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[ CAS No. 6781-98-2 ] {[proInfo.proName]}

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Chemical Structure| 6781-98-2
Chemical Structure| 6781-98-2
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Product Details of [ 6781-98-2 ]

CAS No. :6781-98-2 MDL No. :MFCD00000565
Formula : C8H9Cl Boiling Point : -
Linear Structure Formula :- InChI Key :VDXLAYAQGYCQEO-UHFFFAOYSA-N
M.W : 140.61 Pubchem ID :32885
Synonyms :

Calculated chemistry of [ 6781-98-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.38
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -4.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.28
Log Po/w (WLOGP) : 2.96
Log Po/w (MLOGP) : 3.53
Log Po/w (SILICOS-IT) : 3.41
Consensus Log Po/w : 3.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.27
Solubility : 0.0752 mg/ml ; 0.000535 mol/l
Class : Soluble
Log S (Ali) : -2.95
Solubility : 0.156 mg/ml ; 0.00111 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.0244 mg/ml ; 0.000174 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 6781-98-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6781-98-2 ]

* 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 [ 6781-98-2 ]
  • Downstream synthetic route of [ 6781-98-2 ]

[ 6781-98-2 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 6781-98-2 ]
  • [ 61563-28-8 ]
  • [ 15068-35-6 ]
YieldReaction ConditionsOperation in experiment
95% at 70 - 75℃; Autoclave 500mL stainless steel autoclave,Add 140g (1.0mol) of 2,6-dimethylchlorobenzene,Add 0.14g of cobalt acetylacetonate,Add 0.14g potassium bromide,After vacuum nitrogen replacement for 2 times,Adding the first oxygen to a pressure of 0.3 to 0.5 MPa,Warm the system to 70-75 ° C,Turn on the stirring reaction,When the pressure in the kettle is less than 0.1 MPa,Supplementing the second oxygen to a pressure of 0.3 to 0.5 MPa,Add a total of 4 parts of oxygen,A total of 64g (2.0mol) of oxygen was added.The reaction time is 5-6 hours.Sampling and testing products accounted for 20percent,Raw materials account for 55percent,The intermediate product 2-chloro-3-methylbenzaldehyde accounts for 20percent.Cool down to room temperature,filter,Drain,The mother liquor is directly applied to the next batch (only 10percent catalyst can be added).The filter cake is dried,Get the target product,Weighing 33.1g, purity 98.0percent,The yield was 95percent (calculated as the raw material consumed).
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0079; 0086; 0087
  • 2
  • [ 6781-98-2 ]
  • [ 13049-16-6 ]
  • [ 15068-35-6 ]
YieldReaction ConditionsOperation in experiment
30% at 95℃; for 6.7 h; In the reaction system, 140 g of raw material 2,6-dimethylchlorobenzene was added.Co(OAc)2 0.14g,NaBr 0.14g and 14g acetic acid,Warm the system to 95 ° C,Stir until the catalyst is completely dissolved.64 g of atmospheric pressure was introduced into the system for 6.7 h.Sampling test,Raw material 2,6-dimethylchlorobenzene 20percent,The product 2-chloro-3-methylbenzoic acid is 40percent,2,6-dicarboxychlorobenzene 30percent,2-chloro-3-carboxybenzaldehyde 5percent,2-chloro-3-methylbenzaldehyde 5percent,The reaction solution was cooled to room temperature.After workup, the solid product 2-chloro-3-methylbenzoic acid is obtained.The yield was 30percent.
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0103; 0104
  • 3
  • [ 6781-98-2 ]
  • [ 13049-16-6 ]
  • [ 61563-28-8 ]
  • [ 15068-35-6 ]
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0107; 0108; 0109; 0110
  • 4
  • [ 876-99-3 ]
  • [ 6781-98-2 ]
YieldReaction ConditionsOperation in experiment
97% at 190℃; Large scale 7500 ml of 1,2,4-trichlorobenzene was placed in the reaction vessel.50g aluminum trichloride,Warming up to 190 ° C,2280 g of phenyl 2,6-dimethylchloroformate was added dropwise to the reaction kettle.Distilling 2,6-dimethylchlorobenzene at the same time,The target product was obtained 1690g,The yield was calculated to be 96 to 97percent.
