[ CAS No. 88-58-4 ] {[proInfo.proName]}

Name: 88-58-4|2,5-Di-tert-butylhydroquinone|98%
Brand: Ambeed
SKU: A348334
Price: 5.0 USD
Availability: InStock
Rating: 98 (22 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 88-58-4

Structure of 88-58-4 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 88-58-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 88-58-4 ]

SDS Specification

Alternatived Products of [ 88-58-4 ]

Product Details of [ 88-58-4 ]

CAS No. :	88-58-4	MDL No. :	MFCD00008825
Formula :	C₁₄H₂₂O₂	Boiling Point :	-
Linear Structure Formula :	C₆H₂(OH)₂(C(CH₃)₃)₂	InChI Key :	JZODKRWQWUWGCD-UHFFFAOYSA-N
M.W :	222.32	Pubchem ID :	2374
Synonyms :	BHQ

Calculated chemistry of [ 88-58-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.57
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	69.03
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.91
Log Po/w (XLOGP3) :	4.55
Log Po/w (WLOGP) :	3.69
Log Po/w (MLOGP) :	3.21
Log Po/w (SILICOS-IT) :	3.35
Consensus Log Po/w :	3.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.23
Solubility :	0.0131 mg/ml ; 0.0000588 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.12
Solubility :	0.00168 mg/ml ; 0.00000754 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.67
Solubility :	0.047 mg/ml ; 0.000211 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.46

Safety of [ 88-58-4 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P201-P202-P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P308+P313-P333+P313-P391-P405-P501	UN#:	3077
Hazard Statements:	H302-H317-H318-H341-H351-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 88-58-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 88-58-4 ]
Downstream synthetic route of [ 88-58-4 ]

[ 88-58-4 ] Synthesis Path-Upstream 1~30

1
[ 637-81-0 ]
[ 88-58-4 ]
[ 6630-33-7 ]
[ 103858-52-2 ]

Reference： [1] Patent: US2002/68756, 2002, A1,

2
[ 123-31-9 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 2460-77-7 ]
[ 88-58-4 ]
[ 1948-33-0 ]

Yield	Reaction Conditions	Operation in experiment
48.8%	With porous pillared-zirconium phosphate functionalized with methyl group In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4 h; Autoclave	Alkylation of hydroquinone with tert-butanol was carried outin an autoclave equipped with a magnetic stirrer. Typically, 0.5 ghydroquinone, 1.0 g tert-butanol, and 0.20 g catalyst were addedto the autoclave, along with 2 g of xylene as a solvent. The reac-tion lasted 4 h under 150C. The products were analyzed witha gas chromatograph equipped with a SE-30 capillary column(30 m × 0.25 mm × 0.3 m) and a flame ionization detector. Thetemperature of the capillary column was set at 180C. The mainproducts were 2-tert-butyl hydroquinone (2-TBHQ), 2,5-di-tert-butyl hydroquinone (2,5-TBHQ), 2,5-di-tert-butyl benzoquinone(2,5-DTBBQ) and tert-butyl phenol ether (TBPE).

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 380, p. 84 - 89
[2] Chinese Journal of Catalysis, 2014, vol. 35, # 11, p. 1874 - 1882

3
[ 1634-04-4 ]
[ 123-31-9 ]
[ 2444-28-2 ]
[ 88-58-4 ]
[ 2460-87-9 ]
[ 1948-33-0 ]

Reference： [1] Applied Catalysis A: General, 2013, vol. 450, p. 34 - 41

4
[ 123-31-9 ]
[ 115-11-7 ]
[ 88-58-4 ]
[ 2467-52-9 ]
[ 1948-33-0 ]

Reference： [1] Australian Journal of Chemistry, 1997, vol. 50, # 5, p. 515 - 516

5
[ 88-58-4 ]
[ 2460-77-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH₃CN)₄]PF₆; dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 0.0833333 h;	General procedure: To a solution of dihydroxy arene (0.34 mmol) and 2a (1.98 mg,0.0034 mmol) in THF (1.0 mL) was added H2O2 (30percent aq, 50.0 mL,0.44 mmol) at 0 C. After 5 min the starting material had completelyoxidized to the quinone product. The quinone product wasthen extracted by ether or dichloromethane, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford thedesired product. Pleasingly, the resulted quinone products werepure enough and there is no necessity for column chromatographyin most of the cases.
99%	With silica gel supported cerium(IV) ammonium nitrate-NaBrO₃ In dichloromethane; water at 40℃; for 2 h;	General procedure: A solution of CAN (0.056 g, 0.102 mmoles) and sodium bromate (0.780 g, 5.17 mmoles) in H2O (3 mL) was added slowly to vigorously stirred anhydrous silica gel (5 g) that was contained in a 100 mLround-bottom flask containing a magnetic stirring bar and fitted with a rubber septum. After complete addition of the aqueous solution, stirring was continued until a free-flowing powder was obtained.CH2Cl2 (25 mL) was then added to the flask and a solution of hydroquinone 1A (220.23 mg, 2.0 mmol), in CH2Cl2 (5 mL) was added slowly to the stirred heterogeneous mixture. A condenser was attached to the flask and the reaction was heated to reflux. Disappearance of 1A was monitored by thin-layer chromatography (EtOAc–hexane, 1:4; panisaldehyde/sulfuric acid as staining agent). Upon complete disappearance of 1A (ca. 2 h), the reaction mixture was filtered through a sintered glass funnel, the solid residue was washed with additional CH2Cl2 (3 × 10 mL), and the washings were added to the filtrate. Removal of solvent from the organic solution under vacuum gave an orange solid. Radial chromatography of the crude product (EtOAc–hexane,1:9) gave 1,4-benzoquinone 2A (89 mg, 82percent) as an orange solid.

Reference： [1] Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 336 - 338
[2] Organic and Biomolecular Chemistry, 2009, vol. 7, # 7, p. 1445 - 1453
[3] Synthesis, 2012, vol. 44, # 8, p. 1183 - 1189
[4] Tetrahedron, 1987, vol. 43, # 17, p. 3963 - 3974
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2970 - 2973
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 509 - 511
[7] Tetrahedron, 1987, vol. 43, # 17, p. 3963 - 3974
[8] Synthetic Communications, 2006, vol. 36, # 12, p. 1751 - 1759
[9] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8391 - 8394
[10] Tetrahedron, 2013, vol. 69, # 40, p. 8612 - 8617
[11] Synthesis (Germany), 2015, vol. 47, # 20, p. 3207 - 3211
[12] Synthesis, 1985, # 6/7, p. 641 - 643
[13] Tetrahedron, 1993, vol. 49, # 1, p. 105 - 112
[14] Advanced Synthesis and Catalysis, 2005, vol. 347, # 4, p. 517 - 520
[15] Chemistry - A European Journal, 2014, vol. 20, # 32, p. 9914 - 9917
[16] Tetrahedron, 1987, vol. 43, # 8, p. 1753 - 1758
[17] Synthetic Communications, 1980, vol. 10, # 8, p. 615 - 622
[18] Synthetic Communications, 1980, vol. 10, # 8, p. 615 - 622
[19] Tetrahedron, 1986, vol. 42, # 8, p. 2319 - 2324
[20] Polish Journal of Chemistry, 2007, vol. 81, # 5-6, p. 1049 - 1061
[21] Organic and Biomolecular Chemistry, 2006, vol. 4, # 2, p. 200 - 202
[22] Tetrahedron Letters, 1994, vol. 35, # 28, p. 5083 - 5084
[23] Tetrahedron Letters, 1988, vol. 29, # 22, p. 2671 - 2674
[24] Journal of the American Chemical Society, 2002, vol. 124, # 41, p. 12261 - 12267
[25] Journal of Organic Chemistry, 1987, vol. 52, # 22, p. 5053 - 5055
[26] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 6, p. 1655 - 1660
[27] Synthesis, 1980, # 9, p. 706 - 708
[28] Synthetic Communications, 1989, vol. 19, # 7,8, p. 1317 - 1324
[29] Justus Liebigs Annalen der Chemie, 1955, vol. 597, p. 196,211
[30] Acta Chemica Scandinavica (1947-1973), 1953, vol. 7, p. 938,939
[31] Patent: US2577505, 1950, ,
[32] Journal of the Chemical Society, 1952, p. 4666,4674
[33] Journal of the American Chemical Society, 1947, vol. 69, p. 1057,1063
[34] Chemistry Letters, 1976, p. 1293 - 1296
[35] Journal of Organic Chemistry, 1983, vol. 48, # 24, p. 4764 - 4766
[36] Zeitschrift fuer Physikalische Chemie (Leipzig), 1989, vol. 270, # 5, p. 887 - 896
[37] Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4545 - 4551
[38] Canadian Journal of Chemistry, 1986, vol. 64, p. 225 - 231
[39] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3215 - 3218
[40] Journal of Organic Chemistry, 1981, vol. 46, # 16, p. 3215 - 3218
[41] Journal of the American Chemical Society, 1980, vol. 102, # 15, p. 4999 - 5004
[42] Journal of the American Chemical Society, 1980, vol. 102, # 15, p. 4999 - 5004
[43] Patent: EP812816, 1997, A1,

6
[ 123-31-9 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 2460-77-7 ]
[ 88-58-4 ]
[ 1948-33-0 ]

Yield	Reaction Conditions	Operation in experiment
48.8%	With porous pillared-zirconium phosphate functionalized with methyl group In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4 h; Autoclave	Alkylation of hydroquinone with tert-butanol was carried outin an autoclave equipped with a magnetic stirrer. Typically, 0.5 ghydroquinone, 1.0 g tert-butanol, and 0.20 g catalyst were addedto the autoclave, along with 2 g of xylene as a solvent. The reac-tion lasted 4 h under 150C. The products were analyzed witha gas chromatograph equipped with a SE-30 capillary column(30 m × 0.25 mm × 0.3 m) and a flame ionization detector. Thetemperature of the capillary column was set at 180C. The mainproducts were 2-tert-butyl hydroquinone (2-TBHQ), 2,5-di-tert-butyl hydroquinone (2,5-TBHQ), 2,5-di-tert-butyl benzoquinone(2,5-DTBBQ) and tert-butyl phenol ether (TBPE).

