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Cas Database

589-15-1

589-15-1

Identification

  • Product Name:4-Bromobenzyl bromide

  • CAS Number: 589-15-1

  • EINECS:209-636-5

  • Molecular Weight:249.933

  • Molecular Formula: C7H6Br2

  • HS Code:29036990

  • Mol File:589-15-1.mol

Synonyms:Toluene,p,a-dibromo- (6CI,7CI,8CI);1-(Bromomethyl)-4-bromobenzene;1-Bromo-4-(bromomethyl)benzene;4-Bromo-1-bromomethylbenzene;4-Bromobenzylbromide;NSC 113584;p-Bromobenzyl bromide;a,p-Dibromotoluene;Benzene,1-bromo-4-(bromomethyl)-;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damageH334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

  • 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

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  • Manufacture/Brand:Usbiological
  • Product Description:4-Bromobenzyl bromide 98+%
  • Packaging:25g
  • Price:$ 159
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:4-Bromobenzyl bromide
  • Packaging:5g
  • Price:$ 70
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  • Manufacture/Brand:TRC
  • Product Description:4-Bromobenzyl bromide
  • Packaging:50g
  • Price:$ 95
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  • Manufacture/Brand:TRC
  • Product Description:4-Bromobenzyl bromide
  • Packaging:250g
  • Price:$ 165
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  • Manufacture/Brand:TRC
  • Product Description:4-Bromobenzyl bromide
  • Packaging:100g
  • Price:$ 120
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Bromobenzyl Bromide
  • Packaging:500G
  • Price:$ 293
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Bromobenzyl Bromide
  • Packaging:25G
  • Price:$ 18
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Bromobenzyl Bromide
  • Packaging:100G
  • Price:$ 71
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Bromobenzyl bromide 98.0%
  • Packaging:100 g
  • Price:$ 49
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Bromobenzyl bromide 98.0%
  • Packaging:25 g
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Relevant articles and documentsAll total 95 Articles be found

Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives

Yagiz, Güler,Noma, Samir Abbas Ali,Altundas, Aliye,Al-khafaji, Khattab,Taskin-Tok, Tugba,Ates, Burhan

, (2021/01/28)

This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) activity. All dimethanol and dicarboxylate derivatives exhibited significant inhibition activities with IC50 values ranging from 0.71 to 2.25 μM. Especially, (1-(3-bromobenzyl)-1H-1,2,3-triazole-4,5-diyl)dimethanol (5c) and dimethyl 1-(4-chlorobenzyl)-1H-1,2,3-triazole-4,5-dicarboxylate (6 g) compounds were found to be the most promising derivatives on the XO enzyme inhibition with IC50 values 0.71 and 0.73 μM, respectively. Moreover, the double docking procedure was to evaluate compound modes of inhibition and their interactions with the protein (XO) at atomic level. Surprisingly, the docking results showed a good correlation with IC50 [correlation coefficient (R2 = 0.7455)]. Also, the docking results exhibited that the 5c, 6f and 6 g have lowest docking scores ?4.790, ?4.755, and ?4.730, respectively. These data were in agreement with the IC50 values. These results give promising beginning stages to assist in the improvement of novel and powerful inhibitor against XO.

[1,3]-Claisen rearrangement via removable functional group mediated radical stabilization

Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip

supporting information, p. 890 - 895 (2021/02/01)

A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

Gaikwad, Nikhil B.,Bansode, Sapana,Biradar, Shankar,Ban, Mayuri,Srinivas, Nanduri,Godugu, Chandraiah,Yaddanapudi, Venkata M.

, (2021/08/07)

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Continuous Synthesis and Separation ofp-Bromobenzyl Bromide Using Atom-Efficient Bromination ofp-Bromotoluene without Any Organic Effluent: Potential for Green Industrial Practice

Sancheti, Sonam V.,Yadav, Ganapati D.

