[ CAS No. 17938-06-6 ] {[proInfo.proName]}

Name: 17938-06-6|Triethoxy(naphthalen-1-yl)silane|95%
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SKU: A429964
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2D 3D

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Quality Control of [ 17938-06-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 17938-06-6 ]

Product Details of [ 17938-06-6 ]

CAS No. :	17938-06-6	MDL No. :	MFCD00094090
Formula :	C₁₆H₂₂O₃Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZJEYUFMTCHLQQI-UHFFFAOYSA-N
M.W :	290.43	Pubchem ID :	4208568
Synonyms :

Calculated chemistry of [ 17938-06-6 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.38
Num. rotatable bonds :	7
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	84.6
TPSA :	27.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.7
Log Po/w (XLOGP3) :	4.31
Log Po/w (WLOGP) :	3.1
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	2.39
Consensus Log Po/w :	3.11

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.26
Solubility :	0.0158 mg/ml ; 0.0000545 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.61
Solubility :	0.00721 mg/ml ; 0.0000248 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.77
Solubility :	0.000495 mg/ml ; 0.00000171 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.14

Safety of [ 17938-06-6 ]

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

Application In Synthesis of [ 17938-06-6 ]

* 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.

Downstream synthetic route of [ 17938-06-6 ]

[ 17938-06-6 ] Synthesis Path-Downstream 1~49

1
[ 693-03-8 ]
[ 17938-06-6 ]
[ 1521-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	In not given

Reference： [1]Petrow; Tschugunow [Doklady Akademii Nauk SSSR, 1950, vol. 73, p. 323,325][Chem.Abstr., 1951, p. 2921]
[2]Petrov, A. D.; Chugunov, V. S. [Doklady Akademii Nauk SSSR, 1950, vol. 73, p. 323 - 326][C. A., 1951, p. 2921] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 28, page 86 - 90]

2
[ 917-64-6 ]
[ 17938-06-6 ]
[ 18052-80-7 ]

Reference： [1]Sanin [Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1286,1287;engl.Ausg.S.1371]

3
[ 78-10-4 ]
[1]naphthyl magnesium ⁽¹⁺⁾; bromide [ No CAS ]
[ 17938-06-6 ]

Reference： [1]Khotinsky; Seregenkoff [Chemische Berichte, 1908, vol. 41, p. 2951]

4
[ 1521-08-0 ]
[ 64-17-5 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In tetrahydrofuran for 2h;

Reference： [1]Melzer [Chemische Berichte, 1908, vol. 41, p. 3393]
[2]Melzer [Chemische Berichte, 1908, vol. 41, p. 3393] Sanin [Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1286,1287;engl.Ausg.S.1371]
[3]Fox, Marye Anne; Nobs, Frederic J.; Voynick, Tamara A. [Journal of the American Chemical Society, 1980, vol. 102, # 12, p. 4029 - 4036]

5
[ 17938-06-6 ]
[ 3761-92-0 ]
[ 18759-65-4 ]

Yield	Reaction Conditions	Operation in experiment
	In not given

6
[ 17938-06-6 ]
[ 1589-82-8 ]
[ 18769-68-1 ]

Reference： [1]Tschugunow; Petrow [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1953, p. 713; engl.Ausg.S.639]

7
[ 17938-06-6 ]
phenylmagnesium bromide [ No CAS ]
[ 18768-92-8 ]

Reference： [1]Petrow; Tschugunow [Doklady Akademii Nauk SSSR, 1950, vol. 73, p. 323,325][Chem.Abstr., 1951, p. 2921]

8
[ 17938-06-6 ]
4-et3SiC₆H₄MgBr [ No CAS ]
[ 18765-44-1 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene

Reference： [1]Sanin [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 986; engl.Ausg.S.1029]
[2]Sanin, P. S. [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 986 - 988][C. A., 1954, p. 8765] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 82, page 228 - 229]

9
[ 17938-06-6 ]
[ 591-51-5 ]
[ 18768-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	In not given
	In not given

Reference： [1]Gilman; Brannen [Journal of the American Chemical Society, 1951, vol. 73, p. 4640,4642]
[2]Gilman, H.; Brannen, C. G. [Journal of the American Chemical Society, 1951, vol. 73, p. 4640 - 4641]
[3]Gilman, H.; Brook, A. G.; Miller, L. S. [Journal of the American Chemical Society, 1953, vol. 75, p. 4531 - 4534] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 28, page 86 - 90]

