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Cas Database

21852-50-6

21852-50-6

Identification

Synonyms:Toluene, a-bromo-3,4,5-trimethoxy-(7CI,8CI);1-(Bromomethyl)-3,4,5-trimethoxybenzene;3,4,5-Trimethoxybenzylbromide;5-(Bromomethyl)-1,2,3-trimethoxybenzene;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • 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.

  • 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:5-(Bromomethyl)-1,2,3-trimethoxybenzene
  • Packaging:100mg
  • Price:$ 60
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  • Manufacture/Brand:Crysdot
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95+%
  • Packaging:25g
  • Price:$ 1664
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  • Manufacture/Brand:Crysdot
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95+%
  • Packaging:10g
  • Price:$ 842
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  • Manufacture/Brand:Crysdot
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95+%
  • Packaging:5g
  • Price:$ 505
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3,4,5-TRIMETHOXYBENZYL BROMIDE 95.00%
  • Packaging:5MG
  • Price:$ 495.1
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  • Manufacture/Brand:Ambeed
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95%
  • Packaging:1g
  • Price:$ 169
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  • Manufacture/Brand:Ambeed
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95%
  • Packaging:250mg
  • Price:$ 71
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  • Manufacture/Brand:Ambeed
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95%
  • Packaging:100mg
  • Price:$ 49
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  • Manufacture/Brand:Ambeed
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene 95%
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  • Manufacture/Brand:Alichem
  • Product Description:5-(Bromomethyl)-1,2,3-trimethoxybenzene
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Relevant articles and documentsAll total 97 Articles be found

Asakawa et al.

, p. 1057 (1976)

Erianin, a novel dibenzyl compound in Dendrobium extract, inhibits bladder cancer cell growth via the mitochondrial apoptosis and JNK pathways

Zhu, Qiyu,Sheng, Yuwen,Li, Wenhua,Wang, Jing,Ma, Yulin,Du, Baowen,Tang, Yaxiong

, p. 41 - 54 (2019)

Erianin, a component extracted from the traditional Chinese herbal medicine Dendrobium, has shown significant anti-tumour activity in various cancers but not in bladder cancer. In this study, we assessed the effects of Erianin on bladder cancer growth and elucidated the related mechanisms. First, Erianin was synthesized with high yields, and markedly suppressed EJ and T24 cell proliferation. It induced G2/M-phase arrest in vitro. Furthermore, Erianin triggered apoptosis via caspase cascades activation and the mitochondrial-mediated apoptotic pathway. Bim up-regulation and Bcl-2 down-regulation as the symbol of apoptosis which were found to play the dominant role in the effects of Erianin. We further showed that JNK pathway activation is necessary for the Erianin-mediated anti-proliferation and apoptotic response. Finally, Erianin exhibited anti-tumour activity and induced apoptosis in tumour tissue in vivo. Collectively, these results suggest that Erianin induced cell cycle G2/M-phase arrest and apoptosis via the JNK signalling pathway in bladder cancer, indicating the potential usefulness of Erianin for the therapy of bladder cancer.

Synthesis of colchifulvin, a colchicine–griseofulvin hybrid

Marset, Azucena,Caprioglio, Diego,Torretta, Simone,Appendino, Giovanni,Minassi, Alberto

, p. 1540 - 1543 (2016)

Since the antimitotic agent colchicine (4) and the antifungal antibiotic griseofulvin (5) bind the same target (tubulin), we have explored the possibility of combining the potency of 4 and the low-toxicity of 5 into a hybrid [colchifulvin (6)], where the aromatic A-ring of 4 is bound to a dienone C-ring in a spiro fashion reminiscent of 5. To this purpose, the intramolecular oxidative cyclization of bibenzyl and stilbenoid precursors of spiro[4.5]decadienones was investigated, eventually taming the unexpected subtleties of the reaction. Disappointingly, rac-6 did not share the biological profile of the two inspiring lead structures.

Synthesis and Insecticidal Activity of Spinosyns with C9- O -Benzyl Bioisosteres in Place of the 2′,3′,4′-Tri- O -methyl Rhamnose

Oliver, M. Paige,Crouse, Gary D.,Demeter, David A.,Sparks, Thomas C.