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 380, p. 84 - 89
[2] Chinese Journal of Catalysis, 2014, vol. 35, # 11, p. 1874 - 1882

7
[ 88-58-4 ]
[ 2460-77-7 ]
[ 23803-85-2 ]

Reference： [1] Russian Chemical Bulletin, 1998, vol. 47, # 10, p. 1952 - 1955

8
[ 88-58-4 ]
[ 2406-04-4 ]
[ 2460-77-7 ]
[ 122-37-2 ]

Reference： [1] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 306 - 312

9
[ 2460-77-7 ]
[ 88-58-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With (^iPr₄PCP)IrH₄; hydrogen In toluene at 120℃; for 24 h;	General procedure: To a Teflon stoppered tube shaped glass ampoule ∼4.8mL in volume, 0.166mmol of the desired para-benzoquinone, a stir bar, and 0.25mL toluene containing 0.5mg ^iPrPCPIrH₄ are added. Then the solution is freeze–pump-thaw degassed twice, and 1atm H₂ applied. The sealed vessel is heated at a given temperature in an aluminum heat block with stirring for a prescribed period of time. When the reaction is ceased, volatiles are removed until only several μL toluene remain, and then the ampoule is quickly sealed. After this, 0.5mL THF-d₈ is added and the solution transferred to an NMR tube for analysis.

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3774 - 3783
[2] Tetrahedron, 1993, vol. 49, # 1, p. 105 - 112
[3] Asian Journal of Chemistry, 2010, vol. 22, # 4, p. 2549 - 2553
[4] Polyhedron, 2018, vol. 143, p. 209 - 214
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 4087

10
[ 123-31-9 ]
[ 115-11-7 ]
[ 88-58-4 ]

Reference： [1] Patent: US2572019, 1950, ,
[2] Patent: WO2005/14568, 2005, A2, . Location in patent: Page/Page column 12-13

11
[ 2460-77-7 ]
[ 3200-73-5 ]
[ 88-58-4 ]
[ 74785-31-2 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3774 - 3783

12
[ 2460-77-7 ]
[ 24850-33-7 ]
[ 88-58-4 ]
[ 73685-60-6 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 11, p. 3774 - 3783

13
[ 123-31-9 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 2460-77-7 ]
[ 88-58-4 ]
[ 1948-33-0 ]

Yield	Reaction Conditions	Operation in experiment
48.8%	With porous pillared-zirconium phosphate functionalized with methyl group In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 4 h; Autoclave	Alkylation of hydroquinone with tert-butanol was carried outin an autoclave equipped with a magnetic stirrer. Typically, 0.5 ghydroquinone, 1.0 g tert-butanol, and 0.20 g catalyst were addedto the autoclave, along with 2 g of xylene as a solvent. The reac-tion lasted 4 h under 150C. The products were analyzed witha gas chromatograph equipped with a SE-30 capillary column(30 m × 0.25 mm × 0.3 m) and a flame ionization detector. Thetemperature of the capillary column was set at 180C. The mainproducts were 2-tert-butyl hydroquinone (2-TBHQ), 2,5-di-tert-butyl hydroquinone (2,5-TBHQ), 2,5-di-tert-butyl benzoquinone(2,5-DTBBQ) and tert-butyl phenol ether (TBPE).

Reference： [1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 380, p. 84 - 89
[2] Chinese Journal of Catalysis, 2014, vol. 35, # 11, p. 1874 - 1882

14
[ 110-87-2 ]
[ 2460-77-7 ]
[ 88-58-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 5, p. 1115 - 1121

15
[ 507-19-7 ]
[ 123-31-9 ]
[ 88-58-4 ]

Reference： [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4161 - 4165
[2] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4161 - 4165

16
[ 1634-04-4 ]
[ 123-31-9 ]
[ 2444-28-2 ]
[ 88-58-4 ]
[ 2460-87-9 ]
[ 1948-33-0 ]

Reference： [1] Applied Catalysis A: General, 2013, vol. 450, p. 34 - 41

17
[ 124700-28-3 ]
[ 88-58-4 ]

Reference： [1] Journal of the American Chemical Society, 2003, vol. 125, # 27, p. 8318 - 8329

18
[ 123-31-9 ]
[ 75-65-0 ]
[ 88-58-4 ]

Reference： [1] Journal of the American Chemical Society, 1942, vol. 64, p. 937

19
[ 2460-77-7 ]
[ 88-58-4 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 25, p. 9256 - 9260

20
[ 2460-77-7 ]
[ 88-58-4 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 25, p. 9256 - 9260

21
[ 96455-63-9 ]
[ 2460-77-7 ]
[ 88-58-4 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 25, p. 9256 - 9260

22
[ 123-31-9 ]
[ 88-58-4 ]

Reference： [1] Angewandte Chemie, 1957, vol. 69, p. 699,700

23
[ 2460-77-7 ]
[ 88-58-4 ]
[ 77501-99-6 ]
[ 127558-27-4 ]

Reference： [1] Zeitschrift fuer Physikalische Chemie (Leipzig), 1989, vol. 270, # 5, p. 887 - 896

24
[ 123-31-9 ]
[ 115-11-7 ]
[ 88-58-4 ]
[ 2467-52-9 ]
[ 1948-33-0 ]

Reference： [1] Australian Journal of Chemistry, 1997, vol. 50, # 5, p. 515 - 516

25
[ 2460-77-7 ]
[ 88-58-4 ]

Reference： [1] Chemistry - A European Journal, 2015, vol. 21, # 25, p. 9256 - 9260

26
[ 507-20-0 ]
[ 123-31-9 ]
[ 88-58-4 ]

Reference： [1] Patent: US2439421, 1944, ,

27
[ 2460-77-7 ]
[ 100-99-2 ]
[ 88-58-4 ]
[ 77501-99-6 ]
[ 127558-27-4 ]

Reference： [1] Zeitschrift fuer Physikalische Chemie (Leipzig), 1989, vol. 270, # 5, p. 887 - 896
[2] Zeitschrift fuer Physikalische Chemie (Leipzig), 1989, vol. 270, # 5, p. 887 - 896

28
[ 88-58-4 ]
[ 74-88-4 ]
[ 7323-63-9 ]

Reference： [1] Journal of Materials Chemistry A, 2015, vol. 3, # 14, p. 7332 - 7337
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 6, p. XX682-692

29
[ 88-58-4 ]
[ 77-78-1 ]
[ 7323-63-9 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 1672

30
[ 88-58-4 ]
[ 7323-63-9 ]

Reference： [1] Tetrahedron, 1994, vol. 50, # 23, p. 6727 - 6758

[ 88-58-4 ] Synthesis Path-Downstream 1~100

1
[ 108-31-6 ]
[ 14296-80-1 ]
[ 88-58-4 ]
[ 71-43-2 ]
1,2,3,4,5,6-hexahydro-cyclobutabenzene-4r,5c-dicarboxylic acid-anhydride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 109,111

2
[ 2460-77-7 ]
[ 88-58-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With (iPr4PCP)IrH4; hydrogen; In toluene; at 120℃; under 760.051 Torr; for 24.0h;	General procedure: To a Teflon stoppered tube shaped glass ampoule ?4.8mL in volume, 0.166mmol of the desired para-benzoquinone, a stir bar, and 0.25mL toluene containing 0.5mg iPrPCPIrH4 are added. Then the solution is freeze-pump-thaw degassed twice, and 1atm H2 applied. The sealed vessel is heated at a given temperature in an aluminum heat block with stirring for a prescribed period of time. When the reaction is ceased, volatiles are removed until only several muL toluene remain, and then the ampoule is quickly sealed. After this, 0.5mL THF-d8 is added and the solution transferred to an NMR tube for analysis.

