under Ar atm. to soln. tphb in 1,3,5-trimethylbenzene was added Ag(CF3SO3); mixt. was filtered, filtrate was layered with n-hexane and left standing at room temp. for 2 weeks; elem. anal.;	60%

: 4233-33-4
4-Phenyl-1,2,4-triazolidine-3,5-dione

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 2-Hendo-5-(2,2-diphenylvinyl)-N,N',6-triphenyl-3,4,9,10-tetraazatricyclo<6.2.2.02,7>dodeca-6,11-diene-3,4:9,10-bisdicarboximide

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 20h;	49%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: silver perchlorate

: [Ag2(1,1,4,4-tetraphenyl-1,3-butadiene)(ClO4)2]

Conditions

Conditions	Yield
In 1,3,5-trimethyl-benzene under Ar atm. to soln. tphb in 1,3,5-trimethylbenzene was added AgClO4; mixt. was filtered, filtrate was layered with n-hexane and left standing at room temp. for 2 weeks; elem. anal.;	47%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 141-97-9
ethyl acetoacetate

A: 2491-41-0
phenyl-1,3,3-triphenyl-prop-2-enyl ketone

B: 134643-51-9
3-Ethoxycarbonyl-2-methyl-4-(2,2-diphenylethenyl)-5,5-diphenyl-4,5-dihydrofuran

Conditions

Conditions	Yield
With manganese triacetate In acetic acid for 0.0833333h; Heating;	A 12% B 46%

...Expand

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: Tris(2,4-pentanedionato)cobalt(III)

: 134643-33-7
3-Acetyl-2-methyl-4-(2,2-diphenylethenyl)-5,5-diphenyl-4,5-dihydrofuran

Conditions

Conditions	Yield
In acetic acid for 2h; Heating; other 1,3-dicarbonyl compound-manganese(III) acetate;	42%
In acetic acid for 2h; Heating;	42%

: 1450-63-1
1,1,4,4-tetraphenyl-1,3-butadiene

: 2491-41-0
phenyl-1,3,3-triphenyl-prop-2-enyl ketone

Conditions

Conditions	Yield
With iodine tris(trifluoroacetate) In tetrachloromethane at 23℃; for 3h;	37%
With 3-chloro-benzenecarboperoxoic acid
Multi-step reaction with 2 steps 1: 77 percent / sodium bicarbonate, m-chloroperbenzoic acid / CHCl3 / 26 h / 0 - 20 °C 2: TFA / CDCl3 View Scheme

1,1,4,4-Tetraphenylbutadiene Chemical Properties

Chemical Name: 1,1,4,4-Tetraphenyl-1,3-butadiene
IUPAC NAME: 1,4,4-Triphenylbuta-1,3-dienylbenzene
CAS No.: 1450-63-1
EINECS: 215-914-7
RTECS: CY9040630
Molecular Formula: C₂₈H₂₂
Molecular Weight: 358.47 g/mol
Melting Point: 207-209 °C(lit.)
Density: 1.079 g/cm³
Flash Point: 289 °C
Boiling Point: 556.1 °C at 760 mmHg
Following is the structure of 1,1,4,4-Tetraphenylbutadiene (1450-63-1):

Product Categories about 1,1,4,4-Tetraphenylbutadiene (1450-63-1) are Scintillators ; Electronic ; Electroluminescence ; Functional Materials
The chemical synonymous of 1,1,4,4-Tetraphenylbutadiene (1450-63-1) are Tpb ; 1,1,4,4-Tetraphenyl-1,3-butadiene ; 1,1,4,4-Tetraphenylbutadiene ; (1,4,4-Triphenyl-1,3-butadienyl)benzene ; 1,1,4,4-Tetraphenyl-3-butadiene ; 1,1’,1’’,1’’’-(1,3-Butadiene-1,4-diylidene)tetrabenzene ; 1,1’,1’’,1’’’-(1,3-Butadiene-1,4-diylidene)tetrakis-benzen

1,1,4,4-Tetraphenylbutadiene Toxicity Data With Reference

1.		orl-mus LD50:>14 g/kg		EJTXAZ European Journal of Toxicology and Environmental Hygiene. 9 (1976),99.
2.		ipr-mus LD50:>10 g/kg		EJTXAZ European Journal of Toxicology and Environmental Hygiene. 9 (1976),99.

1,1,4,4-Tetraphenylbutadiene Consensus Reports

Reported in EPA TSCA Inventory.

1,1,4,4-Tetraphenylbutadiene Safety Profile

Low toxicity by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Note: Irritant
Hazard Codes:
Xi: Irritant
Risk Statements about 1,1,4,4-Tetraphenylbutadiene (1450-63-1):
R36/37/38 Irritating to eyes, respiratory system and skin.
Safety Statements about 1,1,4,4-Tetraphenylbutadiene (1450-63-1):
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39 Wear suitable gloves and eye/face protection.
Attentions:
1. Storage: Store in a cool, dry place. Store in a tightly closed container.
2. Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.

Product Name

1,1,4,4-TETRAPHENYL-1,3-BUTADIENE

Synthetic route

1,1,4,4-Tetraphenylbutadiene Chemical Properties

1,1,4,4-Tetraphenylbutadiene Toxicity Data With Reference

1,1,4,4-Tetraphenylbutadiene Consensus Reports

1,1,4,4-Tetraphenylbutadiene Safety Profile

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