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[ CAS No. 104-76-7 ] {[proInfo.proName]}

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Chemical Structure| 104-76-7
Chemical Structure| 104-76-7
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Product Details of [ 104-76-7 ]

CAS No. :104-76-7 MDL No. :MFCD00004746
Formula : C8H18O Boiling Point : -
Linear Structure Formula :- InChI Key :YIWUKEYIRIRTPP-UHFFFAOYSA-N
M.W : 130.23 Pubchem ID :7720
Synonyms :

Calculated chemistry of [ 104-76-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.73
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.5
Log Po/w (XLOGP3) : 3.08
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 2.22
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 2.39

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.26
Solubility : 0.719 mg/ml ; 0.00552 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.0876 mg/ml ; 0.000673 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.12
Solubility : 0.999 mg/ml ; 0.00767 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 104-76-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104-76-7 ]

* 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 [ 104-76-7 ]
  • Downstream synthetic route of [ 104-76-7 ]

[ 104-76-7 ] Synthesis Path-Upstream   1~22

  • 1
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Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1872
[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1942, vol. 274, p. 180
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  • [ 124-04-9 ]
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  • [ 103-23-1 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 17, p. 5769 - 5772
[2] Kobunshi Kagaku, 1945, vol. 2, p. 287,296[3] Chem.Abstr., 1950, p. 5144
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  • [ 117-81-7 ]
YieldReaction ConditionsOperation in experiment
100% for 2 h; Dean-Stark; Reflux General procedure: The typical procedure for esterification of phthalic anhydride withbutanol is as follows: phthalic anhydride (1 mmol, 0.15 g), butanol(5 mmol, 0.46 mL, 0.37 g) and HFDAIL as catalyst (10 molpercent to phthalicanhydride, 0.05 g) were charged into a 50 mL round bottom flask witha dean-stark apparatus, reflux condenser and a magnetic stirrer. Thenthe mixture was stirred at 125 °C for 7 h. The completion of reactionwas monitored by TLC using (EtOAC/Hexane 2:8) as eluent. After completionof the reaction as indicated by TLC, the product (dibutyl phthalate)was separated simply by extraction with ethyl acetate (3 × 5 mL)and ethyl acetatewas evaporated under vacuum to afford desired productas yellowoil liquid at 95percent yield (0/26 g, boiling point=340 °C). Theobtained product dried under vacuumat 70 °C for 5 h. Viscous ionic liquidcould be reused after removal ofwater under vacuumat 80 °C for 5 hwithout any disposal.
100% With diacidic ionic liquid supported on magnetic-silica nanoparticles In neat (no solvent) at 118℃; for 1 h; Dean-Stark The required amounts of phthalic anhydride (1 mmol, 0.15 g), 2-methoxyethanol (5 mmol, 0.39 mL, 0.38 g) and SDAILmagnetic nanoSiO2as catalyst (10 wtpercent to phthalic anhydride, 0.01 g) were added successively into a 50 mL round bottom flask with a dean–stark apparatus, reflux condenser and a magnetic stirrer. The esterification reaction was allowed to proceed at 130 °C for 8 h under vigorous stirring. The completion of reaction was monitored by TLC using(EtOAC/Hexane 2:8) as eluent. After completion of the reaction, the catalyst was recovered from the reaction mixture using an external magnet and subjected to drying under high vacuum at 70 C for 6 h to remove water, leaving behind the SDAILatmagnetic nanoSiO2 (recovery 98percent) which was recycled. Then, the product (bis(2-methoxyethyl) phthalate)was separated simply by extraction with ethyl acetate(3 × 5 mL) and ethyl acetate was evaporated under vacuum to afford desired product as colorless oily liquid at 98percent yield(0/25 g, boiling point = 340 °C). The obtained product dried under vacuum at 70 °C for 6 h.