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 13655 - 13664
[2]Journal of the American Chemical Society,1980,vol. 102,p. 3774 - 3783
[3]Tetrahedron,1993,vol. 49,p. 105 - 112
[4]Asian Journal of Chemistry,2010,vol. 22,p. 2549 - 2553
[5]Polyhedron,2018,vol. 143,p. 209 - 214
[6]Journal of the American Chemical Society,1952,vol. 74,p. 4087

3
[ 88-58-4 ]
[ 2460-77-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [(4,5-dihydro-4,4-dimethyl-2-phenyloxazole)Ru(CH3CN)4]PF6; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20℃; for 0.08333330000000001h;	General procedure: To a solution of dihydroxy arene (0.34 mmol) and 2a (1.98 mg,0.0034 mmol) in THF (1.0 mL) was added H2O2 (30% aq, 50.0 mL,0.44 mmol) at 0 C. After 5 min the starting material had completelyoxidized to the quinone product. The quinone product wasthen extracted by ether or dichloromethane, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford thedesired product. Pleasingly, the resulted quinone products werepure enough and there is no necessity for column chromatographyin most of the cases.
99%	With silica gel supported cerium(IV) ammonium nitrate-NaBrO3; In dichloromethane; water; at 40℃; for 2.0h;	General procedure: A solution of CAN (0.056 g, 0.102 mmoles) and sodium bromate (0.780 g, 5.17 mmoles) in H2O (3 mL) was added slowly to vigorously stirred anhydrous silica gel (5 g) that was contained in a 100 mLround-bottom flask containing a magnetic stirring bar and fitted with a rubber septum. After complete addition of the aqueous solution, stirring was continued until a free-flowing powder was obtained.CH2Cl2 (25 mL) was then added to the flask and a solution of hydroquinone 1A (220.23 mg, 2.0 mmol), in CH2Cl2 (5 mL) was added slowly to the stirred heterogeneous mixture. A condenser was attached to the flask and the reaction was heated to reflux. Disappearance of 1A was monitored by thin-layer chromatography (EtOAc-hexane, 1:4; panisaldehyde/sulfuric acid as staining agent). Upon complete disappearance of 1A (ca. 2 h), the reaction mixture was filtered through a sintered glass funnel, the solid residue was washed with additional CH2Cl2 (3 × 10 mL), and the washings were added to the filtrate. Removal of solvent from the organic solution under vacuum gave an orange solid. Radial chromatography of the crude product (EtOAc-hexane,1:9) gave 1,4-benzoquinone 2A (89 mg, 82%) as an orange solid.
	In acetone;	EXAMPLE 16 The reaction was made under the same conditions as those in the procedure of EXAMPLE 1 except that the aromatic diol compound was 111.2g (0.5 mole) of 2,5-di-t-butylhydroquinone and 500 ml of acetone was used as the solvent. No unreacted 2,5-di-t-butylhydroquinone was detected and the yield of 2,5-di-t-butylbenzoquinone was 98.5%.

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 336 - 338
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 1445 - 1453
[3]Synthesis,2012,vol. 44,p. 1183 - 1189
[4]Tetrahedron,1987,vol. 43,p. 3963 - 3974
[5]Journal of the Chemical Society. Perkin transactions I,1981,p. 2970 - 2973
[6]Journal of the Chemical Society. Perkin transactions I,1982,p. 509 - 511
[7]Tetrahedron,1987,vol. 43,p. 3963 - 3974
[8]Synthetic Communications,2006,vol. 36,p. 1751 - 1759
[9]Journal of Organic Chemistry,2000,vol. 65,p. 8391 - 8394
[10]Tetrahedron,2013,vol. 69,p. 8612 - 8617
[11]Synthesis,2015,vol. 47,p. 3207 - 3211
[12]Synthesis,1985,p. 641 - 643
[13]Tetrahedron,1993,vol. 49,p. 105 - 112
[14]Advanced Synthesis and Catalysis,2005,vol. 347,p. 517 - 520
[15]Chemistry - A European Journal,2014,vol. 20,p. 9914 - 9917
[16]Tetrahedron,1987,vol. 43,p. 1753 - 1758
[17]Synthetic Communications,1980,vol. 10,p. 615 - 622
[18]Synthetic Communications,1980,vol. 10,p. 615 - 622
[19]Tetrahedron,1986,vol. 42,p. 2319 - 2324
[20]Polish Journal of Chemistry,2007,vol. 81,p. 1049 - 1061
[21]Organic and Biomolecular Chemistry,2006,vol. 4,p. 200 - 202
[22]Tetrahedron Letters,1994,vol. 35,p. 5083 - 5084
[23]Tetrahedron Letters,1988,vol. 29,p. 2671 - 2674
[24]Journal of the American Chemical Society,2002,vol. 124,p. 12261 - 12267
[25]Journal of Organic Chemistry,1987,vol. 52,p. 5053 - 5055
[26]Bulletin of the Chemical Society of Japan,1995,vol. 68,p. 1655 - 1660
[27]Synthesis,1980,p. 706 - 708
[28]Synthetic Communications,1989,vol. 19,p. 1317 - 1324
[29]Justus Liebigs Annalen der Chemie,1955,vol. 597,p. 196,211
[30]Acta Chemica Scandinavica (1947),1953,vol. 7,p. 938,939
[31]Journal of the Chemical Society,1952,p. 4666,4674
[32]Journal of the American Chemical Society,1947,vol. 69,p. 1057,1063
[33]Chemistry Letters,1976,p. 1293 - 1296
[34]Journal of Organic Chemistry,1983,vol. 48,p. 4764 - 4766
[35]Zeitschrift fur Physikalische Chemie (Leipzig),1989,vol. 270,p. 887 - 896
[36]Journal of Organic Chemistry,1981,vol. 46,p. 4545 - 4551
[37]Canadian Journal of Chemistry,1986,vol. 64,p. 225 - 231
[38]Journal of Organic Chemistry,1981,vol. 46,p. 3215 - 3218
[39]Journal of Organic Chemistry,1981,vol. 46,p. 3215 - 3218
[40]Journal of the American Chemical Society,1980,vol. 102,p. 4999 - 5004
[41]Journal of the American Chemical Society,1980,vol. 102,p. 4999 - 5004
[42]Patent: EP812816,1997,A1
[43]Dalton Transactions,2019,vol. 48,p. 6445 - 6454

4
[ 88-58-4 ]
[ 124700-28-3 ]

Reference： [1]Journal of Chemical Physics,1958,vol. 28,p. 774
[2]Journal of the American Chemical Society,2003,vol. 125,p. 8318 - 8329
[3]Journal of the American Chemical Society,2003,vol. 125,p. 8318 - 8329
[4]Angewandte Chemie - International Edition,2009,vol. 48,p. 8348 - 8351

5
[ 88-58-4 ]
[ 108-24-7 ]
[ 900-02-7 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6132

6
[ 88-58-4 ]
[ 75-36-5 ]
[ 900-02-7 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4087

7
[ 507-20-0 ]
[ 123-31-9 ]
[ 88-58-4 ]

Reference： [1]Patent: US2439421,1944,

8
[ 123-31-9 ]
[ 115-11-7 ]
[ 88-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	methanesulfonic acid; In toluene; at 22 - 70℃; under 900.09 - 2100.21 Torr; for 7.5h;	Example 5 110. 1G (1. OOOMOL) OF HYDROQUINONE and 330G OF TOLUENE are placed into an autoclave. After purging with N2,3. 30g (0. 0343MOL) of methane sulfonic acid are added. Then the reaction vessel is slowly flooded with iso-buten causing a slight rise of reaction temperature. Altogether 127.6g (2. 274MOL) of the alkene is added during 3h at 22- 35C giving a pressure of 1. 6bar. Stirring is continued overnight at 22-31C causing the pressure decrease to 1.2 bar. Heating to 70C increases the pressure to 2.8bar followed by gradual decrease to 1. 5bar after 4. 5H. After ventilation, 25.7g (8%, 0. 0245MOL) NAHCO3-SOLUTION along with 74. 1G of the buffer solution (I) are added under stirring. Simultaneously the reaction mixture was heated until it became clear. At 106C-the heavy, aqueous phase is drained off. Thereafter, the organic phase is treated with 196.3g of the above used buffer solution (II) at 106-115C. For removal of salt impurities, the reaction mixture is washed with 171.3g deionised water at elevated temperature. After an initial cooling to-30C within 2h, the temperature is further decreased to 0C. Filtering, washing with 100g of cold toluene and drying at max. 90C at 3 mbar yields 113.2g (50.9% rel HYDROQUINE) of 2,5-di-tertiary-butyl hydroquinone. Analytics Value Colour (5g + 95 g acetone) [Apha] 3 Melting point [C] 217 pH (aqueous suspension) 7.3 Volatiles (2g/2h/80C) [%] 0. 02 Ash (5g/800C) [%] 0. 01 Purity (GC) [%] * 98. 1 * The structure/identity has also been confirmed BY H-NMR-SPECTROSCOPY.

