*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
1,3,5-Trimethoxybenzene is a potential biomarker of flavonoid intake in human. It is a human xenobiotic metabolite.
Synonyms: TRIMETHYL PHLOROGLUCINOL
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Tasnim, Tarannum ; Shafiei, Negin ; Laminack, Katelyn ; Robertson, Bailey ; Nevels, Nash ; Fennell, Christopher , et al.
Abstract: While charge-transfer complexes involving halogen-bonding interactions have emerged as an alternative strategy for the photogeneration of carbon radicals, examples using (fluoro)alkyl bromides are limited. This report describes adual catalytic approach for radical generation from α-bromodifluoroesters and amides under visible light irradiation. Mechanistic studies suggest that the reaction proceeds through in-situ bromide displacement using a catalytic iodide salt, generat_x005f_x0002_ing a C–I bond that can be engaged by our halogen-bonding photocatalysis platform.
Show More >
Photocatalytic α-arylation of cyclic ketones
Md Mubarak Hossain ; Aslam C. Shaikh ; Jules Moutet ; Thomas L. Gianetti ;
Abstract: The direct α-arylation of carbonyl compounds using aryl halides represents a powerful method to synthesize critical building blocks for diverse useful compounds. Numerous synthetic methods exist to forge C(sp2)–C(sp3) bonds although mild and metal-free direct α-arylation of ketones remains a challenging transformation. Here we report a green-light-mediated α-arylation of ketones from readily available aryl halides via activation of a C(sp2)–X bond (X = I, Br, Cl) and an α-carbonyl C(sp3)–H bond in a single photocatalytic cycle. This approach is characterized by its mild reaction conditions, operational simplicity and wide functional group tolerance. Importantly, the impressive outcome of the multigram photocatalytic reaction underpins the strength of this method as a potentially practical and attractive approach for scale-up industrial purposes. The utility and scope of this reaction were further demonstrated by formal syntheses of several feedstock chemicals that are commercially expensive but critical for synthesizing numerous pharmaceutical agents.
Show More >
CAS No. : | 621-23-8 |
Formula : | C9H12O3 |
M.W : | 168.19 |
SMILES Code : | COC1=CC(OC)=CC(OC)=C1 |
Synonyms : |
TRIMETHYL PHLOROGLUCINOL
|
MDL No. : | MFCD00008385 |
InChI Key : | LKUDPHPHKOZXCD-UHFFFAOYSA-N |
Pubchem ID : | 69301 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P501-P270-P264-P301+P312+P330 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | The title compound was prepared using an adapted procedure for the same compound reported by Chaumeil et al.17 To a stirring solution of 1,3,5-trimethoxybenzene 7 (11.3 g, 67.2 mmol) in THF (200 mL) at 0 C, n-BuLi (45 mL, 1.60 M, 72.0 mmol) was added dropwise over 10 min. The resulting white suspension was stirred at this temperature for 2 h and then cooled to -78 C. B(OMe)3 (15.0 mL, 135 mmol) in THF (15 mL) was added dropwise over 1 h and the resulting mixture was stirred at -78 C for 1 h before being allowed to slowly warm in the cold bath to room temperature overnight. The resulting cloudy, white mixture was cooled to 0 C and water (100 mL) was added dropwise with stirring over 30 min. The mixture was poured into water (200 mL) and CH2Cl2 (300 mL) and stirred vigorously for 15 min. The phases were separated and the aqueous phase was extracted with CH2Cl2 (4×50 mL), and the combined organics were dried (Na2SO4), filtered and concentrated to provide a white powdery solid. The solid was dissolved in minimal boiling CHCl3 and a roughly equal portion of hot Et2O was added. The mixture was cooled to room temperature and placed in a -20 C freezer overnight to allow crystallization of the product. The resulting white crystals were isolated by suction, washed with cold Et2O (10 mL) and allowed to dry to provide 10.1 g (71%) of the desired boronic acid 9a. 1H NMR (400 MHz, CDCl3) delta 7.00 (s, 2H), 6.14 (s, 2H), 3.87 (s, 6H), 3.83 (s, 3H). NMR data for the synthesized compound corresponded to those reported for the title compound by