[ CAS No. 529-34-0 ] {[proInfo.proName]}

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2D 3D

Structure of 529-34-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 529-34-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 529-34-0 ]

SDS Specification

Alternatived Products of [ 529-34-0 ]

Product Details of [ 529-34-0 ]

CAS No. :	529-34-0	MDL No. :	MFCD00001688
Formula :	C₁₀H₁₀O	Boiling Point :	-
Linear Structure Formula :	C₆H₄(CH₂)₃CO	InChI Key :	XHLHPRDBBAGVEG-UHFFFAOYSA-N
M.W :	146.19	Pubchem ID :	10724
Synonyms :	3,4-Dihydro-1(2H)-naphthalenone	Chemical Name :	3,4-Dihydronaphthalen-1(2H)-one

Calculated chemistry of [ 529-34-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.3
TPSA :	17.07 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
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) :	1.89
Log Po/w (XLOGP3) :	2.02
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	2.01
Log Po/w (SILICOS-IT) :	3.06
Consensus Log Po/w :	2.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.42
Solubility :	0.552 mg/ml ; 0.00378 mol/l
Class :	Soluble
Log S (Ali) :	-2.01
Solubility :	1.44 mg/ml ; 0.00987 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.37
Solubility :	0.0619 mg/ml ; 0.000424 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.45

Safety of [ 529-34-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P270-P301+P312-P312-P330-P501	UN#:	N/A
Hazard Statements:	H302-H312	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 529-34-0 ]

* 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 [ 529-34-0 ]
Downstream synthetic route of [ 529-34-0 ]

[ 529-34-0 ] Synthesis Path-Upstream 1~4

1
[ 75-91-2 ]
[ 119-64-2 ]
[ 21032-12-2 ]
[ 529-33-9 ]
[ 529-34-0 ]
[ 106477-02-5 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 12, p. 2063 - 2066
[2] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 11, p. 2429 - 2434

2
[ 119-64-2 ]
[ 21032-12-2 ]
[ 529-33-9 ]
[ 529-34-0 ]

Reference： [1] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 6, p. 744 - 748

3
[ 529-34-0 ]
[ 21032-12-2 ]

Reference： [1] Journal of the American Chemical Society, 1989, vol. 111, # 1, p. 410 - 411
[2] Chemistry - A European Journal, 2016, vol. 22, # 41, p. 14567 - 14575
[3] ChemCatChem, 2018, vol. 10, # 14, p. 2962 - 2968

4
[ 119-64-2 ]
[ 771-29-9 ]
[ 21032-12-2 ]
[ 19070-56-5 ]
[ 529-33-9 ]
[ 529-34-0 ]

Reference： [1] Chemistry Letters, 1991, # 5, p. 813 - 816

[ 529-34-0 ] Synthesis Path-Downstream 1~13

1
[ 1070-62-8 ]
[ 529-34-0 ]
5-oxo-5-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-valeric acid [ No CAS ]
5-oxo-5-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-valeric acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1926,1929

2
[ 50-00-0 ]
[ 20388-87-8 ]
[ 529-34-0 ]
2-[(2-Phenyl-propylamino)-methyl]-3,4-dihydro-2H-naphthalen-1-one [ No CAS ]

Reference： [1]Patent: DE1913199,1970,
Chem.Abstr.,1971,vol. 74

3
[ 17823-69-7 ]
[ 529-34-0 ]
[ 28559-55-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1325 - 1331

4
[ 5780-66-5 ]
[ 529-34-0 ]
2-(Hydroxy-pyrazin-2-yl-methyl)-3,4-dihydro-2H-naphthalen-1-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 834 - 841

5
[ 1003-61-8 ]
[ 529-34-0 ]
[ 173988-88-0 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 834 - 841

6
[ 529-34-0 ]
[ 771-15-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-Bromosuccinimide; dibenzoyl peroxide; In benzene; for 4h;Reflux; Inert atmosphere;	General procedure: A benzene suspension (30 mL) of 1-tetralone 4, 11, 16 (1.0 equiv), N-bromosuccinimide (NBS) (2.2 equiv) and (PhCOO)2 (5 mol percent) was refluxed under Argon atmosphere for 4 h and then cooled to 20 °C. To the reaction mixture was added triethylamine (1 mL) and the solvent was removed in vacuo. The reaction mixture was diluted with water and extracted with CH2Cl2 (3.x.25 mL). The combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (silica gel, heptane/EtOAc) to give 5, 12 and 17.
59%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In benzene; for 4h;Reflux; Inert atmosphere;	A benzene suspension (30 mL) of 1-tetralone (1.8mL, 13.7 mmol), N-bromosuccinimide (NBS) (4.9 g, 27.5 mmol), and AIBN (0.1 g, 5 molpercent) was refluxed under argon atmosphere for 4 h, and then cooled to 20 . To the reaction mixture was added triethylamine (2 mL) and the solvent was removed in vacuo, added by water and extracted with CH3Cl. The organic layer was dried over MgSO4 and concentrated in vacuo. The product was purified by flash column chromatography using hexane and EtOAc to give 2-bromo-1-naphthol as white solid (1.8 g, 59percent), 1H NMR (300MHz, CDCl3) d 8.24?8.21 (m, 1H), 7.77?7.73 (m, 1H),7.51?7.43(m, 3H), 7.28 (d, J = 8.8 Hz, 1H),5.96 (s, 1H); 13C NMR (75 MHz, CDCl3) d 148.1, 133.7,128.3, 127.5, 126.8, 126.1, 124.3, 122.2, 121.3, 103.9; GC-MS m/z 222, 224 (M+).