10 %Chromat. With nanosilica-supported hydroxyl-functionalized diacidic ionic liquid In neat (no solvent) at 180℃; for 3 h; Dean-Stark; Green chemistry General procedure: The typical procedure for esterification of phthalic anhydridewith butanol as an example, was performed as follows:phthalic anhydride (1 mmol, 0.15 g), butanol (5 mmol, 0.46mL, 0.37 g) and nanosilica (at) [HFDAIL] as catalyst (10 molpercentto phthalic anhydride, 0.05 g) were poured into a 50mL roundbottom flask equipped with a dean-stark apparatus, reflux condenserand a magnetic stirrer. Then the mixture was stirredat 125 °C for 8 h. The completion of reaction was monitoredby TLC using (EtOAC/Hexane 2:8) as eluent. After completionof the reaction as indicated by TLC, ethyl acetate wasadded to dissolve the product and then the reaction mixturewas filtered to separate the catalyst from the reactionmixture.Then, ethyl acetate was evaporated under vacuum to affordthe desired product as yellow oil liquid at 92percent yield (0.25g, B.p.: 340 °C). The obtained product (dibutyl phthalate) was subjected to drying under vacuum at 70 °C for 5 h. Thesolid catalyst was washed with acetone to remove the residualproduct and dried under vacuum at 70 °C.
Reference: [1] Journal of Molecular Liquids, 2017, vol. 227, p. 153 - 160
[2] Journal of the Iranian Chemical Society, 2018, vol. 15, # 11, p. 2615 - 2629
[3] Patent: EP1186593, 2002, A2, . Location in patent: Page 6
[4] RSC Advances, 2014, vol. 4, # 100, p. 57297 - 57307
[5] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 6.1, p. 1133 - 1136
[6] Kobunshi Kagaku, 1945, vol. 2, p. 287,296[7] Chem.Abstr., 1950, p. 5144
[8] Kobunshi Kagaku, 1951, vol. 8, p. 85,91,103[9] Chem.Abstr., 1953, p. 7463
[10] Industrial and Engineering Chemistry, 1945, vol. 37, p. 781
[11] Patent: US2642389, 1950, ,
[12] Patent: US2698340, 1951, ,
[13] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2004, vol. 43, # 5, p. 1039 - 1043
[14] Dalton Transactions, 2004, # 12, p. 1846 - 1851
[15] Patent: EP1186593, 2002, A2, . Location in patent: Page 6
[16] Patent: US2010/152477, 2010, A1, . Location in patent: Page/Page column 6-7
[17] Journal of Chemical Sciences, 2018, vol. 130, # 5,
  • 4
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  • [ 95-47-6 ]
  • [ 117-81-7 ]
Reference: [1] Patent: CN104418748, 2016, B, . Location in patent: Paragraph 0020-0023; 0026
  • 5
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  • [ 4376-20-9 ]
  • [ 117-81-7 ]
Reference: [1] Doklady Chemistry, 1987, vol. 295, # 8, p. 357 - 359[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1987, vol. 295, # 5, p. 1128 - 1130
[3] Applied Catalysis A: General, 2013, vol. 467, p. 430 - 438
  • 6
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  • [ 88-99-3 ]
  • [ 117-81-7 ]
Reference: [1] RSC Advances, 2018, vol. 8, # 66, p. 37835 - 37840
[2] Asian Journal of Chemistry, 2014, vol. 26, # 17, p. 5769 - 5772
[3] Kogyo Kagaku Zasshi, 1956, vol. 59, p. 895,897[4] Technology Reports of the Osaka University, 1957, vol. 7, p. 199,203
  • 7
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  • [ 78-83-1 ]
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  • [ 84-69-5 ]
Reference: [1] Patent: US2005/38283, 2005, A1, . Location in patent: Page/Page column 43
  • 8
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  • [ 71-36-3 ]
  • [ 117-81-7 ]
  • [ 84-74-2 ]
  • [ 85-69-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 1, p. 253 - 266
  • 9
  • [ 85-44-9 ]
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  • [ 117-81-7 ]
  • [ 4376-20-9 ]
  • [ 85-69-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 1, p. 253 - 266
  • 10
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  • [ 4376-20-9 ]
Reference: [1] Environmental Science and Technology, 2001, vol. 35, # 18, p. 3757 - 3763
[2] Chemosphere, 2003, vol. 53, # 8, p. 921 - 926
[3] Applied Catalysis A: General, 2013, vol. 467, p. 430 - 438
[4] Chemosphere, 2017, vol. 173, p. 452 - 459
  • 11
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  • [ 85-69-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 1, p. 253 - 266
  • 12
  • [ 110-86-1 ]
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  • [ 4376-20-9 ]
Reference: [1] Journal of the Chemical Society, 1939, p. 637
  • 13
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  • [ 60-19-5 ]
  • [ 122-01-0 ]
  • [ 108-10-1 ]
  • [ 41859-67-0 ]
Reference: [1] Patent: EP582441, 1994, A1,
  • 14
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  • [ 5232-99-5 ]
  • [ 6197-30-4 ]
Reference: [1] Patent: US5047571, 1991, A,
  • 15
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  • [ 88122-99-0 ]
YieldReaction ConditionsOperation in experiment
