[ CAS No. 2642-63-9 ] {[proInfo.proName]}

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2D 3D

Structure of 2642-63-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2642-63-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2642-63-9 ]

SDS Specification

Alternatived Products of [ 2642-63-9 ]

Product Details of [ 2642-63-9 ]

CAS No. :	2642-63-9	MDL No. :	MFCD00000553
Formula :	C₈H₆Cl₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	189.04	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 2642-63-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.66
TPSA :	17.07 ?2

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) :	2.05
Log Po/w (XLOGP3) :	3.08
Log Po/w (WLOGP) :	3.2
Log Po/w (MLOGP) :	2.94
Log Po/w (SILICOS-IT) :	3.43
Consensus Log Po/w :	2.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.29
Solubility :	0.0969 mg/ml ; 0.000513 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.148 mg/ml ; 0.000784 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.97
Solubility :	0.0204 mg/ml ; 0.000108 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.18

Safety of [ 2642-63-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2642-63-9 ]

* 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 [ 2642-63-9 ]
Downstream synthetic route of [ 2642-63-9 ]

[ 2642-63-9 ] Synthesis Path-Upstream 1~1

1
[ 64-17-5 ]
[ 2642-63-9 ]
[ 28394-58-3 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 3, p. 369 - 372

[ 2642-63-9 ] Synthesis Path-Downstream 1~3

1
[ 1475-11-2 ]
[ 2642-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(IV) oxide; silica gel; In acetonitrile; at 70℃; for 8h;Molecular sieve;	General procedure: The above secondary alcohol was dissolved in acetonitrile (30mL). Molecular sieve (1.5g), silica gel (1.5g) and activated MnO2 (3.5g, 40mmol) were added, and the mixture was stirred at 70C for 8h. upon completion of the oxidation, the resulting suspension was filtered through diatomite, and the filtrate was concentrated by rotary evaporation. Purification of the residue by column chromatography (petroleum ethrt/EtOAc, 15:1) afforded ketone 13.

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1741 - 1746
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3466 - 3471
[3]Arkiv foer Kemi,1955,vol. 7,p. 577,578
[4]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1996 - 2000
[5]European Journal of Medicinal Chemistry,2018,vol. 159,p. 90 - 103

2
[ 391-12-8 ]
[ 2642-63-9 ]
[ 148887-62-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 977 - 984

3
[ 2642-63-9 ]
[ 1475-11-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol; at 82℃; for 6h;Inert atmosphere; Green chemistry;	The 3, 4 - dichloro ethanone (189 mg, 1.0 mmol), cat. [Ir] (1.1 mg, 0 . 002 mmol, 0.2 muM %) and isopropyl alcohol (5 ml) are added to the 25 ml Kjeldahl tube, N2Protection, 82 C reaction 6 h. Cooling to room temperature, rotary evaporation to remove the solvent, then through the column chromatography (developing solvent: petroleum ether/ethyl acetate) to obtain the pure target compound, yield: 97%
94%	With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); hydrogen; In tert-Amyl alcohol; at 30℃; under 760.051 Torr; for 12h;Green chemistry;	General procedure: To an oven-dried 5 mL round-bottom flask were added ketone (1 mmol), cat. 7 (2.7 mg, 0.5 mol %) and tert-amyl alcohol (1 mL). Next, vacuum was applied to the flask followed by filling with H2 gas and keeping the flask attached to a balloon filled with H2 gas. The mixture was heated at 30 C for 12 h. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The alcohols were isolated and purified by filtering a hexanes/ethyl acetate (5:1) solution of the crude product through a pad of silica gel, and then removing the solvent under reduced pressure. The conversion and purity of the alcohol products was assessed using NMR spectroscopy.
80%	With sodium tetrahydroborate; ethanol; at 20℃;Cooling with ice;	2.2 mmol NaBH4 was added to 2.1 mmol of 8a in dry ethanol (10 mL) stirred in an ice bath.The suspension was further stirred at room temperature overnight. After the reaction was completed, it was quenched by the addition of 1.0 N HCl, and the remaining ethanol was evaporated under reduced pressure. The product was extracted with diethyl ether (25 mL x 2),washed with sodium bicarbonate (15 mL), and water (10 mL), dried over MgSO4, and evaporated under reduced pressure. Silica gel column chromatography (hex ane:ethyl acetate4:1) was performed to give the corresponding rac-8b. 9a-11a and 13a (2.21 mmol~2.66 mmol) were also reduced similarly. The 1H-NMR spectra of alcohols 8b [1], 9b-11b [2], and 13b [3] were in agreement with those reported in the literature. 1.2.1 1-(3?,4?-Dichlorophenyl)ethanol, rac-8b. 0.42 g (2.21 mmol) of 8a was converted to 0.34 g of rac-8b (1.77 mmol, 80%, colorless oil). 1H-NMR (400 MHz, CDCl3, 25C, TMS): delta=7.47-7.48 (m, 1H), 7.41(d, J=8.4 Hz, 1H), 7.20 (dd, J=8.4 Hz, 2.0Hz, 1H), 4.85-4.90 (m, 1H), 1.85 (brd,J=3.6 Hz, 1H), 1.48 (d, J=6.4 Hz, 3H).

