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[ CAS No. 118-45-6 ] {[proInfo.proName]}

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Product Details of [ 118-45-6 ]

CAS No. :118-45-6 MDL No. :MFCD00152354
Formula : C8H3ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BTTRMCQEPDPCPA-UHFFFAOYSA-N
M.W : 182.56 Pubchem ID :67044
Synonyms :

Calculated chemistry of [ 118-45-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.2
TPSA : 43.37 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) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 1.65
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.9

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.327 mg/ml ; 0.00179 mol/l
Class : Soluble
Log S (Ali) : -2.78
Solubility : 0.306 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.151 mg/ml ; 0.000828 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 118-45-6 ]

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

Application In Synthesis of [ 118-45-6 ]

* 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 [ 118-45-6 ]
  • Downstream synthetic route of [ 118-45-6 ]

[ 118-45-6 ] Synthesis Path-Upstream   1~47

  • 1
  • [ 118-45-6 ]
  • [ 7147-90-2 ]
Reference: [1] Canadian Journal of Chemistry, 1985, vol. 63, p. 121 - 128
[2] Synthetic Communications, 2001, vol. 31, # 12, p. 1927 - 1931
[3] Patent: WO2003/101450, 2003, A1, . Location in patent: Page 79
[4] Patent: US2004/48916, 2004, A1, . Location in patent: Page/Page column 30
[5] Patent: WO2010/43711, 2010, A1, . Location in patent: Page/Page column 95
[6] Patent: US2012/46307, 2012, A1, . Location in patent: Page/Page column 46
  • 2
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  • [ 57-13-6 ]
  • [ 7147-90-2 ]
Reference: [1] Patent: US2692267, 1952, ,
  • 3
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  • [ 319-03-9 ]
Reference: [1] Patent: US2891074, 1954, ,
[2] Patent: DE1018042, 1953, ,
  • 4
  • [ 85-44-9 ]
  • [ 118-45-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1959, vol. 32, p. 691
[2] Patent: CN108164452, 2018, A, . Location in patent: Paragraph 0041; 0042
  • 5
  • [ 1204-28-0 ]
  • [ 118-45-6 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 15, p. 4142 - 4145
  • 6
  • [ 89-20-3 ]
  • [ 118-45-6 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 15, p. 2465 - 2468
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1388 - 1391
[3] Organic Letters, 2010, vol. 12, # 21, p. 4796 - 4799
[4] Chemische Berichte, 1882, vol. 15, p. 320
[5] Oef. Sv., 1881, # 9, p. 10[6] Bulletin de la Societe Chimique de France, 1881, vol. <2> 36, p. 434
[7] Chemische Berichte, 1892, vol. 25, p. 2115
[8] Justus Liebigs Annalen der Chemie, 1886, vol. 233, p. 226[9] Journal of the Chemical Society, 1886, vol. 49, p. 518
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1834 - 1840
[11] Patent: US5739135, 1998, A,
[12] Patent: US5049682, 1991, A,
  • 7
  • [ 615-60-1 ]
  • [ 118-45-6 ]
  • [ 89-20-3 ]
Reference: [1] Patent: US4124593, 1978, A,
[2] Patent: US4025505, 1977, A,
  • 8
  • [ 56047-23-5 ]
  • [ 118-45-6 ]
Reference: [1] Canadian Journal of Chemistry, 1985, vol. 63, p. 121 - 128
[2] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[3] Patent: US2012/46307, 2012, A1, . Location in patent: Page/Page column 45
  • 9
  • [ 1204-28-0 ]
  • [ 85-44-9 ]
  • [ 118-45-6 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 4, p. 371 - 372
[2] Tetrahedron Letters, 1982, vol. 23, # 4, p. 371 - 372
  • 10
  • [ 89-20-3 ]
  • [ 27563-65-1 ]
  • [ 118-45-6 ]
  • [ 117-21-5 ]
Reference: [1] Patent: US2006/4223, 2006, A1, . Location in patent: Page/Page column 9
[2] Patent: US2006/4223, 2006, A1, . Location in patent: Page/Page column 9
  • 11
  • [ 7440-44-0 ]
  • [ 118-45-6 ]
Reference: [1] Patent: US5003088, 1991, A,
  • 12
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Reference: [1] Patent: US5059697, 1991, A,