Reference： [1]Patent: US2572019,1950,
[2]Patent: WO2005/14568,2005,A2 .Location in patent: Page/Page column 12-13

9
[ 123-31-9 ]
[ 75-65-0 ]
[ 88-58-4 ]

Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 937

10
[ 123-31-9 ]
[ 88-58-4 ]

Reference： [1]Angewandte Chemie,1957,vol. 69,p. 699,700

11
[ 88-58-4 ]
[ 57-11-4 ]
1,4-di-tert-butyl-2,5-bis-stearoyloxy-benzene [ No CAS ]

Reference： [1]Journal of the American Oil Chemists' Society,1955,vol. 32,p. 170

12
[ 88-58-4 ]
[ 77-78-1 ]
[ 7323-63-9 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 1672

13
[ 108-31-6 ]
[ 88-58-4 ]
1,2,3,4,5,6-hexahydro-cyclobutabenzene-4r,5c-dicarboxylic acid-anhydride [ No CAS ]
[ 71-43-2 ]
[ 96983-75-4 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 109,111

14
[ 67-56-1 ]
[ 88-58-4 ]
[ 17208-03-6 ]

Reference： [1]Tetrahedron,1972,vol. 28,p. 5119 - 5129

15
[ 67-56-1 ]
[ 88-58-4 ]
[ 17208-05-8 ]

Reference： [1]Tetrahedron,1972,vol. 28,p. 5119 - 5129

16
[ 75-77-4 ]
[ 88-58-4 ]
[ 18724-29-3 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 4999 - 5004

17
[ 994-30-9 ]
[ 88-58-4 ]
[ 73759-44-1 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 4999 - 5004

18
[ 2460-77-7 ]
[ 100-99-2 ]
[ 88-58-4 ]
[ 77501-99-6 ]
[ 127558-27-4 ]

Reference： [1]Zeitschrift fur Physikalische Chemie (Leipzig),1989,vol. 270,p. 887 - 896
[2]Zeitschrift fur Physikalische Chemie (Leipzig),1989,vol. 270,p. 887 - 896

19
[ 2460-77-7 ]
[ 24850-33-7 ]
[ 88-58-4 ]
[ 73685-60-6 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 3774 - 3783

20
[ 2460-77-7 ]
[ 3200-73-5 ]
[ 88-58-4 ]
[ 74785-31-2 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 3774 - 3783

21
[ 2460-77-7 ]
[ 88-58-4 ]
[ 77501-99-6 ]
[ 127558-27-4 ]

Reference： [1]Zeitschrift fur Physikalische Chemie (Leipzig),1989,vol. 270,p. 887 - 896

22
[ 88-58-4 ]
[ 69739-34-0 ]
[ 73759-45-2 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 4999 - 5004
[2]Journal of Organic Chemistry,1981,vol. 46,p. 3215 - 3218

23
[ 88-58-4 ]
[ 79520-52-8 ]
[ 85629-71-6 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1020 - 1027

24
[ 88-58-4 ]
[ 7323-63-9 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 6727 - 6758

25
[ 88-58-4 ]
[ 18162-48-6 ]
[ 73759-45-2 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 12832 - 12833
[2]Canadian Journal of Chemistry,1986,vol. 64,p. 225 - 231

26
[ 88-58-4 ]
[ 143-15-7 ]
[ 130442-22-7 ]
1,4-Di-tert-butyl-2,5-bis-dodecyloxy-benzene [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

27
[ 507-19-7 ]
[ 123-31-9 ]
[ 88-58-4 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4161 - 4165
[2]Journal of Organic Chemistry,1984,vol. 49,p. 4161 - 4165

28
[ 75-77-4 ]
[ 88-58-4 ]
[ 999-97-3 ]
[ 18724-29-3 ]

Reference： [1]Journal of Organic Chemistry,1981,vol. 46,p. 3215 - 3218

29
[ 506-68-3 ]
[ 88-58-4 ]
[ 1969-47-7 ]

Yield	Reaction Conditions	Operation in experiment
10%	With triethylamine; In diethyl ether; at 0℃; for 0.5h;	General procedure: Phenyl cyanates should be freshly prepared before use, a mixture of phenol (20 mmol), BrCN (20 mmol), Et3N (20 mmol) in ethyl ether (20 ml) in ice bath for 0.5 h. At the end of reaction, the mixture filtered with Buchner funnel, washed with ethyl ether. The organic layer was transferred to round bottom flask and concentrated in vacuum, purification by column chromatography on silica gel.

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 1327 - 1330
[2]Tetrahedron,2016,vol. 72,p. 5749 - 5753
[3]Bulletin de la Societe Chimique de France,1967,p. 428 - 430

30
[ 88-58-4 ]
[ 4693-41-8 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1965,vol. 74,p. 397 - 406

31
[ 96-49-1 ]
[ 88-58-4 ]
2-[2,5-Di-tert-butyl-4-(2-hydroxy-ethoxy)-phenoxy]-ethanol [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5707 - 5738

32
[ 123-31-9 ]
[ 115-11-7 ]
[ 88-58-4 ]
[ 2467-52-9 ]
[ 1948-33-0 ]

Reference： [1]Australian Journal of Chemistry,1997,vol. 50,p. 515 - 516

33
[ 88-58-4 ]
[ 2460-77-7 ]
[ 23803-85-2 ]

Reference： [1]Russian Chemical Bulletin,1998,vol. 47,p. 1952 - 1955

34
[ 88-58-4 ]
2,5-di-t-butyl-1,4-benzoquinone [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 2351 - 2356

35
[ 64-17-5 ]
[ 507-20-0 ]
[ 123-31-9 ]
ZnCl₂ [ No CAS ]
[ 88-58-4 ]

Reference： [1]Patent: US2439421,1944,

Yield	Reaction Conditions	Operation in experiment
58.3%		Use of tert-butanol 6.2 g of hydroquinone (0.056 mol), 6.2 ml of methanol, 6.2 ml of water and 35.4 g (0.224 mol, 4 eq.) of benzenesulphonic acid are introduced, under a stream of nitrogen, into a 250 ml reactor. The medium is brought to 55 C. and 20.9 g (0.282 mol, 5 eq.) of tertbutanol are added rapidly (5 min). After maintaining these conditions for 24 hours, the reaction medium is cooled to room temperature and processing and purification are carried out as above. A yield of isolated product of 67.5% is obtained, for an 87% degree of conversion of the hydroquinone. b: Use of methyl tert-butyl ether (MTBE) 12.4 g (0.113 mol) of hydroquinone, 49.8 g of MTBE (0.566 mol, 5 eq.) and 21.5 g (0.113 mol, 1 eq.) of 85% benzenesulphonic acid are introduced, under a stream of nitrogen, into a 250 ml reactor. The medium is then brought to 60 C. After maintaining these conditions for 5 hours, 25 ml of hexane are added and the reaction medium is cooled to 20 C. and then filtered in order to obtain 17.8 g of wet cake. This filter cake is placed in an oven (35 C.) under maximum vacuum for 12 h to give 14.6 g (58.3% yield for an 80% degree of conversion) of 2,5-di-tert-butylhydroquinone.
		Examples of hydroquinones and alkylated hydroquinones of group c) are 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate and bis(3,5-di-tert-butyl-4-hydroxyphenyl)adipate.
		Alkylated Monophenols ... 2,6-di-octa-decyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octa-decyloxyphenol. 4,4'-thio-bis-(6-tert-butyl-3-methylphenol), 4,4'-thio-bis-(6-tert-butyl-2-methylphenol). 2,2'-Methylene-bis-(6-tert-butyl-4-methylphenol), 2,2'-methylene-bis-(6-tert-butyl-4-ethylphenol), ...