	With sodium tetrahydroborate; In methanol; at 0 - 20℃;	To a stirred solution of 3,4-dichloroacetophenone (4 g, 21.15 mmol, Aldrich) in dry MeOH (80 mL), sodium borohydride (0.96 g, 25.39 mmol, spectrochem) was added portionwise at 0 C. The reaction mixture was stirred at rt overnight. It was cooled to 0 C and quenched using ice water (10 mL). Solvents were removed under reduced pressure and resulting residue was dissolved in DCM (50 mL). The organic layer was washed with water (25 mL), brine (20 mL), dried over Na2SO4 and concentrated. The crude product was used for next step without further purification. Yield: 95% (3.8 g, colorless liquid). 1H NMR (400 MHz, DMSO-d6): delta 7.57-7.55 (m, 2H), 7.33 (d, J = 1.9 Hz, 1H), 5.38 (d, J = 4.4 Hz, 1H), 4.76-4.70 (m, 1H), 1.30 (d, J = 6.4 Hz, 3H).
	With methanol; sodium tetrahydroborate; at 0 - 20℃;	General procedure: Ten mmol of NaBH4 was added to a cooled (0C) solution of 2.5 mmol of each specific substrate(1a-1f, 1m and 1n) in 50 mL of methanol. After stirring for 10 min, the mixture was warmed to room temperature and stirred for another 3-4 h to complete the reduction. After quenching with 2 M HCl topH 7.0, the mixture was extracted with EtOAc (50 mL 3). The organic phases were washed withbrine, dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by flashchromatography on silica gel (eluent: EtOAc/PE 1:20) to give the racemic alcohol 2a-2f, 2m and 2n(see Supplementary Materials for NMR spectroscopic data).

Reference： [1]Synthesis,2009,p. 4058 - 4062
[2]Patent: CN109384645,2019,A .Location in patent: Paragraph 0060; 0061; 0062; 0063
[3]Tetrahedron,2019,vol. 75
[4]Journal of Medicinal Chemistry,1997,vol. 40,p. 3905 - 3914
[5]Molecular catalysis,2018,vol. 448,p. 153 - 161
[6]Tetrahedron Letters,2020,vol. 61
[7]Patent: WO2016/30443,2016,A1 .Location in patent: Page/Page column 93
[8]Marine Drugs,2018,vol. 16

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 2642-63-9 ]

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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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[ CAS No. 2642-63-9 ] {[proInfo.proName]}

Quality Control of [ 2642-63-9 ]

Related Doc. of [ 2642-63-9 ]

Product Details of [ 2642-63-9 ]

Calculated chemistry of [ 2642-63-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2642-63-9 ]

Application In Synthesis of [ 2642-63-9 ]

[ 2642-63-9 ] Synthesis Path-Upstream 1~1

[ 2642-63-9 ] Synthesis Path-Downstream 1~3

Technical Information

Related Functional Groups of [ 2642-63-9 ]

Aryls

Chlorides

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2642-63-9 ]