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[ CAS No. 6334-18-5 ] {[proInfo.proName]}

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Chemical Structure| 6334-18-5
Chemical Structure| 6334-18-5
Structure of 6334-18-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6334-18-5 ]

CAS No. :6334-18-5 MDL No. :MFCD00010127
Formula : C7H4Cl2O Boiling Point : -
Linear Structure Formula :- InChI Key :LLMLNAVBOAMOEE-UHFFFAOYSA-N
M.W : 175.01 Pubchem ID :35745
Synonyms :

Calculated chemistry of [ 6334-18-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.85
TPSA : 17.07 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) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.81
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 3.26
Consensus Log Po/w : 2.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.119 mg/ml ; 0.000679 mol/l
Class : Soluble
Log S (Ali) : -2.98
Solubility : 0.183 mg/ml ; 0.00104 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.57
Solubility : 0.0467 mg/ml ; 0.000267 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 6334-18-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P273-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310 UN#:1759
Hazard Statements:H314-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 6334-18-5 ]

* 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 [ 6334-18-5 ]
  • Downstream synthetic route of [ 6334-18-5 ]

[ 6334-18-5 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 32768-54-0 ]
  • [ 6334-18-5 ]
YieldReaction ConditionsOperation in experiment
29% at 90℃; (1) Device: Refer to Figure 2 to determine the connection of the tubular reactor, the type of pipe: (3a + 3e) DC channel + Corningde Heart Cel 1 structure, pipe diameter and volume according to the flow rate and reaction time to determine the heat transfer Medium for the heat transfer oil. [0040] (2) 6.06 g of cobalt acetate and 6.06 g of sodium molybdate were dissolved in 200 ml of 2,3-dichlorotoluene and 200 ml of acetic acid to form a mixed solution at which time η (cobalt acetate): η (2,3-dichlorotoluene ) = 0.015: 1, 6.06 g of sodium bromide was dissolved in 25percent H22 to form H22-acetic acid solution, where η (sodium bromide): η (2,3-dichlorotoluene) = 0.015: 1 , 2,3-dichlorotoluene-acetic acid solution and H22-acetic acid solution were injected into the continuous heat transfer tubular reactor at a flow rate of 5.56 ml / min and ll.llml / min, respectively, when η (H2? 2):? (2,3-dichlorotoluene) = 2: 1, using Figure 2 microchannel reactor, Control reaction temperature 90 ° C, residence time 1200s. The outlet material was cooled at 0 ° C and the reaction was quenched with dichloromethane. The yield of 2,3-dichlorotoluene was 42.8percent and the yield of 2,3-dichlorobenzaldehyde was 29.0percent by GC analysis
Reference: [1] Patent: CN106699525, 2017, A, . Location in patent: Paragraph 0039; 0040
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 861,863[3] Industrial and Engineering Chemistry, 1947, vol. 39, p. 1486,1487
[4] Journal of the Chemical Society. Perkin transactions 1, 1965, p. 5976 - 5983
[5] Patent: CN107032968, 2017, A,
  • 2
  • [ 38594-42-2 ]
  • [ 6334-18-5 ]
YieldReaction ConditionsOperation in experiment
48.19 g With hydrogen bromide; dihydrogen peroxide In 1,4-dioxane at 25℃; for 7 h; In a 1L reactor,add 61.5 g of 2,3-dichlorotoluene, 3.075 g of azobisisobutyronitrile (5percent), 215.25 g of 2-dichloroethane, heat the mixture at 75 ° C and add 44 g of bromine drop wise,reflux reaction till red bromine fades , Intermittent drip and 136.2g27.5percent hydrogen peroxide continues to react till red bromine no longer generates. Add a 49.2g30percent aqueous solution of sodium carbonate to the reaction solution, reflux reaction for 8 h ,at the same time recover1,2-dichloroethane.The hydrolyzate is heated and filtered at 80° C, into organic phase add 246g 1,4-Dioxane , add 40percent of the catalyst HBr6.15g, add 27.5percent hydrogen peroxide 38.3g,react at 25 ° C for 7 h. The reaction system is extracted three times with 1,2-dichloroethane,the organic phase is concentrated and obtained crude 2,3-dichlorobenzaldehyde, re-crystallization from ethanol and obtained 48.19 g of 2,3-dichlorobenzaldehyde, GC purity is 99.26percent and yield is 72.1percent.
