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[ CAS No. 28188-41-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Chemical Structure| 28188-41-2

Chemical Structure| 28188-41-2

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Quality Control of [ 28188-41-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 28188-41-2 ]

SDS Specification

Alternatived Products of [ 28188-41-2 ]

Product Citations

Product Details of [ 28188-41-2 ]

CAS No. :	28188-41-2	MDL No. :	MFCD00001809
Formula :	C₈H₆BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVKOOKPNCVYHNY-UHFFFAOYSA-N
M.W :	196.04	Pubchem ID :	97249
Synonyms :

Calculated chemistry of [ 28188-41-2 ] 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 :	43.99
TPSA :	23.79 ?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) :	-9.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	-3.31
Log Po/w (WLOGP) :	2.3
Log Po/w (MLOGP) :	2.25
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.65
Solubility :	879.0 mg/ml ; 4.49 mol/l
Class :	Highly soluble
Log S (Ali) :	3.38
Solubility :	475000.0 mg/ml ; 2420.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0353 mg/ml ; 0.00018 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 28188-41-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 28188-41-2 ]

* 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 [ 28188-41-2 ]
Downstream synthetic route of [ 28188-41-2 ]

[ 28188-41-2 ] Synthesis Path-Upstream 1~2

1
[ 201230-82-2 ]
[ 28188-41-2 ]
[ 2084-13-1 ]

Reference： [1] Tetrahedron Letters, 1983, vol. 24, # 37, p. 4005 - 4008

2
[ 544-97-8 ]
[ 28188-41-2 ]
[ 34136-57-7 ]
[ 620-22-4 ]

Reference： [1] Journal of Organic Chemistry, 1993, vol. 58, # 24, p. 6908 - 6910

[ 28188-41-2 ] Synthesis Path-Downstream 1~10

1
[ 23218-93-1 ]
[ 28188-41-2 ]
3-(3-Cyano-benzylamino)-5-nitro-benzoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,p. 854 - 859
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 972 - 978

2
[ 28188-41-2 ]
[ 5294-61-1 ]
[ 185407-96-9 ]

Reference： [1]Bioorganic and medicinal chemistry,1996,vol. 4,p. 1629 - 1635

3
[ 85416-75-7 ]
[ 28188-41-2 ]
3-[(R)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-ylmethyl]-benzonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3430 - 3433

4
[ 16001-93-7 ]
[ 28188-41-2 ]
[2-(3-cyano-phenyl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5804 - 5814

5
[ 16732-80-2 ]
[ 28188-41-2 ]
1-(3-cyano-benzyl)-4-methyl-1H-indole-2-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: US6337344,2002,B1 .Location in patent: Page column 61

6
[ 28188-41-2 ]
[ 612832-83-4 ]
[ 847148-94-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 80℃; for 5h;	A mixture of <strong>[612832-83-4]2-benzyloxy-5-chlorophenylboronic acid</strong> (2. 1G), 3-cyanobenzyl bromide (1.57g), sodium carbonate (1.7g) and tetrakis (triphenylphosphine) palladium (0) (0.46g) in ethylene glycol dimethyl ether (30ML) was heated at 80C for 5H. The mixture was cooled, partitioned between WATER/DIETHYLETHER, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5% ethylacetate/isohexane, yield 0.53g. H NMR DMSO-D6 : 8 7.68-7. 24 (11H, m); 7.08 (1H, d); 5.10 (2H, s); 3.97 (2H, s)

Reference： [1]Patent: WO2005/18529,2005,A2 .Location in patent: Page/Page column 55-56

7
[ 28188-41-2 ]
[ 137215-27-1 ]
[ 1362586-01-3 ]

Yield	Reaction Conditions	Operation in experiment
10%	With potassium carbonate; In acetone; at 20℃;	General procedure: A mixture of 44 (300 mg, 1.56 mmol), K2CO3 (372 mg, 2.34 mmol), and halogenated compound (1 equiv) in acetone (10 mL) was stirred for 0.5-3.5 h at rt. After filtering the mixture and removing the solvent in vacuo, the residue was purified by column chromatography (eluent: hexane/EtOAc 85:15) to obtain the target compounds (11-23) as white solids.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 49,p. 74 - 85

8
[ 2296-23-3 ]
[ 28188-41-2 ]
[ 1456777-72-2 ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: Potassium carbonate (1-1.6 equiv) was added to a stirred solution of the phenol (1 equiv) in DMF. After 30 min the cyanobenzyl bromide (1-1.2 equiv) was added, and the mixture was stirred until completion (1-4 days). The reaction mixture was poured over ice or diluted with water. The precipitated product was filtered off and recrystallized if needed.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 67,p. 310 - 324

9
[ 52022-77-2 ]
[ 28188-41-2 ]
3-((3-nitrophenethoxy)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.41 g		A solution of <strong>[52022-77-2]2-(3-nitrophenyl)ethanol</strong> (1 .3 g, 7.78 mmol) in DMF (40 mL) was treated with sodium hydride (95%, 0.236 g, 9.33 mmol) at 0 C and the mixture stirred at 0 C for 30 min. 3- (Bromomethyl)benzonitrile (1 .525 g, 7.78 mmol) was then added and the mixture was stirred at room temperature for 1 h. The reaction mixture was cooled to 0 C, quenched with saturated aqueous NH4CI aqueous, and extracted with EtOAc (3x). The extract was dried (Na2S04), evaporated and the residue was purified by chromatography (silica gel, gradient 0 to 50% EtOAc/hexanes) to give the desired product (1 .41 g) as a pale brown oil. 1H NMR (400 MHz, CDCI3) delta ppm 3.08 (t, J = 6.46 Hz, 2H), 3.80 (t, J = 6.46 Hz, 2H), 4.58 (s, 2H), 7.42 - 7.66 (m, 6H), 8.10 - 8.20 (m, 2H).

Reference： [1]Patent: WO2019/53617,2019,A1 .Location in patent: Page/Page column 113

10
[ 52022-77-2 ]
[ 28188-41-2 ]
tert-butyl 3-((3-nitrophenethoxy)methyl)benzylcarbamate [ No CAS ]

Reference： [1]Patent: WO2019/53617,2019,A1

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction ? Vilsmeier-Haack Reaction

Historical Records

Related Functional Groups of
[ 28188-41-2 ]

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4-Cyanobenzyl bromide

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4-Cyanobenzyl bromide

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2-Cyanobenzyl bromide

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