[ CAS No. 2142-63-4 ] {[proInfo.proName]}

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Structure of 2142-63-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2142-63-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2142-63-4 ]

SDS Specification

Alternatived Products of [ 2142-63-4 ]

Product Details of [ 2142-63-4 ]

CAS No. :	2142-63-4	MDL No. :	MFCD00000083
Formula :	C₈H₇BrO	Boiling Point :	-
Linear Structure Formula :	C₆H₄(Br)(COCH₃)	InChI Key :	JYAQYXOVOHJRCS-UHFFFAOYSA-N
M.W :	199.05	Pubchem ID :	16502
Synonyms :

Calculated chemistry of [ 2142-63-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
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 :	44.34
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) :	-5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	2.47
Log Po/w (WLOGP) :	2.65
Log Po/w (MLOGP) :	2.52
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	2.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.01
Solubility :	0.195 mg/ml ; 0.000981 mol/l
Class :	Soluble
Log S (Ali) :	-2.47
Solubility :	0.67 mg/ml ; 0.00337 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.59
Solubility :	0.0512 mg/ml ; 0.000257 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.25

Safety of [ 2142-63-4 ]

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 [ 2142-63-4 ]

* 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 [ 2142-63-4 ]
Downstream synthetic route of [ 2142-63-4 ]

[ 2142-63-4 ] Synthesis Path-Upstream 1~6

1
[ 2142-63-4 ]
[ 74877-08-0 ]
[ 176707-77-0 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 45, p. 8960 - 8962,3
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 45, p. 8960 - 8962
[3] Patent: WO2015/178846, 2015, A1, . Location in patent: Page/Page column 5; 6; 7

2
[ 2142-63-4 ]
[ 176707-77-0 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 11, p. 5314 - 5327
[2] Organic Process Research and Development, 2014, vol. 18, # 6, p. 788 - 792
[3] Green Chemistry, 2017, vol. 19, # 2, p. 474 - 480

3
[ 74877-08-0 ]
[ 2142-63-4 ]
[ 176707-77-0 ]

Reference： [1] ChemCatChem, 2014, vol. 6, # 4, p. 992 - 995

4
[ 87227-77-8 ]
[ 2142-63-4 ]
[ 109-97-7 ]
[ 176707-77-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 10, p. 1618 - 1624

5
[ 2142-63-4 ]
[ 110-60-1 ]
[ 5724-81-2 ]
[ 74877-08-0 ]
[ 176707-77-0 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 2, p. 361 - 366

6
[ 2142-63-4 ]
[ 411235-57-9 ]
[ 408359-52-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate tribasic heptahydrate; C₄₅H₅₃ClFeNO₂PPd In water; toluene at 100℃; for 3 h; Inert atmosphere	General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.

Reference： [1] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
[2] Patent: WO2016/201168, 2016, A1, . Location in patent: Paragraph 0703
[3] Patent: WO2017/214505, 2017, A1, . Location in patent: Paragraph 000559; 000560

Yield	Reaction Conditions	Operation in experiment
		34 g of 3-cyclopropyl bromobenzene was synthesized from 50 g of 3-bromoacetophenone by a method described in J. Org. Chem., 41, 2263 (1976), and 2 9 of this product was used to prepare 520 mg of the title compound as a white solid by the method described in Production Example 427.1H-NMR (DMSO-d6) delta: 0.63(m, 2H), 0.90(m, 2H), 1.83(m, 1H), 3.20(m, 4H), 3.30(m, 4H), 6.54(d, J=8.0Hz, 1H), 6.68(s, 1H), 6.72(d, J=8.0Hz, 1H), 7.10(t, J=8.0Hz, 1H)

Yield	Reaction Conditions	Operation in experiment
		A 100-ml round-bottom flask fitted with a stirbar, condenser, and septum was flushed with N2 and charged with 3-bromoacetophenone (2.50 g) and anhydrous pyridine (20 mL), followed by selenium dioxide (2.8 g). The reaction mixture was heated to 100 C. After one hour, the reaction was cooled to room temperature and pyridine was distilled off under reduced pressure. The resulting thick oil was partitioned between 50 ml 1N HCl and 50 ml EtOAc. The aqueous phase was extracted once more with 50 ml EtOAc, and the combined organic phase was dried over sodium sulfate and concentrated in vacuo. The resulting crude acid was azeotroped with 10 ml of anhydrous toluene. To a 100-ml round-bottom flask containing the crude acid were added anhydrous DMF (20 ml), Cs2C03 (4.11 g), and methyl iodide (3.58 g) sequentially. The mixture was heated at 40 C for 1 hour under N2, cooled to room temperature, diluted with 200 ml saturated NH4Cl solution, and extracted two times with 200 ml EtOAc/hexanes (1/1). The combined organic phase was dried over Na2S04, concentrated in vacuo, and purified by column chromatography on silica gel (25% EtOAc/hexanes) to provide the desired product. 1H NMR (CDCl3) : 8.22 (s, 1H), 8.01 (d, J=8 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 7.44 (t, J=8 Hz, 1H), 4.0 (s, 3H) MS: m/e 243/245 (M+1)+
	With pyridine; selenium(IV) oxide; at 100℃; for 16h;	[000969] A suspension of Compound 261 A (6.00 g, 30.15 mmol) and Se02 (5.02 g, 45.22 mmol) in pyridine (50 mL) was stirred at 100 C for 16 h. It was filtered to remove the resultant solid and the filtrate was evaporated to remove pyridine. The residue was dissolved in aqueous NaOH solution (5% w/w, 200 mL) and extracted with diethyl ether (100 mL x 2). The aqueous was adjusted to pH 1 with con. HCl to form a solid, which was filtered and dried to afford Compound 261B.

Yield	Reaction Conditions	Operation in experiment
90%	With mesitylenesulfonylhydroxylamine; In acetonitrile; at 20 - 70℃; for 3h;	General procedure: To a round bottom flask, equipped with a magnetic stirring bar, was added ketone 1 (0.5 mmol, 1.0 equiv.) and acetonitrile (2 mL) at room temperature. To this stirred solution, freshly prepared O-(Mesitylsulfonyl)hydroxylamine 2 (2.0 equiv.) was added. The reaction mixture was stirred for the specified duration and temperature. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ethyl acetate (10 mL) and washed with a saturated aqueous NaHCO3 solution (3 x 5 mL). The combined organic layer was washed with brine solution and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to get the crude product. The reaction that required elevated temperature was stirred first at room temperature for 2 hours after addition of MSH and then heated at 70 C for the specified time.

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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 ? Reactions of Dihalides ? 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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[ 2142-63-4 ]

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H401	Toxic to aquatic life
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[ CAS No. 2142-63-4 ] {[proInfo.proName]}

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