10
[ 17938-06-6 ]
[ 106-95-6 ]
[ 18663-17-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With Mg In not given
	With magnesium

Reference： [1]Petrov, A. D.; Shchukovskaja, L. L. [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 564 - 565][C. A., 1953, p. 3792] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 28, page 86 - 90]
[2]Petrow; Schtschukowskaja [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 564;engl.Ausg.S.537]

11
[ 78-10-4 ]
[ 14474-59-0 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
56%	addn. of (C10H7)Li to Si(OC2H5)4;;
56%	addn. of (C10H7)Li to Si(OC2H5)4;;

Reference： [1]Gilman, H.; Brannen, C. G. [Journal of the American Chemical Society, 1951, vol. 73, p. 4640 - 4641]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 78, page 217 - 218]
[3]Gilman; Brannen [Journal of the American Chemical Society, 1951, vol. 73, p. 4640,4642]

12
[ 17938-06-6 ]
[ 14474-59-0 ]
[ 18750-75-9 ]

Reference： [1]Gilman; Brannen [Journal of the American Chemical Society, 1951, vol. 73, p. 4640,4642]

13
[ 17938-06-6 ]
[ 14474-59-0 ]
[ 18765-03-2 ]

Yield	Reaction Conditions	Operation in experiment
24%	In diethyl ether on boiling;;

Reference： [1]Petrov, A. D.; Tsuganov, V. S. [Doklady Akademii Nauk SSSR, 1951, vol. 77, p. 815 - 818][C. A., 1952, p. 480] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 78, page 217 - 218]
[2]Petrow; Tschugunow [Doklady Akademii Nauk SSSR, 1951, vol. 77, p. 815,818][Chem.Abstr., 1952, p. 480]

14
[ 17938-06-6 ]
[ 4294-57-9 ]
[ 18840-24-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	In toluene
70%	In toluene

Reference： [1]Sanin, P. S.; Petrov, A. D. [Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1124 - 1127][C. A., 1953, p. 8029]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 78, page 217 - 218]
[3]Sanin; Petrow [Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1124,1126;engl.Ausg.S.1167]

15
[ 17938-06-6 ]
[ 4294-57-9 ]
[ 18769-67-0 ]

Yield	Reaction Conditions	Operation in experiment
20%	In not given

Reference： [1]Chugunov, V. S.; Petrov, A. D. [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1953, p. 713 - 720][C. A., 1954, p. 12716] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 28, page 86 - 90]
[2]Tschugunow; Petrow [Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1953, p. 713; engl.Ausg.S.639]

16
[ 78-10-4 ]
[ 703-55-9 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether
	In not given
	In not given

Reference： [1]Khotinsky; Seregenkoff [Chemische Berichte, 1908, vol. 41, p. 2951]
[2]Khotinsky, E. [Chemische Berichte, 1909, vol. 42, p. 3088 - 3089]
[3]Khotinsky, E.; Seregenkov, B. [Chemische Berichte, 1908, vol. 41, p. 2946 - 2953] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 78, page 217 - 218]

17
[ 17938-06-6 ]
[ 1521-11-5 ]

Reference： [1]Petrow; Tschugunow [Doklady Akademii Nauk SSSR, 1950, vol. 73, p. 323,325][Chem.Abstr., 1951, p. 2921] Sanin [Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1286,1287;engl.Ausg.S.1371]

18
[ 17938-06-6 ]
[ 18985-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene 2: C₆H₅MgBr / toluene

Reference： [1]Sanin [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 986; engl.Ausg.S.1029]
[2][Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 82, page 228 - 229]

19
[ 17938-06-6 ]
[ 18840-26-1 ]

Reference： [1]Sanin; Petrow [Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1124,1126;engl.Ausg.S.1167]

20
[ 17938-06-6 ]
[ 18765-68-9 ]

Reference： [1]Sanin [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 986; engl.Ausg.S.1029]

21
[ 17938-06-6 ]
[ 18848-25-4 ]

Reference： [1]Sanin; Petrow [Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1124,1126;engl.Ausg.S.1167]

22
[ 17938-06-6 ]
[ 18764-98-2 ]

