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[ CAS No. 1948-33-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1948-33-0
Chemical Structure| 1948-33-0
Chemical Structure| 1948-33-0
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Product Details of [ 1948-33-0 ]

CAS No. :1948-33-0 MDL No. :
Formula : C10H14O2 Boiling Point : -
Linear Structure Formula :C6H3C(CH3)3(OH)2 InChI Key :BGNXCDMCOKJUMV-UHFFFAOYSA-N
M.W : 166.22 Pubchem ID :16043
Synonyms :
tert-Butylhydroquinone
Chemical Name :2-(tert-Butyl)benzene-1,4-diol(may occur to produce black solid)

Calculated chemistry of [ 1948-33-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 49.76
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 2.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.183 mg/ml ; 0.0011 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.0764 mg/ml ; 0.00046 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.45
Solubility : 0.591 mg/ml ; 0.00356 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 1948-33-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1948-33-0 ]

* 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 [ 1948-33-0 ]
  • Downstream synthetic route of [ 1948-33-0 ]

[ 1948-33-0 ] Synthesis Path-Upstream   1~25

  • 1
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YieldReaction ConditionsOperation in experiment
99.9% With phosphoric acid In water at 59 - 81℃; for 2 h; 1) 3 parts by weight of phosphoric acid, 0.1 part by weight of water was poured into a stirring cylinder, and 6 parts by weight of hydroquinone was added to the stirring cylinder to carry out stirring;2) After stirring, the mixed solution was placed in a reaction kettle and heated to 59 ° C, and then the reaction vessel was charged with t-butanolCopies;3) heating to 81 ° C, the insulation for 2 hours to react;4) the reaction product by centrifugal separation, washing, dehydration after TBHQ crude;5) 1 part by weight of acid and 95 parts by weight of water were mixed and then heated. After heating to 81 ° C, 6.5 parts by weight of TBHQ was added and heated to 95 ° C with stirring.6) The solution of step 5) was centrifuged for the first time, the DTBHQ insoluble in water in the crude TBHQ was separated, and then the solution was cooled. When the solution was cooled to 45C or lower, the second centrifugation was carried out, and the obtained TBHQ crystal washing, dehydration, drying, that was TBHQ boutique.Wherein the drying in step 6) is carried out by pouring the wet TBHQ boutique into a vibrating screen sieve, laying the sieved TBHQ boutique on a drying tray, having a thickness of 5 cm and drying for 8 hours.The TBHQ was obtained, where the weight percentage of TBHQ was 99.9percent and the weight percentage of DTBHQ was 0.1percent.
Reference: [1] Patent: CN103864580, 2016, B, . Location in patent: Paragraph 0095-0104
[2] Patent: US2511193, 1947, ,
[3] Patent: US2722556, 1952, ,
[4] Patent: CN105541560, 2016, A, . Location in patent: Paragraph 0011
[5] Patent: WO2018/214039, 2018, A1, . Location in patent: Page/Page column 12-15
[6] Patent: CN108929200, 2018, A, . Location in patent: Paragraph 0009; 0011; 0014; 0017
  • 2
  • [ 3602-55-9 ]
  • [ 1948-33-0 ]
YieldReaction ConditionsOperation in experiment
99% With (iPr4PCP)IrH4; hydrogen In toluene at 60℃; for 2 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] Polyhedron, 2018, vol. 143, p. 209 - 214
[2] Agricultural and Biological Chemistry, 1988, vol. 52, # 11, p. 2843 - 2850
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 28, p. 8196 - 8200[4] Angew. Chem., 2017, vol. 129, # 28, p. 8308 - 8312,5
[5] Molecular Catalysis, 2018, vol. 456, p. 49 - 56
  • 3
  • [ 88-18-6 ]
  • [ 3602-55-9 ]
  • [ 1948-33-0 ]
YieldReaction ConditionsOperation in experiment
97% With dihydrogen peroxide In water; acetic acid at 50 - 60℃; for 1.25 h; Preparation of 2-tert-butyl-1, 4-benzoquinone A mixture of 2-t-butylphenol (5 mmol) and Ti-superoxide catalyst (125 mg, 20percent w/w) in acetic acid (5 ml) was heated with stirring at 50-60 C under inert atmosphere. To this reaction mixture was added aq. 30percent H202 (20 mmol) drop wise over 15 min. and heated for 1 h. The catalyst was recovered by simple filtration and 2-tert-butyl-1, 4-benzoquinone formed (97percent) was separated by chromatographic purification.Table 1: Ti-superoxide (1) catalyzed oxidation of phenols to quinines and hydroquinones with aq. 30percent H202 : a Ex. Substrate t/h Conversion ProductU Selectivity (percent) c

No. (percent)



