2,5-Di-tert-Butylhydroquinone supplier

Name
2,5-Di-tert-butylhydroquinone
EINECS 201-841-8
CAS No. 88-58-4
Article Data84
CAS DataBase
Density 1.012 g/cm³
Solubility insoluble in water
Melting Point 216-218 °C(lit.)
Formula C₁₄H₂₂O₂
Boiling Point 334.4 °C at 760 mmHg
Molecular Weight 222.327
Flash Point 151.5 °C
Transport Information
Appearance White or light yellow crystals
Safety 26-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms BHQ;DBH;DTBHQ;Dibug;NSC 11;NSC 9886;Naugard 451;Nocrac NS 7;NonflexAlba;Santovar O;Hydroquinone,2,5-di-tert-butyl- (8CI);1,4-Dihydroxy-2,5-di-tert-butylbenzene;2,5-Di-tert-butyl-1,4-benzenediol;2,5-Di-tert-butyl-1,4-benzohydroquinone;2,5-Di-tert-butyl-1,4-hydroquinone;2,5-Di-tert-butylquinol;2,5-Dihydroxy-1,4-di-tert-butylbenzene;Antage DBH;
PSA 40.46000
LogP 3.69280

Synthetic route

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: C72H116Fe4S8(3-)*2C16H36N(1+)

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: C72H116Fe4S8(2-)*2C16H36N(1+)

Conditions

Conditions	Yield
With [hydrogen(diethyl ether)][tetra[3,5-bis(trifluoromethyl)phenyl]borate]	A 100% B 100%

...Expand

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: C39H17F33Fe4S8(3-)*2C16H36N(1+)

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: C39H17F33Fe4S8(2-)*2C16H36N(1+)

Conditions

Conditions	Yield
With [hydrogen(diethyl ether)][tetra[3,5-bis(trifluoromethyl)phenyl]borate]	A 65% B 100%

...Expand

: 507-19-7
t-butyl bromide

: 123-31-9
hydroquinone

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
silica gel In tetrachloromethane at 70℃; for 24h; Product distribution; addition of Na2CO3;	92%
With sodium carbonate; silica gel In tetrachloromethane at 70℃; for 24h;	92%

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With 2,5-dihydrotoluene; trifluoroacetic acid In toluene at 30℃; for 15h; Solvent; Temperature; Reagent/catalyst;	90%
With boron trifluoride diethyl etherate; prenyl tributylstannane In dichloromethane at -78℃;	88%
With sodium dithionite In solid	85%

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: thiol

: C47H72Fe4NS7(1-)

A: {Fe4S4(S-2,4,6-(i-Pr)3C6H2)4}(1-)

B: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With 2,4,6-tri-tert-butylphenoxyl	A 50% B 90%

...Expand

: 96455-63-9
{Fe4S4(S-2,4,6-(i-Pr)3C6H2)4}(3-)

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

A: {Fe4S4(S-2,4,6-(i-Pr)3C6H2)4}(2-)

B: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With [hydrogen(diethyl ether)][tetra[3,5-bis(trifluoromethyl)phenyl]borate]	A 80% B 85%

...Expand

: methanesulfonic acid 2,5-di-tert-butyl-4-methanesulfonyloxyphenyl ester

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.5h;	70%

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: 3200-73-5
trans-2-butenyltrimethylstannane

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: 74785-31-2
2-(2-butenyl)-5-tert-butylhydroquinone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78℃;	A 56% B n/a

...Expand

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: 100-99-2
triisobutylaluminum

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: 77501-99-6
2,5-di-t-butyl-1-isobutylbenzene

C: 127558-27-4
2-t-butyl-5-isobutyl-1,4-dihydroxybenzene

Conditions

Conditions	Yield
In benzene for 10h; Heating;	A 32% B 16% C 52%
In benzene for 10h; Mechanism; Heating;	A 32 % Chromat. B 16 % Chromat. C 52 % Chromat.

