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Cas Database

100-39-0

100-39-0

Identification

  • Product Name:Benzyl bromide

  • CAS Number: 100-39-0

  • EINECS:202-847-3

  • Molecular Weight:171.037

  • Molecular Formula: C7H7Br

  • HS Code:2903 99 80

  • Mol File:100-39-0.mol

Synonyms:Toluene,a-bromo- (8CI);(Bromomethyl)benzene;(Bromophenyl)methane;1-Bromomethylbenzene;NSC 8041;Phenylmethyl bromide;a-Bromotoluene;w-Bromotoluene;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. Vapors cause severe eye irritation; liquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach. (USCG, 1999) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Water spray, dry chemical, foam or carbon dioxide is effective. Water is effective not only for dispersing of leaked chemicals prior to its ignition, but also for cooling fire-exposed containers. Special Hazards of Combustion Products: Irritating hydrogen bromide gas may be formed. Behavior in Fire: Forms vapor that is a powerful tear gas. (USCG, 1999) 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. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus. Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

  • 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. Separated from strong oxidants, strong bases and food and feedstuffs. Dry. Well closed.In general, materials which are toxic as stored or which can decomposition into toxic components due to heat, moisture, acids, or acid fumes, should be stored in cool, well ventilated place, out of sun, away from area of high fire hazard and should be periodically inspected and monitored. Incompatible materials should be isolated.

  • 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:TRC
  • Product Description:Benzyl bromide
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Benzyl Bromide (stabilized with Propylene Oxide) >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Benzyl Bromide (stabilized with Propylene Oxide) >98.0%(GC)
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  • Manufacture/Brand:TCI Chemical
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Benzyl bromide
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  • Product Description:Benzyl bromide
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  • Product Description:Benzyl bromide
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  • Manufacture/Brand:SynQuest Laboratories
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Benzyl bromide for synthesis. CAS No. 100-39-0, EC Number 202-847-3., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 370 Articles be found

Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid

Klein, Suzane M.,Zhang, Cungen,Jiang, Yu Lin

, p. 2638 - 2641 (2008)

A simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid (HI) is reported. The alkyl iodides were obtained in quick and easy work-up with good to excellent yields (66-94%) and very high purities (97-99%). Freshly prepared iodomethane and 1-iodobutane were applied to synthesize biologically relevant 3,7-dimethyladenine and 9-butyladenine, which were characterized thoroughly using 1D and 2D NMR, individually.

-

Kubiczek,Neugebauer

, p. 917,919 (1950)

-

Organic synthesis in water/carbon dioxide emulsions

Jacobson,Lee C.T.,DaRocha,Johnston

, p. 1207 - 1210 (1999)

The synthetic reaction between a hydrophobe, benzyl chloride, and a hydrophilic nucleophile, KBr, is reported in water-in-carbon dioxide (w/c) and carbon dioxide-in-water (c/w) emulsions. Emulsions containing equal amounts of water and CO2 were

Chlorotrimethylsilane/Lithium Bromide and Hexamethyldisilane/Pyridinium Bromide Perbromide: Effective and Selective Reagents for the Conversion of Alkyl (Cycloalkyl and Aralkyl) Alcohols into Bromides

Olah, George A.,Gupta, B. G. Balaram,Malhotra, Ripudaman,Narang, Subhash C.

, p. 1638 - 1639 (1980)

Alkyl bromides were obtained in high yield in the reaction of the corresponding alcohols with chlorotrimethylsilane/lithium bromide.The reaction was equally applicable to primary, secondary, and tertiary alcohols as well as to allylic and benzylic alcohols.High regioselectivity was observed in related conversions in which hexamethyldisilane/pyridinium bromide perbromide was used.Tertiary alcohols, for example, were converted selectively into the corresponding tertiary bromides in the presence of primary and secondary hydroxylic functions.The reactions were also highly steroselective.

Simple and rapid determination of the activation parameters of organic reactions by temperature-dependent NMR spectroscopy II. Application to reversible reactions

Satoh, Masahiro,Hirota, Minoru

, p. 2619 - 2624 (1996)

A non-isothermal (NIT) method for evaluating the activation enthalpies and entropies of reactions in solutions was applied to several reversible reactions. This was realized by a stepwise elevation of the temperature of a reaction system using a variable-temperature apparatus comprising on NMR spectrometer and a quick collection of FID (free induction decay) at every plateau of the step. The rate from NIT experiments agreed well with the previously measured rates by the conventional methods.

