[ CAS No. 2489-87-4 ] {[proInfo.proName]}

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Quality Control of [ 2489-87-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 2489-87-4 ]

CAS No. :	2489-87-4	MDL No. :	MFCD07775098
Formula :	C₁₃H₁₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	168.23	Pubchem ID :	-
Synonyms :

Safety of [ 2489-87-4 ]

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Hazard Statements:		Packing Group:

Application In Synthesis of [ 2489-87-4 ]

* 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.

Downstream synthetic route of [ 2489-87-4 ]

[ 2489-87-4 ] Synthesis Path-Downstream 1~9

1
[ 91-20-3 ]
[ 106-42-3 ]
[ 107-18-6 ]
[ 2489-86-3 ]
[ 42918-26-3 ]
[ 2489-87-4 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1982,vol. 18,p. 305 - 307
Zhurnal Organicheskoi Khimii,1982,vol. 18,p. 352 - 355

2
[ 580-13-2 ]
[ 106-95-6 ]
[ 2489-87-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 2-bromonaphthalene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: allyl bromide In tetrahydrofuran at 20℃; Reflux; Stage #3: With ammonium chloride In tetrahydrofuran at 20℃;	37 A two necks round bottom flask equipped with a condenser and a pressure compensated ad dition funnel was charged with magnesium turnings (28 mg, 0.96 mmol) and a few iodine pellets. The system was flamed under vacuum and cooled under argon atmosphere. Dry THF (0.6 mL) was added to the round bottom flask and the compensated addition funnel was charged with a solution of 2-bromonaphthalene (200 mg, 0.96 mmol) in dry THF (1 mL). This solution was slowly added to the suspension, which was heated under reflux for 2 h. The reaction mixture was cooled to room temperature and then it was treated with a solution of allyl bromide (0.09 mL, 1 mmol) in dry THF (0.5 mL). After heating under reflux for 2 h and cooling to room temperature saturated NH4Cl was added. The organic layer was separated and the aqueous phase was ex- tracted with dichloromethane (x2). The combined organic extracts were dried (anh. Na2SO4), filtered and concentrated under reduced pressure. Purification by flash chromatography eluting with hexane gave 2-allylnaphthalene (31) (158 mg, 99%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 7.91-7.85 (m, 3H, 3xArH), 7.71 (s, IH, ArH), 7.58-7.40 (m, 3H, 3xArH), 6.23-6.07 (m, IH, CH=CH2), 5.28-5.19 (m, 2H, CH=CH2), 3.63 (d, J= 7.8 Hz, 2H, CH2) ppm. 13C NMR (75 MHz, CDCl3) δ 137.5 (C), 137.3 (CH), 133.6 (C), 132.1 (C), 127.9 (CH), 127.6 (CH), 127.4 (CH), 127.3 (CH), 126.6 (CH), 125.9 (CH), 125.2 (CH), 116.0 (CH2) and 40.3 (CH2) ppm. MS (CI) m/z (%) 169 (MH+). HRMS calcd. for Ci3Hi3 (MH+): 169.1017, found, 169.1023.
99%	Stage #1: 2-bromonaphthalene With iodine; magnesium In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Reflux; Stage #2: allyl bromide In tetrahydrofuran for 2h; Reflux; Inert atmosphere;
75%	With magnesium In tetrahydrofuran for 5h; Heating;

	(i) Mg, Et₂O, (ii) /BRN= 605308/; Multistep reaction;
	Stage #1: 2-bromonaphthalene With magnesium In tetrahydrofuran Stage #2: allyl bromide In tetrahydrofuran Stage #3: With ammonium chloride In water
	Stage #1: 2-bromonaphthalene With magnesium In tetrahydrofuran Stage #2: allyl bromide With ammonium chloride In water
	Stage #1: 2-bromonaphthalene With iodine; magnesium In tetrahydrofuran Stage #2: allyl bromide In tetrahydrofuran for 1h; Stage #3: With ammonium chloride In tetrahydrofuran; water
	Stage #1: 2-bromonaphthalene With iodine; magnesium In tetrahydrofuran Stage #2: allyl bromide With ammonium chloride In tetrahydrofuran; water