96% With sodium methylate In toluene at 110 - 115℃; To the reactor was added 2000 mL of toluene,Sodium methoxide 103.6g and 1210mL isooctanol, heated and dissolved to dissolve,And heated to 110 ~ 115 ° C, containing 1036g slowly added dropwiseMethyl triazone 1500mL toluene solution was added dropwise,Insulation reaction 8-10h, the reaction was continuously distilled to remove the methanol produced,The reaction is completed, the solvent was distilled off,After the solvent is evaporated to dryness, 2500 mL of absolute ethanol is added,Crystallization of octyl triazone (UVT-150) product, filtration,Washed with anhydrous ethanol and water to obtain a UV absorber (UVT-150)Product 1549g, the resulting UVT-150The results of liquid chromatography analysis of the product as shown in the following table:The amount of each raw material and the process conditions in Example 1 are the best technical solutions of the present invention. The yield of the obtained UVT-150 product is 96percent. According to the liquid chromatographic analysis,Purity of 99.74percent, fully meet the requirements of the cosmetics industry,Suitable for use in oil-soluble sunscreen products.
Reference: [1] Patent: CN106986839, 2017, A, . Location in patent: Paragraph 0017; 0019; 0021
  • 16
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  • [ 88122-99-0 ]
YieldReaction ConditionsOperation in experiment
93.74% With toluene-4-sulfonic acid In toluene at 105 - 115℃; To a 5000ML four-necked flask, 470.64 g (0.97 mol) of a white solid H3TATAB,Isooctanol 504.40 g (3.88 mol),Toluene 600ml, p-toluenesulfonic acid 30g,Stirring heated to reflux and water separation,Reaction temperature 105-115°C , Until H3TATAB is completely converted Then cooled to 90 insulation, caustic washing, washing,The organic phase was recovered by vacuum distillation xylene and isooctanol,Get UVT-150 crude.The insolubles were cooled to 85°C., 600 g of methanol was added,Heated and stirred until completely dissolved, and then cooled;Cyclohexane 3500ml added 5000ML glass reactor,Stir frozen to -10 , and keep the frozen water cycle, Then dropping the above solution; rapid precipitation of crystals;Dropping is completed, suction filtration, drying,748.46 g (0.91 mol) of white crystal UVT-150 product was obtained.HPLC: 99.18percentStructure by 1H-NMR,MS was confirmed as the target product. Yield 93.74percentThe total yield of the two-step reaction: 90.93percent.
Reference: [1] Patent: CN105061345, 2017, B, . Location in patent: Paragraph 0044-0061
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  • [ 96474-94-1 ]
  • [ 88122-99-0 ]
Reference: [1] Patent: EP2774921, 2014, A1, . Location in patent: Paragraph 0063-0064
[2] Patent: US2014/255324, 2014, A1, . Location in patent: Paragraph 0095-0096
  • 18
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  • [ 88122-99-0 ]
Reference: [1] Patent: CN104860893, 2017, B,
[2] Patent: CN104860893, 2017, B,
  • 19
  • [ 104-76-7 ]
  • [ 122-04-3 ]
  • [ 26218-04-2 ]
YieldReaction ConditionsOperation in experiment
65.8 g
Stage #1: With triethylamine In toluene at 0℃; for 1 h; Cooling with ice
Stage #2: With palladium 10% on activated carbon In ethanol; water at 20 - 50℃; for 1.66667 h; Cooling with ice
With cooling with ice, 4-nitrobenzoyl chloride (60.00 g, 0.323 mol) was added to a mixture of 2-ethyl-1-hexanol (54.3 mL, 0.346 mol), toluene (200 mL) and triethylamine (56.8 mL, 0.407 mol). After the addition, this was stirred still at 0° C. for 1 hour, then water was added thereto, and the aqueous layer was extracted with chloroform. The chloroform layer was dried with anhydrous sodium sulfate, and the filtrate after filtration was concentrated. Hexane (300 mL) was added thereto, and the precipitated solid was removed through filtration, and the filtrate was concentrated to give an oily substance. Ethanol (400 ml) was added to the resultant oily substance, then 10percent palladium carbon (containing 55percent water, manufactured by Tokyo Chemical Industry, 5 g) was added thereto, cooled in an ice bath, and while the internal temperature was kept at 20° C. or lower, hydrazine monohydrate (25.9 g, 808 mmol) was dropwise added thereto, taking 40 minutes, and thereafter while the internal temperature was kept at 40 to 50° C., this was stirred for 1 hour. After cooled in an ice bath, the palladium carbon was removed through filtration, the filtrate was concentrated under reduced pressure, water was added to the resultant oily substance, the formed agglomerate was collected through filtration, washed with methanol/water=2/1 (by volume) (400 ml), and dried under reduced pressure to give an intermediate B-1 (65.8 g) as a white solid.
Reference: [1] Patent: US2015/191601, 2015, A1, . Location in patent: Paragraph 0288
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  • [ 26218-04-2 ]
Reference: [1] Patent: CN104860893, 2017, B,
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  • [ 1160823-77-7 ]
Reference: [1] Polymer, 2015, vol. 56, p. 171 - 177
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  • [ 1160823-78-8 ]
Reference: [1] Polymer, 2015, vol. 56, p. 171 - 177
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