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0079; 0085; 0098; 0100
[2] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2493 - 2496
[3] Patent: US5420364, 1995, A,
[4] Patent: US5306849, 1994, A,
[5] Patent: US5306849, 1994, A,
  • 5
  • [ 100379-00-8 ]
  • [ 6781-98-2 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 6, p. 1192 - 1195
[2] RSC Advances, 2017, vol. 7, # 2, p. 764 - 770
  • 6
  • [ 576-22-7 ]
  • [ 6781-98-2 ]
  • [ 1595253-60-3 ]
  • [ 1595253-66-9 ]
  • [ 1595253-68-1 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: With tert.-butyl lithium In hexane; tert-butyl methyl ether at -70℃; Inert atmosphere
Stage #2: at -70 - 45℃; for 23 h; Inert atmosphere
A solution of pure bromo-2,6-dimethylbenzene (3.22mL, 24.1mmol) in anhydrous t-BuOMe (41mL) was stirred at −70°C during the slow addition of t-BuLi (48.3mmol) in hexane (28.4mL), then kept at rt for 30min so as to destroy the byproduct t-BuBr,30 and stirred at −70°C during the dropwise addition of the dichloroalkene 17 (2.50g, 12.1mmol) in t-BuOMe (8mL) within 20min. The mixture was warmed at 40–45°C for ≥23h, poured onto solid CO2, warmed up, treated with aqueous NaOH (2M, 150mL), and shaken with Et2O (3×50mL). The combined organic layers were extracted with NaOH (2×), washed with distilled water until neutral, dried over Na2SO4, and concentrated to yield a yellow liquid (2.41g) that contained a roughly 1:6:2:1 mixture of 20, 23, 28, and 29 accompanied by traces of further products. Column chromatography on silicagel with low-boiling petroleum ether afforded first 23 (1535mg, ca. 46percent containing some 29), followed by the isomer 28 (490mg, ca. 15percent), which crystallized slowly from pentane at −70°C or from methanol at rt: transparent rods, mp 58–59.5°C; bp 80–85°C/0.04mbar. 1H NMR of 28 (CDCl3, 400MHz) δ 0.98 (s, 6H, 2×6-CH3), 1.25 (s, 6H, 2×3-CH3), 1.67 and 1.84 (AA′MM′ system, 2H+2H, CH2-5 and CH2-4), 2.18 (s, 6H, 2×o-CH3), 7.03 and 7.07 (AA′B system, 2H+1H, 2×m-H and p-H)ppm, assigned through the NOESY correlations m-H↔o-CH3↔6-CH3↔CH2-5↔CH2-4↔3-CH3; 13C NMR (CDCl3, 100.6MHz) δ 20.66 (qm, 1J 126.0Hz, 2×o-CH3), 28.35 (qsext, 1J 126.6 Hz, 3J 4.4Hz, 2×3-CH3), 28.80 (qqt, 1J 126.3 Hz, 3J 4.8 Hz, 3J 4.5Hz, 2×6-CH3), 35.75 (tm, 1J 123Hz, CH2-4), 36.00 (tm, 1J 123Hz, CH2-5), 37.98 (m, C-3), 39.86 (m, C-6), 126.19 (sharp d, 1J 158.5Hz, C-p), 127.28 (ddq, 1J 156.5Hz, 3J 7.5Hz, 3J 5Hz, 2×C-m), 136.19 (apparent qi, 3J=2J=6.0Hz, 2×C-o with reduced intensity due to the prolonged relaxation time T1=12±3s), 138.67 (m, C-ipso), 139.35 (tm, 3J 3.5Hz, C-1), 140.21 (tm, 3J 4.5Hz, C-2) ppm, assigned through HETCOR and the following selective {1H} decoupling experiments: {6-CH3}→C-1 as a t 3J 3.5Hz, C-6 sharpened, CH2-5 simplified; {3-CH3}→C-2 as a t 3J 4.5Hz, C-3 sharpened, CH2-4 simplified; {CH2-5}→6-CH3 as a qq, C-6 sharpened; confirmed through HMBC experiments showing the 3JC,H correlations 6-CH3↔C-1↔CH2-5↔C-3, 3-CH3↔C-2↔CH2-4↔C-6, C-4↔3-CH3↔3-CH3↔CH2-4, C-5↔6-CH3↔6-CH3↔CH2-5, m-H↔C-m↔o-CH3↔C-ipso↔m-H↔o-CH3, p-H↔C-o, and the 2JC,H correlations 6-CH3↔C-6↔CH2-5, 3-CH3↔C-3↔CH2-4, and o-CH3↔C-o. Anal. Calcd for C18H25Cl (276.85): C, 78.09; H, 9.10. Found: C, 78.20; H, 9.00.
