[ CAS No. 1823-14-9 ] {[proInfo.proName]}

Name: 1823-14-9|5-Phenyl-1-pentyne|98%
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SKU: A832273
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Quality Control of [ 1823-14-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1823-14-9 ]

Product Details of [ 1823-14-9 ]

CAS No. :	1823-14-9	MDL No. :	MFCD00039813
Formula :	C₁₁H₁₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KOSORCNALVBYBP-UHFFFAOYSA-N
M.W :	144.21	Pubchem ID :	74573
Synonyms :

Safety of [ 1823-14-9 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330	UN#:	3082
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1823-14-9 ]

* 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 [ 1823-14-9 ]

[ 1823-14-9 ] Synthesis Path-Downstream 1~23

1
[ 1823-14-9 ]
[ 135643-82-2 ]
7-phenyl-1-(tetrahydro-pyran-2-yloxy)-hept-3-yn-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 95 - 98

2
[ 1823-14-9 ]
[ 630-19-3 ]
2,2-dimethyl-8-phenyl-4-octyn-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 5-phenyl-1-pentyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: pivalaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	2,2-Dimethyl-8-phenyloct-4-yn-3-ol (rac-51) To a solution of 1-(Pent-4-ynyl)benzene (50, 5.0 g, 34.672 mmol) in anhydrous THF (115 mL) was dropwise added n-BuLi (2.76 M in n-hexane, 13.8 mL, 38.139 mmol) at -78 °C under an argon atmosphere. The reaction mixture was stirred at -78 °C for 10 min. To the reaction mixture was dropwise added pivalaldehyde (4.14 mL, 38.139 mmol) at -78 °C, and the reaction mixture was stirred at rt for 1 h, quenched with saturated NH4Cl, and extracted with AcOEt (x 2). The combined organic layers were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography onsilica gel (n-hexane/AcOEt = 100/1 ~ 10/1) to give rac-51 (7.99 g, quant) as a colorless oil.
	Stage #1: 5-phenyl-1-pentyne With lithium diisopropyl amide In tetrahydrofuran at -30℃; for 0.666667h; Stage #2: pivalaldehyde In tetrahydrofuran at -30 - 20℃; for 2h;

Reference： [1]Higashino, Masato; Ikeda, Naoko; Shinada, Tetsuro; Sakaguchi, Kazuhiko; Ohfune, Yasufumi [Tetrahedron Letters, 2011, vol. 52, # 3, p. 422 - 425]
[2]Dieter, R. Karl; Chen, Ningyi; Gore, Vinayak K. [Journal of Organic Chemistry, 2006, vol. 71, # 23, p. 8755 - 8760]

3
[ 1823-14-9 ]
[ 162363-46-4 ]
C₂₃H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-phenyl-1-pentyne With Schwartz's reagent In tetrahydrofuran Stage #2: 4-Chloro-6,7-diethoxyquinazoline In tetrahydrofuran Further stages.;

Reference： [1]Kitano, Yasunori; Suzuki, Tsuyoshi; Kawahara, Eiji; Yamazaki, Takahisa [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 21, p. 5863 - 5867]

4
[ 1823-14-9 ]
[ 70557-99-2 ]
C₁₈H₂₅BO₂ [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5458 - 5461
[2]Organic Letters,2010,vol. 12,p. 88 - 91

5
[ 21702-84-1 ]
[ 1823-14-9 ]
[ 1228274-21-2 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 2330 - 2336