		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol. 2,2'-Thio-bis-(6-tert-butyl-4-methylphenol), ...
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octa-decyloxyphenol. 4,4'-thio-bis-(6-tert-butyl-3-methylphenol), 4,4'-thio-bis-(6-tert-butyl-2-methylphenol). ...
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-tnethoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octa-decyloxyphenol. 2,2'-Thio-bis-(6-ten-butyl-4-methylphenol), ...
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol and o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone and 2,6-diphenyl-4-octadecyloxyphenol. 2,2'-Thio-bis-(6-tert-butyl-4-methylphenol), ...
		Alkylated Monophenols ... 2,6-Di-octadecyl-4-methylphenol 2,4,6-Tri-cyclohexylphenol 2,6-Di-tert.butyl-4-methoxymethylphenol 2,6-Di-tert.-butyl-4-methoxyphenol 2,5-Di-tert.-butyl-hydroquinone 2,5-Di-tert.-amyl-hydroquinone 2,6-Diphenyl-4-octadecyloxyphenol 2,2'-Thio-bis-(6-tert.butyl-4-methylphenol) ...
		Alkylated monophenols ... 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol 2,2'-Thio-bis-(6-tert-butyl-4-methylphenol), ...
		Alkylated monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol and o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone and 2,6-diphenyl-4-octadecyloxyphenol. 2,2'-Thio-bis-(6-tert-butyl-4-methylphenol), ...
		Alkylated Monophenols ... 2,6-di-octadecyl-4-methylphenol 2,4,6-tri-cyclohexylphenol 2,6-di-tert.-butyl-4-methoxymethylphenol 2,6-Di-tert.-butyl-4-methoxyphenol 2,5-di-tert.-butyl-hydroquinone 2.5-di-tert-amyl-hydroquinone 2,6-diphenyl-4-octadecyloxyphenol 2,2'-Thio-bis-(6-tert.-butyl-4-methylphenol) ...
		A method as claimed in claim 3, in which the host compound is at least one compound selected from the group consisting of the following substances: ... 2,2'-Methylene-bis(4-methyl-6-t-butylphenol) 4. 4'-Thio-bis(3-methyl-6-t-butylphenol) 2,2'-Methylenbis(4-chlorophenol) T-butylhydroquinone 2,5-Di-t-butylhydroquinone.
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octa-decyloxyphenol. 2,2'-Thio-bis-(6-tert-butyl-4-methylphenol), ...
		Alkylated Monophenols ... 2,6-Di-octadecyl-4-methylphenol 2,4,6-Tri-cyclohexylphenol 2,6-Di-tert.-butyl-4-methoxymethylphenol 2,6-Di-tert.-butyl-4-methoxyphenol 2,5-Di-tert.-butyl-hydroquinone 2,5-Di-tert.-amyl-hydroquinone 2,6-diphenyl-4-octadecyloxyphenol 2,2'-Thio-bis(6-tert.-butyl-4-methylphenol) ...
		Alkylated monophenols ... 2,6-di-octadecyl-4-methylphenol 2,4,6-tricyclohexylphenol 2,6-di-tert-butyl-4-methoxymethylphenol 2,6-di-tert-butyl-4-methoxyphenol 2,5-di-tert-butyl-hydroquinone 2,5-di-tert-amyl-hydroquinone 2,6-diphenyl-4-octadecyloxyphenol 2,2'-thio-bis(6-tert-butyl-4-methylphenol) ...
		Alkylated monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol. 2,2'-Thio-bis-(6-tert-butyl-4-methylphenol), ...
		Illustrative examples of such compounds are 2,5-di-t-butylhydroquinone 2,6-di-t-butylhydroquinone 2,5-di-t-butyl-4-hydroxyanisole
		Alkylated monophenols ... 2,4,6-Tri-cyclohexylphenol 2,6-Di-tert-butyl-4-methoxymethylphenol o-tert-Butylphenol 2,6-Di-tert-butyl-4-methoxyphenol 2,5-Di-tert-butyl-hydroquinone 2,5-Di-tert-amyl-hydroquinone 2,6-Diphenyl-4-octadecyloxyphenol 2,2'-Thio-bis-(6-tert-butyl-4-methyphenol) ...
		illustrative examples of such compounds are: 2,5-di-t-butylhydroquinone 2,6-di-t-butylhydroquinone 2,5-di-t-butyl-4-hydroxyanisole
		Illustrative examples of such compounds are: 2,5-di-t-butylhydroquinone 2,6-di-t-butylhydroquinone 2,5-di-t-butyl-4-hydroxyanisole
		illustrative examples of such compounds are 2,5-di-t-butylhydroquinone 2,6-di-t-butylhydroquinone 2,5-di-t-butyl-4-hydroxyanisole.
		illustrative examples of such compounds are 2,5-di-t-butylhydroquinone 2,6-di-t-butylhydroquinone 2,5-di-t-butyl-4-hydroxyanisole
		(20) A slime preventing/removing agent according to (19), in which the multi-molecular host compound is one or more compounds selected from the group consisting of the following compounds: tetrakisphenols ... deoxycholic acid, cholic acid, alpha, alpha, alpha', alpha'-tetraphenyl-1,1'-biphenyl-2,2'-dimethanol, t-butylhydroquinone, 2,5-di-tert-butylhydroquinone,
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol. 2,2--Thio-bis-(6-tert-butyl-4-methylphenol), 2,2--thio-bis-(4-octylphenol), 4,4--thio-bis-(6-tert-butyl-3-methylphenol), 4,4--thio-bis-(6-tert-butyl-2-methylphenol).
		1. Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol,2,6-di-tert-butyl-4-ethyl-phenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(beta-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octa-decyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octa-decyloxyphenol. 4,4--thio-bis-(6-tert-butyl-3-methylphenol), 4,4--thio-bis-(6-tert-butyl-2-methylphenol).
		Alkylated Monophenols ... 2,6-di-tert.-butyl-4-methoxymethylphenol 2,6-Di-tert.-butyl-4-methoxyphenol 2,5-di-tert.-butyl-hydroquinone 2,5-di-tert.-amyl-hydroquinone ...
		1. Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octadecyloxyphenol. 2,2--Thio-bis-(6-tert-butyl-4-methylphenol), 2,2--thio-bis-(4-octyl-phenol), 4,4--thio-bis-(6-tert-butyl-3-methylphenol), 4,4--thio-bis-(6-tert-butyl-2-methylphenol).
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol. 2,2--Thio-bis-(6-tert-butyl-4-methylphenol), 2,2--thio-bis-(4-octylphenol), 4,4--thio-bis-(6-tert-butyl-3-methylphenol), 4,4--thio-bis-(6-tert-butyl-2-methylphenol).
		Alkylated Monophenols ... 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl- 4-methoxymethylphenol, o-tert-butylphenol. 2,6-Di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4-octa-decyloxyphenol.
		Illustrative examples of such compounds are 2,5-di-t-butylhydroquinone 2,6-di-t-butylhydroquinone 2,5-di-t-butyl-4-hydroxyanisole

39
[ 88-58-4 ]
[ 150985-87-8 ]
1,4-dimethyl-3-(2,5-di-tert-butyl-4-hydroxyl-1-carbophenoxy)-7-isopropylazulene [ No CAS ]
C₄₆H₅₄O₄ [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 5003 - 5018

40
[ 124700-28-3 ]
[ 88-58-4 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 8318 - 8329

41
[ 88-58-4 ]
[ 124-63-0 ]
methanesulfonic acid 2,5-di-tert-butyl-4-methanesulfonyloxyphenyl ester [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 1513 - 1514

42
methanesulfonic acid 2,5-di-tert-butyl-4-methanesulfonyloxyphenyl ester [ No CAS ]
[ 88-58-4 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 1513 - 1514

43
[ 88-58-4 ]
[ 2406-04-4 ]
[ 2460-77-7 ]
[ 122-37-2 ]

Reference： [1]Russian Chemical Bulletin,2004,vol. 53,p. 306 - 312

44
[ 31643-49-9 ]
[ 88-58-4 ]
[ 135848-91-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In water; dimethyl sulfoxide;	Example 5 Preparation of 1,4-bis-(3,4-dicyanophenoxy)-2,5-di-tert-butyl benzene 17.38 g (0.1 moles) of 4-nitrophthalonitrile, prepared according to Example 3, was dissolved in 150 ml anhydrous dimethyl sulphoxide (DMSO) in a 250 ml three-necked flask fitted with a stirrer, nitrogen-gas inlet and thermometer. 11.1 g (0.05 moles) of 2,5-di-tert-butyl hydroquinone (supplied by Aldrich) was added to the mixture followed by 20 g of anhydrous potassium carbonate. The mixture was stirred at room temperature with a stream of dry, oxygen-free (white spot) nitrogen passing through the flask for 24 hours. The reaction mixture was then poured into 1200 ml of water to produce a solid product which was washed five times with water and three times with methanol. The product (20 g, 85% yield) in the form of a white powder was recrystallized from acetonitrile to yield white crystals of 1,4-bis-(3,4-dicyanophenoxy)-2, 5-di-tert-butylbenzene having the formula: The melting point of this product was above 300C. Theoretical analysis of C30H26N4O2: C,75.94%; H,5.48%; N,11.81%; found: C,76.05%; H,5.50%; N,11.89%.