Reference： [1]Gilman; Brannen [Journal of the American Chemical Society, 1951, vol. 73, p. 4640,4642]

23
[ 17938-06-6 ]
[ 18764-92-6 ]

Reference： [1]Sanin [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 986; engl.Ausg.S.1029]

24
[ 17938-06-6 ]
[ 17049-49-9 ]
[ 18759-15-4 ]

Yield	Reaction Conditions	Operation in experiment
27%	In not given

25
[ 17938-06-6 ]
[ 925-90-6 ]
[ 1521-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	In not given purity: 95%;;

Reference： [1]Petrov, A. D.; Chugunov, V. S. [Doklady Akademii Nauk SSSR, 1950, vol. 73, p. 323 - 326][C. A., 1951, p. 2921] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 28, page 86 - 90]

26
[ 78-10-4 ]
[ 14474-59-0 ]
[ 18750-75-9 ]
[ 18765-03-2 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
8%	addn. of Si(OC2H5)4 to (C10H7)Li;;
8%	addn. of Si(OC2H5)4 to (C10H7)Li;;

27
[ 17938-06-6 ]
[ 6921-34-2 ]
[ 18769-68-1 ]

Yield	Reaction Conditions	Operation in experiment
10%	In not given

28
[ 1521-08-0 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	With C₂H₅OH

Reference： [1]Melzer, W. [Chemische Berichte, 1908, vol. 41, p. 3390 - 3395] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 78, page 217 - 218]

29
[ 17938-06-6 ]
[ 18768-92-8 ]

Yield	Reaction Conditions	Operation in experiment
	With C₆H₅MgBr In not given (CH3CH2O)3Si(C10H7) and C6H5MgBr; hydrolysis;;

30
[ 17938-06-6 ]
[ 703-55-9 ]
[ 18765-03-2 ]

Yield	Reaction Conditions	Operation in experiment
0%	In further solvent(s) heating of (C10H7)Si(OC2H5)3 and (C10H7)MgBr in petroleum at 250°C for a longer period of time;;

31
[ 998-30-1 ]
naphthalene-1-diazonium 4-methylbenzenesulfonate [ No CAS ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: naphthalene-1-diazonium 4-methylbenzenesulfonate With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetra-(n-butyl)ammonium iodide; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: Triethoxysilane In N,N-dimethyl-formamide at 20 - 100℃; Inert atmosphere;

Reference： [1]Tang, Zhi Yong; Zhang, Yuan; Wang, Tao; Wang, Wei [Synlett, 2010, # 5, p. 804 - 808]

32
[ 17938-06-6 ]
[ 321-38-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 2,6-dimethylpyridine; Selectfluor; silver(l) oxide In acetone at 23 - 90℃; for 2h; regioselective reaction;	4.3.2. General procedure B (for non-volatile compounds) General procedure: To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (46.4 mg, 0.200 mmol, 2.00 equiv), barium oxide (17.2 mg, 0.110 mmol, 1.10 equiv) or 2,6-lutidine (12.8 μL, 0.110 mmol, 1.10 equiv) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial. The reaction mixture was cooled to 23 °C and concentrated under reduced pressure. To the residue was added CH2Cl2 and the mixture was filtered through a pad of Celite eluting with CH2Cl2. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silica gel or preparative TLC.

Reference： [1]Tang, Pingping; Ritter, Tobias [Tetrahedron, 2011, vol. 67, # 24, p. 4449 - 4454]

33
[ 17938-06-6 ]
[ 18769-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene 2: toluene

Reference： [1]Sanin, P. S. [Zhurnal Obshchei Khimii, 1953, vol. 23, p. 986 - 988][C. A., 1954, p. 8765] [Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 82, page 228 - 229]

34
[ 703-55-9 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethyl ether 2: C₂H₅OH

Reference： [1]Melzer, W. [Chemische Berichte, 1908, vol. 41, p. 3390 - 3395]