, p. 5571 - 5577 (2015)

The spinosyns are fermentation-derived natural products active against a wide range of insect pests. They are structurally complex, consisting of two sugars (forosamine and rhamnose) coupled to a macrocyclic tetracycle. Removal of the rhamnose sugar results in a >100-fold reduction in insecticidal activity. C9-O-benzyl analogues of spinosyn D were synthesized to determine if the 2′,3′,4′-tri-O-methyl rhamnose moiety could be replaced with a simpler, synthetic bioisostere. Insecticidal activity was evaluated against larvae of Spodoptera exigua (beet armyworm) and Helicoverpa zea (corn earworm). Whereas most analogues were far less active than spinosyn D, a few of the C9-O-benzyl analogues, such as 4-CN, 4-Cl, 2-isopropyl, and 3,5-diOMe, were within 3-15 times the activity of spinosyn D for larvae of S. exigua and H. zea. Thus, although not yet quite as effective, synthetic bioisosteres can substitute for the naturally occurring 2′,3′,4′-tri-O-methyl rhamnose moiety.

Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming

Sheng, Yuwen,Chen, Yuwen,Zeng, Zhongqiu,Wu, Wenbi,Wang, Jing,Ma, Yuling,Lin, Yuan,Zhang, Jichao,Huang, Yulan,Li, Wenhua,Zhu, Qiyu,Wei, Xiao,Li, Suiyan,Wisanwattana, Wisanee,Li, Fu,Liu, Wanli,Suksamrarn, Apichart,Zhang, Guolin,Jiao, Wei,Wang, Fei

, p. 460 - 484 (2022/01/03)

Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.

Synthesis method of selenium-containing isochroman compound

-

, (2021/05/29)

The invention discloses a synthesis method of a selenium-containing isochroman compound. The synthesis method comprises the following steps: under the protection of nitrogen, adding N-phenylseleno saccharin (NPSSac) into a reactor, then adding dichloromethane to completely dissolve the N-phenylseleno saccharin, adding a 1-[(cinnamoxy) methyl]-3, 4, 5-trimethoxy benzene compound and boron trifluoride diethyl etherate after the N-phenylseleno saccharin is completely dissolved, stirring at 20-60 DEG C for 2-6 hours until the reaction is complete, and after the reaction is finished, quenching, extracting, combining organic phases, drying, concentrating, separating and purifying to obtain the selenium-containing isochroman compound. The synthesis method disclosed by the invention is relatively easy to operate, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrial production.

Synthesis method of 2-benzoxepin compound

-

, (2021/05/29)

The invention discloses a synthesis method of a 2-benzoxepin compound. The method comprises the following specific steps: under the protection of nitrogen, adding N-phenylseleno-phthalimide into a reactor, then adding anhydrous dichloromethane to dissolve the N-phenylseleno-phthalimide, then adding a 1-[(cinnamyl) methyl]-3, 4, 5-trimethoxybenzene compound, taking zinc chloride as a catalyst, reacting at room temperature, adding saturated sodium bicarbonate for quenching after the reaction is finished, extracting by dichloromethane, combining organic phases, drying by anhydrous magnesium sulfate, concentrating under reduced pressure, and performing silica gel rapid chromatographic purification by thin-layer chromatography silica gel to obtain the 2-benzoxepin compound. The method is simple in reaction operation, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrialized production.

Synthesis method of isochroman compound

-

, (2021/05/15)

The invention discloses a synthesis method of an isochroman compound, which comprises the following steps of adding dichloromethane and phosphorus tribromide into 3, 4, 5-trimethoxy benzyl alcohol, and reacting to obtain 1-bromomethyl-3, 4, 5-trimethoxy benzene, adding tetrahydrofuran, cinnamyl alcohol, sodium hydride and 1-bromomethyl-3, 4, 5-trimethoxybenzene into a reactor, and reacting to obtain 1-[(cinnamyl oxy)methyl]-3, 4, 5-trimethoxybenzene, adding cyanuric acid into a reactor containing a potassium hydroxide aqueous solution to react, dropwise adding a silver nitrate aqueous solution, and reacting to obtain silver isocyanurate, adding silver isocyanurate, phenyl selenium bromide and anhydrous dichloromethane into a reactor, and reacting to obtain N, N, N-triphenyl seleno isocyanurate, reacting N, N, N-triphenyl seleno isocyanurate, dichloromethane, boron trifluoride diethyl etherate and a 1-[(cinnamyl oxy)methyl]-3, 4, 5-trimethoxybenzene compound to obtain a target product. The method is simple in reaction operation, mild in reaction condition, relatively high in yield and environment-friendly.

