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[ CAS No. 328-67-6 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 328-67-6

Chemical Structure| 328-67-6

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Quality Control of [ 328-67-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 328-67-6 ]

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Product Details of [ 328-67-6 ]

CAS No. :	328-67-6	MDL No. :	MFCD03412186
Formula :	C₈H₄BrF₃O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	AMZBKZQMAZWIJM-UHFFFAOYSA-N
M.W :	269.02	Pubchem ID :	11086788
Synonyms :

Calculated chemistry of [ 328-67-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.1
TPSA :	37.3 ?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) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.7
Log Po/w (XLOGP3) :	3.02
Log Po/w (WLOGP) :	4.32
Log Po/w (MLOGP) :	3.38
Log Po/w (SILICOS-IT) :	2.95
Consensus Log Po/w :	3.07

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.6
Solubility :	0.0683 mg/ml ; 0.000254 mol/l
Class :	Soluble
Log S (Ali) :	-3.47
Solubility :	0.0915 mg/ml ; 0.00034 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0831 mg/ml ; 0.000309 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.69

Safety of [ 328-67-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 328-67-6 ]

* 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 [ 328-67-6 ]
Downstream synthetic route of [ 328-67-6 ]

[ 328-67-6 ] Synthesis Path-Upstream 1~1

1
[ 822-36-6 ]
[ 328-67-6 ]
[ 641571-13-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide In 1,4-dioxane at 115℃; for 72 h; Molecular sieve	Coupling reaction: A reaction flask was charged with 3-bromo-5-trifluoromethylbenzoic acid (compound 2, 2.7 g, 0.01 mol), 4-methyl-1H- imidazole (1.64 g, 1), trans- N, N'-dimethylcyclohexanediamine (0.28 g, 0.002 mol), 1,4-dioxane (10 vol./g), anhydrous potassium phosphate , 0.03mol) and 4A molecular sieves (0. lg / g), to form a mixed system; the mixed system is purged with nitrogen to have an oxygen content of 500ppm, finally adding cuprous iodide (0.38g, 0.002mol) The system was heated to 115 ° C, the reaction was stirred for 72 hours, TLC showed compound 2 disappeared to give the product system; and then the system was cooled to room temperature, transferred to 2M hydrochloric acid quenched, concentrated filtered without fraction To be purified solution. Adding n-butanol, extracting and separating the organic phase, extracting with n-butanol twice, and combining the organic phases; concentrating the organic phase to remove n-butanol to obtain 3- (4-methyl- -5- (trifluoromethyl) benzoic acid (Compound 3) crude. Recrystallization from methanol (4: 1 ./g) gave 1.76 g of a khaki-colored solid in 65percent yield.

Reference： [1] Patent: CN104592122, 2018, B, . Location in patent: Paragraph 0102- 0103

[ 328-67-6 ] Synthesis Path-Downstream 1~3

1
[ 124-38-9 ]
[ 481075-59-6 ]
[ 328-67-6 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 2508 - 2517

2
[ 328-67-6 ]
[ 172023-97-1 ]

Yield	Reaction Conditions	Operation in experiment
69%		16). Synthesis of 1-bromomethyl-3-methanesulfonyl-5-trifluoromethyl-benzene; To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (5 mmol, 1.35 g) in THF (8 mL) is added 1M boran in THF (16 mmol, 16 ml_) under nitrogen. The solution is allowed to warm to 65 0C and stirred for 2 hours. The mixture is cooled to room temperature, then poured into saturated aq. NaHCO3. The mixture is extracted with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: hexane / EtOAc) to give (3-bromo-5-trifluoromethyl-phenyl)-methanol (418 mg, 69%).
57%		Step C: (3-Bromo-5-(trifluoromethyl)phenyl)methanol To a solution of 3-bromo-5-(trifluoromethyl)benzoic acid (2.13 gm, 7.92 mmol) in anhydrous THF under nitrogen was added borane dimethylsulfide complex (15.83 mmol, 7.91 mL) and the mixture was stirred at room temperature for 16 hours. A further aliquot of borane dimethylsulfide complex (15.83 mmol, 7.91 mL) was then added and stirring was continued at room temperature for a further 4 hours. LC-MS indicated complete consumption of starting material. Methanol was added cautiously until effervescence ceased then 2N hydrochloric acid (20 mL) was added. The mixture was stirred at room temperature for 20 hours then concentrated to dryness under reduced pressure. The residue was extracted with diethyl ether and the solution washed with water. The organic layer was dried with anhydrous sodium sulfate and the solvent removed under vacuum. The residue was dissolved in a mixture of dichloromethane and methanol, silica gel was added and the solvent removed under vacuum. The solid was placed on a column of silica gel (50 gm) and eluted with hexane-ethyl acetate (85:15) to give the title compound as a yellow oil which crystallized on standing (1.16 gm, 57%). LC-MS (ES-) Calc: 255, Found: 254 (M-H). 1H NMR (CDCl3) delta ppm 7.72 (brs, 1H), 7.69 (brs, 1H), 7.57 (brs, 1H), 4.77 (s, 2H), 1.86 (brs, 1H).
	With hydrogenchloride; In tetrahydrofuran; water; ethyl acetate;	Step 1: (3-bromo-5-(trifluoromethyl)phenyl)methanol To a stirred solution of 3-bromo-5-(trifluoromethyl)benzoic acid (1 g, 3.72 mmol) in THF (5 ml) at -78 C. with stirring under nitrogen was added dropwise over 10 mins borane tetrahydrofuran complex 1M in THF (18.59 ml, 18.59 mmol) and then the reaction mixture was warmed to RT over 20 hours. The reaction mixture was cooled in an ice/water bath and quenched dropwise with MeOH (10 ml) followed by 1M HCl until effervescence ceased. Water was added and stirred at RT for 30 mins. THF was removed under reduced pressure, and the compound extracted into EtOAc. The organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-50% EtOAc in Hexanes as eluent to afford the title product. 1H NMR (400 MHz, d6-DMSO): delta 7.83 (s, 1H), 7.83 (s, 1H) 7.69 (s, 1H), 5.54-5.51 (t, 1H), 4.60-4.59 (d, 2H)

Reference： [1]Patent: WO2008/9435,2008,A1 .Location in patent: Page/Page column 162
[2]Patent: US2007/213371,2007,A1 .Location in patent: Page/Page column 71
[3]Patent: US2014/171403,2014,A1 .Location in patent: Page/Page column

3
[ 328-67-6 ]
[ 1150271-61-6 ]

Reference： [1]Patent: WO2012/139775,2012,A1

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Technical Information

? Alkyl Halide Occurrence ? Arndt-Eistert Homologation ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hunsdiecker-Borodin Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Passerini Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Reactions of Dihalides ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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