  • 13
  • [ 96-02-6 ]
  • [ 1122-17-4 ]
  • [ 92-84-2 ]
  • [ 126-99-8 ]
  • [ 118-45-6 ]
Reference: [1] Patent: US5322954, 1994, A,
  • 14
  • [ 5466-84-2 ]
  • [ 118-45-6 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 469,471[2] Chem.Abstr., 1958, p. 18325
  • 15
  • [ 2065-70-5 ]
  • [ 118-45-6 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 320
  • 16
  • [ 88-99-3 ]
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Reference: [1] Journal of the Chemical Society, 1929, p. 255
  • 17
  • [ 56-23-5 ]
  • [ 5466-84-2 ]
  • [ 118-45-6 ]
Reference: [1] Ukrainskii Khimicheskii Zhurnal (Russian Edition), 1958, vol. 24, p. 68[2] Chem.Abstr., 1958, p. 18325
  • 18
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  • [ 117-21-5 ]
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  • [ 51971-64-3 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 15, p. 2465 - 2468
[2] Journal of Organic Chemistry, 1983, vol. 48, # 15, p. 2465 - 2468
[3] Journal of Organic Chemistry, 1983, vol. 48, # 15, p. 2465 - 2468
  • 19
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Reference: [1] Chemische Berichte, 1882, vol. 15, p. 320
  • 20
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Reference: [1] Journal of the Chemical Society, 1929, p. 255
  • 21
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  • [ 86-90-8 ]
Reference: [1] Patent: US4962206, 1990, A,
  • 22
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  • [ 1823-59-2 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In water; 1,2-dichloro-benzene for 3.5 h; Heating / reflux 4-Chlorophthalic anhydride, 16 grams (g) (87.7 mmol), was weighed into a 150 milliliter (ml) three-necked flask fitted with a distillation head and containing about 100 ml of distilled o-dichlorobenzene having a water content of less than 5 ppm. The mixture was heated at reflux for 0.5 hour in a nitrogen atmosphere and about 80 ml of o-dichlorobenzene was removed by distillation. [00022] Powdered potassium carbonate, 6.06 g (43.8 mmol), was added to another flask with 50 ml of dry o-dichlorobenzene. The suspension was heated at reflux for 0.5 hour under nitrogen and 40 ml of o-dichlorobenzene was distilled. The 4-chlorophthalic anhydride solution was transferred to the flask containing carbonate. The mixture was stirred and 468 mg (1.77 mmol) of hexaethylguanidinium chloride (in the form of an 18percent solution in o-dichlorobenzene containing less than 15 ppm of water) was added, whereupon the solution turned yellow as refluxing was continued. Periodic analysis of the mixture showed a 93percent yield of the desired 4,4'-ODPA after 3 hours. In a control experiment employing tetraphenylphosphonium bromide at the same mole percent level and powdered potassium carbonate, a period of 13 hours was required to attain the same yield. The procedure of Example 1 was repeated except that granular potassium carbonate was used and the level of hexaethylguanidinium chloride was 2.0 mole percent based on 4-chlorophthalic anhydride. Product formation leveled off after 3 hours at a minimum of about 85percent total yield. [00024] While typical embodiments have been set forth for the purpose of illustration, the foregoing descriptions and examples should not be deemed to be a limitation on the scope of the invention. Accordingly, various modifications, adaptations, and alternatives may occur to one skilled in the art without departing from the spirit and scope of the present invention.