Pd-catalyzed sp-sp3cross-coupling of benzyl bromides using lithium acetylides

Buter, Jeffrey,Doze, Anna M.,Feringa, Ben L.,Mondal, Anirban,Visser, Paco

supporting information, p. 7529 - 7532 (2021/08/05)

Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C-C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp2, and sp3) with aromatic (pseudo) halides (sp2). Here we present an efficient method for the cross-coupling of benzyl bromides (sp3) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products.

Process route upstream and downstream products

Process route

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
With polymethylhydrosiloxane; dimethylbromosulphonium bromide; In chloroform; at 20 ℃; for 5h;
98%
Multi-step reaction with 2 steps
1: NaBH4 / methanol / 20 °C
2: PBr3 / diethyl ether / -40 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; diethyl ether;
Multi-step reaction with 2 steps
1: 95 percent / NaBH4 / methanol
2: 97 percent / PBr3 / diethyl ether / -40 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; diethyl ether;
Multi-step reaction with 2 steps
1: 95 percent / NaBH4; MeOH
2: PBr3 / diethyl ether
With methanol; sodium tetrahydroborate; phosphorus tribromide; In diethyl ether; 1: Reduction / 2: Bromination;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / dichloromethane / 0.5 h / 20 °C
2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C
With sodium tetrahydroborate; phosphorus tribromide; In dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol
2: phosphorus tribromide
With sodium tetrahydroborate; phosphorus tribromide; In methanol;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 1 h / 0 °C
2: phosphorus tribromide / diethyl ether / 2 h / -20 °C
With sodium tetrahydroborate; phosphorus tribromide; In diethyl ether; ethanol;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / Inert atmosphere
2: phosphorus tribromide / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 3 h / 15 - 20 °C
2: phosphorus tribromide / dichloromethane / 2 h / 15 - 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C
2: phosphorus tribromide / dichloromethane / 4 h / 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere; Schlenk technique
2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 2 h / 20 °C
2: phosphorus tribromide / diethyl ether / 0.5 h / 0 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; diethyl ether;
3,4,5-trimethoxy-benzaldehyde; With sodium tetrahydroborate; In methanol; at 0 ℃;
With phosphorus tribromide; In dichloromethane; at 0 ℃;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 0 - 20 °C
2: phosphorus tribromide / diethyl ether / 0 - 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; diethyl ether;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; water / 0.17 h / 0 - 10 °C
2: phosphorus tribromide / diethyl ether / 0.08 h / 0 °C
With sodium tetrahydroborate; phosphorus tribromide; In tetrahydrofuran; diethyl ether; water;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 2 h / 0 - 20 °C
2: phosphorus tribromide / dichloromethane / 0.5 h / 0 - 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 2 h / 0 °C
2: phosphorus tribromide / dichloromethane / 1 h / 0 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 0.75 h / 40 °C / Heating / reflux
2: phosphorus tribromide / dichloromethane / 0.83 h / 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / ethanol / 0.75 h / 40 °C / Heating / reflux
1.2: 20 °C
2.1: phosphorus tribromide / dichloromethane / 0.83 h / 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / ethanol / 0.75 h / Heating / reflux
1.2: 20 °C
2.1: phosphorus tribromide / dichloromethane / 0.83 h / 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C
2: phosphorus tribromide / dichloromethane / 0.5 h / 0 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol
2: phosphorus tribromide / dichloromethane
With methanol; sodium tetrahydroborate; phosphorus tribromide; In dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C
2: phosphorus tribromide / dichloromethane / 0.67 h / 0 °C
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; ethanol / 0.2 h / 25 °C / 5171.62 Torr / Microwave irradiation
2: phosphorus tribromide / tetrahydrofuran / 0.1 h / 50 °C / 5171.62 Torr / Microwave irradiation
With sodium tetrahydroborate; ethanol; phosphorus tribromide; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / -5 - 20 °C
2: phosphorus tribromide / dichloromethane / -10 - 20 °C / Inert atmosphere
With sodium tetrahydroborate; phosphorus tribromide; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C
2: phosphorus tribromide / dichloromethane / 1 h / 0 °C / Inert atmosphere
With sodium tetrahydroborate; phosphorus tribromide; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / ethanol / 1 h / 0 °C
2: phosphorus tribromide / dichloromethane / 1 h / 0 °C / Inert atmosphere
With sodium tetrahydroborate; phosphorus tribromide; In ethanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 0.33 h / 0 - 20 °C
2: phosphorus tribromide / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere
With sodium tetrahydroborate; phosphorus tribromide; In methanol; dichloromethane;
CF<sub>3</sub>O<sub>3</sub>S<sup>(1-)</sup>*C<sub>15</sub>H<sub>21</sub>N<sub>2</sub>O<sub>3</sub>S<sup>(1+)</sup>
847778-92-1