Reference: [1] Tetrahedron, 2014, vol. 70, # 17, p. 2703 - 2710
  • 7
  • [ 876-99-3 ]
  • [ 95-49-8 ]
  • [ 6781-98-2 ]
YieldReaction ConditionsOperation in experiment
43.8% at 80 - 110℃; for 3 h; In a 1L four-neck bottle,Add 110.8 g of phenyl 2,6-dimethylchloroformate,Add 110.8g of anhydrous aluminum trichloride,Warming up to 80 ° C,554g (3. Omol) was added dropwise to the reaction system.Phenyl 2,6-dimethyl chloroformate,After the addition,The reaction is exothermic,The temperature of the system gradually rises to 100~110 °C,Keep the temperature at 100~110 °C,After the addition is completed,Insulation for 3.0h,Sampling test,When the raw material remains 15~17percent,The target product 2,6-dimethylchlorobenzene accounts for 40percent.2-Chlorotoluene accounts for 40percent.Adjust the vacuum to 20~25mbar,Collecting the top temperature of 80~85 °C is the target product 2,6-dimethylchlorobenzene; the liquid fraction weighs 185g.Purity (GC) 99.0percent,The yield was 43.8percent.
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0101; 0102
  • 8
  • [ 576-22-7 ]
  • [ 6781-98-2 ]
Reference: [1] Synlett, 2003, # 8, p. 1145 - 1148
  • 9
  • [ 576-22-7 ]
  • [ 6781-98-2 ]
  • [ 1595253-60-3 ]
  • [ 1595253-61-4 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 17, p. 2703 - 2710
  • 10
  • [ 67-66-3 ]
  • [ 103724-97-6 ]
  • [ 6781-98-2 ]
Reference: [1] Synthesis, 1985, # 6/7, p. 647 - 649
  • 11
  • [ 576-26-1 ]
  • [ 6781-98-2 ]
Reference: [1] Patent: US5420364, 1995, A,
[2] Patent: CN108530297, 2018, A,
[3] Patent: CN108530297, 2018, A,
  • 12
  • [ 87-62-7 ]
  • [ 6781-98-2 ]
Reference: [1] Monatshefte fuer Chemie, 1934, vol. 64, p. 361,364, 365[2] Monatshefte fuer Chemie, 1935, vol. 65, p. 6,14
[3] Journal of the American Chemical Society, 1977, vol. 99, # 19, p. 6405 - 6410
[4] European Journal of Organic Chemistry, 2000, # 14, p. 2663 - 2668
[5] Canadian Journal of Chemistry, 2005, vol. 83, # 3, p. 213 - 219
  • 13
  • [ 108-38-3 ]
  • [ 95-66-9 ]
  • [ 6781-98-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 5175,5178
[2] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5260 - 5269
[3] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 6, p. 2096 - 2098
[4] Monatshefte fur Chemie, 1999, vol. 130, # 12, p. 1493 - 1497
  • 14
  • [ 876-99-3 ]
  • [ 120-82-1 ]
  • [ 6781-98-2 ]
Reference: [1] Patent: US5874655, 1999, A,
  • 15
  • [ 95-47-6 ]
  • [ 95-66-9 ]
  • [ 556-97-8 ]
  • [ 95-72-7 ]
  • [ 6781-98-2 ]
  • [ 615-60-1 ]
  • [ 608-23-1 ]
  • [ 20824-80-0 ]
  • [ 68266-67-1 ]
  • [ 34060-72-5 ]
  • [ 52331-02-9 ]
  • [ 70172-92-8 ]
  • [ 552-45-4 ]
  • [ 55676-90-9 ]
Reference: [1] Patent: EP1508557, 2005, A1, . Location in patent: Page/Page column 23-24
[2] Patent: EP1508557, 2005, A1, . Location in patent: Page/Page column 24
  • 16
  • [ 876-99-3 ]
  • [ 124-38-9 ]
  • [ 6781-98-2 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2493 - 2496
  • 17
  • [ 7782-50-5 ]
  • [ 64-19-7 ]
  • [ 108-38-3 ]
  • [ 95-66-9 ]
  • [ 6781-98-2 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 5175,5178
  • 18
  • [ 7553-56-2 ]
  • [ 7782-50-5 ]
  • [ 108-38-3 ]
  • [ 95-66-9 ]
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1317
  • 19
  • [ 6781-98-2 ]
  • [ 4703-15-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3773 - 3777[2] Angew. Chem., 2015, vol. 127, # 12, p. 3844 - 3848,5
  • 20
  • [ 6781-98-2 ]
  • [ 100379-00-8 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[2] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
  • 21
  • [ 6781-98-2 ]
  • [ 61563-28-8 ]
  • [ 15068-35-6 ]
YieldReaction ConditionsOperation in experiment
95% at 70 - 75℃; Autoclave 500mL stainless steel autoclave,Add 140g (1.0mol) of 2,6-dimethylchlorobenzene,Add 0.14g of cobalt acetylacetonate,Add 0.14g potassium bromide,After vacuum nitrogen replacement for 2 times,Adding the first oxygen to a pressure of 0.3 to 0.5 MPa,Warm the system to 70-75 ° C,Turn on the stirring reaction,When the pressure in the kettle is less than 0.1 MPa,Supplementing the second oxygen to a pressure of 0.3 to 0.5 MPa,Add a total of 4 parts of oxygen,A total of 64g (2.0mol) of oxygen was added.The reaction time is 5-6 hours.Sampling and testing products accounted for 20percent,Raw materials account for 55percent,The intermediate product 2-chloro-3-methylbenzaldehyde accounts for 20percent.Cool down to room temperature,filter,Drain,The mother liquor is directly applied to the next batch (only 10percent catalyst can be added).The filter cake is dried,Get the target product,Weighing 33.1g, purity 98.0percent,The yield was 95percent (calculated as the raw material consumed).
