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Cas Database

491-35-0

491-35-0

Identification

  • Product Name:Quinoline, 4-methyl-

  • CAS Number: 491-35-0

  • EINECS:207-734-2

  • Molecular Weight:143.188

  • Molecular Formula: C10H9N

  • HS Code:29334900

  • Mol File:491-35-0.mol

Synonyms:Lepidine(6CI,8CI);4-Lepidine;4-Methylquinoline;Cincholepidine;Lepidin;NSC 3412;g-Methylquinoline;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xi,Xn

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:4-Methylquinoline
  • Packaging:10g
  • Price:$ 120
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Lepidine >97.0%(GC)(T)
  • Packaging:25mL
  • Price:$ 60
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Lepidine >97.0%(GC)(T)
  • Packaging:100mL
  • Price:$ 175
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Lepidine >97.0%(GC)(T)
  • Packaging:500mL
  • Price:$ 561
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylquinoline
  • Packaging:100 g
  • Price:$ 285
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methylquinoline
  • Packaging:25 g
  • Price:$ 128
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Methylquinoline ≥99%
  • Packaging:100g
  • Price:$ 152
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Lepidine 99%
  • Packaging:100g
  • Price:$ 97.1
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Lepidine 99%
  • Packaging:25g
  • Price:$ 84.8
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Methylquinoline ≥99%
  • Packaging:1 SAMPLE
  • Price:$ 50
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Relevant articles and documentsAll total 103 Articles be found

A novel approach to vapor-phase synthesis of 2- and 4-methylquinoline from lactic acid and aniline

Li, An,Huang, Chen,Luo, Cai-Wu,Li, Li-Jun,Yi, Wen-Jun,Liu, Tian-Wei,Chao, Zi-Sheng

, p. 13 - 16 (2017)

A novel and green route for vapor-phase synthesis of 2- and 4-methylquinoline was provided in this work, in which lactic acid as one of the reactants was for the first time employed. Various influencing factors, including types of catalysts, reaction temperature and stability of catalyst were investigated systematically. The results showed that a 67.6% total yield of quinolines was obtained over the HBeta catalyst. The characterization by using BET, NH3-TPD and pyridine-IR techniques revealed that strong Br?nsted acid sites are favorable for generation of 2- and 4-methylquinoline whereas Lewis acid sites could increase the proportion of 4-methylquinoline in target products. Besides, a feasible reaction pathway to synthesize 2- and 4-methylquinoline was proposed on the basis of the reaction products.

Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution

Legros, Jean-Yves,Primault, Gaelle,Toffano, Martial,Riviere, Marie-Alix,Fiaud, Jean-Claude

, p. 433 - 436 (2000)

(Formula presented) Quinolylmethyl, 1-(isoquinolyl)ethyl, and 1-(quinolyl)ethyl acetates reacted with dimethylmalonate anion in the presence of a Pd(0) catalyst to give products of nucleophilic substitution and/or byproducts, depending upon the substitution pattern. The observed side reactions were reduction in the case of primary acetates and elimination or elimination/Michael-type addition sequence for secondary substrates.

-

Tsuchiya,Kurita

, p. 419 (1976)

-

Vapour-phase synthesis of 2-methyl- and 4-methylquinoline over BEA* zeolites

Brosius, Roald,Gammon, David,Van Laar, Frederik,van Steen, Eric,Sels, Bert,Jacobs, Pierre

, p. 362 - 368 (2006)

4-Methylquinoline and 2-methylquinoline were synthesized from acetaldehyde and aniline in the gas phase over BEA* zeolite catalysts. High combined yields of 2- and 4-methyl-substituted quinolines were obtained with H-BEA* zeolite and with BEA*-F synthesized in fluoride medium, with 4-methylquinoline being the predominant isomer. Postsynthesis fluorination of the H-BEA* with ammonium fluoride leads to dealumination and formation of extra-framework aluminium fluoride compounds. Product selectivities changed with time over this catalyst, such that 2-methylquinoline became the predominant product. New insight into the reaction mechanism is offered, and previous propositions can be rationalized based on these new results.