Reference： [1]Synlett,2011,p. 1827 - 1830
[2]Tetrahedron,2012,vol. 68,p. 6305 - 6313
[3]Tetrahedron Letters,2005,vol. 46,p. 4187 - 4191
[4]Tetrahedron Letters,2014,vol. 55,p. 3355 - 3357

7
[ 529-34-0 ]
ethyl halide [ No CAS ]
[ 771-15-3 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4187 - 4191

8
[ 703-67-3 ]
[ 103-67-3 ]
2-(N-benzylmethylamino)methyl-6-fluoro-3,4-dihydro-2H-naphthalene-1-one hydrochloride [ No CAS ]
[ 529-34-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; paraformaldehyde; In ethanol; water;	Step D 2-(N-Benzylmethylamino)methyl-6-fluoro-3,4-dihydro-2H-naphthalene-1-one hydrochloride To an ice-cooled solution of N-benzylmethylamine (5.67 cm3) in ethyl alcohol (60 cm3) was added hydrochloric acid (5 M, 10 cm3). <strong>[703-67-3]6-Fluoro-3,4-dihydro-2H-naphthalene-1-one</strong> (6.00 g) and paraformaldehyde (1.32 g) were then added and the resulting mixture was stirred and heated to reflux for 4 h. Upon cooling, the alcohol was removed under reduced pressure and water (100 cm3) was added. The remaining tetralone was extracted into diethyl ether (100 cm3) and the aqueous mixture was then extracted further with dichloromethane (2*100 cm3). The combined extracts were dried (Na2SO4) and concentrated under reduced pressure. Trituration with diethyl ether and filtration provided the title compound (3.18 g) as a white solid.

Reference： [1]Patent: US6410592,2002,B1

9
[ 1409956-58-6 ]
[ 14472-80-1 ]
[ 529-34-0 ]

Yield	Reaction Conditions	Operation in experiment
	With zirconium(IV) chloride; In toluene; at 20 - 50℃; for 2h;	To a reactor equipped with reflux condenser, dropping funnel and thermo-pocket, was charged 2-(4-(4-chlorophenyl)-1-hydroxy cyclohexyl)-3,4-dihydronaphthalen-1-(2H)-one (5.0 g, 0.04 mol) and dissolved in toluene (50 mL) at room temperature. To the above solution was added ZrCl4 (0.33 g, 1.4 mmol) and the reaction mass was stirred at 50 °C for 2 h. The reaction mass showed complete conversion of starting material to a-tetralone and 4-(4- chlorophenyl) cyclohexanone in 1 :1 ratio and no olefin product could be identified and isolated.

Reference： [1]Patent: WO2013/14486,2013,A1 .Location in patent: Page/Page column 20

10
[ 1409956-58-6 ]
[ 14472-80-1 ]
[ 1409956-62-2 ]
[ 529-34-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With toluene-4-sulfonic acid; In toluene; at 60℃; for 6h;	2-(4-(4-chlorophenyl)-1-hydroxycyclohexyl)-3,4-dihydronaphthalen-1-(2H)-one (12.0 g, 0.0.034 mol) was charged in a reactor equipped with overhead stirrer, reflux condenser and thermo-pocket. Toluene (200 mL) was added to suspend the material and p-toluene sulfonic acid (0.3 g, 2.5 mol percent) was added to the reaction mass which was then heated to 60 °C and stirred for 6 h. Progress of reaction was monitored on TLC. After completion of reaction, reaction mass was cooled to RT and solvent was evaporated under pressure to obtain residue. To the residue, was added ethyl acetate (150 mL) and washed with sat. NaHC03 soln. and brine followed by evaporation of solvent to give crude product which was further recrystallised from methanol to afford white solid compound (5.3 g, 50 percent yield). The mother liquor obtained after re-crystallisation was subjected to GC analysis wherein both a-tetralone and 4-(4-chlorophenyl) cyclohexanone were identified to be present in approx. 1 : 1 ratio (by respective retention times and AUCs in the mother liquor) and in 50 percent yield. GC retention time: a-tetralone (XII): 17.21 min (Area percent : 46)

Reference： [1]Patent: WO2013/14486,2013,A1 .Location in patent: Page/Page column 19

11
[ 5417-17-4 ]
[ 529-34-0 ]
2-(2-chloro-3,4-dimethoxybenzylidene)-1-tetralone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 3549 - 3561
[2]Chemical Biology and Drug Design,2016,vol. 88,p. 889 - 898

12
[ 529-34-0 ]
[ 52927-23-8 ]
[ 91270-69-8 ]

Reference： [1]Patent: US2003/225281,2003,A1

13
[ 14135-38-7 ]
[ 529-34-0 ]
(2-fluorophenyl)(naphthalen-2-yl)sulfane [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2154 - 2158

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Isomers

Technical Information

? 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 ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? 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 Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

Historical Records

Similar Product of
[ 529-34-0 ]

A1267883[ 189811-58-3 ]

3,4-Dihydronaphthalen-1(2H)-one-4a,5,6,7,8,8a-13C6

Reason: Stable Isotope

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[ 529-34-0 ]

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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 529-34-0 ] {[proInfo.proName]}

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