Reference: [1] RSC Advances, 2014, vol. 4, # 91, p. 49974 - 49978
[2] European Journal of Organic Chemistry, 2013, # 21, p. 4503 - 4508
[3] Patent: CN107032968, 2017, A, . Location in patent: Paragraph 0015; 0017; 0018; 0019; 0022
  • 3
  • [ 4414-54-4 ]
  • [ 6334-18-5 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 6, p. 1153 - 1158
[2] Synthetic Communications, 2000, vol. 30, # 17, p. 3121 - 3125
  • 4
  • [ 288-43-7 ]
  • [ 1820-80-0 ]
  • [ 6287-38-3 ]
  • [ 6334-18-5 ]
Reference: [1] Patent: US2003/22890, 2003, A1,
  • 5
  • [ 95-50-1 ]
  • [ 6334-18-5 ]
Reference: [1] Patent: US4572908, 1986, A,
[2] Patent: US4572909, 1986, A,
[3] Patent: US4559351, 1985, A,
  • 6
  • [ 29027-17-6 ]
  • [ 6334-18-5 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 861,863[2] Industrial and Engineering Chemistry, 1947, vol. 39, p. 1486,1487
  • 7
  • [ 111011-80-4 ]
  • [ 6334-18-5 ]
  • [ 115578-90-0 ]
Reference: [1] Synthesis, 1993, # 7, p. 705 - 713
[2] Synthesis, 1993, # 7, p. 705 - 713
  • 8
  • [ 57915-78-3 ]
  • [ 6334-18-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 91, p. 49974 - 49978
  • 9
  • [ 75-17-2 ]
  • [ 608-27-5 ]
  • [ 6334-18-5 ]
Reference: [1] Archiv der Pharmazie, 1962, vol. 295 /67, p. 16 - 19
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 385 - 390
[3] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
  • 10
  • [ 6705-49-3 ]
  • [ 68-12-2 ]
  • [ 6334-18-5 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 32, p. 5819 - 5822
  • 11
  • [ 17257-79-3 ]
  • [ 68-12-2 ]
  • [ 6334-18-5 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 32, p. 5819 - 5822
[2] Tetrahedron Letters, 1995, vol. 36, # 32, p. 5819 - 5822
  • 12
  • [ 6334-18-5 ]
  • [ 89583-90-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 385 - 390
  • 13
  • [ 6334-18-5 ]
  • [ 38594-42-2 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate In methanol at 0℃; Inert atmosphere General procedure: Aldehyde (1 mmol) was dissolved in 10 ml ofmethanol(ethanol for ketones) and cooled to 0oC. NaBH4 (3 mmol) was then added inone portion and the reaction was allowed to stir until completion as indicatedby TLC (9:1 heptanes/ethyl acetate). The reaction was quenched with 0.1 N NaOH(10 ml) and extracted three times with ethyl actetate. The organic layer waswashed with brine and dried over Na2SO4. The solvent wasremoved under reduced pressure and the resulting yellow oil was subjected toflash chromatography.
92% With sodium borohydrid In methanol; sodium hydroxide 1.
Preparation of 2,3-Dichlorobenzyl alcohol
To 2,3-dichlorobenzaldehyde (500 g, 2.85 mole) in methanol (3.5 liters) was added an alkaline solution of sodium borohydride (113.5 g, 2.975 mole) in 0.2N sodium hydroxide solution (241 ml) over a period of 1 hour.
After 2 hours the reaction mixture was quenched into water (3.7 liters) and the pH was adjusted to pH 6 using glacial acetic acid (125 ml).
Filtration afforded 2,3-dichlorobenzyl alcohol as a white solid (467 g, 92percent yield).