35
[ 78-10-4 ]
[ 90-11-9 ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 1-Bromonaphthalene With magnesium; ethylene dibromide In tetrahydrofuran at 25℃; Sonication; Stage #2: tetraethoxy orthosilicate In tetrahydrofuran at 25℃; for 0.75h; Sonication;
30 g	With sodium at 70 - 80℃; for 2h;	3 1) naphthyl triethoxy silane synthesis: Synthesis of naphthyltriethoxysilane: To a 1 L four-necked flask equipped with a mechanical stirrer, a thermometer, a constant pressure dropping funnel and a spherical condenser was charged with 8.2 g of sodium, 100 ml of tetraethoxysilane and heated to 70 ° C; keep the temperature at 70 ° C, add 25 ml of 1-bromonaphthalene to the constant pressure dropping funnel and slowly drip into a four-necked flask to control the drip rate, raise the temperature to 70 ° C for 2 h ; Dropping tetrachlorosilane 8.3ml, stirring reflux, control the reaction temperature does not exceed 80 ° C. The resulting mixture was then filtered and the resulting liquid was distilled off under normal pressure to remove the remaining tetraethoxysilane, distilled under reduced pressure, and 150-135 ° C fractions were collected at 5 mmHg to give naphthyltriethoxy Silane crude product 30g
98 g	With magnesium In tetrahydrofuran at 30 - 70℃;	3 Embodiment 3, naphthyl of triethoxy silane synthesis and purification: 1) naphthyl triethoxy silane synthesis: to is equipped with a mechanical stirrer, thermometer, constant pressure dropping funnel and spherical condenser 5 L four bottle adding 29.2 g (1.2 µM) magnesium piece, 832 g (4 µM) four-ethoxy silane and 1152 g (16 µM) tetrahydrofuran, and heated to 30 °C;Keeping temperature at 30 °C, will 165.6 g (0.8 µM) 1 - bromonaphthalene adding constant pressure dropping in the funnel, and slowly drips into the four-mouth bottle in, control drop acceleration, after finishing dripping, heating up to 70 °C reaction 2 h;Then the reaction obtained after filtering the mixed solution, and the resulting filtrate under normal pressure distillation to remove the solvent and the remaining four ethoxy silane, reduced pressure distillation, in 5 mmHg collected under a 150 - 135 °C distillate, get the naphthyl triethoxy silane crude product 140 g.2) naphthyl triethoxy silane purification: to is provided with a thermometer, a stirrer and a spherical condenser 250 ml three-neck bottle is added in step 1) in the prepared naphthyl triethoxy silicon hydride alkane crude product 120 g and 1.8 g of sodium hydroxide solid powder, raising the temperature to 80 °C, stirring 24 h; then reduced pressure distillation, in 5 mmHg lower collection 130 - 135 °C fraction, to obtain purified naphthyl triethoxy silane 98 g

Stage #1: 1-Bromonaphthalene With magnesium In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: tetraethoxy orthosilicate In tetrahydrofuran at -30 - 20℃; for 13h; Inert atmosphere;

Reference： [1]Jorapur, Yogesh R.; Shimada, Toyoshi [Synlett, 2012, vol. 23, # 7, p. 1064 - 1068]
[2]Current Patent Assignee: JIUJIANG UNIVERSITY - CN106188125, 2016, A Location in patent: Paragraph 0022; 0023
[3]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Institute of Chemistry (in: CAS) - CN104788488, 2017, B Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046
[4]Li, Xiaolan; Sun, Kai; Shen, Wenjuan; Zhang, Yong; Lu, Ming-Zhu; Luo, Xuzhong; Luo, Haiqing [Organic Letters, 2021, vol. 23, # 1, p. 31 - 36]

36
[ 17938-06-6 ]
[ 1380681-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diethyl ether / 10 h / 0 - 20 °C 2: triethyloxonium fluoroborate / acetonitrile / 0.5 h / 50 °C / Inert atmosphere

Reference： [1]Jorapur, Yogesh R.; Shimada, Toyoshi [Synlett, 2012, vol. 23, # 7, p. 1064 - 1068]

37
[ 17938-06-6 ]
[ 1730-25-2 ]
[ 1380681-14-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	In diethyl ether at 0 - 20℃; for 10h;

Reference： [1]Jorapur, Yogesh R.; Shimada, Toyoshi [Synlett, 2012, vol. 23, # 7, p. 1064 - 1068]

38
[ 17938-06-6 ]
[ 33513-42-7 ]
[ 86-53-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With ammonium iodide; potassium fluoride; copper(II) nitrate trihydrate; oxygen at 140℃; for 25h; Schlenk technique;

