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[ CAS No. 83-38-5 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
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3d Animation Molecule Structure of 83-38-5
Chemical Structure| 83-38-5
Chemical Structure| 83-38-5
Structure of 83-38-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 83-38-5 ]

CAS No. :83-38-5 MDL No. :MFCD00003307
Formula : C7H4Cl2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :175.01 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 83-38-5 ]

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) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 2.64
Log Po/w (WLOGP) : 2.81
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 3.26
Consensus Log Po/w : 2.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.189 mg/ml ; 0.00108 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.393 mg/ml ; 0.00224 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 : 1.09

Safety of [ 83-38-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 UN#:1759
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 83-38-5 ]

* 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 [ 83-38-5 ]
  • Downstream synthetic route of [ 83-38-5 ]

[ 83-38-5 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 83-38-5 ]
  • [ 66490-33-3 ]
Reference: [1] Patent: WO2013/15456, 2013, A1,
[2] Patent: WO2013/15456, 2013, A1,
[3] Organic Process Research and Development, 2016, vol. 20, # 1, p. 86 - 89
  • 2
  • [ 83-38-5 ]
  • [ 4659-45-4 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1939, vol. <2> 152, p. 49,67
  • 3
  • [ 83-38-5 ]
  • [ 89978-31-4 ]
Reference: [1] Journal of the Indian Chemical Society, 1990, vol. 67, # 11, p. 927 - 929
[2] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 5, p. 611 - 618
[3] Archiv der Pharmazie, 2015, vol. 348, # 1, p. 10 - 22
  • 4
  • [ 83-38-5 ]
  • [ 68-11-1 ]
  • [ 23967-57-9 ]
YieldReaction ConditionsOperation in experiment
30.5 g
Stage #1: With potassium hydroxide In water for 2.5 h; Reflux
Stage #2: With hydrogenchloride In water for 1 h;
After potassium hydroxide (30.8 g) was dissolved in water (179 ml), thioglycolic acid (19.4 g) was added to the solution, and 2 , 6-dichlorobenzaldehyde (32.0 g) was further added. The resulting mixture was heated under reflux for 2.5 hours. The mixture was allowed to cool, and then allowed to stand at room temperature overnight. The precipitated crystals (potassium 4- chlorobenzo[b] thiophen-2-carboxylate) was collected by filtration and washed with cold water. Further, the crystals were dispersed in water (256 ml). After concentrated hydrochloric acid (20 ml) was added thereto, the resulting mixture was stirred for 1 hour. The precipitated crystals were collected by filtration and washed with water. Crude crystals of this 2-carboxy-4- chlorobenzo[b] thiophene were dispersed in ethyl acetate (96 ml), and washed at room temperature. The precipitated crystals were washed with ethyl acetate, and then dried to yield 29.12 g of a dried product. The dried product was further washed with ethyl acetate, and the wash was concentrated to 70 ml. The precipitated secondary crystals were collected and dried to obtain 2-carboxy- 4-chlorobenzo[b]thiophene (1.35 g) . Yield: 30.5 g White crystals ^-NMRiDMSO-de) δρρπΐ; 7.53 (1H, t, J= 7.7 Hz), 7.58 (1H, dd, J= 7.7. 1.3 Hz), 8.03 (1H, d, J= 0.5 Hz), 8.07 (1H, d, J= 7.6 Hz).
Reference: [1] Organic Process Research and Development, 2016, vol. 20, # 1, p. 86 - 89