-

Harnish,Tarbell

, p. 4123,4125, 4126 (1948)

-

Visible light induced 'on water' benzylic bromination with N-bromosuccinimide

Podgor?ek, Ajda,Stavber, Stojan,Zupan, Marko,Iskra, Jernej

, p. 1097 - 1099 (2006)

Benzylic bromination of various 4-substituted toluenes (Me, tert-Bu, COOEt and COMe) was effectively conducted with NBS in pure water and with a 40 W incandescent light-bulb as an initiator of the radical chain process, while electron donating groups (OMe and NHAc) directed the reaction to electrophilic aromatic substitution.

Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination

Ghorbani-Vaghei, Ramin,Chegini, Mohammad,Veisi, Hojat,Karimi-Tabar, Mehdi

, p. 1861 - 1865 (2009)

N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], and novel poly(N,N′-dibromo-N-phenylbenzene-1,3-disulfonamide) [PBPS] can be used for bromination of benzylic positions in solvent.

-

Olah,G.A.,Welch,J.

, p. 652 (1974)

-

A facile conversion of thiols to alkyl halides by triphenylphosphine/N-halosuccinimides

Iranpoor,Firouzabadi,Aghapour

, p. 1176 - 1178 (2001)

Thiols are efficiently converted to alkyl halides in high to excellent yields when treated with triphenylphosphin/N-halosuccinimide (halogen: Br,Cl, and I) in dichloromethane at room temperature.

Pure branch effect on the optical properties of novel conjugated derivatives

Yang, Long,Gao, Fang,Liu, Jian,Zhong, Xiaolin,Li, Hongru,Zhang, Shengtao

, p. 582 - 583 (2010)

Pure cooperative branch effects on one- and two-photon optical properties of conjugated derivatives are presented. AMI calculations demonstrate that the electron density distribution of the frontier orbital and the dipole moment changes of the derivatives are related to the number of branches. The theoretical results show that not only the energy level of the frontier orbital could be mediated by the number of branches, but the HOMOLUMO gap could be regulated.

-

Jung,M.E.,Hatfield,G.L.

, p. 4483 - 4486 (1978)

-

Direct halogenation of alcohols and their derivatives with tert-Butyl halides in the ionic liquid [pmIm]Br under sonication conditions - A novel, efficient and green methodology

Ranu, Brindaban C.,Jana, Ranjan

, p. 755 - 758 (2005)

A novel halogenating reagent system for direct halogenation of alcohols has been developed. tert-Butyl bromide, chloride and iodide in combination with the ionic liquid [pmIm]Br have been found to convert alcohols into the corresponding bromides, chlorides and iodides under sonication conditions (or heating) in good yields. Although a variety of primary and secondary alcohols participated in this reaction without any difficulty, tertiary alcohols remained inert. Several alcohol derivatives such as OTMS, OTBDMS, OAc, OTS and OTHP are also transformed into the corresponding halides in one-pot fashion by this procedure. A plausible rationale for this transformation is also presented. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Tribromoisocyanuric acid/triphenylphosphine: A new system for conversion of alcohols into alkyl bromides

De Andrade, Vitor S.C.,De Mattos, Marcio C.S.

, p. 975 - 979 (2014)

An efficient and facile method has been developed for the conversion of alcohols into alkyl bromides under neutral conditions using tribromoisocyanuric acid and triphenylphosphine (molar ratio 1.0:0.7:2.0, alcohol/ tribromoisocyanuric acid/triphenylphosphine) in dichloromethane at room temperature. This method can be applied for the conversion of primary, secondary, benzylic and allylic alcohols, and their corresponding bromides are obtained in 67-82 percent yield. Tertiary alcohols do not react under these conditions.

Direct bromination of hydrocarbons catalyzed by Li2MnO 3 under oxygen and photo-irradiation conditions

Nishina, Yuta,Morita, Junya,Ohtani, Bunsho

, p. 2158 - 2162 (2013)

A method for the direct bromination of hydrocarbons with Br2 using a ubiquitous and inexpensive catalyst is highly desirable. Herein, we report the selective mono-bromination of hydrocarbons in good yield using Li2MnO3 as a catalyst under irradiation with a fluorescent room light. This new catalyst can be recycled. The effect of light was investigated using action spectra, which revealed that the reaction occurred on the surface of the catalyst.