Reference： [1]Wang, Zhen; Chang, Sukbok [Organic Letters, 2013, vol. 15, # 8, p. 1990 - 1993]

39
[ 17938-06-6 ]
[ 100-63-0 ]
[ 605-02-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h;	Typical procedure forthe product General procedure: A mixture of arylhydrazine (1 mmol), triethoxy(phenyl)silane (1.2 mmol), Pd(PhCN)2Cl2 (5 mol%) and CSA (camphorsulfonic acid, 1 mmol) was stirred in thesolvent of TBAF (1 M in THF, 1.0 ml) at 50oC for 3 hours under air. After cooling down to room temperature, the insoluble was firstremoved by filtration and then the solvent was removed undera reduced pressure. The cross-coupling products were purified by silica gelchromatography with a mixture of petroleum ether and ethyl acetate. Thecross-coupling products were confirmed by melting point and spectroscopic (1HNMR, 13C NMR and HRMS-EI) analysis, which wereall consistent with the literature results.

Reference： [1]Zhang, Hui; Wang, Chunjie; Li, Zhiwei; Wang, Ziyun [Tetrahedron Letters, 2015, vol. 56, # 40, p. 5371 - 5376]

40
[ 78-10-4 ]
C₁₀H₇BrMg*Li⁽¹⁺⁾*Cl^(1-) [ No CAS ]
[ 17938-06-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran at -30 - 10℃; for 8h;

Reference： [1]Delpozo, Juan; Casares, Juan A.; Espinet, Pablo [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4274 - 4284]

41
[ 455-13-0 ]
[ 17938-06-6 ]
1-(4-(trifluoromethyl)phenyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95 %Spectr.	With copper (II)-fluoride; [PdCl₂(1,3-dimethyl-imidazol-2-ylidene)(AsPh₃)] In N,N-dimethyl-formamide at 110℃; Schlenk technique; Inert atmosphere;

Reference： [1]Delpozo, Juan; Casares, Juan A.; Espinet, Pablo [Chemistry - A European Journal, 2016, vol. 22, # 12, p. 4274 - 4284]

42
6-methoxynaphthalen-2-yl dimethylcarbamate [ No CAS ]
[ 17938-06-6 ]
[ 64184-79-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper (II)-fluoride; bis(1,5-cyclooctadiene)nickel⁽⁰⁾; potassium dihydrogenphosphate; 1,2-bis-(dicyclohexylphosphino)ethane In hexane at 120℃; for 12h; Schlenk technique; Glovebox; Sealed tube;

Reference： [1]Shi, Wen-Juan; Zhao, Hong-Wei; Wang, Yang; Cao, Zhi-Chao; Zhang, Li-Sheng; Yu, Da-Gang; Shi, Zhang-Jie [Advanced Synthesis and Catalysis, 2016, vol. 358, # 15, p. 2410 - 2416]

43
[ 401-55-8 ]
[ 17938-06-6 ]
[ 24021-14-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 1-naphthyltriethoxysilane With (1,2-dimethoxyethane)dichloronickel(II); cesium fluoride; 4,4'-di-tert-butyl-2,2'-bipyridine In 1,4-dioxane for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: ethyl bromofluoroacetate In 1,4-dioxane at 100℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Wu, Yun; Zhang, Hao-Ran; Cao, Yi-Xuan; Lan, Quan; Wang, Xi-Sheng [Organic Letters, 2016, vol. 18, # 21, p. 5564 - 5567]

44
[ 17938-06-6 ]
[ 762-04-9 ]
[ 25944-75-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 1-naphthyltriethoxysilane With bis-triphenylphosphine-palladium(II) chloride; potassium fluoride; silver carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Sealed tube; Stage #2: phosphonic acid diethyl ester In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube;

