Home Cart 0 Sign in  
X

[ CAS No. 38594-42-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 38594-42-2
Chemical Structure| 38594-42-2
Chemical Structure| 38594-42-2
Structure of 38594-42-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 38594-42-2 ]

Related Doc. of [ 38594-42-2 ]

Alternatived Products of [ 38594-42-2 ]

Product Details of [ 38594-42-2 ]

CAS No. :38594-42-2 MDL No. :MFCD00238581
Formula : C7H6Cl2O Boiling Point : -
Linear Structure Formula :- InChI Key :STVBVTWXWZMRPZ-UHFFFAOYSA-N
M.W : 177.03 Pubchem ID :228603
Synonyms :

Calculated chemistry of [ 38594-42-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.59
TPSA : 20.23 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) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.02
Solubility : 0.168 mg/ml ; 0.000949 mol/l
Class : Soluble
Log S (Ali) : -2.79
Solubility : 0.288 mg/ml ; 0.00163 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.062 mg/ml ; 0.00035 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 38594-42-2 ]

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 [ 38594-42-2 ]

* 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 [ 38594-42-2 ]
  • Downstream synthetic route of [ 38594-42-2 ]

[ 38594-42-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 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
  • 2
  • [ 38594-42-2 ]
  • [ 57915-78-3 ]
YieldReaction ConditionsOperation in experiment
83% With phosphorus tribromide In toluene at 20℃; for 2 h; To a solution of (2,3-dichlorophenyl)methanol (75 g, 0.431 mol), in toluene (800 ml),tribromophosphine (40.7 g, 0.151 mol) was added dropwise at room temperature withstirring. Then the reaction mixture was stirred at room temperature for 2 h andconcentrated. The resulting residue was neutralized with aq. NaHC03 and extracted withDCM (300 ml * 3). The organic layer was washed with brine, dried over Na2S04 , filteredand the filtrate was concentrated to provide the titled compound (84.7 g, 83percent), as a deepred solid.
Reference: [1] Patent: WO2013/28263, 2013, A1, . Location in patent: Page/Page column 79
[2] Pest Management Science, 2000, vol. 56, # 10, p. 875 - 881
  • 3
  • [ 38594-42-2 ]
  • [ 7789-60-8 ]
  • [ 57915-78-3 ]
Reference: [1] Patent: US9096605, 2015, B2,
  • 4
  • [ 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
  • 5
  • [ 2905-54-6 ]
  • [ 38594-42-2 ]
YieldReaction ConditionsOperation in experiment
88% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; A suspension of LiAIH4 (7.4 g, 0.195 mol) in THF (500 ml) was stirred at 0 °C. A solutionof methyl 2,3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 ml) was added dropwiseinto the above mixture at 0 - 5 °C. Then the mixture was stirred at room temperature for 2h. The reaction mixture was quenched with ethyl acetate (15 ml), water (7.5 ml), 15percentNaOH (7.5 ml) and water (22.5 ml), filtered and the filtrate was concentrated. Theresulting residue was dissolved with DCM (500 ml) and washed with brine. The organiclayer was dried over Na2S04 , filtered and the filtrate was concentrated to provide the titledcompound (37 g, 88percent), as a white solid; 1H NMR (300 MHz, CDCI3) 8 ppm 4.81 (d, J=6.3Hz, 2 H), 7.24 (t, J=7.8 Hz, 1 H), 7.42- 7.45 (m, 2 H).
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 31, p. 6021 - 6022
[2] Patent: WO2013/28263, 2013, A1, . Location in patent: Page/Page column 78; 79
[3] Patent: US2004/180890, 2004, A1, . Location in patent: Page/Page column 6; 10
  • 6
  • [ 2905-54-6 ]
  • [ 38594-42-2 ]
  • [ 96042-30-7 ]
YieldReaction ConditionsOperation in experiment
88% With lithium aluminium tetrahydride In tetrahydrofuran; ethyl acetate b)
(2,3-dichlorophenyl)methanol
A suspension of LiAlH4 (7.4 g, 0.195 mol) in THF (500 mL) was stirred at 0° C. A solution of methyl 2,3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 mL) was added dropwise into the above mixture at 0-5° C.
Then the mixture was stirred at room temperature for 2 h.
The reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15percent NaOH (7.5 mL) and water (22.5 mL), filtered and the filtrate was concentrated.
The resulting residue was dissolved with DCM (500 mL) and washed with brine.
The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (37 g, 88percent), as a white solid; 1H NMR (300 MHz, CDCl3) δ ppm 4.81 (d, J=6.3 Hz, 2H), 7.24 (t, J=7.8 Hz, 1H), 7.42-7.45 (m, 2H).
Reference: [1] Patent: US9096605, 2015, B2,
  • 7
  • [ 50-45-3 ]
  • [ 38594-42-2 ]
Reference: [1] Patent: US9096605, 2015, B2,
[2] Patent: US3966758, 1976, A,
[3] Patent: WO2013/28263, 2013, A1,
[4] Patent: US2004/180890, 2004, A1,
  • 8
  • [ 57915-78-3 ]
  • [ 38594-42-2 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 91, p. 49974 - 49978
[2] Patent: CN107032968, 2017, A, . Location in patent: Paragraph 0015; 0017; 0019; 0021
  • 9
  • [ 6334-18-5 ]
  • [ 38594-42-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 57, p. 46026 - 46030
  • 10
  • [ 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
  • 11
  • [ 608-27-5 ]
  • [ 38594-42-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
  • 12
  • [ 32768-54-0 ]
  • [ 38594-42-2 ]
Reference: [1] Patent: CN107032968, 2017, A,
  • 13
  • [ 6334-18-5 ]
  • [ 38594-42-2 ]
  • [ 50-45-3 ]
Reference: [1] Monatshefte fuer Chemie, 1959, vol. 90, p. 683,687
  • 14
  • [ 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,
  • 15
  • [ 38594-42-2 ]
  • [ 124-63-0 ]
  • [ 3218-45-9 ]
YieldReaction ConditionsOperation in experiment
83% With 2-(Dimethylamino)pyridine; triethylamine In water; toluene; Petroleum ether 2.
Preparation of 2,3-Dichlorophenylacetonitrile
To the 2,3-dichlorobenzyl alcohol (470.5 g, 2.658 mole) in toluene (1.97 liters) was added triethylamine (322.8E g, 3.19 mole) and dimethylaminopyridine (16.23 g, 0.13 mole).
Methanesulphonyl chloride (365.4 g, 3.19 mole) was added over a period of 1 hour.
After 2 hours the toluene solution was washed with water.
To the methanesulphonate in toluene was added a solution of tetrabutylammonium hydrogen sulphate (180.5 g, 0.53 mole) in water (641 ml) followed by aqueous potassium cyanide solution (259.6 g 3.987 mole) in water (712 ml).
The two phase reaction mixture was stirred overnight, separated and the organic phase was washed with water (1069 ml).
The toluene was removed under vacuum and the product was precipitated from petroleum ether 60/80 (1069 ml), filtered and washed with petroleum ether 60/80 (356 ml) to give the crude 2,3-dichlorophenylacetonitrile (406 g, 83percent yield).
Reference: [1] Patent: US6124308, 2000, A,
  • 16
  • [ 38594-42-2 ]
  • [ 3218-45-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
[2] Patent: US2004/180890, 2004, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 38594-42-2 ]