85% With potassium carbonate; sodium nitrite In N,N-dimethyl acetamide; toluene at 162 - 170℃; for 5 h; 150 g (0 · 82 mol) of 4-chlorophthalic anhydride, 11 g (0 · 08 mol) of potassium carbonate, 22 g of sodium nitrite was placed in a reactor containing 504 g of dimethylacetamide and 144 g of toluene, and the temperature was raised to 162 ° C, the reaction was carried out at 162 ° C to 170 ° C for 5 hours, followed by distillation under reduced pressure to distill the solvent, and distillation was carried out for 20 min, thereafter, 600 g of pure water was added to the vacuum, and the mixture was further stirred and refluxed for 1 to 2 hours, filtered at 102 ° C, and washed with water, the mixture was filtered and dried to obtain 107 g of 3,3',4,4'-diphenyl ether tetracarboxylic dianhydride, the yield was 85percent, mp 226 ° C, and the purity of liquid chromatography was 99.6percent.
82%
Stage #1: With monopotassium carbonate In 2,4-dichlorotoluene for 7.5 h; Heating / reflux; Nitrogen atmosphere
Stage #2: Heating / reflux
The procedure of Example 1 was repeated, substituting 2,4-dichlorotoluene for the o-dichlorobenzene and reducing the tetraphenylphosphonium bromide amount to 200 mg. Reflux time was 7.5 hours after the final addition of K2CO3. Product yield was 82percent of theoretical
80% With monopotassium carbonate In 1,2-dichloro-benzeneHeating / reflux 4-Chlorophthalic anhydride (16 grams [g], 87.7 mmol) was weighed into a 50 milliliter (ml) round-bottomed flask containing about 17 ml of o-dichlorobenzene. The mixture was heated at reflux for 0.5 hour in a nitrogen atmosphere with distillation of solvent until less than 20 ppm of water was present, whereupon about 7 ml of solvent had been removed. Tetraphenylphosphonium bromide, 400 milligrams (mg) (0.95 mmol) was added with stirring, whereupon the solution turned yellow. Potassium bicarbonate, 22 mg (0.22 mmol), was added, followed by 5.45 g (39.5 mmol) of potassium carbonate in a stepwise fashion over 5-10 minutes. The mixture was heated at reflux (bath temperature 200° C.) after the first addition of K2CO3. The mixture was heated under reflux for 17 hours after the final addition of K2CO3. At the end of the reaction, additional o-dichlorobenzene was added to form a 10percent solution and the by-product KCl was removed by filtration while hot. The filtrate was cooled to room temperature, whereupon the desired 4,4'-ODPA precipitated and was collected by suction filtration. 11.56 g of slightly pink-colored powder was obtained. Recrystallization from o-dichlorobenzene afforded 10.87 g of product (80percent of theoretical) as an off-white powder, m.p. 225-226° C. 4-Chlorophthalic anhydride (4800 g, 26.3 moles) and 7836 g of o-dichlorobenzene were charged to a 3.8 liter (L) stainless steel reactor. The mixture was heated at reflux for about 0.5 hour in a nitrogen atmosphere and 1020 g of o-dichlorobenzene was removed to dry the system. With stirring, 120 g (0.29 mole) of tetraphenylphosphonium bromide was added. After mixing, 6.6 g (0.066 mole) of potassium bicarbonate was added, followed by 1650 g (11.95 moles) of potassium carbonate in 7 portions. The mixture was heated under reflux for 27 hours after the last addition of K2CO3 and periodically analyzed. About 60percent of conversion was achieved at this point. To make sure that the reaction went to completion, an additional 50 g (0.119 mole) of tetraphenylphosphonium bromide was added. The mixture was heated overnight, whereupon conversion reached about 90percent. o-Dichlorobenzene, 39,500 g, was added to dilute the reaction mixture and the temperature was brought to 165° C. A hot filtration was performed through a 1-micron filter bag. The filtrate was cooled to room temperature and the desired 4,4'-ODPA was collected in about 80percent crude yield and 95percent purity. Recrystallization from o-dichlorobenzene gave pure product, m.p. 225-226° C. While typical embodiments have been set forth for the purpose of illustration, the foregoing descriptions and examples should not be deemed to be a limitation on the scope of the invention. Accordingly, various modifications, adaptations, and alternatives may occur to one skilled in the art without departing from the spirit and scope of the present invention.