6
[ 497-25-6 ]
[ 1823-14-9 ]
[ 1274906-19-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: dimethylenecyclourethane With pyridine; sodium carbonate; copper dichloride In toluene at 70℃; for 0.5h; Stage #2: 5-phenyl-1-pentyne In toluene at 70℃;	General procedure of synthesis of ynamides General procedure: In a 250 cm3 two-neck round-bottom flask equipped with astir-bar, CuCl2(0.2 equiv.), nitrogen nucleophile (5 equiv.),and Na2CO3(2 equiv.) were combined. The reaction flask was purged with oxygen gas. A solution of pyridine(2 equiv.) in dry toluene (0.06 M) was added to the reactionflask and stirred at 70 °C. After 0.5 h, a solution ofthe respective alkyne (1.0 equiv.) in dry toluene (0.033 M)was added to the flask over 4 h using a syringe pump. Afteraddition of alkyne/toluene solution, the reaction mixture wasallowed to stir at 70 °C overnight. After cooling to r.t., thecrude mixture was concentrated under reduced pressure. Theresidue was purified by column chromatography on silicagel.3-(5-Phenylpent-1-yn-1-yl)oxazolidin-2-one (1a,C14H15NO2)According to the general procedure, the ynamide1a was isolated after purification by column chromatography(pentane/EE = 5:1-1:1) as a yellow oil (1555 mg,6.8 mmol, 68%). 1H NMR (400 MHz, CDCl3):δ = 7.30 (t,2H), 7.21 (dd, J = 9.9, 4.1 Hz, 3H), 4.43 (t, 2H), 3.89 (t, 1H),2.75 (m, 2H), 2.35 (t, J = 7.1 Hz, 2H), 1.88 (p, 2H) ppm; 13CNMR (100 MHz, CDCl3):δ = 141.6, 128.7, 128.5, 126.0,70.9, 62.9, 47.2, 34.9, 30.4, 18.0 ppm; IR: = 3060, 3026,2924, 2861, 2270, 1766, 1603, 1479, 1454, 1415, 1302,1207, 1113, 1035, 972, 748, 701 cm-1; HRMS (ESI): m/zcalculated for [M]+ 229.1103, found 229.1093.
67%	Stage #1: dimethylenecyclourethane With pyridine; oxygen; sodium carbonate; copper dichloride In toluene at 70℃; for 0.25h; Inert atmosphere; Stage #2: 5-phenyl-1-pentyne In toluene at 70℃; for 16h; Inert atmosphere;
	Stage #1: dimethylenecyclourethane With oxygen; sodium carbonate; copper dichloride for 0.25h; Stage #2: With pyridine In toluene at 70℃; for 0.25h; Stage #3: 5-phenyl-1-pentyne In toluene at 70℃; for 16h;

Reference： [1]Brutiu, Bogdan R.; Bubeneck, Wilhelm Andrei; Cvetkovic, Olivera; Li, Jing; Maulide, Nuno [Monatshefte fur Chemie, 2019, vol. 150, # 1, p. 3 - 10]
[2]Peng, Bo; Huang, Xueliang; Xie, Lan-Gui; Maulide, Nuno [Angewandte Chemie - International Edition, 2014, vol. 53, # 33, p. 8718 - 8721]
[3]Pinto, Alexandre; Kaiser, Daniel; Maryasin, Boris; Di Mauro, Giovanni; González, Leticia; Maulide, Nuno [Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2515 - 2519]