Reference： [1]Luo, Haiqing; Liu, Haidong; Chen, Xingwei; Wang, Keke; Luo, Xuzhong; Wang, Kejun [Chemical Communications, 2017, vol. 53, # 5, p. 956 - 958]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: With magnesium; ethylene dibromide In tetrahydrofuran; Triethylene glycol dimethyl ether; toluene at 40 - 45℃; Stage #2: at 80 - 85℃; for 2h;	7 synthesis of 1-naphthyl trimethoxysilane General procedure: The magnesium 98.6g (4.06 mol) and THF1200mL were added to the 3L four-lot flask provided with the agitator, the reflux condenser, the tap funnel, and the thermometer, and the temperature rise was carried out to 40 degrees C. Subsequently, after adding a small amount of 1,2-dibromoethane as an initiator, 800 g (3.86 mol) of 1-bromonaphthalene was dropped in 40-45 degrees C. By the time it carried out half dropping, after supplying 850 mL of toluene, and 250 mL of triethylene glycol wood ether, 1-bromonaphthalene was dropped succeedingly and the Grignard reagent was prepared. There was no precipitation of a salt in a Grignard reagent, and unreacted magnesium was the black slightly remaining transparent solution.Next, 1,764 g (11.6 mol) of tetramethyl orthosilicate was charged in a 5 L four-necked flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, the temperature in the can was raised to 80 ° C., The obtained Grignard reagent was added dropwise over 2 hours at a temperature of 80 to 85 ° C. After completion of the dropwise addition, the mixture was cooled and the magnesium salt was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. Next, under reduced pressure, naphthalene (boiling point: 218 ° C / 760 mmHg, melting point: 80-82 ° C) produced as by-product and triethylene glycol dimethyl ether (boiling point: 216 ° C / 760 mmHg) used in the Grignard reagent preparation were concentrated under reduced pressure . During removal, there was no adhesion of sublimate naphthalene to the cooling tube and there was no problem in operation. After the removal of the solvent was completed, distillation was carried out and 593.5 g of a fraction of 120-125 ° C./0.3 mmHg was recovered. As a result of GC analysis, the purity was 98.5%, and from the results of NMR and IR, it was 1-naphthyltrimethoxysilane.

46
[ 17938-06-6 ]
[ 254454-54-1 ]
tert-butyl 3-(naphthalen-1-yl)azetidine-1-carboxylate [ No CAS ]
C₁₈H₂₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 60℃; for 12h; Inert atmosphere; Overall yield = 54percent; Overall yield = 76 mg; regioselective reaction;

Reference： [1]Liu, Zhenwei; Luan, Nannan; Shen, Linhua; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie [Journal of Organic Chemistry, 2019, vol. 84, # 19, p. 12358 - 12365]

47
[ 17938-06-6 ]
N-benzyl-N-(1-phenylvinyl)acetamide enamide [ No CAS ]
(Z)-N-benzyl-N-(2-(naphthalen-1-yl)-1-phenylvinyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper (II)-fluoride; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In N,N-dimethyl-formamide at 100℃; for 24h; Sealed tube; stereoselective reaction;

Reference： [1]Li, Xiaolan; Sun, Kai; Shen, Wenjuan; Zhang, Yong; Lu, Ming-Zhu; Luo, Xuzhong; Luo, Haiqing [Organic Letters, 2021, vol. 23, # 1, p. 31 - 36]

48
[ 624-31-7 ]
[ 17938-06-6 ]
[ 13249-99-5 ]

Yield	Reaction Conditions	Operation in experiment
41%	With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide); tetrabutyl ammonium fluoride; N,N`-dimethylethylenediamine In acetonitrile at 120℃; for 24h; Glovebox; Inert atmosphere;

Reference： [1]Adenot, Aurélien; Anthore-Dalion, Lucile; Nicolas, Emmanuel; Berthet, Jean-Claude; Thuéry, Pierre; Cantat, Thibault [Chemistry - A European Journal, 2021, vol. 27, # 72, p. 18047 - 18053]

49
[ 17938-06-6 ]
[ 1972-28-7 ]
diethyl 1-(naphthalene-1-yl)hydrazine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With silver(I) fluoride In butanone at 60℃; for 12h; Inert atmosphere;

Reference： [1]Deng, Shijun; Li, Dong; Shimokawa, Jun; Yorimitsu, Hideki; Zhang, Qian [Chemistry - An Asian Journal, 2022, vol. 17, # 5]

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[ 17938-06-6 ]

Organosilicon

[ 780-69-8 ]

Triethoxy(phenyl)silane

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[ 18052-76-1 ]

1-(Trimethoxysilyl)naphthalene

Similarity: 0.87

[ 18412-57-2 ]

Triethoxy(p-tolyl)silane

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H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 17938-06-6 ] {[proInfo.proName]}

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[ 17938-06-6 ] Synthesis Path-Downstream 1~49

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