REACTIONS IN MICROEMULSION MEDIA. NUCLEOPHILIC DISPLACEMENT REACTION OF BENZYL CHLORIDE WITH BROMIDE ION

Martin, Craig A.,McCrann, Patrick M.,Angelos, George H.,Jaeger, David A.

, p. 4651 - 4654 (1982)

A kinetic and synthetic study of the reaction of benzyl chloride with bromide ion has been performed in microemulsions composed of cetyltrimethylammonium bromide, 1-butanol, water, potassium bromide, and hexane; rates and yields of benzyl bromide formatio

SYNTHESIS OF BENZYL HALIDES FROM ALDEHYDES PROMOTED BY HALOSILANES AND 1,1,3,3-TETRAMETHYLDISILOXANE (TMDS).

Aizpurua, Jesus M.,Palomo, Claudio

, p. 1103 - 1104 (1984)

Direct synthesis of monoalkyl halides from aldehydes by a new reductive halogenation method is briefly described.

Highly Reactive Manganese(IV)-Oxo Porphyrins Showing Temperature-Dependent Reversed Electronic Effect in C-H Bond Activation Reactions

Guo, Mian,Seo, Mi Sook,Lee, Yong-Min,Fukuzumi, Shunichi,Nam, Wonwoo

, p. 12187 - 12191 (2019)

We report that Mn(IV)-oxo porphyrin complexes, MnIV(O)(TMP) (1) and MnIV(O)(TDCPP) (2), are capable of activating the C-H bonds of hydrocarbons, including unactivated alkanes such as cyclohexane, via an oxygen non-rebound mechanism. Interestingly, 1 with an electron-rich porphyrin is more reactive than 2 with an electron-deficient porphyrin at a high temperature (e.g., 0 °C). However, at a low temperature (e.g., -40 °C), the reactivity of 1 and 2 is reversed, showing that 2 is more reactive than 1. To the best of our knowledge, the present study reports the first example of highly reactive Mn(IV)-oxo porphyrins and their temperature-dependent reactivity in C-H bond activation reactions.

Mild Aliphatic and Benzylic Hydrocarbon C-H Bond Chlorination Using Trichloroisocyanuric Acid

Combe, Sascha H.,Hosseini, Abolfazl,Parra, Alejandro,Schreiner, Peter R.

, p. 2407 - 2413 (2017)

We present the controlled monochlorination of aliphatic and benzylic hydrocarbons with only 1 equiv of substrate at 25-30 °C using N-hydroxyphthalimide (NHPI) as radical initiator and commercially available trichloroisocyanuric acid (TCCA) as the chlorine source. Catalytic amounts of CBr4 reduced the reaction times considerably due to the formation of chain-carrying ·CBr3 radicals. Benzylic C-H chlorination affords moderate to good yields for arenes carrying electron-withdrawing (50-85%) or weakly electron-donating groups (31-73%); cyclic aliphatic substrates provide low yields (24-38%). The products could be synthesized on a gram scale followed by simple purification via distillation. We report the first direct side-chain chlorination of 3-methylbenzoate affording methyl 3-(chloromethyl)benzoate, which is an important building block for the synthesis of vasodilator taprostene.

THE CINE O-ALKYLATION OF OXIRANYLCARBINOLS

Bird, C. W.,Hormozi, N.

, p. 705 - 706 (1988)

The reaction of the alkoxides derived from some oxyranylcarbinols with alkyl halides occurs by electrophilic attack on the oxiranyl oxygen rather than the alkoxide one leading to formation of the rearranged oxiranylcarbinyl ether.

BORON TRIFLUORIDE ETHERATE/HALIDE ION, A NOVEL REAGENT FOR THE CONVERSION OF ALLYL, BENZYL AND TERTIARY ALCOHOLS TO THE HALIDES

Mandal, Arun K.,Mahajan, S. W.

, p. 3863 - 3866 (1985)

A combination of boron trifluoride etherate and halide ion is found to be an excellent reagent for the conversion of allyl, benzyl and tertiary alcohols to the halides.