...Expand

: 123-31-9
hydroquinone

: 75-65-0
tert-butyl alcohol

A: 6669-13-2
t-butyl phenyl ether

B: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

C: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

D: 1948-33-0
tert-butylhydroquinone

Conditions

Conditions	Yield
With porous pillared-zirconium phosphate functionalized with methyl group In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4h; Reagent/catalyst; Autoclave;	A n/a B n/a C n/a D 48.8%
With perfluorosulfonicacid-functionalized carbon nanotubes (PFSA-CNT-0.5) In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Catalytic behavior; Reagent/catalyst; Autoclave;

...Expand

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

: 24850-33-7
allyltributylstanane

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: 73685-60-6
2-(1,1-dimethylethyl)-5-(2-propenyl)-1,4-benzenediol

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at -78℃;	A 35% B 36%

...Expand

: 123-31-9
hydroquinone

: 75-65-0
tert-butyl alcohol

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With sulfuric acid; acetic acid

: 123-31-9
hydroquinone

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With aluminium at 150℃; anschliessendes Erhitzen mit Isobutylen auf 240grad;

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: 77501-99-6
2,5-di-t-butyl-1-isobutylbenzene

C: 127558-27-4
2-t-butyl-5-isobutyl-1,4-dihydroxybenzene

Conditions

Conditions	Yield
With triisobutylaluminum In benzene for 10h; Heating;	A 32 % Chromat. B 16 % Chromat. C 52 % Chromat.

...Expand

: 123-31-9
hydroquinone

: 115-11-7
isobutene

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: 2467-52-9
2-t-Butyl-4-t-butoxyphenol

C: 1948-33-0
tert-butylhydroquinone

Conditions

Conditions	Yield
With Amberlyst IR120 H(1+) In diethyl ether Ambient temperature;

...Expand

: 64-17-5
ethanol

: 507-20-0
tertiary butyl chloride

: 123-31-9
hydroquinone

ZnCl2: ZnCl2

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

...Expand

: 124700-28-3
2,5-Di-tert-butyl-4-hydroxy-phenoxyl

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

Conditions

Conditions	Yield
With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol In benzene at 19.85℃; Equilibrium constant; Thermodynamic data; Further Variations:; Solvents;

: 1634-04-4
tert-butyl methyl ether

: 123-31-9
hydroquinone

A: 2444-28-2
2,6-di-tert-butyl-4-hydroxyphenol

B: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

C: 2460-87-9
4-(tert-butoxy)phenol

D: 1948-33-0
tert-butylhydroquinone

Conditions

Conditions	Yield
With 3-(4-sulfobutylamino)propylsilanized MCM-41 In nitrobenzene at 150℃; for 0.133333h; Catalytic behavior; Concentration; Friedel-Crafts Alkylation; Microwave irradiation; Green chemistry; chemoselective reaction;

...Expand

: acid blue 5

A: 1450-72-2
5-methyl-2-hydroxyacetophenone

B: 591-81-1
4-hydroxybutanoic acid

C: 617-48-1
malic acid

D: 19071-34-2
2-hydroxyacrylic acid

E: 83-56-7
1,5-dihydroxynaphthalene

F: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

G: 1-aminoethenol

Conditions

Conditions	Yield
With dihydrogen peroxide pH=3; Kinetics; Reagent/catalyst; Concentration; pH-value;

...Expand

: 123-31-9
hydroquinone

: 75-65-0
tert-butyl alcohol

A: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

B: 1948-33-0
tert-butylhydroquinone

Conditions

Conditions	Yield
With phosphoric acid In toluene at 70 - 105℃;

...Expand

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

Conditions

Conditions	Yield
With benzyltrimethylammonium tribromide In water; acetic acid for 0.166667h; Ambient temperature;	100%
With 3-[3,6-dioxo-2-(pyridinium-1-yl)cyclohexa-1,4-dienyl]-2-oxo-2H-chromen-4-olate In methanol; dichloromethane at 20℃; for 2.5h;	100%
With μ-Oxo-I,I'-bis(trifluoroacetato-O)-I,I'-diphenyldiiodine(III) In water; acetonitrile at 0℃; for 2h;	100%

