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Chemical Structure| 34907-53-4 Chemical Structure| 34907-53-4

Structure of 34907-53-4

Chemical Structure| 34907-53-4

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Product Details of [ 34907-53-4 ]

CAS No. :34907-53-4
Formula : C11H17BO2
M.W : 192.06
SMILES Code : CC1=C(B(OC)OC)C(C)=CC(C)=C1
MDL No. :MFCD32068248
InChI Key :NCEUIABFEQHUQB-UHFFFAOYSA-N
Pubchem ID :15920607

Safety of [ 34907-53-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 34907-53-4 ]

* 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 [ 34907-53-4 ]

[ 34907-53-4 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 27126-76-7 ]
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  • [ 3976-35-0 ]
  • 2
  • [ 34907-53-4 ]
  • diphenyliodonium tetrafluoroborate [ No CAS ]
  • [ 3976-35-0 ]
  • 3
  • [ 69907-27-3 ]
  • [ 34907-53-4 ]
  • 8-mesityl-8-borafluorazene [ No CAS ]
  • 4
  • bis(2-bromophenyl)mesitylphosphane [ No CAS ]
  • [ 34907-53-4 ]
  • B,P-dimesitylphosphaborin [ No CAS ]
  • 6
  • [ 97437-81-5 ]
  • [ 34907-53-4 ]
  • 3,6,9-trimethyl-10-mesityl-9,10-dihydro-9-aza-10-boraanthracene [ No CAS ]
  • 7
  • 4,6-dibromo-N,N'-bis(2-bromo-4-butylphenyl)-N,N'-dimethylbenzene-1,3-diamine [ No CAS ]
  • [ 34907-53-4 ]
  • 2,10-dibutyl-5,7-dimethyl-12,14-dimesityl-5,7,12,14-tetrahydro-5,7-diaza-12,14-diborapentacene [ No CAS ]
  • 8
  • 2,5-dibromo-N,N'-bis(2-bromo-4-butylphenyl)-N,N'-dimethylbenzene-1,4-diamine [ No CAS ]
  • [ 34907-53-4 ]
  • 2,9-dibutyl-5,12-dimethyl-7,14-dimesityl-5,7,12,14-tetrahydro-5,12-diaza-7,14-diborapentacene [ No CAS ]
  • 9
  • [ 891780-12-4 ]
  • [ 34907-53-4 ]
  • 2,12-didodecyl-5,9,16-trimethyl-7,14,18-trimesityl-5,7,9,14,16,18-hexahydro-5,9,16-triaza-7,14,18-triboraheptacene [ No CAS ]
  • 10
  • [ 949586-26-9 ]
  • [ 4627-22-9 ]
  • [ 34907-53-4 ]
  • (C6H13N(C6H3N(C6H4C(CH3)3)2)BC6H2(CH3)3)2C6H2 [ No CAS ]
  • 11
  • [ 949586-26-9 ]
  • [ 37500-95-1 ]
  • [ 34907-53-4 ]
  • (C6H13N(C6H3N(C6H3C(CH3)3)2)BC6H2(CH3)3)2C6H2 [ No CAS ]
  • 12
  • [ 949586-26-9 ]
  • [ 34907-53-4 ]
  • C48H58B2Br2N2 [ No CAS ]
  • 13
  • [ 949586-26-9 ]
  • [ 111-26-2 ]
  • [ 34907-53-4 ]
  • (C6H13N(C6H3NHC6H13)BC6H2(CH3)3)2C6H2 [ No CAS ]
  • 14
  • [ 93994-38-8 ]
  • [ 34907-53-4 ]
  • [ 949586-25-8 ]
  • 15
  • C15H17Br2N [ No CAS ]
  • [ 34907-53-4 ]
  • 3,6,9-trimethyl-10-mesityl-9,10-dihydro-9-aza-10-boraanthracene [ No CAS ]
  • 16
  • [ 21848-84-0 ]
  • [ 34907-53-4 ]
  • 10-mesityl-10H-thia-10-boraanthracene [ No CAS ]
  • 17
  • 1,4-dibromo-2,5-bis(2-bromo-4-butylphenylsulfanyl)benzene [ No CAS ]
  • [ 34907-53-4 ]
  • 2,9-dibutyl-7,14-dimesityl-7,14-dihydro-5,12-dithia-7,14-diborapentacene [ No CAS ]
  • 18
  • 1,5-dibromo-2,4-bis(2-bromo-4-butylphenylsulfanyl)benzene [ No CAS ]
  • [ 34907-53-4 ]
  • 2,10-dibutyl-12,14-dimesityl-12,14-dihydro-5,7-dithia-12,14-diborapentacene [ No CAS ]
  • 19
  • [ 121-43-7 ]
  • [ 576-83-0 ]
  • [ 34907-53-4 ]
YieldReaction ConditionsOperation in experiment