, p. 2071 - 2080 (2021/09/13)

This work focuses on the bromination ofp-bromotoluene (PBT) using different brominating agents such as liquid Br2, NaBr-NaBrO3, NaBr-NaBrO3-NaCl, NaBr-H2O2, and HBr-H2O2. NaBr-NaBrO3-NaCl is an eco-friendly brominating agent obtained from a bromine recovery plant. Both NaBr-NaBrO3and NaBr-NaBrO3-NaCl were found to be nonhazardous and efficient brominating agents. Pure NaBr-NaBrO3resulted in the best PBT conversion with 79.7% Br atom efficiency in water and 98.2% average Br atom efficiency using dichloroethane as a solvent. Dichloroethane is de facto no longer used in the US and Europe and is not eco-friendly; the process with water as a solvent is the best. The substrate to active bromine molar ratio of 3:1 was found to be sufficient to get the maximum selectivity ofp-bromobenzyl bromide (PBBB). The low-temperature crystallization method was used for separation cum purification of the product. Unreacted PBT was recycled along with the dibromo byproduct obtained. The dibromo product, which was built up gradually in the reaction mixture over 10 successive batches, was converted back into PBBB/PBT through NaBH4treatment of the mother liquor. This continuous process is highly sustainable and produces zero organic waste, making it potentially attractive toward green industrial implementation.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

Houle, Camille,Savoie, Paul R.,Davies, Clotilde,Jardel, Damien,Champagne, Pier Alexandre,Bibal, Brigitte,Paquin, Jean-Fran?ois

supporting information, p. 10620 - 10625 (2020/07/24)

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

Process route upstream and downstream products

Process route

para-bromotoluene
106-38-7

para-bromotoluene

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With tert.-butylhydroperoxide; copper(ll) bromide; In acetic anhydride;
3%
95%
para-bromotoluene
106-38-7

para-bromotoluene

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With N-Bromosuccinimide; In tetrachloromethane; Heating;
95.8%
With N-Bromosuccinimide; dibenzoyl peroxide; In Diethyl carbonate; for 0.333333h; Reflux; Microwave irradiation;
95%
With bromine; at 40 ℃; for 4h; Inert atmosphere; Irradiation;
95%
With hydrogen bromide; sodium bromide; In chloroform; water; at 0 - 2 ℃; Electrolysis;
89%
With hydrogen bromide; sodium bromide; In chloroform; water; at 10 - 25 ℃; Electrolysis;
89%
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; dibenzoyl peroxide; In ethyl acetate; for 3h; Reflux;
87%
With N-Bromosuccinimide; trityl tetrafluoroborate; In dichloromethane; at 20 ℃; chemoselective reaction; Irradiation; Inert atmosphere;
86%
With N-Bromosuccinimide; tetrachlorosilane; In acetonitrile; at 20 ℃; for 8h;
84%
With sodium bromate; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium bromide; dibenzoyl peroxide; In dichloromethane; water; Reflux;
83%
With Oxone; water; potassium bromide; In dichloromethane; at 20 ℃; for 18h; Irradiation; Sealed tube;
80%
With boron tribromide; In tetrachloromethane; at 20 ℃; for 48h; Inert atmosphere;
79.5%
With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 0.216667h; Flow reactor; Irradiation;
78%
With hydrogen bromide; dihydrogen peroxide; In water; at 20 ℃; for 28h; Irradiation;
77%
With hydrogen bromide; dihydrogen peroxide; In water; at 27 ℃; for 28h; Irradiation;
77%
With sodium bromate; sodium hydrogensulfite; In water; ethyl acetate; at 20 ℃; for 4h;
76%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In cyclohexane; at 100 ℃; for 4h;
75%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In various solvent(s); at 60 - 65 ℃; for 1h;
72%
With hydrogen bromide; dihydrogen peroxide; In water; at 0 ℃; Incandescent lamp light;
70.1%
With bromine; lanthanum(III) acetate; In tetrachloromethane; at 60 ℃; for 4h; Irradiation;
65%
With N-Bromosuccinimide; Perbenzoic acid; In tetrachloromethane; for 1.5h; Heating;
60%
With [FeIV(1,1-di(pyridin-2-yl)-N,N-bis(quinolin-2-ylmethyl)methanamine)(O)]2+; [FeII(1,1-di(pyridin-2-yl)-N,N-bis(quinolin-2-ylmethyl)methanamine)(Br)]Br; In acetonitrile; at 25 ℃; for 0.5h; Inert atmosphere; Glovebox;
60%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 3h; Reflux; Inert atmosphere;
58.9%
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide;
With bromine; Irradiation;
With tetrachloromethane; bromine; Irradiation;
With tetrachloromethane; bromine; dibenzoyl peroxide;
With bromine; im direkten Sonnenlicht;
With air; bromine;
With tetrachloromethane; bromine; Irradiation.UV-Licht;
With N-Bromosuccinimide; In chloroform; Heating;
(bromination);
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;
With N-Bromosuccinimide; Perbenzoic acid; In tetrachloromethane; Heating; Irradiation;
With N-Bromosuccinimide; Perbenzoic acid; for 3h; Heating;
With bromine; at 110 ℃;
90 g
With N-Bromosuccinimide; Perbenzoic acid; carbon tetrabromide; In toluene;
With N-Bromosuccinimide;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 4h; Heating;
With N-Bromosuccinimide; In tetrachloromethane; Heating;
With N-Bromosuccinimide; In benzene; at 80 ℃; Rate constant; Irradiation;
With N-Bromosuccinimide;
With bromine; silica gel; In tetrachloromethane; at 20 ℃; for 5h;
65 % Chromat.
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; Heating;
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 4h; Heating;
With N-Bromosuccinimide; In tetrachloromethane; for 4h; Heating;
With N-Bromosuccinimide; at 36 ℃; Reactivity; Irradiation; neat (no solvent);
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 0.666667h; Reflux;
With N-Bromosuccinimide; In tetrachloromethane;
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In acetonitrile; at 20 ℃; for 2h; Reagent/catalyst; Time; Solvent; Temperature; Irradiation;
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); In acetonitrile; at 20 ℃; for 2h; Reagent/catalyst; Solvent; Reflux;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 1h; Reflux; Irradiation;
With N-Bromosuccinimide; In tetrachloromethane;
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h; Inert atmosphere; Heating;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 3h; Reflux;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 50 ℃;
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 1h; Reflux; Irradiation;
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; Reflux; Inert atmosphere;
With benzophenone; Bromotrichloromethane; In neat (no solvent); Heating; Irradiation; Flow reactor;
4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With isopinocampheyl-boron dibromide dimethylsulfide complex; In hexane; at 20 ℃; for 3h;
87%
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
2: acetic acid; hydrogen bromide / 0.5 h / 0 °C
With sodium tetrahydroborate; hydrogen bromide; acetic acid; In methanol;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C
2: hydrogen bromide / acetic acid / 0.5 h / 0 °C
With sodium tetrahydroborate; hydrogen bromide; In methanol; acetic acid;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / 0 °C
2: phosphorus tribromide / dichloromethane / 5 °C
With methanol; sodium tetrahydroborate; phosphorus tribromide; In dichloromethane;
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 2 h / 0 - 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 h / 0 - 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 h / 0 - 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 / tetrahydrofuran / 3 h / 0 - 20 °C
2: phosphorus tribromide / chloroform / 1 h / 0 - 20 °C
With sodium tetrahydroborate; phosphorus tribromide; In tetrahydrofuran; chloroform;
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With hydrogen bromide; ferric(III) bromide; In dichloromethane; at 25 ℃; for 0.2h;
96%
1,1-dimethoxy-1-(4-bromophenyl)methane
24856-58-4