Chaumeil et al.17 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; hexane; water; | EXAMPLE H 2,4,6-Trimethoxybenzoic acid To a stirred solution of 1,3,5-trimethoxybenzene (10.0 g, 59.4 mmol) in 150 mL of dry THF at 0 C. in nitrogen atmosphere was added 27.3 mL (68.31 mmol) of 2.5 M n-BuLi in hexane dropwise via syringe. The resulting solution was stirred at room temperature overnight. The mixture was cooled to -20 C. and 30 g of dry ice was added. Stirring was continued for 1 hr before hydrolysis with 200 mL of water. The mixture was evaporated under reduced pressure to remove THF. The aqueous phase was extracted with ether, acidified with hydrochloric acid to pH 3 and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and concentrated. The solid residue was washed with ether and dried in vacuo to give 6.7 g of the title compound: mp 152-153 C. dec (lit.: 147 C. dec.; Beilsteins, 10, 1988). 1 H NMR (CDCl3): 6.16 (2 H, s), 3.91 (6 H, s), 3.86 (3 H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium persulfate; ethanol; at 60℃; for 18h;Sealed tube; Green chemistry; | General procedure: A solution of aromatic carboxylic acid (0.1 mmol), Na2S2O8 (1.0 equiv) in ethanol (1 mL) was stirred in a sealed tube under an atmosphere of air at 60 oC for 18 h. The reaction mixture was then evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (TLC) on silica gel with petroleum ether and ethyl acetate to achieve the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 20% | With bis-triphenylphosphine-palladium(II) chloride; water; sodium hydroxide; In tetrahydrofuran; at 70℃; for 24h;Inert atmosphere; | General procedure: A 25 mL round bottom flask was charged with 9a (ca. 320 mg, 1.51 mmol), either anhydrous NaOH or K2CO3 (ca. 3 mmol) and Pd(PPh3)2Cl2 (1 mol %). THF (10 mL) was then added and the mixture was stirred until the boronic acid and catalyst dissolved. The resulting mixture was degassed with an Argon sparge for 30 min. Neat BnBr (120 muL, 1 mmol) was added via syringe, followed by water (2 mL) for the aqueous reactions. The resulting mixtures were stirred for 24 h at 70 C, then cooled to room temperature and quenched by the addition of satd aq NH4Cl (10 mL). The resulting mixture was extracted with CH2Cl2 (2×20 mL) and the combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The title product 10 was obtained in 10% isolated yield using aqueous K2CO3 as the base and 20% using aqueous NaOH as the base. In both cases the product was isolated as a white, powdery solid following silica gel chromatography (CH2Cl2/hexanes, 1:1) of the crude mixtures. 1H NMR (400 MHz, CDCl3) delta 7.24-7.07 (m, 5H), 6.15 (s, 2H), 3.93 (s, 2H), 3.80 (s, 3H), 3.77 (s, 6H). 13C NMR (100 MHz, CDCl3) delta 159.5, 159.1, 142.5, 128.6, 128.1, 125.4, 110.6, 90.9, 55.9, 55.5, 28.5. Mp 93-94 C (lit. Mp 93-95 C). NMR and mp data for the synthesized compound corresponded to those reported by Katritzky et al.24 for the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With p-toluenesulfonic acid immobilized on silica; In toluene; at 0 - 20℃; for 2h; | General procedure: The corresponding benzyl acetate (0.16 mmol) was dissolved intoluene or 4:1 EtOH/toluene (see details in each reaction) (1 mL)and then aromatic compound (0.80e1.6 mmol) and PTS-Si(0.17 mmol) were sequentially added at 0 C. The stirring wascontinued (for time and temperature noted in each Table) and thenthe mixture was filtered through a short pad cotton wool. Removalof the solvent afforded the crude product, which was purified bypreparative thin-layer chromatography (PTLC). Following the general procedure and purification by PTLC, the product was obtained as colorless oil (0.038 g, 0.13 mmol, 81%). Rf 0.50 (10% EtOAc/hexanes, developed three times). FTIR (UATR): numax 2937, 2836, 1595, 1116 cm-1. 1H NMR (CDCl3, 300 MHz): delta 3.74 (s, 3H), 3.78 (s, 9H), 3.86 (s, 2H), 6.14 (s, 2H), 6.75 (d, J=8.1 Hz, 2H), 7.15 (d, J=8.1 Hz, 2H). 13C NMR (CDCl3, 75 MHz): delta 27.3, 55.1, 55.3, 55.7 (2C), 90.6 (2C), 110.7, 113.3 (2C), 129.2 (2C), 134.4, 157.3, 158.7 (2C), 159.5. LRMS (EI) m/z (rel intensity) 288 (M+, 36), 257 (15), 181 (27), 121 (100), 91 (23). ESITOF-HRMS calcd for C17H20NaO4 (M+Na+) 311.1253, found 311.1252. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Compounds 46: 7-hyroxycitronellal (140 mu, 0.75 mmol), Cu(OTf)2 (2.2 mg, 2.5 mol %), ethanethiol (108 mu, 1.5 mmol) and 1,3,5- trimethoxybenzene (42 mg, 0.25 mmol) were reacted according to method B. The mixture was stirred for 2 h at rt. After the addition of Et3SiH (116 mu, 0.75 mmol) the reaction was stirred for 1 h at room temperature. The residual material was purified by column chromatography (silica gel 40-60, hexane / ethyl acetate 80:20) affording compound 46 (64 mg, 79% yield) as a thick oil. Characterization data of compound 46: lH NMR (CDCl3/400 MHz): delta 6.13 (s, 2H), 3.80 (s, 3H), 6.79 (s, 6H), 2.60 - 2.48 (m, 2H), 1.49 - 1.24 (m, 9H), 1.21 (s, 6H), 0.93 (d, J = 6.2, Hz, 3H); 13C NMR (CDCl3/100 MHz): 6 159.0, 158.7, 112.3, 90.6, 71.1, 55.7, 55.3, 44.4, 37.3, 36.6, 32.9, 29.3, 29.2, 21.6, 20.1, 19.7; HRMS (ESI): m/z calcd for Ci9H3204 [M+H]+ 325.2373 found 325.2363. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With copper(II) bis(trifluoromethanesulfonate); In 2,2,2-trifluoroethanol; at 20℃; for 2h; | Compound 33: 7-hyroxycitronellal (140 mu, 0.75 mmol), Cu(OTf)2 (2.2 mg, 2.5 mol ethanethiol (108 mu, 1.5 mmol) and 1,3,5- trimethoxybenzene (42 mg, 0.25 mmol) were reacted according to method A. The mixture was stirred for 2 h at room temperature. The residual material was purified by column chromatography (silica gel 40-60, hexane / ethyl acetate 80:20) affording compound 33 (68 mg, 71% yield) as a thick oil. Characterization data of compound 33: lH NMR (CDCl3/400 MHz): delta 6.12 (s, 1H), 6.09 (s, 1H), 4.54 - 4.46 (m, 1H), 3.80 (s, 3H), 3.78 (s, 6H), 2.51 - 2.32 (m, 3H), 1.96 - 1.84 (m, 1H), 1.56 - 1.47 (m, 1H), 1.40 - 1.32 (m, 4H), 1.24 - 1.19 (m, 5H), 1.17 (s, 3H), 1.15 (s, 3H), 0.82 (t, J = 4.5 Hz, 3H); 13C NMR (CDCl3/100 MHz): delta 160.2, 159.8, 158.2, 112.4, 111.4, 91.7, 90.3, 71.0, 55.9, 55.7, 55.2, 44.2, 41.3, 38.1, 37.1, 31.4, 29.1, 26.3, 21.6, 20.0, 19.4, 15.0; HRMS (ESI): m/z calcd for C2iH3604S [M+Na]+ 407.2227 found 407.2218. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Compound 48: Prepared according to method B with <strong>[40359-32-8]3-(allyloxy)benzaldehyde</strong> (81 mg, 0. 5 mmol), Cu(OTf)2 (2.2 mg, 2.5 mol %),ethanethiol (72 iii, 1.0 mmol) and 1,3,5-trimethoxybenzene (42 mg, 0.25 mmol). The mixture was stirred for 1.5 h at rt. After the addition of Et3SiH (116 mu, 0.75 mmol) the reaction was stirred at room temperature for 0.5 h. The residual material was purified by column chromatography (silica gel 40-60, hexane / ethyl acetate 93:7) to obtain compound 48 (74 mg, 94% yield) as a thick oil. Characterization data of compound 48: 1H NMR (CDCl3/400 MHz): delta 7.12 (d, = 7.8 Hz, 1H), 6.84 (d, = 7.8 Hz, 1H), 6.82 (s, 1H), 6.68 (dd, = 8.3, 1.8 Hz, 2H), 6.15 (s, 2H), 6.05 (ddt, = 17.0, 10.7, 5.2, 1H), 5.39 (dd, J = 17.0, 1.2 Hz, 1H), 5.39 (dd, = 10.5, 0.7 Hz, 1H), 4.49 (d, = 10.5, 5.2, 2H), 3.91 (s, 2H), 3.81 (s, 3H), 3.79 (s, 6H); 13C NMR (CDCl3/100 MHz): delta 159.7, 158.9, 158.5, 144.0, 133.7, 128.8, 121.2, 117.5, 115.1, 111.3, 110.0, 90.6, 68.7, 55.7, 55.4, 28.3; HRMS (ESI): m/z calcd for Ci9H2204 [M+H]+ 337.1410 found 337.1406. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: A solution of acetophenone 1 (1 mmol), SeO2 (2 mmol) and ytterbium chloride (0.3 mmol) inDMSO:H2O (9:1) (3 mL) was well stirred at 110 oC for 15 h. Then the 2-methylfuran/thiophene (2or 3) was added to the reaction mixture at room temperature and stir again for 10 min at 70 oC. Aftercompletion of the reaction, the reaction mixture brought to room temperature, and it was filteredthrough a short pad of Celite, excess SeO2 and other selenium-containing byproducts were removedby adsorption on Celite. Water was added to the filtrate and the mixture was extracted withdichloromethane. The combined organic layers were dried over anhydrous Na2SO4, concentrated invacuo and purified by chromatography on silica gel to afford required products (4 or 5). Therecovered