Reference： [1]Patent: EP413415,1991,A1
[2]Macromolecules,2006,vol. 39,p. 7534 - 7548

45
[ 88-58-4 ]
[ 51762-67-5 ]
[ 135848-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; dimethyl sulfoxide;	Example 6 Preparation of 1,4-bis-(2,3-dicyanophenoxy)-2,5-di-tert-butyl benzene The same apparatus as was used in Example 5 was used in this example. 8.8 g (0.051 moles) of 3-nitrophthalonitrile, prepared according to Example 4, was dissolved in 75 ml of anhydrous dimethyl sulphoxide in the three-necked flask. 5.55 g (0.025 moles) of 2,5-di-tert-butyl hydroquinone and 10 g of potassium carbonate were added to the reaction mixture. The mixture was stirred at room temperature with a stream of dry, oxygen-free nitrogen passing through the flask for 26 hours. The product was isolated by pouring the reaction mixture into 500 ml of water. The resultant solid precipitate was filtered and washed until the effluent was neutral. The product was further washed with boiling methanol until it became a greyish-white powder 10.6 g (90.2% yield). After recrystallisation from boiling acetonitrile white crystals of 1,4-bis-(2,3-dicyanophenoxy)-2,5-di-tert-butyl benzene were obtained having the formula: The melting point of this product was above 300C. Theoretical analysis of C30H26N4O2: C,75.94%; H,5.48%; N,11.81%; found: C,75.61%; H,5.48%; N,11.98%.

Reference： [1]Macromolecules,2006,vol. 39,p. 7534 - 7548
[2]Patent: EP413415,1991,A1

46
[ 2143-67-1 ]
[ 88-58-4 ]
[ 124700-28-3 ]
[ 122-39-4 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 91 - 96

47
[ 88-58-4 ]
[ 135771-48-1 ]

Reference： [1]Macromolecules,2006,vol. 39,p. 7534 - 7548

48
[ 88-58-4 ]
[ 135771-46-9 ]

Reference： [1]Macromolecules,2006,vol. 39,p. 7534 - 7548

49
[ 88-58-4 ]
[ 135848-93-0 ]

Reference： [1]Macromolecules,2006,vol. 39,p. 7534 - 7548

50
[ 88-58-4 ]
C₃₀H₃₀O₁₀ [ No CAS ]

Reference： [1]Macromolecules,2006,vol. 39,p. 7534 - 7548

51
[ 88-58-4 ]
[ 177539-55-8 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 5707 - 5738

52
[ 88-58-4 ]
[ 99758-88-0 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 6727 - 6758

53
[ 88-58-4 ]
[ 140466-64-4 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

54
[ 88-58-4 ]
[ 130442-23-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

55
[ 88-58-4 ]
Phosphorochloridic acid 3-bromomethyl-phenyl ester 2,5-di-tert-butyl-4-dodecyloxy-phenyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

56
[ 88-58-4 ]
C₃₆H₅₄NO₅PS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

57
[ 88-58-4 ]
C₃₇H₅₆NO₅PS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

58
[ 88-58-4 ]
C₃₇H₅₆NO₅PS [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

59
[ 88-58-4 ]
[ 77501-99-6 ]

Reference： [1]Zeitschrift fur Physikalische Chemie (Leipzig),1989,vol. 270,p. 887 - 896

60
[ 88-58-4 ]
[ 127558-27-4 ]

Reference： [1]Zeitschrift fur Physikalische Chemie (Leipzig),1989,vol. 270,p. 887 - 896

61
[ 88-58-4 ]
[ 4857-75-4 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1955,vol. 597,p. 196,211

62
[ 88-58-4 ]
[ 1969-45-5 ]

Reference： [1]Bulletin de la Societe Chimique de France,1967,p. 428 - 430

63
[ 88-58-4 ]
[ 1969-46-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1967,p. 428 - 430

64
[ 637-81-0 ]
[ 88-58-4 ]
[ 6630-33-7 ]
[ 103858-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; sodium; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; hexane;	Step 1 Ethyl 4-bromo-indolecarboxylate A solution of 23 mL of ethyl azidoacetate and 7.6 mL of 2-bromobenzaldehyde in 40 mL ethanol was added dropwise to a solution of 4.5 g sodium in 180 mL ethanol, in a bath at -10 C., at a rate such that the reaction temperature does not rise above 8 C. After the addition is complete, the mixture is stirred at 5-10 C. for 30 min. The reaction mixture is then poured into a mixture of 28 g of NH4Cl in 1 L ice, and extracted with 1:4 CH2Cl2/hexane. The organic phase is filtered through 150 mL silica gel, which is rinsed with 200 mL of the same solvent. This is evaporated to near dryness, diluted with 300 mL xylene, and stabilised with 60 mg of 2,5-di-t-butylhydroquinone. This mixture is heated with a distillation head until 50 mL of xylene has distilled. The mixture is cooled and evaporated in vacuo to a volume of 80 mL, which is diluted with 80 mL of hexane. A white solid forms upon cooling to 0 C., which is filtered off. 1H NNR (acetone-d6) delta 1.37 (t, 3H), 4.37 (q, 2H), 7.13 (t, 1H), 7.21 (t, 1H), 7.33 (d, 1H), 7.55 (d, 1H), 11.3 (s, 1H).

Reference： [1]Patent: US2002/68756,2002,A1

65
[ 88-58-4 ]
[ 75-98-9 ]
[ 216314-03-3 ]

Yield	Reaction Conditions	Operation in experiment
78%	sulfuric acid; In hexane; di-isopropyl ether; ethyl acetate; acetonitrile;	1) Synthesis of 2,5-di-t-butyl-4-trimethylacetoxyphenol Under argon atmosphere, a solution of 11.12 g of 2,5-di-t-butylhydroquinone and 10.1 ml of anhydrous trimethylacetic acid in 200 ml of acetonitrile was stirred with a catalytic amount of sulfuric acid at room temperature for a whole day and night. After the reaction mixture was evaporated under reduced pressure, the concentrate was dissolved in diisopropyl ether. This solution was washed with a saturated aqueous sodium bicarbonate solution, then saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 5% ethyl acetate) to give 11.9 g of 2,5-di-t-butyl-4-trimethylacetoxyphenol as a white solid (yield 78%). 1H NMR (270 MHz, CDCl3) delta ppm: 1.30 (s, 9H), 1.37 (s, 9H), 1.38 (s, 9H), 4.67 (s, 1H), 6.64 (s, 1H), 6.67 (s, 1H).

Reference： [1]Patent: US6403639,2002,B1

66
[ 71771-78-3 ]
[ 88-58-4 ]
[ 108-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium bromide; sodium iodide; potassium carbonate; In acetonitrile;	EXAMPLE 10 Phenol, 2,5-bis(1,1-dimethylethyl)-4-[(2-furanyidimethylsilyl)methoxy]-- STR20 Stir a mixture of chloromethyl(dimethyl)furanylsilane (0.3 mol, Example 1, step a), 2,5-di-t-butylhydroquinone (0.3 mol, Aldrich Chemical Co., Milwaukee, Wis. 53233), lithium bromide (0.1 mol), potassium carbonate (0.3 mol) sodium iodide (2.0 g) and acetonitrile (600 mL) at reflux for 3 days. Cool the mixture, dilute with water and extract with ether. Wash the ether layer with water and evaporate to dryness to give a residue. Distill and chromatograph the residue on silica gel to give the title compound.

Reference： [1]Patent: US6121463,2000,A

67
[ 88-58-4 ]
[ 143-15-7 ]
[ 130442-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;	EXAMPLE 51 2,5-Bis(1,1-dimethylethyl)-4-(dodecyloxy)phenol To a suspension of 42.08 g of hexanes washed sodium hydride, under inert gas, in 400 ml of N,N-dimethylformamide was added 10.12 g of sodium iodide. White stirring, a solution of 150 g of <strong>[88-58-4]2,5-di-tert-butylhydroquinone</strong> in 400 ml of N,N-dimethylformamide and 300 ml of tetrahydrofuran was added dropwise over 1.5 hours. Over an additional 30 minutes, 168.16 g of 1-bromododecane was added dropwise. Stirring was continued at ambient temperature for 24 hours. The mixture was diluted with crushed ice and cold dilute hydrochloric acid followed by ether extraction. The organic layer was dried with magnesium sulfate and the solvent removed in vacuo to afford a syrup which was distilled in a Kugelrohr apparatus. The fraction boiling 160-205 C. was collected and purified by chromatography on silica gel with ether-hexanes giving 23.6 g of the desired compound as an orange oil.

Reference： [1]Patent: US4983592,1991,A

68
[ 2004-70-8 ]
[ 930-60-9 ]
[ 88-58-4 ]
[ 52894-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene;	a. 4-Methyl-cis-3a,4,7,7a-tetrahydroindane-1,3-dione A solution of 4-cyclopentene-1,3-dione (5.84g; 0.06 mole) in dry benzene (20ml.) was stood for 4 days with 1,3-pentadiene (8.9g; 0.122 mole) and a little 2,5-di-t-butyl hydroquinone (10mg.) and the crystalline solid filtered off and recrystallized from methanol to yield the title dione, m.p. 139- 40 C. (Found; C, 72.96; H, 7.51; C10 H12 02 requires; C, 73.15; H, 7.34%).