CF3O3S(1-)*C15H21N2O3S(1+)

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
With KBr-K222 complex; 1,2-dimethoxy-4-methylbenzene; In tetrahydrofuran; at 60 ℃; for 0.0833333h;
43%
3,4,5-trimethoxytoluene
6443-69-2

3,4,5-trimethoxytoluene

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
With bromine; In tetrachloromethane; Irradiation; heating;
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 82 - 84 ℃; for 0.5h; Product distribution / selectivity; Heating / reflux;
With benzophenone; Bromotrichloromethane; In neat (no solvent); Heating; Irradiation; Flow reactor;
(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

phosphorus tribromide
7789-60-8

phosphorus tribromide

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
With pyridine; hydrogenchloride; sodium borohydrid; In tetrahydrofuran; water;
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 70 percent / LAH / tetrahydrofuran
2: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp.
With lithium aluminium tetrahydride; phosphorus tribromide; triethylamine; In tetrahydrofuran; tetrachloromethane;
Multi-step reaction with 2 steps
1: lithium borohydride / methanol / 20 °C
2: phosphorus tribromide / benzene / 20 °C
With lithium borohydride; phosphorus tribromide; In methanol; benzene;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice
2: phosphorus tribromide / dichloromethane / 4 h / Cooling with ice; Inert atmosphere
With lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: phosphorus tribromide / dichloromethane / 0 - 20 °C
With lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
2: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice
With lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice
2: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice
With lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; dichloromethane;
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice
3: phosphorus tribromide / dichloromethane / 4 h / Cooling with ice; Inert atmosphere
With lithium aluminium tetrahydride; phosphorus tribromide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
3: phosphorus tribromide / dichloromethane / 0 - 20 °C
With lithium aluminium tetrahydride; phosphorus tribromide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 4.5 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
3: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice
With lithium aluminium tetrahydride; phosphorus tribromide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 4.5 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice
3: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice
With lithium aluminium tetrahydride; phosphorus tribromide; potassium carbonate; In tetrahydrofuran; dichloromethane; acetone;
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 82 percent / LiAlH4 / tetrahydrofuran / 3 h / 0 °C
2: 57 percent / CBr4, PPh3 / tetrahydrofuran / 12 h / Ambient temperature
With lithium aluminium tetrahydride; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran;
Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 11 h / 0 - 20 °C
2: phosphorus tribromide / dichloromethane / 2 h / 0 °C
With lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; dichloromethane;
(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
With phosphorus tribromide; In benzene; at 20 ℃;
100%
With pyridine; phosphorus tribromide; In diethyl ether; at 40 ℃; for 3h;
100%
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
100%
With pyridine; phosphorus tribromide; In diethyl ether; for 3h; Schlenk technique; Inert atmosphere; Reflux;
100%
With phosphorus tribromide; In dichloromethane; at -5 ℃; for 0.75h; Inert atmosphere;
99%
With phosphorus tribromide; In tetrahydrofuran; at 50 ℃; for 0.1h; under 5171.62 Torr; Microwave irradiation;
98%
With chloro-trimethyl-silane; lithium bromide; In acetonitrile;
97%
With phosphorus tribromide; In diethyl ether; at -40 ℃;
97%
With phosphorus tribromide; In diethyl ether; at 0 - 20 ℃; for 5h; Inert atmosphere;
95%
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 4h;
93%
With functionalised triphenylphosphine monolith; In dichloromethane; for 1h; Inert atmosphere;
92%
With carbon tetrabromide; triphenylphosphine; In benzene; at 0 ℃; for 2h;
90%
With phosphorus tribromide; In diethyl ether; at 0 ℃; for 0.0833333h;
90%
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
89%
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
89%
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃;
86%
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
86%
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 0.5h;
86%
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 0.666667h;
86%
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 0.5h;
