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Cas Database

694-80-4

694-80-4

Identification

  • Product Name:Benzene,1-bromo-2-chloro-

  • CAS Number: 694-80-4

  • EINECS:211-775-1

  • Molecular Weight:191.455

  • Molecular Formula: C6H4BrCl

  • HS Code:29039990

  • Mol File:694-80-4.mol

Synonyms:1-Bromo-2-chlorobenzene;1-Chloro-2-bromobenzene;2-Bromo-1-chlorobenzene;2-Bromochlorobenzene;2-Bromophenyl chloride;2-Chlorobromobenzene;2-Chlorophenyl bromide;o-Bromochlorobenzene;o-Bromophenyl chloride;o-Chlorobromobenzene;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn; IrritantXi; ToxicT

  • Hazard Codes:Xi,T,Xn,F

  • 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 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:1-Bromo-2-chlorobenzene
  • Packaging:1g
  • Price:$ 45
  • Delivery:In stock
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  • Product Description:1-Bromo-2-chlorobenzene
  • Packaging:500G
  • Price:$ 211
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1-Bromo-2-chlorobenzene
  • Packaging:25G
  • Price:$ 22
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chlorobromobenzene 99.0%
  • Packaging:100 g
  • Price:$ 50
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chlorobromobenzene 99.0%
  • Packaging:250 g
  • Price:$ 88
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chlorobromobenzene 99.0%
  • Packaging:25 g
  • Price:$ 18
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-Bromo-2-chlorobenzene 99%
  • Packaging:10g
  • Price:$ 25.8
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1-Bromo-2-chlorobenzene 99%
  • Packaging:100g
  • Price:$ 116
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:1-Bromo-2-chlorobenzene
  • Packaging:1 g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1-Bromo-2-chlorobenzene 95+%
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Relevant articles and documentsAll total 40 Articles be found

Direct bromodeboronation of arylboronic acids with CuBr2 in water

Tang, Yan-Ling,Xia, Xian-Song,Gao, Jin-Chun,Li, Min-Xin,Mao, Ze-Wei

supporting information, (2021/01/05)

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi

, p. 18040 - 18049 (2021/05/29)

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

Liu, Mingyang,Zhang, Zhanrong,Liu, Huizhen,Wu, Tianbin,Han, Buxing

supporting information, p. 7120 - 7123 (2020/07/14)

We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.

Metal- and base-free synthesis of aryl bromides from arylhydrazines

Phuc Tran, Dat,Nomoto, Akihiro,Mita, Soichiro,Dong, Chun-ping,Kodama, Shintaro,Mizuno, Takumi,Ogawa, Akiya

supporting information, (2020/05/08)

An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.

Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation

Rogers, David A.,Bensalah, Adam T.,Espinosa, Alvaro Tomas,Hoerr, John L.,Refai, Fares H.,Pitzel, Amy K.,Alvarado, Juan J.,Lamar, Angus A.

supporting information, p. 4229 - 4233 (2019/06/17)

Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone.

Process route upstream and downstream products

Process route

1-chloro-1,2,3,4,5,6-hexabromocyclohexane
88400-64-0

1-chloro-1,2,3,4,5,6-hexabromocyclohexane

bromochlorobenzene
106-39-8

bromochlorobenzene

1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

benzyl bromide
100-39-0

benzyl bromide

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

chlorobenzene
108-90-7

chlorobenzene

Conditions
Conditions Yield
at 55 ℃; for 16h; Product distribution; Irradiation; other solvents;
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2,4,6-trimethylphenyl bromide
576-83-0

2,4,6-trimethylphenyl bromide

chlorobenzene
108-90-7

chlorobenzene

3-Bromo-2'-chloro-2,4,6-trimethyl-biphenyl

3-Bromo-2'-chloro-2,4,6-trimethyl-biphenyl

Conditions
Conditions Yield
With bromine; In diethyl ether; for 0.5h; Yield given; Ambient temperature;
bromobenzene
108-86-1,52753-63-6

bromobenzene

bromochlorobenzene
106-39-8

bromochlorobenzene

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

Conditions
Conditions Yield
With Nitryl chloride; trifluoroacetic acid; at 20 ℃; for 8h; Product distribution; Mechanism;
bromobenzene
108-86-1,52753-63-6

bromobenzene

bromochlorobenzene
106-39-8

bromochlorobenzene

para-dichlorobenzene
106-46-7,84348-21-0

para-dichlorobenzene

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

chlorobenzene
108-90-7

chlorobenzene

2,3-dibromobenzene
583-53-9

2,3-dibromobenzene

Conditions
Conditions Yield
With potassium chloride; cobalt(III) acetate; trifluoroacetic acid; at 20 ℃; for 15h; Product distribution; Mn(CH3COO)3, 600 - 216 h, various conc. of aq. CF3COOH;
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2-chloro-1,1'-biphenyl
2051-60-7,108321-69-3