Synthesis of bis(4-bromophenyl)(mesityl)borane To a stirred solution of 2-bromo-1,3,5-trimethylbenzene (5.9 g, 30.0 mmol) in dry Et2O (100 mL) is added dropwise n-butyllithium (1.60 M in hexane, 18.75 mL, 30.0 mmol) at -78 C. After stirring for 1 h, the mixture is added trimethyl borate (6.2 g, 60.0 mmol) and is stirred overnight at room temperature. The solvent of mixture is evaporated, and the residue is distilled under reduced pressure (200 torr) to afford clear liquid dimethyl mesitylboronate intermediate. To the solution of dimethyl mesitylboronate (1 g, 5.21 mmol) in dry THF (20 mL) is added (4-bromophenyl)magnesium bromide (0.5 M in THF, 32 mL, 16 mmol) at -78 C. under nitrogen atmosphere. The reaction mixture is allowed to stir at room temperature and poured into a large amount of water, and extracted with chloroform. The combined organic layer is washed with water, and dried over anhydrous Na2SO4. The residue is purified by column chromatography on silica gel (eluent: hexane/CHCl3=8:1, v/v) to afford a white solid (8.4 g, 63%).
  • 21
  • [ 188290-36-0 ]
  • [ 34907-53-4 ]
  • [ 1172602-73-1 ]
  • 22
  • [ 632-15-5 ]
  • [ 34907-53-4 ]
  • [ 1172602-74-2 ]
  • 23
  • [ 34907-53-4 ]
  • [ 95-15-8 ]
  • [ 1172602-75-3 ]
  • 24
  • [ 1202254-86-1 ]
  • [ 34907-53-4 ]
  • [ 1202254-83-8 ]
  • 25
  • [ 34907-53-4 ]
  • [ 97516-53-5 ]
  • [ 1202254-84-9 ]
  • 26
  • [ 34907-53-4 ]
  • [ 117402-74-1 ]
  • [ 1202254-85-0 ]
  • 27
  • [ 1239910-79-2 ]
  • [ 34907-53-4 ]
  • [ 1239910-76-9 ]
  • 28
  • [ 1245701-79-4 ]
  • [ 34907-53-4 ]
  • [ 1245701-78-3 ]
  • 29
  • [ 1181972-67-7 ]
  • [ 34907-53-4 ]
  • [ 1181972-68-8 ]
  • 30
  • [ 1181972-62-2 ]
  • [ 34907-53-4 ]
  • [ 1181972-64-4 ]
YieldReaction ConditionsOperation in experiment
68.8% In a 3-neck 2 L flask, 34.1 g (64.5 mmol) of the intermediate (2) was dissolved in 645 mL of diethyl ether, and then cooled to -78 C. 57 mL (142 mmol) of n-butyllithium (n-BuLi, 2.5 M in Hexanes) was slowly added dropwise. After stirring at the same temperature for 1 hour, 13.6 g (70.9 mmol) of <strong>[34907-53-4]dimethyl mesitylboronate</strong> was slowly added dropwise. The mixture was stirred while slowly raising the temperature to room temperature. After the reaction was terminated using distilled water, the separated organic layer was dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The reactant was solidified using methanol (MeOH) to form a beige solid compound (Intermediate (3))22.0 g (yield: 68.8%) was obtained.
  • 31
  • bis(3-bromo-2-naphthyl)methylamine [ No CAS ]
  • [ 34907-53-4 ]
  • [ 1245701-78-3 ]
  • 32
  • bis(3-bromo-2-naphthyl)methylamine [ No CAS ]
  • [ 34907-53-4 ]
  • [ 3557-48-0 ]
  • [ 1245701-78-3 ]
  • 33
  • [ 87345-09-3 ]
  • [ 34907-53-4 ]
  • [ 144776-63-6 ]
YieldReaction ConditionsOperation in experiment
55% Compound X was prepared according to the literature procedure {Org. Lett. 2006, 8, 2241). 2-bromo-N-(2-bromophenyl)-N-methylaniline (0.5 g, 1.5 mmol) was dissolved in 50 mL of diethyl ether and the solution cooled to -78 C. tert-Butyllithium (4.3 mL of 1.7 molar solution in pentane, 7.3 mmol) was added dropwise and the reaction mixture allowed to warm to 0 C and stirred for 30 minutes. Dimethylmesityldiboronate ester (0.37 g, 1.9 mmol) was dissolved in 10 mL of ether and added to reaction mixture dropwise. The reaction mixture was allowed to warm to room temperature, refluxed for 2 h, cooled, filtered through Celite with dichlormethane and concentrated. The crude product was chromatographed on silica gel with 9/1 hexane/ethyl acetate and further crystallized from hexane to give 0.13 g (55%) of the Compound X.
  • 34
  • [ 1418317-60-8 ]
  • [ 34907-53-4 ]