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material

-

Paragraph 0010-0011; 0014-0015, (2021/06/26)

The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee

supporting information, p. 2876 - 2894 (2021/02/01)

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami

, p. 1237 - 1242 (2021/06/01)

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

Smyrnov, Vladyslav,Muriel, Bastian,Waser, Jerome

, p. 5435 - 5439 (2021/07/21)

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

Quan, Yangjian,Lan, Guangxu,Shi, Wenjie,Xu, Ziwan,Fan, Yingjie,You, Eric,Jiang, Xiaomin,Wang, Cheng,Lin, Wenbin

supporting information, p. 3115 - 3120 (2020/12/09)

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Process route upstream and downstream products

Process route

C<sub>17</sub>H<sub>18</sub>N<sub>2</sub>
54683-47-5

C17H18N2

indole
120-72-9

indole

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

8-methylquinoline
611-32-5

8-methylquinoline

<i>o</i>-toluidine
95-53-4

o-toluidine

Conditions
Conditions Yield
at 800 ℃; for 0.75h; under 0.004 Torr; Further byproducts given. Title compound not separated from byproducts;
40 % Chromat.
40 % Chromat.
4 % Chromat.
C<sub>17</sub>H<sub>18</sub>N<sub>2</sub>
54683-47-5

C17H18N2

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

8-methylquinoline
611-32-5

8-methylquinoline

aniline
62-53-3

aniline

<i>o</i>-toluidine
95-53-4

o-toluidine

Conditions
Conditions Yield
at 850 ℃; for 3h; under 0.003 Torr; Further byproducts given;
methyl vinyl ketone
78-94-4,25038-87-3

methyl vinyl ketone

aniline
62-53-3

aniline

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With iron(III) chloride hexahydrate; at 110 ℃; for 8h;
87%
With indium(III) chloride; silica gel; for 0.0833333h; Irradiation;
85%
With indium(III) chloride; silica gel; for 0.0833333h; microwave irradiation;
85%
potassium dodecatangestocobaltate trihydrate; for 0.133333h; microwave irradiation;
75%
In hexafluoropropan-2-ol; at 58 ℃; for 6h;
56%
methyl vinyl ketone; aniline; With acetic acid; at 70 - 75 ℃; for 1.33333h;
zinc(II) chloride; for 2h; Heating / reflux;
With sodium hydroxide; In water;
55%
aniline; iron(III) chloride adsorbed on silica gel; In acetic acid; for 0.0833333h;
methyl vinyl ketone; In acetic acid; at 70 - 75 ℃; for 1h;
zinc(II) chloride; In acetic acid; for 2h; Heating / reflux;
55%
4-methyl-1,2,3,4-tetrahydroquinoline
19343-78-3,74459-14-6