2-chloro-1,1'-biphenyl

Conditions
Conditions Yield
With bromine; In diethyl ether; for 0.5h; Yield given; Ambient temperature;
2-Chlorobenzeneboronic acid
3900-89-8

2-Chlorobenzeneboronic acid

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

Conditions
Conditions Yield
With tetrabutylammomium bromide; copper(ll) bromide; In water; at 100 ℃; Sealed tube;
82%
With potassium bromide; In water; at 80 ℃;
(2-bromophenyl)(mesityl)iodonium trifluoromethanesulfonate

(2-bromophenyl)(mesityl)iodonium trifluoromethanesulfonate

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

Conditions
Conditions Yield
With copper(l) chloride; In acetonitrile; at 80 ℃; for 2h;
80%
o-chlorophenylhydrazine hydrochloride
41052-75-9

o-chlorophenylhydrazine hydrochloride

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

Conditions
Conditions Yield
With boron tribromide; dimethyl sulfoxide; at 80 ℃; for 1h;
81%
chlorobenzene
108-90-7

chlorobenzene

bromochlorobenzene
106-39-8

bromochlorobenzene

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

Conditions
Conditions Yield
With N-Bromosuccinimide; iron(III) chloride; In acetonitrile; for 2h;
57%
38%
With potassium bromate; In sulfuric acid; acetic acid; for 1h; Yields of byproduct given; Heating;
52%
With potassium bromate; In sulfuric acid; acetic acid; for 1h; Yield given; Heating;
52%
With cobalt(III) acetate; trifluoroacetic acid; potassium bromide; for 15h; Product distribution; Ambient temperature; Mn(CH3COO)3, 90percent aq. CF3COOH, 72 - 10 h;
With potassium nitrate; potassium bromide; In water; trifluoroacetic acid; at 20 ℃; for 24h; Product distribution; under argon;
With oxygen; potassium bromide; sodium nitrite; In water; trifluoroacetic acid; at 20 ℃; for 48h; Product distribution; other solvent, other time;
With lead(II,IV) oxide; trifluoroacetic acid; potassium bromide; at 20 ℃; Product distribution;
With lead(IV) acetate; trifluoroacetic acid; potassium bromide; at 25 ℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With bromine; ZnBr2 on silica (100 Angstroem); In hexane; at 25 ℃; for 1.33333h; Yield given. Yields of byproduct given;
With ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; bromine; zinc(II) oxide; In dichloromethane; for 4h; Heating;
With N-Bromosuccinimide; boron trifluoride; at 20 ℃; for 18h;
With sulfuryl dichloride; Ca(2+)-Y zeolite; bromine; at 25 ℃; for 24h; Further Variations:; Catalysts; Reaction partners; Reagents; Product distribution;
96.7 % Chromat.
3.3 % Chromat.
With sulfuryl dichloride; Ca(2+)-Y zeolite; bromine; at 25 ℃; for 24h;
96.7 % Chromat.
3.3 % Chromat.
With Fe(3+)-Y zeolite; bromine; at 25 ℃; for 24h;
16.0 % Chromat.
84.0 % Chromat.
With thallium (III) oxide; trifluoroacetic acid; potassium bromide; at 20 ℃; for 47h;
With N-Bromosuccinimide; 1,1,2,2-tetrafluoroethanesulfonic acid; at 20 ℃; for 8h; Overall yield = 87 %Chromat.;
With bromine; In dichloromethane; at 40 ℃; for 2h; Darkness; Inert atmosphere; Green chemistry;
85%Chromat.
7%Chromat.
With 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione; In trifluoroacetic acid; at 20 ℃; for 0.5h; Overall yield = 68 %;
With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 60 ℃; for 12h; Overall yield = 97 %; Sealed tube;
With bromine; In hexane; at 25 ℃; for 1.33333h; Darkness;
2-Chlorobenzenediazonium o-benzenedisulfonimide

2-Chlorobenzenediazonium o-benzenedisulfonimide

2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

Conditions
Conditions Yield
With tetrabutylammomium bromide; copper; In acetonitrile; at 20 ℃; for 0.75h;
61%
With tetrabutylammomium bromide; In acetonitrile; at 60 ℃; for 0.75h;
52%

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