Reference: [1] Patent: US6706897, 2004, B1, . Location in patent: Page column 3-4
[2] Patent: CN108250168, 2018, A, . Location in patent: Paragraph 0009-0010; 0011-0012; 0013-0014; 0015-0016
[3] Patent: US6727370, 2004, B1, . Location in patent: Page column 4
[4] Patent: US6727370, 2004, B1, . Location in patent: Page column 4
[5] Patent: US2007/117990, 2007, A1, . Location in patent: Page/Page column 12-13
[6] Patent: US2009/247725, 2009, A1, . Location in patent: Page/Page column 5; 6
[7] Patent: WO2009/120215, 2009, A1, . Location in patent: Page/Page column 14-16; 17
[8] Patent: US2009/247727, 2009, A1, . Location in patent: Page/Page column 11-12
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Reference: [1] Patent: WO2009/120212, 2009, A1, . Location in patent: Page/Page column 34-39
  • 24
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  • [ 1823-59-2 ]
Reference: [1] Patent: US4870194, 1989, A,
  • 25
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  • [ 2751-90-8 ]
  • [ 74-11-3 ]
  • [ 1823-59-2 ]
Reference: [1] Patent: US5153335, 1992, A,
[2] Patent: US5153335, 1992, A,
[3] Patent: US5153335, 1992, A,
[4] Patent: US5153335, 1992, A,
  • 26
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Reference: [1] Patent: US5153335, 1992, A,
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Reference: [1] Patent: US5153335, 1992, A,
  • 28
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Reference: [1] Patent: US5153335, 1992, A,
  • 29
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Reference: [1] Patent: US5153335, 1992, A,
  • 30
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Reference: [1] Patent: US5153335, 1992, A,
  • 31
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Reference: [1] Patent: US5153335, 1992, A,
  • 32
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Reference: [1] Patent: US5153335, 1992, A,
  • 33
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Reference: [1] Patent: US5153335, 1992, A,
  • 34
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Reference: [1] Patent: US5153335, 1992, A,
  • 35
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Reference: [1] Patent: US5153335, 1992, A,
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Reference: [1] Patent: US5153335, 1992, A,
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Reference: [1] Patent: US5153335, 1992, A,
  • 38
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Reference: [1] Patent: US5153335, 1992, A,
  • 39
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Reference: [1] Patent: US5153335, 1992, A,
  • 40
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  • [ 36978-41-3 ]
YieldReaction ConditionsOperation in experiment
87.7% at 30℃; for 8 h; Inert atmosphere In a 1000 ml three-necked flask, 18.3 g (0.1 mol) of 4-chlorophthalic anhydride and 18.3 g (0.1 mol) were added 3-chlorophthalic anhydride, 300 g of anisole as solvent, 0.13 g (0.001 mol) of nickel chloride as a catalyst, 0.198 g (0.001 mol) of C-1 as a catalyst ligand, and 0.03 g (0.0003 mol) of sodium bromide as a catalyst Auxiliary, 13 g (0.2 mol) of zinc powder was used as a reducing agent, and the reaction was stirred at 30 ° C for 8 hours under a nitrogen atmosphere. The reaction solution was filtered to remove insoluble solids in the reaction liquid. 300 g of methanol was added to the filtration mother liquor, and the product was precipitated, filtered, and dried to obtain 25.8 g of the product 2,3,3',4'-biphenyltetracarboxylic dianhydride, yield 87.7percent.
Reference: [1] Patent: CN108250169, 2018, A, . Location in patent: Paragraph 0010; 0052-0055; 0058; 0061; 0064; 0071
  • 41
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  • [ 89-20-3 ]
Reference: [1] Patent: US4124593, 1978, A,
[2] Patent: US4025505, 1977, A,
  • 42
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  • [ 89-20-3 ]
  • [ 27563-65-1 ]
Reference: [1] Patent: US6670487, 2003, B1, . Location in patent: Page column 13-15
  • 43
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  • [ 89-20-3 ]
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Reference: [1] Patent: WO2009/120212, 2009, A1, . Location in patent: Page/Page column 39-40
  • 44
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  • [ 89-20-3 ]
Reference: [1] Journal of Chemical and Engineering Data, 2009, vol. 54, # 3, p. 1135 - 1137
  • 45
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  • [ 7732-18-5 ]
  • [ 89-20-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1886, vol. 233, p. 226[2] Journal of the Chemical Society, 1886, vol. 49, p. 518
  • 46
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  • [ 38103-06-9 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 85 - 172℃; for 15 h;
Stage #2: at 130 - 145℃; for 5 h;
79 g (0.63 mol) of a 32percent by weight aqueous sodium hydroxide solution and 62.4 g (0.3 mol) of bisphenol A were charged into the reactor.Stir and dissolve,The temperature rises to 85 ° C and the solution is transparent.Next, 510 g of a trimethylbenzene solvent and 4.2 g of a benzyltriethylammonium chloride catalyst were added.Warming and refluxing,The temperature rose to 172 ° C,Stirring reaction for 15 hours,Then cool down to 130 ° C,108 g (0.6 mol) of 4-chlorophthalic anhydride and 4.86 g of benzyltriethylammonium chloride catalyst were added.Heating from 140 ° C to 145 ° C,Reflow reaction for 5 hours,Then filter hot,Pumping the filtrate into the crystallization kettle,The filtrate is cooled to room temperature.Crystallized for 12 hours,filter,The precipitate is washed with ion-free water,Filtration, precipitation was obtained and washed with 250 g of ethanol.Stirring for 2 hours,filter,Get wet material 125g,After drying, 120 g of bisphenol A diether dianhydride product (yield 85percent),The product is white powder,
Reference: [1] Patent: CN108148029, 2018, A, . Location in patent: Paragraph 0011; 0012; 0014
  • 47
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YieldReaction ConditionsOperation in experiment
25% at 180℃; for 5 h; A dry 100 mL flask was charged with 2.0 g (7.3 mmol) of the disodium salt of bisphenol A, 2.67 g (14.6 mmol) of 4-chlorophthalic anhydride, 4 mL (14 mmol) of hexaethylguanidinium chloride as a 15 weight percent solution in o-dichlorobenzene, 48 g of dry o-dichlorobenzene, and 100 mg of o-terphenyl (internal standard). The flask was immersed in an oil bath maintained at 180° C. and the mixture was stirred magnetically. The reaction was followed as in Example 1. The yield of biphenol dianhydride had reached 25percent after 5 hours.
Reference: [1] Patent: US2006/205958, 2006, A1, . Location in patent: Page/Page column 6
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