A new synthesis and application of N, N'-dibromo-N, N'-1,2-ethylene bis(2,5-dimethyl benzene sulfonamide); as a novel selective bromination agent for aromatic compounds

Ardeshir, Khazaei,Abbas, Shirdarreh

, p. 4079 - 4085 (1999)

Reaction Between Novel Compound; N, N' dibromo-N, N'-1,2- ethylene bis(2,5- dimethyl benzene sulfonamide) and aromatic compounds in the carbontetrachloride produces bromo aromatic compounds. In the case of benzene rings that contain mono activated substituted, only para - bromo isomer was formed. At the presence of benzoyl peroxide in the reaction mixture α - Hydrogen from alkyl side chain was substituted with bromine.

Free-Radical Bromination of Selected Organic Compounds in Water

Shaw, Henry,Perlmutter, Howard D.,Gu, Chen,Arco, Susan D.,Quibuyen, Titos O.

, p. 236 - 237 (1997)

-

A new synthetic approach to novel spiro-β-lactams

Bhalla, Aman,Venugopalan, Paloth,Bari, Shamsher S.

, p. 4943 - 4950 (2006)

An operationally simple and efficient approach for the synthesis of novel spiro-β-lactams is described. The key reaction is a halogen-mediated intrasulfenyl cyclization of a cis-3-benzylthio-3-(prop-2-ynyloxy/-enyloxy)- β-lactam procured through a Lewis acid-mediated C-3-alkylation of the trans-3-benzylthio-3-chloro-β-lactam carbocation equivalent. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

-

Koeroesi,J.

, p. 1222 - 1232 (1969)

-

NHC-palladium-catalyzed ionic liquid-accelerated regioselective oxyarylation of alkynes with diaryl ethers?

Cen, Liying,He, Dan,Jiang, Huanfeng,Li, Jianxiao,Lin, Zidong,Wu, Wanqing

supporting information, p. 1983 - 1988 (2022/04/03)

The first NHC-palladium-catalyzed regioselective oxyarylation of oxime ether in a task-specific ionic liquid via C(sp3)-O and C(sp2)-O bond cleavage of two different types of ethers for the assembly of structurally diverse 4-arylisoxazoles is described. Both the basic ionic liquid [C3NH2mim]Br and NHC-Pd catalyst IPr-Pd-Im-Cl2 played an important role in this transformation. Notably, this new approach provides a practical and straightforward route to access a broad range of privileged 4-arylisoxazole structures with good yields and excellent regioselectivities. Significantly, this catalytic system can be recycled up to eight times without significant loss of catalytic activity.

[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.

Process route upstream and downstream products

Process route

1,2-propylene cyclic carbonate
108-32-7

1,2-propylene cyclic carbonate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

chloranil
118-75-2

chloranil

para-bromotoluene
106-38-7

para-bromotoluene

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
at 100 ℃; Product distribution;
1,2-propylene cyclic carbonate
108-32-7

1,2-propylene cyclic carbonate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

para-bromotoluene
106-38-7

para-bromotoluene

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
at 100 ℃; Product distribution;
1,2-propylene cyclic carbonate
108-32-7

1,2-propylene cyclic carbonate

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

para-bromotoluene
106-38-7

para-bromotoluene

2-methylphenyl bromide
95-46-5

2-methylphenyl bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
at 100 ℃; Product distribution;
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

dibutyl ether
142-96-1

dibutyl ether

benzyl 2,4,6-trimethylbenzoate
4909-77-7

benzyl 2,4,6-trimethylbenzoate

mesitylenecarboxylic acid
480-63-7

mesitylenecarboxylic acid

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

benzyl 2,4,6-trimethylbenzoate
4909-77-7

benzyl 2,4,6-trimethylbenzoate

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
With dibutyl ether;
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dibenzyl ether
103-50-4

dibenzyl ether

benzyl bromide
100-39-0

benzyl bromide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
UV-Licht.Irradiation;
tetrachloromethane
56-23-5

tetrachloromethane

N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
ethyl bromide
74-96-4

ethyl bromide

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

benzoic acid ethyl ester
93-89-0,99341-95-4

benzoic acid ethyl ester

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
With magnesium; benzene;
diethyl ether
60-29-7,927820-24-4

diethyl ether

phenylmagnesium bromide

phenylmagnesium bromide

benzyl bromide
100-39-0

benzyl bromide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
phenylmagnesium bromide

phenylmagnesium bromide

benzyl bromide
100-39-0

benzyl bromide

Conditions
Conditions Yield
With diethyl ether;

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