7
fmoc-Leu-Alko Resin [ No CAS ]
[ 1823-14-9 ]
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 188970-92-5 ]
C₃₄H₄₇N₉O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of piperidine (1 mL) in anhydrous DMF (2 mL) and DCM (2 mL) was added to the peptide vessel containing the swelled resin (0.1 mmol). The mixture was allowed to rock for 30 minutes at room temperature. The solution was drained, and the resin was rinsed with DMF (3 mL x 2). A solution of 1:1 DCM/DMF (3 mL x 2) was added to the resin and the peptide vessel was allowed to rock for 3 minutes. The solution was drained, and DMF (3 mL) was added. The vessel was rocked for 3 minutes, and the solvent was drained. General procedure for peptide synthesis:1 Fmoc-amino acid (0.5 mmol), HOBT (0.068 g, 0.5 mmol), and HBTU (0.190 g, 0.5 mmol) were dissolved in anhydrous DMF (3 mL) and DCM (1 mL). DIEA (0.087 mL, 0.5 mmol) was added and the resulting solution was added to the peptide vessel containing the resin (0.1 mmol). The vessel was allowed to rock for 3 hours at room temperature, the solution was drained, and the resin was rinsed with DMF (3 mL x 2). A solution of 1:1 DCM/DMF (3 mL x 2) was added to the resin and the peptide vessel was allowed to rock for 3 minutes. The solution was drained, and DMF (3 mL) was added. The vessel was rocked for 3 minutes, and the solvent was drained. The resin 5 (0.05 mmol) was suspended in anhydrous DCM (3 mL) in a peptide vessel. Pd(PPh3)4 (0.046 g, 0.04 mmol) and phenylsilane (0.12 mL, 1.0 mmol) were added. The vessel was allowed to rock for 2 hours, and the solution was drained under vacuum. The resin was rinsed with DCM (3 mL x 2), followed by washing the resin with DCM (3 mL x 2) by rocking for 3 minutes. Generation of the side chain primary amine to generate resin-bound peptide 6 was confirmed by orange resin coloration upon testing with TNBS. Sodium azide (39 mg, 0.6 mmol) was dissolved in water (1 mL). Toluene (1 mL) was added and the solution was cooled to 0C. Trifluoromethanesulfonic anhydride (Tf2O, 0.05 mL, 0.3 mmol) was added dropwise to the solution. The reaction mixture was stirred at 0C for 30 minutes, followed by warming to room temperature and was stirred for 4 hours at room temperature. A saturated sodium carbonate solution was added until the reaction mixture became basic, and the organic layer was separated. The aqueous layer was extracted with toluene (2 mL x 3) and organic layers were combined. To the combined organic layers were added triethyl amine (0.02 mL, 0.15 mmol) and methanol (2 mL). The solution was transferred to the fritted vessel containing resin charged with peptide 6 (0.1 mmol). Solid zinc chloride (2.7 mg, 0.02 mmol) was then added and the mixture was rocked for 12 hours. The peptide was rinsed with DCM/DMF (1:1, 5 mL x 3) and solvent was drained under vacuum. The conversion of amine 6 to azide 7 was confirmed by the negativeTNBS test result, with the resin exhibiting a pale gray color. CuI (0.248 g, 1.3 mmol), ascorbic acid (0.228 g, 1.3 mmol) and DIEA (0.3 mL, 1.7 mmol) were dissolved in DMF (2.5 mL) and pyridine (1.5 mL). The solution was poured into the peptide vessel containing resin charged with azide peptide 7 (0.1 mmol). The appropriate substituted alkyne (0.3 mmol) was dissolved in DMF (1 mL) and transferred to the peptide vessel. Thepeptide vessel was rocked for 12 hours at room temperature. The obtained resin-bound crude products were rinsed with DMF (5 mL x 2), DMF/DCM (5 mL x 2), and DMF (5 mL) for 3 minutes for each rinse, with solvent drained under vacuum after each rinse. The resin-bound peptide 8 (0.05 mmol) was deprotected and cleaved from the resin support per previously reported protocols.1 The Fmoc group was removed according to the general procedure for Fmoc-deprotection described above. Following Fmoc removal, a cleavage cocktail of TFA/H2O/TIPS/anisole (4.5 mL/0.25 mL/0.125 mL/0.125 mL) was added to the vessel, and the vessel was allowed to rock for 3 hours. The solution was collected, and the resin was rinsed with TFA (1 mL x 2) with the rinse added to the collected solution. Ice cold ether (10 mL) was added to a separatory funnel. The combined cleavage solution was poured into the funnel, followed by 5% acetic acid in water (5 mL). The resulting organic layer was extracted with 5% acetic acid in water (5 mL x 3). The aqueous layer and washes were combined and the remaining TFA and acetic acid were removed under reduced pressure. The triazole peptide product 8 was obtained by lyophilization, and for initial screening was dissolved in DMSO and used without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2800 - 2803

8
[ 1823-14-9 ]
[ 77897-23-5 ]
(S)-3-benzyl-4-((S)-4-methyl-1,9-diphenylnon-5-yn-4-yl)morpholine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 987 - 999