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 564 - 576
[2] Patent: US6124308, 2000, A,
[3] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
  • 14
  • [ 6334-18-5 ]
  • [ 38594-42-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 57, p. 46026 - 46030
  • 15
  • [ 6334-18-5 ]
  • [ 38594-42-2 ]
Reference: [1] ChemSusChem, 2015, vol. 8, # 10, p. 1664 - 1675
[2] Journal of Organic Chemistry, 2015, vol. 80, # 12, p. 6375 - 6380
[3] Journal of Organic Chemistry, 2016, vol. 81, # 22, p. 11065 - 11071
  • 16
  • [ 6334-18-5 ]
  • [ 38594-42-2 ]
  • [ 50-45-3 ]
Reference: [1] Monatshefte fuer Chemie, 1959, vol. 90, p. 683,687
  • 17
  • [ 38594-42-2 ]
  • [ 124-63-0 ]
  • [ 6334-18-5 ]
  • [ 3218-45-9 ]
YieldReaction ConditionsOperation in experiment
72% With sodium borohydrid; triethylamine In methanol; water; acetone; toluene; Petroleum ether 1.
Preparation of 2,3-Dichlorophenylacetonitrile
To a suspension of 2,3-dichlorobenzaldehyde (40 kg, 228.6 mole) in toluene (254 liters) and methanol (40 liters), was added sodium borohydride (2.59 kg, 68.6 mole) portionwise over a period of 1 hour.
The mixture was stirred for a period of 30 minutes prior to treatment with acetone (20 liters).
On decomposition of the excess borohydride, water (80 liters) was added.
Toluene (54 liters) was added to the toluene phase and the suspension was warmed to 42° C.+-2° C. to attain a solution prior to separation.
The organic phase was distilled to remove 54 liters of azeotrope and so effect the removal of water, acetone, and isopropyl alcohol.
The resulting toluene solution of 2,3-dichlorobenzyl alcohol was cooled.
To the resulting suspension was added triethylamine (27.8 kg, 274.3 mole) followed by methanesulphonyl chloride (31.4 kg, 274.3 mole) over a period of 11/2 hours so as to maintain the temperature at 0° C.+-2° C.
The mixture was stirred for 1 hour then water (,100 liters) was charged to the suspension and the mixture was stirred vigorously prior to separation.
To the methanesulphonate in the toluene phase was added tetrabutylammonium hydrogen sulphate (15.6 kg, 45.8 mole) and aqueous potassium cyanide solution (22.4 kg, 342.8 mole) in water (70 liters) over a period of 40 minutes.
The two phase mixture was stirred overnight, separated and the organic phase was washed with water (70 liters).
The toluene phase was distilled to remove 130 kg of toluene in the presence of charcoal (2.8 kg) and dicalite (2.8 kg).
Petroleum ether 60/80 (300 liters) was charged to the residue, the mixture was filtered hot and crystallized under vacuum to afford 2,3-dichlorophenylacetonitrile (30 kg, 72percent yield).
Reference: [1] Patent: US6124308, 2000, A,
  • 18
  • [ 6334-18-5 ]
  • [ 3218-45-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
  • 19
  • [ 6334-18-5 ]
  • [ 6574-97-6 ]
Reference: [1] Biochemical Pharmacology, 2015, vol. 96, # 2, p. 93 - 106
  • 20
  • [ 6334-18-5 ]
  • [ 56041-57-7 ]
Reference: [1] Patent: TW2016/4185, 2016, A,
  • 21
  • [ 105-45-3 ]
  • [ 6334-18-5 ]
  • [ 74073-22-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 108 - 116
[2] Applied Catalysis A: General, 2017, vol. 530, p. 203 - 210
  • 22
  • [ 626-34-6 ]
  • [ 105-45-3 ]
  • [ 6334-18-5 ]
  • [ 72509-76-3 ]
YieldReaction ConditionsOperation in experiment
94.3%
Stage #1: With piperidine; pyridine In neat (no solvent) at 75 - 80℃; for 9 h;
Stage #2: for 1 h; Reflux
20.0-dichlorobenzaldehyde 70.0 g (0.40 mol), β-aminocrotonate ethyl ester in a 500 mL round bottom flask55.8g (0.48mol),62.0 g (0.48 mol) of methyl acetoacetate, followed by 4.5 g (0.053 mol) of piperidine and 4.2 g (0.053 mol) of pyridine.The heating was started slowly and the temperature was raised. The reaction was maintained at 75-80 ° C for 9 h, and 200 g of absolute ethanol was added while heating, and the mixture was heated to reflux for 1 h, and filtered while hot.The mixture was cooled to 15 ° C and stirred for 1 h, and suction filtered. The filter cake was washed with a small amount of dry ethanol and dried to give 145 g of pale yellow solid.Yield: 94.3percent, purity 99.1percent