Reference： [1]Current Patent Assignee: UNIVERSITY OF SANTIAGO DE COMPOSTELA - WO2010/146125, 2010, A1 Location in patent: Page/Page column 38
[2]Location in patent: experimental part Blanco, Beatriz; Sedes, Anti; Peon; Lamb, Heather; Hawkins, Alastair R.; Castedo, Luis; Gonzalez-Bello, Concepcion [Organic and Biomolecular Chemistry, 2012, vol. 10, # 18, p. 3662 - 3676]
[3]Efange; Michelson; Dutta; Parsons [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2638 - 2643]
[4]Klemm,L.H.; Kohlik,A.J. [Journal of Organic Chemistry, 1963, vol. 28, p. 2044 - 2049]
[5]Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng [Chemical Communications, 2011, vol. 47, # 44, p. 12224 - 12226]
[6]Chen, Huoji; Yang, Wanfei; Wu, Wanqing; Jiang, Huanfeng [Organic and Biomolecular Chemistry, 2014, vol. 12, # 21, p. 3340 - 3343]
[7]Jiang, Huanfeng; Yang, Wanfei; Chen, Huoji; Li, Jianxiao; Wu, Wanqing [Chemical Communications, 2014, vol. 50, # 54, p. 7202 - 7204]
[8]Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji [Organic and Biomolecular Chemistry, 2015, vol. 13, # 20, p. 5613 - 5616]

3
[ 556-56-9 ]
[ 3857-83-8 ]
[ 2489-87-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With indium; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 1h;
92%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; indium; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere;

Reference： [1]Lee, Kooyeon; Lee, Jinsung; Lee, Phil Ho [Journal of Organic Chemistry, 2002, vol. 67, # 23, p. 8265 - 8268]
[2]Location in patent: scheme or table Lee, Kooyeon; Kim, Hyunseok; Mo, Juntae; Lee, Phil Ho [Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2147 - 2157]

4
[ 591-87-7 ]
[ 3857-83-8 ]
[ 91-20-3 ]
[ 2489-87-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 84% 2: 3%	With indium(III) chloride; indium; lithium chloride In N,N-dimethyl-formamide at 100℃; for 2h;
1: 68 % Chromat. 2: 10 % Chromat.	With indium(III) chloride; indium; lithium chloride In N,N-dimethyl-formamide at 100℃; for 20h;

Reference： [1]Seomoon, Dong; Phil, Ho Lee [Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1165 - 1168]
[2]Seomoon, Dong; Phil, Ho Lee [Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1165 - 1168]

5
[ 2483-57-0 ]
[ 2489-87-4 ]
[ 1073426-87-5 ]
[ 1073426-64-8 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14090 - 14091

6
[ 2489-87-4 ]
[ 6315-96-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; chemoselective reaction;

Reference： [1]Zhao, Jinwu; Liu, Li; Xiang, Shijian; Liu, Qiang; Chen, Huoji [Organic and Biomolecular Chemistry, 2015, vol. 13, # 20, p. 5613 - 5616]

7
[ 76-09-5 ]
[ 375-48-4 ]
[ 13826-27-2 ]
[ 2489-87-4 ]
4,4,5,5-tetramethyl-2-(4,4,5,5,6,6,7,7,7-nonafluoro-1-(naphthalen-2-yl)heptan-2-yl)-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: nonafluoro-1-bromobutane; 2,2'-bis(1,3,2-benzodioxaborole); 2-allylnaphthalene In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Irradiation; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In N,N-dimethyl-formamide for 1h; regioselective reaction;

Reference： [1]Cheng, Ying; Mück-Lichtenfeld, Christian; Studer, Armido [Journal of the American Chemical Society, 2018, vol. 140, # 20, p. 6221 - 6225]

8
[ 2489-87-4 ]
benzene-1,3,5-triyl triformate [ No CAS ]
[ 782-28-5 ]
[ 15410-83-0 ]
[ 107777-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; Inert atmosphere; Sealed tube; Overall yield = 67 %; Overall yield = 45.7 mg;

Reference： [1]Wu, Fu-Peng; Li, Da; Peng, Jin-Bao; Wu, Xiao-Feng [Organic Letters, 2019, vol. 21, # 14, p. 5699 - 5703]

9
[ 1356823-19-2 ]
[ 106-95-6 ]
[ 2489-87-4 ]

Yield	Reaction Conditions	Operation in experiment
91 %Spectr.	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ In 1,4-dioxane; water at 60℃; Sealed tube;

Reference： [1]Brodie, Glen; France, David J.; Memarzadeh, Sarah; Phillips, David; Tang, Gi Lum [RSC Advances, 2020, vol. 10, # 51, p. 30624 - 30630]

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[ CAS No. 2489-87-4 ] {[proInfo.proName]}

Quality Control of [ 2489-87-4 ]

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[ 2489-87-4 ] Synthesis Path-Downstream 1~9

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