9
[ 694-59-7 ]
[ 1823-14-9 ]
[ 82113-65-3 ]
1-((5-phenylpent-1-en-2-yl)oxy)pyridin-1-ium bis((trifluoromethyl)sulfonyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With silver(I) acetate; In 2,2,2-trifluoroethanol; at 60℃; for 12h;	In a 25 ml reaction flask, silver acetate (10%, 66.8 mg)Pyridine nitrogen oxides (1.2 equiv. 4.056 g) were added,Tf2NH (1.1 equiv, 1.232 g),1a (4 mmol, 0.576 g),Trifluoroethanol 4ml, 60 under the conditions of heating and stirring 12 hours TLC monitoring is completed,Rapid column chromatography (eluent dichloromethane: methanol = 60: 1)A reddish brown oily liquid in 80% yield.
		Pre-prepared compound A (1.2 equiv., 90.2 mg) was added to a 4 ml reaction flask in turn, and the substrate alkyne 1k was added.(0.2 mmol, 28.8 mg), PPh3AuNTf2 (2.5%, 3.7 mg), HFIP (0.2 ml), stirred at room temperature for 2.5 hours, charged twice equivalents of hydrazine, heated to 60 C, stirred for 2.5 hours, TLC After the completion of the reaction, rapid column chromatography (eluent petroleum ether: ethyl acetate = 20:1) gave a colorless oily liquid with a yield of up to 80%.

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 5515 - 5518
[2]Patent: CN107162967,2017,A .Location in patent: Paragraph 0049; 0050; 0051; 0052
[3]Organic and Biomolecular Chemistry,2019,vol. 17,p. 966 - 972
[4]Chemistry - A European Journal,2017,vol. 23,p. 14133 - 14137
[5]Patent: CN108383706,2018,A .Location in patent: Paragraph 0034; 0067-0069
[6]Journal of Organic Chemistry,2018,vol. 83,p. 10051 - 10059

10
[ 1823-14-9 ]
[ 274-07-7 ]
[ 161282-94-6 ]

Yield	Reaction Conditions	Operation in experiment
64%		[00132] 5-Phenyl-i-pentyne (6.23 mL, 41.05 mmol, 1.00 eq) and catecholborane (5.25 mL, 49.26 mmol, 1 .20 eq) were dissolved in THF (15.2 mL) and the mixture was refluxed for 18 h. The solvent was evaporated and then H20 (3 mL) was added. The suspension was vigorously stirred for 4 h at room temperature. The solid was filtered and recrystallized with water. (E)-5-phenylpent-i-en-i-ylboronic acid (5.0 g, 26.3 mmol, 64%) was then filtered and dried under vacuum.1H NMR (400 MHz, DMSO-d6) OH /ppm: 7.52 (br. s, 2H), 7.32 -7.23 (m, 2H), 7.23 -7.12 (m, 3H), 6.47 (dt, J= 17.9, 6.4 Hz, 1H), 5.34 (dt, J= 17.8, 1.6 Hz, 1H), 2.62 -2.53 (m, 2H), 2.16-2.03 (m, 2H), 1.66 (p, J= 7.5 Hz, 2H).13C NMR (101 MHz, DMSO) Oc /ppm: 149.6, 142.1, 128.4 (20), 128.3 (20), 125.7, 119.3,34.6, 34.5, 30.0.

Reference： [1]Patent: WO2016/198836,2016,A1 .Location in patent: Paragraph 00132

11
[ 426-65-3 ]
[ 1823-14-9 ]
C₁₄H₁₃F₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of alkyne (1.0 eq) in THF (0.5 M) was added dropwise n-BuLi in solution in hexanes (1.1 eq) at -78 C. The mixture was stirred for 1 h at -78 C and ethyl trifluoroacetate (1.5 eq) was added. After the complete consumption of the alkyne (TLC), the mixture was diluted with MeOH (same volume than THF). The mixture was allowed to warm up to 0 C and NaBH4 (1.0 eq) was added. The mixture was stirred overnight while warming up to room temperature. The reaction was then quenched with a saturated solution of NH4Cl, extracted with Et2O (x3), washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give the alpha-trifluoromethyl secondary propargylic alcohol. The crude product was purified by flash column chromatography to afford the pure product.