  • [ 1418317-63-1 ]
  • 35
  • [ 34907-53-4 ]
  • [ 40033-65-6 ]
  • [ 1605347-20-3 ]
  • 36
  • [ 40033-68-9 ]
  • [ 34907-53-4 ]
  • [ 1605347-19-0 ]
  • 37
  • [ 34907-53-4 ]
  • [ 5980-97-2 ]
  • 38
  • [ 34907-53-4 ]
  • 6-ethynyl-2',4',6'-trimethyl-2,3,4,5-tetrahydro-1,1'-biphenyl [ No CAS ]
  • 39
  • [ 34907-53-4 ]
  • 5,7,9-trimethyl-1,2,3,4-tetrahydrobenzo[a]azulene [ No CAS ]
  • 40
  • [ 19718-35-5 ]
  • [ 34907-53-4 ]
  • C30H30B2N2 [ No CAS ]
  • 41
  • [ 34907-53-4 ]
  • C21H20BBrN2 [ No CAS ]
  • C30H30B2N2 [ No CAS ]
  • 42
  • [ 34907-53-4 ]
  • N-(4-(3-(4-methoxyphenyl)thieno[3,2-b]thiophen-2-yl)phenyl)-N-phenylbenzenamine [ No CAS ]
  • N-(4-(5-(methoxymesitylboryl)-3-(4-methoxyphenyl)thieno[3,2-b]-thiophene-2-yl)phenyl)-N-phenylbenzenamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% EXAMPLE ( Molecule (I*) : R1: -PhOMe, R2: -TP A, R3: -H, R4: -OMe, Ar : -Mesit lene ) A Procedure for the Synthesis of 4-(5-(mesityl(methoxy)boranyl)-3-(4- methoxyphenyl)thieno[3,2-b]thiophen-2-yl)-N,N-diphenylaniline (I*). To a solution of 4- (3-(4-methoxyphenyl)thieno[3,2-b]thiophen-2-yl)-N,N-diphenylaniline (123 mg, 240 μηιο) in 30 mL of dry THF was added -BuLi (185 μL, 290 μηιο) dropwise at -78 C under nitrogen atmosphere. The reaction mixture was stirred at same temperature for 1 h. Then MesB(OMe)2 (51.0 L, 240 μιηο) was added at -78 C and the solution was heated slowly up to room temperature and then stirred for another 12 h. The product was extracted with dichloromethane (3 x 20 mL). The solution was washed with brine and H20, and then dried over NaSC After removal of the solvent under atmospheric, the crude product was purified by column chromatography over silica gel using a mixture of -hexane/dichloromethane (6: 1) as eluent. The product was obtained as a green solid in 45% yield; R = 0.85; M.p. 179-180 C; 1H NMR (500 MHz, CDC13) δ 7.74 (s, 1H), 7.38 (d, J= 9.0 Hz, 2H), 7.26 (t, J= 8.0 Hz, 4H), 7.18 (d, J= 9.0 Hz, 2H), 7.11 (d, J= 7.5 Hz, 4H), 7.05 (t, J= 7.5 Hz, 2H), 6.92 (dd, J = 8.0, 2.5 Hz 4H), 6.82 (s, 2H), 3.83 (s, 3H), 2.32 (s, 3H), 2.10 ppm (s, 6H); 13C NMR (125 MHz, CDCI3): δ 158.9, 152.5, 147.6, 147.2, 146.7, 144.3, 137.6, 136.6, 136.5, 132.5, 131.5, 130.2, 129.8, 129.4, 129.3, 127.8, 127.6, 126.9, 124.9, 123.4, 122.1, 114.2, 55.2, 28.1, 22.3 ppm.
  • 43
  • [ 34907-53-4 ]
  • N-(4-(3-(4-methoxyphenyl)thieno[3,2-b]thiophen-2-yl)phenyl)-N-phenylbenzenamine [ No CAS ]
  • 4-(5-((5-(4-(diphenylamino)phenyl)-6-(4-methoxyphenyl)thieno[3,2-b]thiophen-2-yl)(mesityl)boryl)-3-(4-methoxyphenyl)thieno[3,2-b]thiophen-2-yl)-N,N-diphenylbenzenamine [ No CAS ]
  • 44
  • [ 34907-53-4 ]
  • (Z)-(4-bromo-5-(2-(1-bromonaphthalen-2-yl)vinyl)thiophen-2-yl)triisopropylsilane [ No CAS ]
  • 10-triisopropylsilyl-12-mesitylnaphtho[2′,1′:6,7]borepino[3,2-b]thiophene [ No CAS ]
  • 45
  • [ 34907-53-4 ]
  • (((1Z,1′Z)-(2,5-dibromo-1,4-phenylene)bis(ethene-2,1-diyl))bis(4-bromothiophene-5,2-diyl))bis(triisopropylsilane) [ No CAS ]
  • 2,9-bistriisopropylsilyl-4,11-dimesitylbenzo[1″,2″:6,7;4″,5″:6′,7′]diborepino[3,2-b:3′,2′-b′]dithiophene [ No CAS ]
  • 46
  • [ 34907-53-4 ]
  • (((1Z,1′Z)-(1,5-dibromonaphthalene-2,6-diyl)bis(ethene-2,1-diyl))bis(4-bromothiophene-5,2-diyl))bis(triisopropylsilane) [ No CAS ]
  • 2,10-bistriisopropylsilyl-4,12-dimesitylnaphtho[1″,2″:7,6;6″,7″:6′,7′]diborepino[3,2-b:3′,2′-b′]dithiophene [ No CAS ]
  • 47
  • [ 34907-53-4 ]
  • (Z)-(4-bromo-5-(2-bromostyryl)thiophen-2-yl)triisopropylsilane [ No CAS ]
  • 2-triisopropylsilyl-4-mesitylbenzo[1′,2′:6,7]borepino[3,2-b]thiophene [ No CAS ]
  • 48
  • [ 34907-53-4 ]
  • [ 583-53-9 ]
  • [ 1251846-11-3 ]
YieldReaction ConditionsOperation in experiment
73.3% Synthesis of Intermediate II: Under nitrogen, to 500mL three-necked round bottom flask47.2g (0.2mol) of o-dibromobenzene in 200 mL anhydrous ether. After cooling to -78C, was slowly added dropwise 80mL n-BuLi under magnetic stirring (0.2mol, 2.5mol·L-1 in n-hexane). Maintaining the temperature of the reaction after 1h, the reaction was warmed to room temperature and stirring was continued for 2h. Then cooled again to -78C, was added a solution of 50mL 19.2g (0.1mol) MesitylB (OMe) 2 in ether solution, the reaction was stirred for 1h. It was slowly warmed to room temperature,The reaction was continued overnight, the amount of water hydrolysis, and extracted 2-3 times with ethyl acetate, the combined organic phases. After drying over anhydrous MgSO4, the organic solvent was removed by rotary evaporation to give the crude product. Purified by silica gel chromatography to obtain a white crystal 32.4 g, yield 73.3%.
73.3% under nitrogen, a 500 mL three-necked round flask was added 47.2g (0.2mol) ofo-dibromobenzene, 200 mL anhydrous ether, cooled to -78 C, was slowly added dropwise under magneticstirring 80mL of n-butyl butyllithium (n-BuLi) (0.2mol, 2.5molL in n-hexane). After maintaining thereaction temperature 1h, warmed to room temperature and stirring was continued for a natural response 2h.Then cooled again to -78 C, a solution of 50mL solution of 19.2g (0.1mol) MesityB (OMe) 2 in ethersolution, the reaction was stirred for 1h. Was slowly warmed to room temperature, the reaction was continuedovernight, water was added q.s. hydrolysis, and extracted 3 times with ethyl acetate, the organic phasescombined, dried over anhydrous MgSO 4, the organic solvent was removed by rotary evaporation to give thecrude product. By silica gel column chromatography to give a white crystals 32.4g, a yield of 73.3%.
73.3% Under nitrogen protection, 500 mL three-necked round bottom flask 47.2 g (0.2 mol) of o-dibromobenzene, 200 mL of anhydrous ether was added, and after cooling to -78 C, 80 mL of n-butyllithium (0.2 mol, 2.5 M, the solvent was n-hexane) was slowly added dropwise with magnetic stirring. Maintain the temperature reaction lh, the natural temperature to room temperature to continue stirring reaction 2h. After cooling again to -78 C, 50 mL of a solution of 19.2 g (0.1 mol) of Mesity B (0 Me) 2 in ether was added and stirred for 1 h. Slowly warmed to room temperature, continue to react overnight, add appropriate water hydrolysis, extracted by ethyl acetate 2-3 times, combined organic phase, anhydrous MgS04 dry, rotary evaporation to remove the organic solvent to get the crude product. The white crystals were separated by silica gel column chromatography (32.4 g) and the yield was 73.3%
  • 49
  • [ 70259-70-0 ]
  • [ 34907-53-4 ]
  • C19H17BS2 [ No CAS ]
  • 50
  • [ 70259-68-6 ]
  • [ 34907-53-4 ]
  • C19H17BS2 [ No CAS ]
  • 51
  • [ 40033-62-3 ]
  • [ 34907-53-4 ]
  • C19H17BS2 [ No CAS ]
  • 56
  • [ 34907-53-4 ]
  • C30H26BN [ No CAS ]
 

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