Reference： [1]Patent: US4005219,1977,A

69
[ 626-99-3 ]
[ 930-60-9 ]
[ 88-58-4 ]
[ 52894-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene;	a. 4-Carboxy cis- 3a,4,7,7a-tetrahydroindane-1,3-dione A solution of 4-cyclopentene-1,3-dione (9 6g; 0.1 mole) in dry benzene (30ml.) was added to 1-carboxy butadiene (9 8g; 0.1 mole) and a few crystals of 2,5-di-t-butyl hydroquinone added. The orange solution was stood at room temperature for 3 days and evaporated to small bulk to induce crystallisation. Filtration followed by trituration with anhydrous ether gave the desired product, m.p. 182 C. (H. O. House and G. H. Rasmunsen J. Org. Chem., 1963, 28, 27 quote m.p. 191 C).

Reference： [1]Patent: US4005219,1977,A

70
[ 88-58-4 ]
[ 616-38-6 ]
[ 1991-52-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 3 44.4 parts of 2,5-di-tert.-butylhydroquinone, 18 parts of dimethyl carbonate and 1 part of p-dimethylaminopyridine are kept for 20 hours at 200 C. Working up takes place as described in Example 1. 9.5 parts (26% of theory, based on converted starting material II) of 2,5-di-tert.-butylhydroquinone dimethyl ether of boiling point 71-74 C./0.5 mbar and 22.4 parts (65% of theory) of 2,5-di-tert.-butylhydroquinone monomethyl ether of boiling point 77-79 C./0.5 mbar are obtained. The conversion is 73 percent.

Reference： [1]Patent: US4192949,1980,A

71
[ 71771-78-3 ]
[ 88-58-4 ]
Phenol, 2,5-bis(1,1-dimethylethyl)-4-[(2-furanyldimethylsilyl)methoxy]- [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium bromide; sodium iodide; potassium carbonate; In acetonitrile;	EXAMPLE 10 Phenol, 2,5-bis(1,1-dimethylethyl)-4-[(2-furanyldimethylsilyl)methoxy]- Stir a mixture of chloromethyl(dimethyl)furanylsilane (0.3 mol, Example 1, step a), 2,5-di-t-butylhydroquinone (0.3 mol, Aldrich Chemical Co., Milwaukee, Wis. 53233), lithium bromide (0.1 mol), potassium carbonate (0.3 mol) sodium iodide (2.0 g) and acetonitrile (600 mL) at reflux for 3 days. Cool the mixture, dilute with water and extract with ether. Wash the ether layer with water and evaporate to dryness to give a residue. Distill and chromatograph the residue on silica gel to give the title compound.

Reference： [1]Patent: EP998477,2003,B1

72
[ 88-58-4 ]
[ 74-88-4 ]
[ 7323-63-9 ]

Reference： [1]Journal of Materials Chemistry A,2015,vol. 3,p. 7332 - 7337
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. XX682-692

73
[ 1291-32-3 ]
[ 88-58-4 ]
[(ZrCl(C₅H₅)2)2(OC₆H₂(C₄H₉)2O)] [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 913 - 919

74
[ 107333-47-1 ]
[ 88-58-4 ]
[ 176542-03-3 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 913 - 919

75
[ 88-58-4 ]
[ 40411-25-4 ]
[ 887704-24-7 ]

Reference： [1]Russian Journal of Applied Chemistry,2008,vol. 81,p. 1821 - 1830

76
[ 88-58-4 ]
[ 3320-83-0 ]
[ 887704-26-9 ]

Reference： [1]Russian Journal of Applied Chemistry,2008,vol. 81,p. 1821 - 1830

77
[ 88-58-4 ]
[ 2909-38-8 ]
[ 1186005-98-0 ]

Reference： [1]Russian Journal of Applied Chemistry,2008,vol. 81,p. 1821 - 1830

78
[ 88-58-4 ]
[ 28556-81-2 ]
[ 887704-25-8 ]

Reference： [1]Russian Journal of Applied Chemistry,2008,vol. 81,p. 1821 - 1830

79
[ 88-58-4 ]
[ 51762-67-5 ]
[ 1158537-37-1 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 3357 - 3363

80
[ 88-58-4 ]
[ 139152-08-2 ]
[ 1158537-28-0 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 3357 - 3363

81
[ 57294-38-9 ]
[ 88-58-4 ]
[ 1192363-56-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6613 - 6619

82
[ 57294-38-9 ]
[ 88-58-4 ]
[ 1192363-55-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6613 - 6619

83
[ 627-42-9 ]
[ 88-58-4 ]
[ 1350770-63-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydride; In tetrahydrofuran; at 20℃;	2,5-Di-tert-butylhydroquinone (0.2 mmol) was dissolved in anhydrous THF (20 ml). Sodium hydride (0.6 mmol) and 2-chloroethylethylether (0.4 mmol) was then added to the solution. The reaction mixture was then stirred at room temperature overnight. After removal of the solvent, the residue was partitioned between dichloromethane and aqueous NaHCO3 (0.1M). The organic portion was separated and dried over Na2SO4. After solvent removal in vacuo, the crude product was chromatographed (silica, hexanes/DCM from 5:1 to 1:1) to afford 1,4-bis(2-methoxyethoxy)-2,5-di-tert-butyl-benzene in an 81% yield. The product was characterized by 1H NMR (300 MHz, CDCl3, delta/ppm): 7.14 (s, 2H), 4.11 (t, J=4.5 Hz, 4H), 3.80 (t, J=4.5 Hz, 4H), 3.45 (s, 6H), 1.37 (s, 18H).

Reference： [1]Patent: US2011/294003,2011,A1 .Location in patent: Page/Page column 11

84
[ 448-19-1 ]
[ 88-58-4 ]
[ 1381864-10-3 ]

Reference： [1]Polymer,2012,vol. 53,p. 2783 - 2791

85
[ 88-58-4 ]
[ 1381864-12-5 ]

Reference： [1]Polymer,2012,vol. 53,p. 2783 - 2791

86
[ 88-58-4 ]
[ 1381864-11-4 ]

Reference： [1]Polymer,2012,vol. 53,p. 2783 - 2791

87
[ 1634-04-4 ]
[ 123-31-9 ]
[ 2444-28-2 ]
[ 88-58-4 ]
[ 2460-87-9 ]
[ 1948-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-(4-sulfobutylamino)propylsilanized MCM-41; In nitrobenzene; at 150℃; for 0.133333h;Microwave irradiation; Green chemistry;Catalytic behavior;	Friedel-Crafts reactions were performed with microwave irradiation assistance by modifying the synthesis condition [30]. Prior to reaction, hydroquinone (Merck, 2.0 mmol), methyl tert-butyl ether (MTBE, Merck, 2.0 mmol) and freshly activated SO3H-MCM-41 catalyst (0.1 g, 100 C, 3 h) were loaded into a reactor. The reaction was realized in an Anton Paar Synthos 3000 microwave oven under magnetic stirring and 300 W microwave irradiation, while the reaction temperature was monitored by an infrared pyrometer. The samples were withdrawn after the reaction and the liquid phase was separated and analyzed using a gas chromatograph (Hewlett-Packard 5880) equipped with a Carbowax Equity 1 non-polar capillary column. The identity of the product was confirmed by GC-MS (Perkin-Elmer GC-IR 2000 system).

Reference： [1]Applied Catalysis A: General,2013,vol. 450,p. 34 - 41

88
[ 123-31-9 ]
[ 75-65-0 ]
[ 6669-13-2 ]
[ 2460-77-7 ]
[ 88-58-4 ]
[ 1948-33-0 ]

Yield	Reaction Conditions	Operation in experiment
48.8%	With porous pillared-zirconium phosphate functionalized with methyl group; In 5,5-dimethyl-1,3-cyclohexadiene; at 150℃; for 4.0h;Autoclave;	Alkylation of hydroquinone with tert-butanol was carried outin an autoclave equipped with a magnetic stirrer. Typically, 0.5 ghydroquinone, 1.0 g tert-butanol, and 0.20 g catalyst were addedto the autoclave, along with 2 g of xylene as a solvent. The reac-tion lasted 4 h under 150C. The products were analyzed witha gas chromatograph equipped with a SE-30 capillary column(30 m × 0.25 mm × 0.3 m) and a flame ionization detector. Thetemperature of the capillary column was set at 180C. The mainproducts were 2-tert-butyl hydroquinone (2-TBHQ), 2,5-di-tert-butyl hydroquinone (2,5-TBHQ), 2,5-di-tert-butyl benzoquinone(2,5-DTBBQ) and tert-butyl phenol ether (TBPE).
	With perfluorosulfonicacid?functionalized carbon nanotubes (PFSA?CNT?0.5); In 5,5-dimethyl-1,3-cyclohexadiene; for 4.0h;Autoclave;Catalytic behavior;	Alkylation of hydroquinone was carried out in a stainlesssteel autoclave with a PTFE liner using magnetic stirring. Typically,0.5 g hydroquinone, 1.0 g tert?butanol, and 0.2 g catalystwere added in the autoclave accompanied with 2 g xylene assolvent. The reaction lasted 4 h. The products were analyzedwith a GC122 gas chromatograph equipped with a SE?54 capillarycolumn (30 m 0.25 mm 0.3 m) and a flame ionizationdetector