: 75-77-4
chloro-trimethyl-silane

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 18724-29-3
1,4-bis(trimethylsiloxy)-2,5-di-tert-butylbenzene

Conditions

Conditions	Yield
In acetonitrile	97%

...Expand

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 2,5-di-t-butyl-1,4-benzoquinone

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene In methanol at 20℃; for 2h; Oxidation;	96%

: 1120-71-4
1,3-propanesultone

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: sodium 3-(2,5-di-tert-butyl-4-hydroxy-phenoxy)propane-1-sulfonate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃;	95%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 74-88-4
methyl iodide

: 7323-63-9
1,4-di-tert-butyl-2,5-dimethoxybenzene

Conditions

Conditions	Yield
Stage #1: 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.25h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 40℃; for 2h;	94%
With sodium hydride In N,N-dimethyl-formamide at 40℃; for 2h;

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 69739-34-0
t-butyldimethylsiyl triflate

: 73759-45-2
1,4-bis(tert-butyldimethylsiloxy)-2,5-di-(tert-butyl)benzene

Conditions

Conditions	Yield
With triethylamine In chloroform at 25℃;	88%
With triethylamine In chloroform	83%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 51762-67-5
3-nitrobenzene-1,2-dicarbonitrile

: 135848-92-9
1,4-bis-(2,3-dicyanophenoxy)-2,5-di-tert-butyl benzene

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 24h;	87%
With potassium carbonate In water; dimethyl sulfoxide

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 73759-45-2
1,4-bis(tert-butyldimethylsiloxy)-2,5-di-(tert-butyl)benzene

Conditions

Conditions	Yield
With P(MeNCH2CH2)3N In acetonitrile at 60℃; for 18h;	86%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 0.333333h; Ambient temperature;	84%

: 31643-49-9
4-Nitrophthalonitrile

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 135848-91-8
1,4-bis-(3,4-dicyanophenoxy)-2,5-di-tert-butyl benzene

Conditions

Conditions	Yield
With potassium carbonate In water; dimethyl sulfoxide	85%
With potassium carbonate In dimethyl sulfoxide at 20℃;

: 448-19-1
4-fluoro-2-methoxy-1-nitrobenzene

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 1381864-10-3
1,4-bis(3-methoxy-4-nitrophenoxy)2,5-di-tertbutylbenzene

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 18h;	85%

: 627-42-9
2-chloroethyl methyl ether

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 1350770-63-6
1,4-di-tert-butyl-2,5-bis(2-methoxyethoxy)benzene

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃;	81%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 6482-24-2
2-Bromoethyl methyl ether

: 1350770-63-6
1,4-di-tert-butyl-2,5-bis(2-methoxyethoxy)benzene

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 58 - 70℃; for 5.5h;	79%

: 75-77-4
chloro-trimethyl-silane

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 18724-29-3
1,4-bis(trimethylsiloxy)-2,5-di-tert-butylbenzene

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 12h;	78%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

A: 2460-77-7
2,5-di-tert-butyl-p-benzoquinone

B: 23803-85-2
2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone

Conditions

Conditions	Yield
With air; silica gel	A 78% B 10%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 75-98-9
Trimethylacetic acid

: 216314-03-3
2,5-di-t-butyl-4-trimethylacetoxyphenol

Conditions

Conditions	Yield
sulfuric acid In hexane; di-isopropyl ether; ethyl acetate; acetonitrile	78%

: 96-49-1
[1,3]-dioxolan-2-one

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 2-[2,5-Di-tert-butyl-4-(2-hydroxy-ethoxy)-phenoxy]-ethanol

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 140℃;	77%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 124-63-0
methanesulfonyl chloride

: methanesulfonic acid 2,5-di-tert-butyl-4-methanesulfonyloxyphenyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.25h;	77%

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 16420-13-6
N,N-Dimethylthiocarbamoyl chloride

: 1,4-bis(dimethylthiocarbamoyl)2,5-di-tert-butylbenzene

Conditions

Conditions	Yield
With potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;	70%