Reference： [1]Organic Letters,2016,vol. 18,p. 5162 - 5165
[2]Tetrahedron,2018,vol. 74,p. 5232 - 5239

12
[ 13275-42-8 ]
[ 1823-14-9 ]
1-(3-phenylpropyl)benzo[4,5]imidazo[1,2-c][1,2,3]triazolo[1,5-a]quinazoline [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6445 - 6449

13
[ 1823-14-9 ]
[ 16292-17-4 ]
9-(4-phenylbutyl)acridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; ethylenediamine; at 180℃; for 1.5h;Microwave irradiation; Inert atmosphere;	General procedure: Microwave Heating:To a flame dried 35 mL microwave vial with a teflon coated cap, 25 mL of ethylene diaminewas added via syringe and degassed with nitrogen for 20 minutes. To this vessel was added504 mg (1.5 mmol) of bis(2-bromophenyl)amine (3), 66 mg (0.30 mmol) of copper iodide,and 219 mg (0.30 mmol) of bis(triphenylphosphine)palladium dichloride sequentially whilestirring under nitrogen. Next 3.0 mmol of aryl acetylene was added dropwise via syringe.The reaction flask was heated for 1.5 hours at 180 C in a microwave reactor. Uponcompletion, the reaction was then poured over ice, extracted into dichloromethane (3 x 35mL) and the combined organic layers were washed with water three times before purifyingon an amine treated KP-NH silica flash column using hexanes and ethyl acetate as eluent.Fractions include primarily bis(tolan)amines (4a-f), 9-substituted acridines (5a-f), andcarbazole (6) depending on conditions.

Reference： [1]Molecules,2018,vol. 23

14
[ 1823-14-9 ]
[ 84539-22-0 ]
[ 25015-63-8 ]
4-{5-[5-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentyl]pyrimidin-2-yl}morpholine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 6173 - 6179

15
[ 1823-14-9 ]
[ 253176-94-2 ]
(E)-tert-butyl 3-(6-phenylhex-2-en-1-yl)azetidine-1-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 12464 - 12469

16
[ 1823-14-9 ]
[ 145508-94-7 ]
(E)-tert-butyl 4-(6-phenylhex-2-en-1-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 12464 - 12469

17
[ 1823-14-9 ]
[ 112823-30-0 ]
(E)-3-methyl-3-(6-phenylhex-2-en-1-yl)oxetane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With (tpy')NiI; (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride; lithium isopropoxide; HSiPh₃ In 1,2-dimethoxyethane; 2,2,4-trimethylpentane at 25℃; for 2h; Inert atmosphere; diastereoselective reaction;

Reference： [1]Hazra, Avijit; Chen, Jason; Lalic, Gojko [Journal of the American Chemical Society, 2019, vol. 141, # 32, p. 12464 - 12469]

18
[ 1823-14-9 ]
[ 1256788-71-2 ]
[ 2307449-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / tetrahydrofuran / 16 h / 20 °C 2: hydroxylamine hydrochloride; sodium carbonate / ethanol / 16 h / Reflux

Reference： [1]Baati, Rachid; Brown, Richard C. D.; Jagadeesh, Yerri; Mardy, Keven; Razafindrainibe, Franck; Reddy, Nimmakayala Mallikarjuna; Reihanian-Hadany, Norbert; Tissier, Allan; Voros, Camille [European Journal of Organic Chemistry, 2021, vol. 2021, # 30, p. 4393 - 4397]

19
[ 1823-14-9 ]
[ 1256788-71-2 ]
[ 2308562-17-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 20℃; for 16h;