[2] Patent: WO2013/15456, 2013, A1, . Location in patent: Page/Page column 40; 41
  • 5
  • [ 83-38-5 ]
  • [ 23967-57-9 ]
Reference: [1] Patent: WO2013/15456, 2013, A1,
[2] Patent: WO2013/15456, 2013, A1,
[3] ChemMedChem, 2018, vol. 13, # 15, p. 1517 - 1529
  • 6
  • [ 83-38-5 ]
  • [ 118-69-4 ]
Reference: [1] Chemische Berichte, 1943, vol. 76, p. 1252,1254
  • 7
  • [ 83-38-5 ]
  • [ 437-81-0 ]
YieldReaction ConditionsOperation in experiment
77% With potassium fluoride; tetraphenylphosphonium bromide In sulfolane at 100 - 180℃; for 2 h; Inert atmosphere 34.8 g (0.6 mo) KF is dissolved in 250 m sulfolan under nitrogen for 2h at 100°C. By azeotropic distiNation water is removed. 20 g (0,11 mo) 26-dichlorobenzadehyde and 2.8 g (6.68 mmo) tetrapheny phosphoniumbromide are given to the water-free mixture and heated overnight to 180°C. The resu[ting dark so’ution is fi[tered, the solid washed with ethy’ acetate and the ‘ow-boNing components removed by water pressure evaporation. By vacuum dsUNation (24 mbar, 85-86°C) the color’ess product is obtained, yield 77percent
Reference: [1] Patent: WO2016/102207, 2016, A1, . Location in patent: Page/Page column 32
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Chemistry Letters, 1988, # 9, p. 1355 - 1358
[4] Angewandte Chemie - International Edition, 2006, vol. 45, # 17, p. 2720 - 2725
[5] Patent: US6103659, 2000, A,
[6] Patent: US6103659, 2000, A,
[7] Patent: US6103659, 2000, A,
  • 8
  • [ 83-38-5 ]
  • [ 2751-90-8 ]
  • [ 437-81-0 ]
Reference: [1] Patent: US6127581, 2000, A,
  • 9
  • [ 83-38-5 ]
  • [ 437-81-0 ]
  • [ 387-45-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
  • 10
  • [ 83-38-5 ]
  • [ 15258-73-8 ]
YieldReaction ConditionsOperation in experiment
94% With sodium tetrahydroborate In ethanol at 20℃; for 2 h; To a solution of 3,5-dichlorobenzaldehyde (340 mg, 1.94 mmol) in ethanol (4 mL)Sodium borohydride (74 mg, 1.94 mmol) was added.After stirring at room temperature for 2 hours, 1N hydrochloric acid was added to quench the reaction. The solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate (10 mL), washed with 1N hydrochloric acid and then water (10 mL×2), and the organic phase was dried over anhydrous sodium sulfate. After concentration, the product 3-e (320 mg) was obtained. 94percent).
90%
Stage #1: With Triethoxysilane; [cis-Fe(H)(SPh)(PMe3)4] In tetrahydrofuran at 50℃; for 2 h;
Stage #2: With methanol; sodium hydroxide In tetrahydrofuran; water at 60℃; for 24 h;
General procedure: To a 25 mL Schlenk tube containing a solution of 1 in 2 mL of THF was added an aldehyde (1.0 mmol) and (EtO)3 SiH (0.20 g, 1.2 mmol). The reaction mixture was stirred at 50–55 °C until there was no aldehyde left (monitored by TLC and GC–MS). The reaction was then quenched byMeOH (2mL) and a 10percent aqueous solution of NaOH (5 mL) with vigorous stirring at 60 °C for about 24 h.The organic product was extracted with diethyl ether (10 mL × 3), dried over anhydrous MgSO4, and concentrated under vacuum. The alcohol product was further purified using flash column chromatography (elute with 5–10percent ethyl acetate in petroleum ether). The 1H NMR and 13C NMR spectra of the alcohol products are providedin Supporting information.