1,1-dimethoxy-1-(4-bromophenyl)methane

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With triethylsilane; Acetyl bromide; tin(II) bromide; In dichloromethane; for 7h; Ambient temperature;
97%
bromobenzene
108-86-1,52753-63-6

bromobenzene

1,1-dibromomethane
74-95-3

1,1-dibromomethane

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

Conditions
Conditions Yield
bromobenzene; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;
1,1-dibromomethane; In N,N-dimethyl-formamide; at 60 ℃; for 2h;
4-(methylthio)benzyl alcohol
3446-90-0

4-(methylthio)benzyl alcohol

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
4-(methylthio)benzyl alcohol; With triphenylphosphine dibromide 1:1 addition complex; In acetonitrile; at 0 ℃; for 0.166667h;
With aluminum oxide; Oxone; In chloroform; for 2h; Heating;
100%
ethylbenzene
100-41-4,27536-89-6

ethylbenzene

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80 ℃; for 4h;
77%
para-bromotoluene
106-38-7

para-bromotoluene

azobisisobutyronitrile
34241-39-9

azobisisobutyronitrile

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With N-Bromosuccinimide; In tetrachloromethane;
p-Toluic acid
99-94-5

p-Toluic acid

3-bromo-4-methylbenzoic acid
7697-26-9

3-bromo-4-methylbenzoic acid

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

Conditions
Conditions Yield
With Oxone; sodium carbonate; sodium bromide; In methanol; water; at 20 ℃; for 24h;
71%
8%

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