4-methyl-1,2,3,4-tetrahydroquinoline

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With copper(I) oxide; dmap; N-hydroxyphthalimide; oxygen; In acetonitrile; at 120 ℃; for 12h; Sealed tube;
99%
With copper(I) oxide; dmap; N-hydroxyphthalimide; oxygen; In acetonitrile; at 120 ℃; for 12h;
99%
With [Ru(1,10-phenanthroline-5,6-dione)3](PF6)2; Co(salophen); In acetonitrile; at 27 ℃; for 5.5h;
97%
With diethylazodicarboxylate; In chloroform; toluene; at 20 ℃; for 12h;
97%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; chloropyridinecobaloxime(III); In ethanol; at 30 ℃; for 6h; Schlenk technique; Inert atmosphere; Irradiation;
93%
With potassium tert-butylate; In decane; at 150 ℃; for 36h; Inert atmosphere; Schlenk technique;
91%
With perylene diimide covalent immobilized to SiO2 nanospheres; air; In N,N-dimethyl acetamide; at 20 ℃; UV-irradiation;
91%
With oxygen; potassium carbonate; In methanol; at 60 ℃; for 6h; under 760.051 Torr;
90%
With C21H21ClIrNO2; In tetrahydrofuran; 2,2,2-trifluoroethanol; for 20h; Inert atmosphere;
87%
With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide; In tert-Amyl alcohol; at 95 ℃; for 24h;
86%
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support; In n-heptane; at 100 ℃; for 12h; under 11251.1 Torr; Autoclave;
85%
With potassium tert-butylate; In o-xylene; at 140 ℃; for 36h; Inert atmosphere;
85%
With oxygen; at 100 ℃; for 12h;
82%
With rose bengal; oxygen; In N,N-dimethyl acetamide; at 20 ℃; for 24h; Irradiation;
81%
With rose bengal; In N,N-dimethyl acetamide; at 20 ℃; for 24h; Irradiation;
81%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; Co(dmgH)2(4-MeCO2Py)Cl; In water; at 28 ℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation;
81%
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen; In N,N-dimethyl-formamide; for 11h;
76%
With oxygen; iron(II) chloride; In para-xylene; dimethyl sulfoxide; at 110 ℃; for 24h; Schlenk technique;
75%
With C55H49N4OP2Ru; In o-xylene; at 140 ℃; for 48h; under 750.075 Torr; Inert atmosphere; Schlenk technique; Green chemistry;
75%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammonium tetrafluoroborate; In water; acetonitrile; at 20 ℃; for 4h; Electrochemical reaction;
72%
With iodine; oxygen; In 1,2-dichloro-benzene; toluene; at 160 ℃; for 30h;
71%
With manganese(II) phthalocyanin; 2-(4-nitrophenyl)hydrazin-1-carboxylic acid ethyl ester; oxygen; In acetonitrile; at 70 ℃; for 15h;
70%
With oxygen; 1-(2,2-diphenyl-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinolin-1(2H)-yl)-3-phenylpropan-1-one; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 5h; Irradiation; Green chemistry;
70%
With mesoporous Co3O4; air; In dimethyl sulfoxide; at 140 ℃; for 24h; under 760.051 Torr; Schlenk technique;
68%
With trimethylamine-N-oxide; Co(salophen)-HQ; In dimethyl sulfoxide; at 90 ℃; for 36h; Schlenk technique; Green chemistry;
61%
With [(pentamethylcyclopentadienyl)Ir(5-trifuloromethyl-2-pyridonate)Cl]; In para-xylene; for 20h; Inert atmosphere; Reflux;
76 %Chromat.
With platinum; oxygen; In methanol; at 40 ℃; under 750.075 Torr; Schlenk technique; Sealed tube;
75.1 %Chromat.
With oxygen; In 1,3,5-trimethyl-benzene; at 80 ℃; for 6.5h; under 760.051 Torr;
With tert.-butylhydroperoxide; In water; at 20 ℃; for 18h; Sealed tube;
95 %Spectr.
With tert-butylethylene; C21H26ClIrNOP; sodium t-butanolate; In para-xylene; at 150 ℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
55 %Chromat.
With nickel(II) chloride hexahydrate; In water; acetonitrile; at 20 ℃; for 24h; Inert atmosphere; Irradiation;
88 %Chromat.
quinoline-4-carbonitrile
2973-27-5

quinoline-4-carbonitrile

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With hydrogen; In chloroform; at 65 ℃; for 0.75h; under 775.743 Torr;
95%
4-methylquinoline 1-oxide
4053-40-1

4-methylquinoline 1-oxide

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With styrene; tris(bipyridine)ruthenium(II) dichloride hexahydrate; hydrazine hydrate; In dimethyl sulfoxide; at 20 ℃; for 5h; chemoselective reaction; Inert atmosphere; Irradiation;
94%
With BER-CuSO4; In methanol; for 2h; Ambient temperature;
92%
With tris(pentafluorophenyl)borate; phenylsilane; In dichloromethane; at 60 ℃; for 8h; Inert atmosphere; Schlenk technique; Green chemistry;
90%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate; In acetonitrile; at 20 ℃; for 0.0833333h; chemoselective reaction; Inert atmosphere; Irradiation;
90%
With phenylsilane; 3-Methyl-1-phenyl-2-phospholene 1-oxide; In acetonitrile; for 16h; chemoselective reaction; Irradiation;
69%
1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-4-hydroxy-4-methylquinoline
179898-74-9

1-tert-butyloxycarbonyl-1,2,3,4-tetrahydro-4-hydroxy-4-methylquinoline

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With acetyl chloride; In ethanol; at 20 - 50 ℃; for 1.16667h;
80%
quinoline
91-22-5

quinoline

methyl iodide
74-88-4

methyl iodide

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With bis(acetylacetonato)palladium(II); caesium carbonate; triphenylphosphine; In toluene; at 60 ℃; for 8h;
89%
2-ethylsulfanyl-4-methyl-quinoline
817166-24-8

2-ethylsulfanyl-4-methyl-quinoline

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

Conditions
Conditions Yield
With triethylsilane; palladium dichloride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
72%
N-(3-methyl-2-butyne)aniline
69611-44-5

N-(3-methyl-2-butyne)aniline

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

C<sub>6</sub>H<sub>4</sub>NCH<sub>2</sub>CHCCH<sub>2</sub>
491-35-0

C6H4NCH2CHCCH2

1,2-dihydrolepidine
22514-60-9

1,2-dihydrolepidine

Conditions
Conditions Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); In methanol; at 40 ℃; under 760.051 Torr; Schlenk technique; Inert atmosphere;
50%
41%

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