20
[ 1823-14-9 ]
[ 60169-72-4 ]
C₂₂H₂₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With di-tert-butyl peroxide In toluene at 110℃; for 12h; Inert atmosphere;	2.3 General Procedure fortheHeterogeneousCopper(I)-Catalyzed Decarboxylative Couplingof-Amino Acids withVarious CarbonNucleophiles. General procedure: To a 10mL reaction tube were added N,N-SBA-15-CuBr(122mg, 0.09mmol), -amino acid 1 (0.6mmol), nucleophile2 or 4 (0.9mmol), di-tert-butyl peroxide (0.84mmol),and toluene (3mL) under Ar. The reaction temperature wasraised to 110°C as soon as possible. The resulting mixturewas stirred at that temperature for 12h, and then was cooledto room temperature. The reaction mixture was diluted withEtOAc (10mL) and filtered. The N,N-SBA-15-CuBr catalystwas washed with toluene (2 × 5mL) and acetone (2 × 5mL),dried at 80°C in vacuo for 2h and reused in the next run.The filtrate was concentrated under reduced pressure, andthe residue was purified by flash silica gel column chromatography(light petroleum ether/diethyl ether) to aford thetarget product 3 or 5.

Reference： [1]Cai, Mingzhong; Huang, Bin; Li, Jianying; Zhao, Ruonan [Catalysis Letters, 2022]

21
[ 33574-02-6 ]
[ 1823-14-9 ]
[ 73183-34-3 ]
C₂₁H₃₁BO₂ [ No CAS ]
C₂₁H₃₁BO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With (1-(2,6-diisopropylphenyl)-3,3-diethyl-5,5-dimethylpyrrolidin-2-ylidene)copper(I) chloride; lithium tert-butylate In N,N-dimethyl acetamide at 20℃; for 16h; regioselective reaction;

Reference： [1]Gao, Yang; Kim, Nana; Mendoza, Skyler D.; Yazdani, Sima; Faria Vieira, Andre; Liu, Mingyu; Kendrick, Aaron; Grotjahn, Douglas B.; Bertrand, Guy; Jazzar, Rodolphe; Engle, Keary M. [ACS Catalysis, 2022, vol. 12, # 12, p. 7243 - 7247]

22
[ 3066-75-9 ]
[ 1823-14-9 ]
[ 73183-34-3 ]
C₂₀H₂₉BO₂ [ No CAS ]
C₂₀H₂₉BO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With (1-(2,6-diisopropylphenyl)-3,3-diethyl-5,5-dimethylpyrrolidin-2-ylidene)copper(I) chloride; lithium tert-butylate In N,N-dimethyl acetamide at 20℃; for 16h; regioselective reaction;

Reference： [1]Bertrand, Guy; Engle, Keary M.; Faria Vieira, Andre; Gao, Yang; Grotjahn, Douglas B.; Jazzar, Rodolphe; Kendrick, Aaron; Kim, Nana; Liu, Mingyu; Mendoza, Skyler D.; Yazdani, Sima [ACS Catalysis, 2022, p. 7243 - 7247]

23
[ 7766-48-5 ]
[ 1823-14-9 ]
[ 73183-34-3 ]
C₂₂H₃₃BO₂ [ No CAS ]
C₂₂H₃₃BO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With (1-(2,6-diisopropylphenyl)-3,3-diethyl-5,5-dimethylpyrrolidin-2-ylidene)copper(I) chloride; lithium tert-butylate In N,N-dimethyl acetamide at 20℃; for 16h; regioselective reaction;

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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P234	Keep only in original container.
P235	Keep cool
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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

[ CAS No. 1823-14-9 ] {[proInfo.proName]}

Quality Control of [ 1823-14-9 ]

Related Doc. of [ 1823-14-9 ]

Product Details of [ 1823-14-9 ]

Safety of [ 1823-14-9 ]

Application In Synthesis of [ 1823-14-9 ]

[ 1823-14-9 ] Synthesis Path-Downstream 1~23

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry