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[ CAS No. 6286-46-0 ]

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2D
Chemical Structure| 6286-46-0
Chemical Structure| 6286-46-0
Structure of 6286-46-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 6286-46-0 ]

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SDS

Product Details of [ 6286-46-0 ]

CAS No. :6286-46-0MDL No. :MFCD00017542
Formula :C9H9BrO4Boiling Point :-
Linear Structure Formula :-InChI Key :HWFCHCRFQWEFMU-UHFFFAOYSA-N
M.W :261.07Pubchem ID :222963
Synonyms :

Computed Properties of [ 6286-46-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 6286-46-0 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6286-46-0 ]

  • Downstream synthetic route of [ 6286-46-0 ]

[ 6286-46-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 591-50-4 ]
  • [ 6286-46-0 ]
  • [ 501-65-5 ]
  • 2,3-dimethoxy-9,10-diphenylphenanthrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetramethyl ammonium acetate; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h;Schlenk technique; Inert atmosphere; General procedure: To a Schlenk tube were added aryl iodides 1 (0.2 mmol, 1.0 equiv),1,2-diphenylethynes 2 (0.2 mmol, 1.0 equiv), 2-bromobenzoic acid 3 (0.24 mmol, 1.2equiv), PdCl2(dppf) (0.01 mmol, 5 mol %), K2CO3 (0.6 mmol, 3.0 equiv), Me4NOAc(0.6 mmol, 3.0 equiv), and DMSO (0.2 M, 1 mL). Then the tube was charged with nitrogen, and was stirred at 140 oC (oil bath temperature) for the indicated time until complete consumption of starting material as monitored by TLC analysis. After the reaction was finished, the resulting suspension was filtered and washed with ethyl acetate. The combined filtrates were concentrated under reduced pressure and purifiedon a silica-gel column chromatography (petroleum ether/EtOAc) to give product 4.
  • 2
  • [ 6286-46-0 ]
  • [ 108-46-3 ]
  • [ 126438-35-5 ]
YieldReaction ConditionsOperation in experiment
A mixture of resorcinol 1 (8.00 g; 72.6 mmol; 2.0 eq.), 2-bromo-4,5- dimethoxybenzoic acid 2 (9.50 g; 36.3 mmol; 1.0 eq.) and NaOH (3.20 g; 79.9 mmol; 2.2 eq.) in water (36 mL) was heated at reflux and stirred for 2 hours. Water (20 mL) and CuS04'5H20 (0.91 g; 3.63 mmol; 0.1 eq.) were added and the mixture was stirred under reflux for an additional 1 hour. The reaction was then cooled down to room temperature and the precipitate was filtered. The product was then dissolved in absolute ethanol and concentrated. The crude was engaged in the next step without further purification.
  • 3
  • [ 93-07-2 ]
  • [ 6286-46-0 ]
YieldReaction ConditionsOperation in experiment
91.6% After putting 182.2 g (1.0 mol) of 3,4-dimethoxy- benzoic acid into a 2,000 mE four-necked flask equipped with a stirrer, a thermometer, and a reflux cooling tube, 800 g of water was added thereto and stirred so as to disperse 3,4-dimethoxybenzoic acid. Subsequently, 133.3 g (1.00 mol) of a 30% sodium hydroxide aqueous solution was added. The liquid temperature was then reduced to 0 C., and 150.1 g (0.53 mol (1.05 equivalent)) of 1,3-dibromo-5, 5-dimethylhydantoin (DI3H) was added at a liquid temperature of 0 to 5 C. Completion of the dropwise addition was followed by stirring for one hour at a liquid temperature of 0 to 5 C. After completion of the reaction, 1.28 g (0.01 mol) of sodium sulfite was added followed by addition of 100 g of toluene and raising the liquid temperature to 70 C. The organic phase was removed by a liquid separation operation, and 104.2 g (1.0 mol) of 35% hydrochloric acid was added dropwise to the acquired aqueous phase and stirred for one hout Precipitated crystals were collected by filtration and dried under reduced pressure to acquire 239.4 g (99.9% purity, 91.6% yield) of [6286-46-0]2-bromo-4,5-dimethoxybenzoic acid.
With bromine; acetic acid; at 50℃; for 72h; Example 3; Synthesis of 4-bromo-6,7-dimethoxyphthalazine; [00196] Step 1. Into a 500 mL round bottom flask containing a solution of 3,4- dimethoxybenzoic acid (18.2 g, 99.91 mmol) in AcOH (250 mL) was added Br2 (17.6 g, 110.00 mmol). The resulting solution was stirred for 3 days while the temperature was maintained at 50 0C. The reaction mixture was cooled to room temperature and the solid product was collected by filtration. The filter cake was washed with hexanes and dried to provide 1O g of crude [6286-46-0]2-bromo-4,5-dimethoxybenzoic acid as a white solid.
With hydrogenchloride; bromine; In water; at 25℃; for 7h; Example 1 (Compound (1)?Compound (2)) 3,4-Dimethoxybenzoic acid (25.0 g) was suspended in concentrated hydrochloric acid (35%) (500 mL), and bromine (23.0 g, 1.05 equivalents) was added dropwise to the resultant suspension at 25 C. Subsequently, the resultant mixture was stirred for seven hours. Water (500 mL) was added to the mixture, and the mixture was stirred for one hour. Thereafter, the precipitated crystals were filtrated, and then dried under reduced pressure, to thereby produce crude crystals of [6286-46-0]2-bromo-4,5-dimethoxybenzoic acid (34.47 g) (yield: 96.2%). 1H-NMR(DMSO-d6, delta): 3.79(s,3H), 3.84(s,3H), 7.21(s,1H), 7.37(s,1H), 13.08(bs,1H).
With hydrogenchloride; bromine; In water; at 25℃; for 7h; General procedure: A 10.0 g of 3,4-dimethoxybenzoic acid, Awas suspended in Conc. HCl (35 %, 200 mL) and Br2 (25 g, 1.1 eq) wasadded drop wise to the resultant suspension at 25 Cand the mixture was stirred for 7 h. Water (200 mL) was added to the mixturefor the precipitation of acid, filtered, and dried the product 2-bromo-4,5-dimethoxybenzoicacid The pure product obtained column chromatography was analyzed byNMRTo a 10.0 g, of 2-bromo-4,5-dimethoxybenzoicacid, B diethylmalonate (100 mL) and copper bromide (551.7 mg, 10 mol %) wasadded and the resulting suspension was degassed under nitrogen at 0 C. Sodium hydride (60 % in mineral oil, 3.7 g)was added in portions over 20-25 min. After addition, the mixture was heated to90 C for 2 h, cooled to room temperature, 500 mlwater was added and the mixture was extracted twice with Ethyl acetate (150 mLX 2). The aqueous layer was acidified with 6N HCl and extracted withdichloromethane. The solvent was removed under vacuum to offer the 2-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4,5-dimethoxybenzoic acid. The above solid wasdissolved in 100 mL THF and then 7.7 g of sodium hydroxide in 100 mL watercontaining was added drop wise. The mixture was stirred overnight at roomtemperature. Reaction progress was monitored by TLC. THF was evaporated, andthen the resulting aqueous layer was extractedwith ethyl acetate (100 mL). The organic layer was dried over sodium sulphate,filtered and concentrated to afford the 4,5-dimethoxy homophthalic acid, C that was confirmed by NMR analysis.
With hydrogenchloride; bromine; In water; at 25℃; for 7h;Sealed tube; A 10.0g of 3,4-dimethoxybenzoic acid was suspended in Conc. HCl (35%, 200 ml) andBr2 (25 g, 1.1 eq) was added drop wise to the resultant suspensionat 25 C and the mixture was stirred for 7h. Water (200 ml) was added to the mixture for the precipitation of acid,filtered, and dried the product [6286-46-0]2-bromo-4,5-dimethoxybenzoic acid The pureproduct obtained column chromatography was analyzed by NMR

  • 4
  • [ 6286-46-0 ]
  • [ 134-32-7 ]
  • 2-bromo-4,5-dimethoxy-N-(naphthalen-1-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.0198 g With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 22℃; for 18h; 2-Bromo-4,5- dimethoxybenzoic acid (0.0701 g , 0.2685 mmol), l-aminonaphthalene (0.0423 g, 0.2953 mmol) and (2-(lH-benzotriazol-l-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate) (HBTU, 0.1119 g, 0.2953 mmol) were dissolved in /V,/V-dimcthylformamidc (DMF, 1 mL) and treated with N,N- diisopropylethylamine (0.14 mL). The mixture was stirred at 22 C for 18 hours. Ethyl acetate (20 mL) was added to dilute the mixture and washed with HC1 (5 mL, 1M, twice), saturated NaHC03 solution, saturated brine, subsequently, concentrated under vacuum, and then purified first with normal phase chromatography (12 g Isco silica column, Ethyl acetate-Hexane, 0-20%) and then further purification on HPLC (CH3CN (0.1% TFA)-H20 (0.1% TFA), 30%~90% (CH3CN%), 15 minutes) to give the title compound (a white solid, 0.0198 g). 'H NMR (300 MHz, CDCl3): d 8.44 (s, 1H), 8.17 (d, / = 6 Hz, 1H), 8.05 (d, / = 9 Hz, 1H), 7.91 (d, / = 9 Hz, 1H), 7.76 (d, / = 9 Hz, 1H), 7.57-7.52 (m, 3H), 7.48 (s, 1H), 7.11 (s, 1H), 3.96 (s, 6H). Calculated MS for Ci9Hi6BrN03, 385.03; observed, (M + H)+ 386.3.
  • 5
  • [ 6286-46-0 ]
  • [ 1774-12-5 ]
  • 2-bromo-4,5-dimethoxy-benzoic acid 5-(4-methoxy-phenyl)-3-oxo-cyclohex-1-enyl ester [ No CAS ]
  • 6
  • [ 6286-46-0 ]
  • 1-(2-(2-iodophenyl)-1H-indol-1-yl)-2-methylprop-2-en-1-one [ No CAS ]
  • 5,6-dimethoxy-8a-methyl-8,8a-dihydro-9H-dibenzo[de,g]indolo[1,2-b]isoquinolin-9-one [ No CAS ]
  • 7
  • [ 6286-46-0 ]
  • 2-(2-iodophenyl)-1-(2-methylallyl)-1H-indole [ No CAS ]
  • 5,6-dimethoxy-8a-methyl-8a,9-dihydro-8H-dibenzo[de,g]indolo[1,2-b]isoquinoline [ No CAS ]
  • 8
  • [ 6286-46-0 ]
  • [ 68-12-2 ]
  • [ 490-63-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a dried flask containing a magnetic stir bar under an atmosphere of dry argon was added 2-bromobenzoic acid (1.0 equiv) and dry THF (0.5 M). The solution was cooled to -78 C followed by drop-wise addition of n-BuLi (2.0 equiv, 2.5 M in hexane). The reaction mixture was stirred at -78 C for 30 min. Then the reaction mixture was drop-wise added with DMF (1.2 equiv), keep stirring for 3 - 4 hours, and quenched by saturated aqueous NH4Cl. The organic phase was extracted with EtOAc, washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude products were used directly for the next step without further purification.
  • 9
  • [ 6286-46-0 ]
  • [ 2113-51-1 ]
  • [ 17825-74-0 ]
  • 10
  • [ 6286-46-0 ]
  • [ 75-04-7 ]
  • [ 1228311-59-8 ]
YieldReaction ConditionsOperation in experiment
85% General procedure: Compound 1a (260mg, 1mmol) was dissolved in THF (10mL), to which DMF (0.1mL) and SOCl2 (0.5mL, 4mmol) were added. The reaction solution was stirred for 2hat 50C and then concentrated to remove THF. The residue was then added to a 30% solution of ethylamine in water (20mL) at 5C and filtered. The cake was purified by column chromatography to give 4 as a pale yellow solid (205mg, 75% yield).
85% General procedure: Compound1a(260 mg, 1 mmol) was dissolved in DCM (10 mL), to which DMF(0.1 mL) and SOCl2 (0.5 mL, 4 mmol) were added. The reaction solutionwas stirred for 2 h at 50 C, and then concentrated to remove DCM. Theresidue was then added to a 30% solution of ethylamine in water(20 mL) at 5 C and filtered. The cake was purified bycolumn chromatographyto give 1b as a pale yellow solid (205 mg, 75% yield). 1H NMR(400 MHz, CDCl3) delta 7.43 (d, J=8.8 Hz, 1H), 7.08 (d, J=3.1 Hz, 1H),6.81 (dd, J=8.8, 3.1 Hz, 1H), 3.80 (s, 3H), 3.49 (q, J=7.0 Hz, 2H),1.26 (t, J=7.3 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 167.23 (C),158.94 (C), 138.53 (C), 134.13 (CH), 117.81 (CH), 114.63 (CH), 109.35(C), 55.66 (CH3), 35.06 (CH2), 14.69 (CH3); HREIMS m/z 257.0050[M]+ (calcd for C10H12BrNO2, 257.0051).
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