catalyst was obtained from the aqueous layer after removing water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With molybdenum(V) chloride; titanium tetrachloride; In dichloromethane; at 22℃; for 0.5h;Inert atmosphere; | General procedure: A solution of the disulfide 5 (1.0 equiv) in anhydrous CH2Cl2was treated with TiCl4 (3.3 equiv) and subsequently MoCl5 (3.0equiv) or with MoCl3(HFIP)2 (3.0 equiv). Subsequently, a solutionof the aromatic compound (5.0 equiv) in anhydrous CH2Cl2was added dropwise,e and the mixture was stirred for the giventime (10-60 min) at r.t. at argon atmosphere. After completionof the reaction, a sat. aq solution of NaHCO3 was added and itwas stirred for additional 5 min. The mixture was extractedwith CH2Cl2, washed with brine, dried over MgSO4, and thesolvent was evaporated. The crude product was purified asdescribed below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.2 g | In a separate dry reaction flask, 33.6 g of 1,3,5-trimethoxybenzene and 27.2 g of anhydrous zinc chloride were added.Dichloromethane 300mL, stirring and cooling to 0-5 degrees after dropping 36.5g 1-pyrrolidinoyl chloride, drops,The reaction was heated to reflux for 2 hours. After the reaction was complete, 15 mL of concentrated hydrochloric acid and 150 mL of pure water were added and washed.The resulting organic phase is washed with saturated sodium bicarbonate solution to a pH of 7-8, and the organic phase is dried over magnesium sulfate and then reduced to dryness.Add 100 mL of anhydrous ethanol to the concentrate.20% hydrochloric acid ethanol100mLAfter stirring the reaction at 60-70C for 1 hour, the ethanol is then reduced to dryness.After adding 400 mL of acetone to the residue and cooling and crystallizing, the white crystal was filtered to obtain 60.2 g of buflomedil hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | General procedure: Aryl iodide (5 mmol, 1 equiv) and acetonitrile (5 mL) were added to a round bottom flask, equipped with a magnetic stir bar. Toluenesulfonic acid (5.05 mmol, 1.01 equiv) was added in one portion followed by one portion of m-CPBA (5.05 mmol, 1.01 equiv). The reaction mixture was stirred at room temperature until a white solid was formed. After 1 h 1,3,5-trimethoxybenzene (5.05 mmol, 1.01 equiv) was added and stirred until it forms clear solution. The reaction mixture was triturated with diethyl ether. The precipitate was isolated by vacuum filtration and washed with diethyl ether (3 × 20 mL). After drying under high vacuum the diaryliodonium salt was obtained in analytical pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With trifluorormethanesulfonic acid; In toluene; at 100℃; for 5h; | General procedure: Prior to the screening, CF3SO3H toluene solution was prepared from CF3SO3H (106 mL, 1.2 mmol) and toluene (10 mL) in a 20 mL vial (SV-20, 27 mm x 55 mm; Nichiden Rika-Glass Co., Kobe, Japan). Entry 17: To a 12 mL vial (S-5, 19 mm x 70 mm; Nichiden Rika-Glass Co.) containing a solution of 1,3,5-trimethoxybenzene (1a) (101 mg, 0.60 mmol) and N-methylmaleimide (2a) (66.7 mg, 0.60 mmol) in dry toluene (1.9 mL) was added CF3SO3H toluene solution (0.50 mL, 0.06 mmol) prepared as above. A cap was attached and closed, and the whole mixture was stirred at 100 C for 5 h. After the mixture was cooled by an ice-bath, an aliquot (0.24 mL) was taken from the mixture, diluted with EtOAc (2 mL), and neutralized with saturated aq. NaHCO3 (2 mL). Conversion was calculated by comparison of the 1H NMR (CDCl3) signal ratios at 4.45 (dd, J = 9.6 and 5.3 Hz, C(3)H of 3a) and 6.70 (s, C(3)H of 2a) to be 94%. The remaining mixture was treated with EtOAc (5 mL) and saturated aq. NaHCO3 (5 mL). The organic phase was separated and the aqueous phase was back-extracted with EtOAc (5 mL X 2). The combined organic phase was dried over Na2SO4, evaporated, and dried under reduced pressure to give a crude product, which was purified together with the NMR sample by the normal-phase MPLC (SI-25, size 20, hexane:EtOAc = 69:31 → 48:52) to afford N-methyl-3-(2,4,6-trimethoxyphenyl)succinimide (3a) (141 mg, 84%) |