85.9%
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 0.833333h; Product distribution / selectivity;
84.44%
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 0.833333h;
84.44%
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 0.833333h;
84.44%
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 0.833333h;
84.44%
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 0.833333h;
84.44%
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;
83%
With phosphorus tribromide; In diethyl ether; at -40 ℃; for 6h;
82%
With phosphorus tribromide; In diethyl ether; dichloromethane; at 0 ℃; for 0.166667h;
81%
With phosphorus tribromide; triethylamine; In tetrachloromethane; 1) 1h, 0 degC 2) 3h, roomtemp.;
80%
With phosphorus tribromide; In diethyl ether; for 0.666667h;
80%
With pyridine; phosphorus tribromide; In diethyl ether; at -20 ℃;
80%
With phosphorus tribromide; In diethyl ether; at -20 ℃; for 2h;
79%
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 6h;
77%
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h;
75%
With phosphorus tribromide; In tetrahydrofuran; Reflux;
70%
With phosphorus tribromide; In diethyl ether; at 0 - 20 ℃;
61%
With hydrogen bromide;
60%
With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; for 12h; Ambient temperature;
57%
With phosphorus tribromide; In dichloromethane; at -5 ℃; for 0.5h;
With hydrogen bromide; In benzene; for 0.166667h;
With phosphorus tribromide; In diethyl ether; at -10 ℃; for 1h;
With phosphorus tribromide;
With chloro-trimethyl-silane; lithium bromide; In acetonitrile;
With carbon tetrabromide; triphenylphosphine; In acetone; at 0 - 22 ℃;
With phosphorus tribromide; In diethyl ether;
With phosphorus tribromide; In dichloromethane; at -5 ℃; for 0.75h;
With phosphorus tribromide; In diethyl ether; at -40 ℃;
With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20 ℃;
With carbon tetrabromide; triphenylphosphine; In acetone; at 20 ℃;
With phosphorus tribromide; In dichloromethane; at 20 ℃;
With hydrogen bromide; In toluene; at 20 ℃; for 0.5h;
With phosphorus tribromide; In diethyl ether; at 0 - 20 ℃; for 12h;
With pyridine; phosphorus tribromide; In benzene; for 3h; Reflux;
With phosphorus tribromide; In tetrahydrofuran; Reflux;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
With phosphorus tribromide; In tetrahydrofuran; Reflux;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 0.5h;
With phosphorus tribromide; In dichloromethane; at 0 - 5 ℃; for 0.75h;
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
7 g
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 2h;
With phosphorus tribromide;
With hydrogen bromide; In diethyl ether; dichloromethane; for 4.5h;
With phosphorus tribromide; In dichloromethane; at 15 - 20 ℃; for 2h;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
With phosphorus tribromide; In dichloromethane; at 20 ℃; for 2h;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 0.5h;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere; Schlenk technique;
With phosphorus tribromide; In diethyl ether; at 0 ℃; for 0.5h;
With phosphorus tribromide; In dichloromethane; at 0 ℃;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 0.5h;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
With phosphorus tribromide; In dichloromethane;
With phosphorus tribromide; In dichloromethane;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h;
9.8 g
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃;
With phosphorus tribromide; In dichloromethane; for 4h; Cooling with ice; Inert atmosphere;
With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃;
With phosphorus tribromide; In diethyl ether; at 0 ℃;
With phosphorus tribromide; In dichloromethane; for 4h; Inert atmosphere; Cooling with ice;
With phosphorus tribromide; In dichloromethane; for 4h; Inert atmosphere; Cooling with ice;
With phosphorus tribromide; In dichloromethane;
With phosphorus tribromide; In chloroform; Reflux;
With phosphorus tribromide; In dichloromethane; at 0 ℃;
With phosphorus tribromide; In dichloromethane; at 0 ℃;
With phosphorus tribromide; In dichloromethane; at -10 - 20 ℃; Inert atmosphere;
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Temperature; Inert atmosphere;
13.1 g
With phosphorus tribromide; In dichloromethane; at 0 ℃; for 1h; Temperature; Inert atmosphere;
13.1 g
1-methyl-2-(3,4,5-trimethoxybenzylthio)-imidazole
847778-88-5

1-methyl-2-(3,4,5-trimethoxybenzylthio)-imidazole

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: dichloromethane / 20 °C
2: KBr-K222 complex; 1,2-dimethoxy-4-methylbenzene / tetrahydrofuran / 0.08 h / 60 °C
With KBr-K222 complex; 1,2-dimethoxy-4-methylbenzene; In tetrahydrofuran; dichloromethane;

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