: 1291-32-3
zirconocene dichloride

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: [(ZrCl(C5H5)2)2(OC6H2(C4H9)2O)]

Conditions

Conditions	Yield
With NEt3 In tetrahydrofuran byproducts: (HNEt3)Cl; (inert atmosphere); stirring (room temp., 2 h); filtration, addn. of hexane, sepn. after 12 h, recrystn. (THF/hexane); elem. anal.;	69%

: 107333-47-1
trimethyl(pentamethylcyclopentadienyl)titanium(IV)

: 88-58-4
2,5-bis(1,1-dimethylethyl)-1,4-benzenediol

: 176542-03-3
[(Ti(CH3)2(C5(CH3)5))2(OC6H2(C4H9)2O)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: methane; (inert atmosphere); stirring (room temp., 1 h); recrystn. (THF); elem. anal.;	66%

2,5-Di-tert-Butylhydroquinone Consensus Reports

Reported in EPA TSCA Inventory.

2,5-Di-tert-Butylhydroquinone Standards and Recommendations

ASSAY: 98.0% min
WATER: 0.1% max

2,5-Di-tert-Butylhydroquinone Specification

The IUPAC name of 2,5-Di-tert-Butylhydroquinone is 2,5-ditert-butylbenzene-1,4-diol. With the CAS registry number 88-58-4, it is also named as 1,4-Benzenediol, 2,5-bis(1,1-dimethylethyl)-. The product's categories are Industrial / Fine Chemicals; Anthraquinones, Hydroquinones and Quinones; Organic Building Blocks; Oxygen Compounds; Polyols; Calcium signaling; Signalling. It is white or light yellow crystals which is soluble in ethanol, acetone, ethyl acetate and carbon disulfide, slightly soluble in benzene, gasoline, insoluble in water. Additionally, this chemical should be sealed in the container ann stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.02; (4)ACD/LogD (pH 7.4): 4.02; (5)ACD/BCF (pH 5.5): 669.78; (6)ACD/BCF (pH 7.4): 669.76; (7)ACD/KOC (pH 5.5): 3667.8; (8)ACD/KOC (pH 7.4): 3667.68; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4 ; (12)Index of Refraction: 1.52; (13)Molar Refractivity: 66.79 cm³; (14)Molar Volume: 219.6 cm³; (15)Polarizability: 26.47×10^-24cm³; (16)Surface Tension: 34.7 dyne/cm; (17)Enthalpy of Vaporization: 60.03 kJ/mol; (18)Vapour Pressure: 6.6E-05 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 4; (21)Exact Mass: 222.16198; (22)MonoIsotopic Mass: 222.16198; (23)Topological Polar Surface Area: 40.5; (24)Heavy Atom Count: 16; (25)Complexity: 208.

Preparation of 2,5-Di-tert-Butylhydroquinone: It can be obtained by the reaction of paradioxybenzene and isobutylene.

Uses of 2,5-Di-tert-Butylhydroquinone: It is useful as an antioxidant for Natural rubber, synthetic rubber and latex. And it can react with chloro-triethyl-silane to get 1,4-bis(triethylsiloxy)-2,5-di-tert-butylbenzene. This reaction needs reagent imidazole and solvent dimethylformamide. The yield is 35%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
1. SMILES:Oc1cc(c(O)cc1C(C)(C)C)C(C)(C)C
2. InChI:InChI=1/C14H22O2/c1-13(2,3)9-7-12(16)10(8-11(9)15)14(4,5)6/h7-8,15-16H,1-6H3

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	> 1800mg/kg (1800mg/kg)		Kodak Company Reports. Vol. 21MAY1971,
rat	LDLo	oral	800mg/kg (800mg/kg)		Kodak Company Reports. Vol. 21MAY1971,

Product Name

2,5-Di-tert-butylhydroquinone

Synthetic route

2,5-Di-tert-Butylhydroquinone Consensus Reports

2,5-Di-tert-Butylhydroquinone Standards and Recommendations

2,5-Di-tert-Butylhydroquinone Specification

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