90% With Triethoxysilane; potassium phenyltrifluoborate In methanol at 20℃; for 0.166667 h; Take a 25mL reaction bottle,Place a magnet in the bottle.Weigh 2,6-dichlorobenzaldehyde (0.131 g, 0.75 mmol),Potassium phenyl trifluoroborate (2.5percent eq. 3.5 mg),Add 3 mL of methanol to the reaction flask as a solvent.The pipette was then used to remove trimethoxysilane (2.2 eq. 202 μL).The reaction is carried out in an air atmosphere at room temperature.The progress of the reaction was detected by TLC.After 10 minutes, it was extracted with dichloromethane (3×40 mL).The dichloromethane phases were combined and washed with 40 mL of deionized water.Dry over anhydrous sodium sulfate,Rotary evaporation to remove the solvent,Column chromatography gave 120 mg of the product as a white solid.Yield 90percent;The NMR is as follows:
Reference: [1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: CN103304571, 2018, B, . Location in patent: Paragraph 0142; 0143; 0144
[3] RSC Advances, 2015, vol. 5, # 64, p. 52000 - 52006
[4] Catalysis Communications, 2017, vol. 94, p. 23 - 28
[5] Patent: CN109020779, 2018, A, . Location in patent: Paragraph 0049; 0050
[6] Organometallics, 2014, vol. 33, # 13, p. 3535 - 3539
[7] Tetrahedron Letters, 1983, vol. 24, # 40, p. 4287 - 4290
[8] Dalton Transactions, 2014, vol. 43, # 30, p. 11716 - 11722
[9] RSC Advances, 2018, vol. 8, # 25, p. 14092 - 14099
[10] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 19, p. 3131 - 3132
[11] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3230 - 3236
[12] Journal of Organic Chemistry, 1956, vol. 21, p. 142
[13] Chemical and pharmaceutical bulletin, 1967, vol. 15, # 12, p. 1990 - 1995
[14] Organometallics, 2013, vol. 32, # 18, p. 5235 - 5238
[15] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
[16] ACS Catalysis, 2015, vol. 5, # 9, p. 5540 - 5544
[17] Journal of the American Chemical Society, 2014, vol. 136, # 45, p. 15813 - 15816
[18] Organometallics, 2016, vol. 35, # 20, p. 3538 - 3545
[19] Catalysis Science and Technology, 2017, vol. 7, # 13, p. 2828 - 2837
[20] Patent: WO2017/212289, 2017, A1, . Location in patent: Page/Page column 19; 20
[21] Dalton Transactions, 2018, vol. 47, # 12, p. 4352 - 4359
[22] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3145 - 3157
[23] Catalysis Communications, 2018, vol. 115, p. 1 - 5
[24] New Journal of Chemistry, 2018, vol. 42, # 20, p. 16583 - 16590
  • 11
  • [ 83-38-5 ]
  • [ 15258-73-8 ]
  • [ 17849-38-6 ]
Reference: [1] Catalysis Communications, 2016, vol. 87, p. 78 - 81
  • 12
  • [ 766-77-8 ]
  • [ 83-38-5 ]
  • [ 15258-73-8 ]
  • [ 73927-56-7 ]
Reference: [1] Catalysis Science and Technology, 2017, vol. 7, # 11, p. 2165 - 2169
  • 13
  • [ 83-38-5 ]
  • [ 5866-97-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 564 - 578
[2] Gazzetta Chimica Italiana, 1993, vol. 123, # 7, p. 409 - 415
[3] Justus Liebigs Annalen der Chemie, 1932, vol. 495, p. 249,275
[4] Patent: DE199943, , ,
[5] Patent: DE199943, , ,
  • 14
  • [ 83-38-5 ]
  • [ 437-81-0 ]
  • [ 387-45-1 ]
Reference: [1] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
[2] Journal of Fluorine Chemistry, 2004, vol. 125, # 6, p. 1031 - 1038
[3] Journal of Fluorine Chemistry, 1990, vol. 46, # 3, p. 529 - 537
  • 15
  • [ 83-38-5 ]
  • [ 387-45-1 ]
Reference: [1] Patent: US6465643, 2002, B1,
  • 16
  • [ 83-38-5 ]
  • [ 2040-05-3 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 916,923
  • 17
  • [ 83-38-5 ]
  • [ 2365-48-2 ]
  • [ 35212-95-4 ]
Reference: [1] ChemMedChem, 2018, vol. 13, # 15, p. 1517 - 1529
  • 18
  • [ 83-38-5 ]
  • [ 1334411-79-8 ]
Reference: [1] Patent: WO2011/113802, 2011, A2,
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 18, p. 4370 - 4376
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