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0079; 0086; 0087
  • 22
  • [ 6781-98-2 ]
  • [ 13049-16-6 ]
  • [ 61563-28-8 ]
  • [ 15068-35-6 ]
Reference: [1] Patent: CN108530297, 2018, A, . Location in patent: Paragraph 0107; 0108; 0109; 0110
  • 23
  • [ 6781-98-2 ]
  • [ 61563-28-8 ]
Reference: [1] Journal of Organometallic Chemistry, 1991, vol. 401, # 3, p. 261 - 272
  • 24
  • [ 6781-98-2 ]
  • [ 87-62-7 ]
  • [ 74443-35-9 ]
YieldReaction ConditionsOperation in experiment
99% With NHC-Pd(II)-Im; potassium <i>tert</i>-butylate In toluene for 4 h; Inert atmosphere; Reflux General procedure: Under N2 atmosphere, KOtBu (114.0 mg, 1.0 mmol), NHC-Pd(II)-Im complex 1 (5.2 mg, 1.0 mol percent), dry toluene (1.0 mL), chlorobenzene 2a (0.8 mmol), and aniline 3a (0.96 mmol) were successively added into a Schlenk reaction tube. The reaction mixture was stirred under reflux for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by a flash chromatography on silica gel to give the pure product 4a.
99% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-yl-isoquinolin-2-yl]palladium dichloride; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 3 h; The Protection of Nitrogen Under, The Reaction Tube to are potassium tertiary Butanol (0.91 mmol) and. 1,. 4 - dioxane (0.5 ml), [Pd (of IPr) (isoquinoline) CI2] Complex (41 is) of The Solution (10 L, (0.84 mmol), 2, 6 - dimethyl chlorobenzene (0.7 mmol), the mixture (2), 2 - 6 - dimethyl - chlorobenzene (0.7 mmol) Is available in 110 ° C ° C stirring for 3 hours, stopping the reaction, cooling to room temperature, pressure reduced on on lathe does solvent, rapid column chromatography separation to obtain the product, yield is 99percent. White solid.
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 17, p. 3732 - 3742
[2] Advanced Synthesis and Catalysis, 2011, vol. 353, # 4, p. 533 - 537
[3] Tetrahedron, 2012, vol. 68, # 10, p. 2414 - 2420
[4] Organometallics, 2012, vol. 31, # 8, p. 3402 - 3409
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 8, p. 2563 - 2571
[6] Patent: CN106892945, 2017, A, . Location in patent: Paragraph 0124; 0141; 0142; 0143; 0144; 0145; 0146
[7] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3047 - 3062
[8] Organometallics, 2011, vol. 30, # 16, p. 4432 - 4436
[9] RSC Advances, 2013, vol. 3, # 12, p. 3840 - 3843
[10] RSC Advances, 2016, vol. 6, # 29, p. 24484 - 24490
[11] Chemistry - A European Journal, 2013, vol. 19, # 51, p. 17358 - 17368
[12] ChemCatChem, 2015, vol. 7, # 24, p. 4021 - 4024
[13] Journal of Organic Chemistry, 2004, vol. 69, # 26, p. 9135 - 9142
[14] Journal of Organic Chemistry, 2013, vol. 78, # 10, p. 4649 - 4664
[15] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9144 - 9155
[16] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1897 - 1901
[17] Organometallics, 2012, vol. 31, # 19, p. 6947 - 6951
[18] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4101 - 4111
[19] Synlett, 2005, # 2, p. 275 - 278
[20] Inorganica Chimica Acta, 2012, vol. 386, p. 22 - 26
[21] Organic Letters, 2011, vol. 13, # 20, p. 5540 - 5543
[22] Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 2914 - 2925
[23] Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6482 - 6486[24] Angew. Chem., 2014, vol. 126, # 25, p. 6600 - 6604,5
[25] Organometallics, 2013, vol. 32, # 1, p. 330 - 339
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