Reference： [1]Journal of Molecular Catalysis A: Chemical,2013,vol. 380,p. 84 - 89
[2]Cuihua Xuebao/Chinese Journal of Catalysis,2014,vol. 35,p. 1874 - 1882

89
[ 88-58-4 ]
[ 6482-24-2 ]
[ 1350770-63-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With caesium carbonate; In N,N-dimethyl-formamide; at 58 - 70℃; for 5.5h;	The reactor was charged with DMF (12 L, BDH 111510D) and the stirring speed set to 120 rpm. 2,5-Di-tert-butylbenzene-1,4-diol (1,312 g, 5.90 mol, 1.0 eq, Aldrich MKBC8025V) was added followed by cesium carbonate (5,758 g, 17.67 mol, 3.0 eq, Alfa B09W012). The circulator was set to control the process (internal reaction mixture) temperature at about 60 C. A gradual addition of 1-bromo-2-methoxyethane was started when the reaction temperature reached about 58 C. The whole amount of the reagent (2,467 g, 17.748 mol, 3.0 eq, Oakwood B12M) was added over 20 minutes. The temperature of the reaction mixture spontaneously rose to 65 C. (exothermic reaction). The mixture was stirred for 1 h at 65 C. The circulator was set to about 70 C. The reaction was sampled after 5.5 h (time since addition of 1-bromo-2-methoxyetane was completed). HPLC analysis (Agilent Eclipse Plus, C18, ACN/water gradient elution, UV 225 nm) revealed complete consumption of the starting benzene-1,4-diol and formation of the desired product (96.52% by peak area integration). (0084) The reaction mixture was cooled to about 20 C. The contents of the reactor were drained onto a filter (polypropylene filtration cloth, 61 cm diameter). The solids were washed with DMF (3 L). The combined filtrates were concentrated under reduced pressure on a Buchi rotary evaporator (R-215, bath temperature of about 70 C., pressure 10-14 mbar, vapor temperature 41-44 C). Thirteen liters of solvent (DMF) were recovered. (0085) The 20 L reactor was cleaned and charged with water (14 L). The concentrate (5 L) was added to the stirred (120 rpm) water at room temperature over 10 minutes. The contents of the reactor were drained onto a filter (polypropylene filtration cloth, 61 cm diameter). The solids were washed on the filter with water (4 L) and air dried to yield 2,285 g of crude product. The combined filtrates were disposed as waste. The cleaned 20 L reactor was charged with the crude material. Isopropyl alcohol (7 L, BDH 11291002) was added to the reactor. The process temperature was set to about 55 C. and the stirring speed was set to 60 rpm. Complete dissolution of the solids occurred at about 37 C. Water (3.5 L) was added to the solution at about 52 C. over a period of 10 minutes. The Huber circulator was programmed to a cooling ramp of about 55 C. to 19 C. over 3 h. The solution was seeded with crystalline ANL-RS2 (2 g) at about 49 C. (0086) The mixture was stirred 1 h at about 19 C. The contents of the reactor were drained onto a filter (polypropylene filtration cloth, 61 cm diameter). The material was air dried to yield 2,085 g of 1,4-di-tert-butyl-2,5-bis(2-methoxyethoxy)benzene. HPLC analysis (Agilent Eclipse Plus, C18, ACN/water gradient elution, UV 225 nm) revealed 99.46% purity of the desired compound. The material was re-crystallized from isopropanol/water (7 L/3 L) mixture in the same fashion as the first crystallization. The material from the second crystallization was suspended in 20 L reactor using isopropanol/water (5 L/5 L) mixture. The suspension was stirred about 2 h at about 20 C. The material was filtered off and dried first on air then in vacuum oven (10 mbar/40 C) until moisture content (monitored by coulometric KF titration) dropped below 20 ppm. Yield 1,582 g (79%) of 1,4-di-tert-butyl-2,5-bis(2-methoxyethoxy)benzene (ANL-RS2). Purity was greater than 99 percent (e.g., 99.92% for average HPLC peak area integration). Moisture was 13 ppm (average per KF coulometric titration).

Reference： [1]Patent: US8921611,2014,B1 .Location in patent: Page/Page column 10

90
[ 88-58-4 ]
[ 1204-28-0 ]
C₃₂H₂₆O₁₀ [ No CAS ]

Reference： [1]Polymer,2015,vol. 74,p. 1 - 15

91
[ 2460-77-7 ]
thiol [ No CAS ]
C₄₇H₇₂Fe₄NS₇^(1-) [ No CAS ]
{Fe₄S₄(S-2,4,6-(i-Pr)3C₆H₂)4}^(1-) [ No CAS ]
[ 88-58-4 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9256 - 9260

92
[ 96455-63-9 ]
[ 2460-77-7 ]
{Fe₄S₄(S-2,4,6-(i-Pr)3C₆H₂)4}^(2-) [ No CAS ]
[ 88-58-4 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9256 - 9260

93
[ 2460-77-7 ]
C₇₂H₁₁₆Fe₄S₈^(3-)*2C₁₆H₃₆N⁽¹⁺⁾ [ No CAS ]
[ 88-58-4 ]
C₇₂H₁₁₆Fe₄S₈^(2-)*2C₁₆H₃₆N⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9256 - 9260

94
[ 2460-77-7 ]
C₃₉H₁₇F₃₃Fe₄S₈^(3-)*2C₁₆H₃₆N⁽¹⁺⁾ [ No CAS ]
[ 88-58-4 ]
C₃₉H₁₇F₃₃Fe₄S₈^(2-)*2C₁₆H₃₆N⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 9256 - 9260

95
[ 88-58-4 ]
[ 16420-13-6 ]
1,4-bis(dimethylthiocarbamoyl)2,5-di-tert-butylbenzene [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 1243 - 1252

96
acid blue 5 [ No CAS ]
[ 1450-72-2 ]
[ 591-81-1 ]
[ 617-48-1 ]
[ 19071-34-2 ]
[ 83-56-7 ]
[ 88-58-4 ]
1-Amino ethenol [ No CAS ]

Reference： [1]RSC Advances,2016,vol. 6,p. 81219 - 81230

97
[ 1120-71-4 ]
[ 88-58-4 ]
sodium 3-(2,5-di-tert-butyl-4-hydroxy-phenoxy)propane-1-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydride; In tetrahydrofuran; at 20℃;	Example 3 (0086) The compound I-4 is prepared by deprotonation of 1 g of <strong>[88-58-4]2,5-di-tert-butylhydroquinone</strong> (DBHQ) (4.50 mmol) in the presence of 0.13 g sodium hydride (5.40 mmol) in 20 mL THF at room temperature. The reaction mixture was stirred at room temperature for 15 minutes, then 0.55 g of 1,3-propanesultone (4.50 mmol) is added slowly and the reaction mixture is stirred overnight. The excess sodium hydride is quenched by slow addition of methanol. Precipitation with Et2O followed by filtration and washing with Et2O yields 1.57 g of a white solid (95%). Anion exchange with methylene blue is performed as described above via extraction from water with dichloromethane.

Reference： [1]Patent: US2016/280673,2016,A1 .Location in patent: Paragraph 0084

98
[ 110-87-2 ]
[ 2460-77-7 ]
[ 88-58-4 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 1115 - 1121

99
[ 88-58-4 ]
[ 141-97-9 ]
7-tert-butyl-6-hydroxy-4-methylcoumarin [ No CAS ]

Reference： [1]Chemistry and biodiversity,2019,vol. 16

100
[ 875770-32-4 ]
[ 88-58-4 ]
C₂₅H₄₀O₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2021,vol. 143,p. 9884 - 9892

Recommend Products

Same Skeleton Products

Related Products

Isomers

Historical Records

Related Functional Groups of
[ 88-58-4 ]

Aryls

[ 19263-36-6 ]

2,6-Di-tert-butyl-4-vinylphenol

Similarity: 0.97

[ 157432-87-6 ]

5,11,17,23-Tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene stereoisomer

Similarity: 0.95

[ 2416-95-7 ]

3,3',5,5'-Tetraisopropylbiphenyl-4,4'-diol

Similarity: 0.94

[ 1948-33-0 ]

2-(tert-Butyl)benzene-1,4-diol

Similarity: 0.94

[ 96-76-4 ]

2,4-Di-tert-butylphenol

Similarity: 0.94

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 88-58-4 ] {[proInfo.proName]}

Quality Control of [ 88-58-4 ]

Related Doc. of [ 88-58-4 ]

Product Details of [ 88-58-4 ]

Calculated chemistry of [ 88-58-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 88-58-4 ]

Application In Synthesis of [ 88-58-4 ]

[ 88-58-4 ] Synthesis Path-Upstream 1~30

[ 88-58-4 ] Synthesis Path-Downstream 1~100

Related Functional Groups of [ 88-58-4 ]

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 88-58-4 ]