Aryls

Chemical Structure| 34145-05-6

[ 34145-05-6 ]

(2,5-Dichlorophenyl)methanol

Similarity: 0.92

Chemical Structure| 17849-38-6

[ 17849-38-6 ]

2-Chlorobenzyl alcohol

Similarity: 0.92

Chemical Structure| 1777-82-8

[ 1777-82-8 ]

(2,4-Dichlorophenyl)methanol

Similarity: 0.90

Chemical Structure| 217479-60-2

[ 217479-60-2 ]

2,4,6-Trichlorobenzyl alcohol

Similarity: 0.86

Chemical Structure| 15258-73-8

[ 15258-73-8 ]

(2,6-Dichlorophenyl)methanol

Similarity: 0.86

Chlorides

Chemical Structure| 34145-05-6

[ 34145-05-6 ]

(2,5-Dichlorophenyl)methanol

Similarity: 0.92

Chemical Structure| 17849-38-6

[ 17849-38-6 ]

2-Chlorobenzyl alcohol

Similarity: 0.92

Chemical Structure| 1777-82-8

[ 1777-82-8 ]

(2,4-Dichlorophenyl)methanol

Similarity: 0.90

Chemical Structure| 217479-60-2

[ 217479-60-2 ]

2,4,6-Trichlorobenzyl alcohol

Similarity: 0.86

Chemical Structure| 15258-73-8

[ 15258-73-8 ]

(2,6-Dichlorophenyl)methanol

Similarity: 0.86

Alcohols

Chemical Structure| 34145-05-6

[ 34145-05-6 ]

(2,5-Dichlorophenyl)methanol

Similarity: 0.92

Chemical Structure| 17849-38-6

[ 17849-38-6 ]

2-Chlorobenzyl alcohol

Similarity: 0.92

Chemical Structure| 1777-82-8

[ 1777-82-8 ]

(2,4-Dichlorophenyl)methanol

Similarity: 0.90

Chemical Structure| 217479-60-2

[ 217479-60-2 ]

2,4,6-Trichlorobenzyl alcohol

Similarity: 0.86

Chemical Structure| 15258-73-8

[ 15258-73-8 ]

(2,6-Dichlorophenyl)methanol

Similarity: 0.86