Quinone HQd 1. Phenol 10 22 2 20e 91. 0 2. Phenol 8 66 5 6 92. 4 3. Phenol 7 65 3 60 92.3 4. Phenol 7 68 3.5 63g 92.7 5. Phenol 1 92 88 2.3 95.7 6. o-Cresol 1 99 96 3.0 97.0 7. 7n-Cresol 1 100 99 0.5 99.0 8. 2,6-Dimethylphenol 1 100 97 2.0 97.0 9. 2-'Butylphenol 1 99 97 0. 7 98.0 10. 2, 6-Dibutylphenol 3 70 65 2. 0 93.0 11.4-Chlorophenol 1 57 55-96.5 12.4-Bromophenol 1 61 60-98. 4 13. 4-Iodophenol 1 77 75-97.4 14.2, 4-Dichlorophenol 1 32 25 5. 0 78.1 (a) See examples for detailed experimental procedure; (b) determined by GC analysis of the crude product; (c) selectivity to hydroquinone ; (d) hydroquinone; (e) aq. 10percent H202; (f) aq.50percent H202; (g) 40percent w/w catalyst.
Reference: [1] Patent: WO2005/63664, 2005, A1, . Location in patent: Page/Page column 7
  • 4
  • [ 540-88-5 ]
  • [ 123-31-9 ]
  • [ 1948-33-0 ]
YieldReaction ConditionsOperation in experiment
99.9% at 85℃; for 8 h; Large scale Reaction1 Hydroquinone 110kg 116kg acetic acid tert-ester and sulfuric acid concentration of 50percent sulfuric acid 294kg added to the reaction kettle was warmed up to 85 ° C to a reaction for 8 hours to complete the reaction, cooling to 65 °C rear centrifugal filtration, filtrate recycling sulfuric acid, the resulting added 1 times warm water washing, the crude product of tert-butyl hydroquinone, wherein the tert-butyl hydroquinone content is 70percent.
Reference: [1] Patent: CN105294403, 2016, A, . Location in patent: Paragraph 0027; 0028
  • 5
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Reference: [1] Applied Catalysis A: General, 2013, vol. 450, p. 34 - 41
  • 6
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  • [ 2460-77-7 ]
  • [ 88-58-4 ]
  • [ 1948-33-0 ]
YieldReaction ConditionsOperation 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
  • [ 3602-55-9 ]
  • [ 100-46-9 ]
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Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8698 - 8706
  • 8
  • [ 4857-74-3 ]
  • [ 1948-33-0 ]
Reference: [1] Patent: WO2012/75053, 2012, A2, . Location in patent: Page/Page column 79
  • 9
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Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8698 - 8706
  • 10
  • [ 1634-04-4 ]
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  • [ 1948-33-0 ]
Reference: [1] Applied Catalysis A: General, 2013, vol. 450, p. 34 - 41
  • 11
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  • [ 123-31-9 ]
  • [ 2444-28-2 ]
  • [ 88-58-4 ]
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Reference: [1] Applied Catalysis A: General, 2013, vol. 450, p. 34 - 41
  • 12
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Reference: [1] Canadian Journal of Chemistry, 2015, vol. 94, # 1, p. 44 - 49
  • 13
  • [ 121-00-6 ]
  • [ 88-32-4 ]
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Reference: [1] Patent: US2004/10166, 2004, A1, . Location in patent: Page 4
[2] Patent: US2004/10166, 2004, A1, . Location in patent: Page 3-4
  • 14
  • [ 123-31-9 ]
  • [ 115-11-7 ]
  • [ 1948-33-0 ]
Reference: [1] Patent: US2722556, 1952, ,
[2] Patent: US2781404, 1953, ,
[3] Angewandte Chemie, 1957, vol. 69, p. 699,700
  • 15
  • [ 533-73-3 ]
  • [ 1948-33-0 ]
Reference: [1] Patent: WO2012/75053, 2012, A2,
  • 16
  • [ 21112-37-8 ]
  • [ 3602-55-9 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 2000, vol. 65, # 6, p. 924 - 940
  • 17
  • [ 507-19-7 ]
  • [ 123-31-9 ]
  • [ 1948-33-0 ]
Reference: [1] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4161 - 4165
  • 18
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  • [ 115-11-7 ]
  • [ 88-58-4 ]
  • [ 2467-52-9 ]
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Reference: [1] Australian Journal of Chemistry, 1997, vol. 50, # 5, p. 515 - 516
  • 19
  • [ 66806-57-3 ]
  • [ 3602-55-9 ]
  • [ 1948-33-0 ]
Reference: [1] Journal of Physical Chemistry, 1995, vol. 99, # 4, p. 1218 - 1227
  • 20
  • [ 123-31-9 ]
  • [ 75-65-0 ]
  • [ 6669-13-2 ]
  • [ 2460-77-7 ]
  • [ 88-58-4 ]
  • [ 1948-33-0 ]
YieldReaction ConditionsOperation 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
  • 21
  • [ 123-31-9 ]
  • [ 75-65-0 ]
  • [ 6669-13-2 ]
  • [ 2460-77-7 ]
  • [ 88-58-4 ]
  • [ 1948-33-0 ]
YieldReaction ConditionsOperation 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
  • 22
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  • [ 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
  • 23
  • [ 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
  • 24
  • [ 1948-33-0 ]
  • [ 88-32-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1979, vol. 22, # 5, p. 569 - 571
[2] Patent: US4469897, 1984, A,
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 41, p. 11056 - 11059[4] Angew. Chem., 2015, vol. 126, # 41, p. 11236 - 11239,4
  • 25
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  • [ 88-32-4 ]
Reference: [1] Patent: WO2007/15260, 2007, A2, . Location in patent: Page/Page column 7-9
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