Reference: [1] Patent: CN108840819, 2018, A, . Location in patent: Paragraph 0014; 0040-0042; 0045-0048; 0051-0053
  • 23
  • [ 105-45-3 ]
  • [ 6334-18-5 ]
  • [ 72509-76-3 ]
  • [ 91189-59-2 ]
  • [ 79925-38-5 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: at 40 - 45℃; for 6 h;
Stage #2: for 4 h; Heating / reflux
To a solution of 2,3-dichlorobenzaldehyde (8.76 g, 0.05 mol) in isopropanol (80 mL) is added picolinic acid (0.65 g, 5.4 mmol), piperidine (0.45 g, 5.4 mmol) and methyl acetoacetate (86.3 g, 0.06 mol). The solution is stirred at 40-45 C. for 6 h, and then isopropanol is distilled under vacuum. The residue is dissolved in ethyl acetate (80 mL) and washed with water (60 mL). Ethyl acetate is then removed under vacuum. To the residue is added ethyl aminocrotonate (7.74 g, 0.06 mol) and isopropanol (60 mL). The mixture is heated under reflux for 4 hours. Isopropanol is distilled and heptanes (60 mL) is added. The resulting solid is filtered and washed with heptanes. After drying 12.7 g (66percent) felodipine is obtained as pale yellow solid with a purity of 94.4percent (diethyl and dimethyl have a concentration of 2.02percent and 3.38percent (a/a), respectively).
Reference: [1] Patent: US2004/204604, 2004, A1, . Location in patent: Page 5
  • 24
  • [ 626-34-6 ]
  • [ 6334-18-5 ]
  • [ 72509-76-3 ]
Reference: [1] Patent: US5977369, 1999, A,
  • 25
  • [ 141-97-9 ]
  • [ 105-45-3 ]
  • [ 6334-18-5 ]
  • [ 72509-76-3 ]
Reference: [1] Chinese Journal of Chemistry, 2014, vol. 32, # 12, p. 1245 - 1250
  • 26
  • [ 5394-63-8 ]
  • [ 6334-18-5 ]
  • [ 14205-39-1 ]
  • [ 138279-32-0 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: WO2011/130852, 2011, A1, . Location in patent: Page/Page column 6
  • 27
  • [ 6334-18-5 ]
  • [ 123853-39-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 8, p. 1579 - 1589
[2] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 108 - 116
[3] Patent: CN102464608, 2016, B,
[4] Patent: CN103242220, 2016, B,
  • 28
  • [ 68-11-1 ]
  • [ 6334-18-5 ]
  • [ 90407-16-2 ]
YieldReaction ConditionsOperation in experiment
82% With potassium hydroxide In diethyl ether at 120℃; for 2 h; First Step
Synthesis of 7-Chloro-1-benzothiophene-2-carboxylic acid
To an aqueous solution (10 mL) of potassium hydroxide (1.3 g, 22 mmol), 2-mercaptoacetic acid (0.70 mL, 10 mmol) and 2,3-dichlorobenzaldehyde (1.8 g, 10 mmol) were added, and the resulting mixture was stirred at 120° C.
Two hours later, the reaction solution was cooled to room temperature, and after adding distilled water until precipitated solid was dissolved, diethyl ether was added thereto.
The reaction solution was separated into an organic layer and water layer, and after adding 1.0 N hydrochloric acid to the water layer until the pH reached 5, the water layer was extracted with ethyl acetate.
The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to obtain the title compound (1.7 g; 82percent) as a colorless liquid.
1H-NMR (400 MHz, DMSO-d6): 7.48-7.54 (1H, m), 7.62-7.70 (1H, m), 7.98-8.04 (1H, m), 8.16-8.22 (1H, m).MS (ESI) [M+H]+213
Reference: [1] Patent: US2014/128606, 2014, A1, . Location in patent: Paragraph 0078; 0079; 0080; 0081; 0082; 0083
  • 29
  • [ 6334-18-5 ]
  • [ 90407-16-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 385 - 390
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 385 - 390
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