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558-13-4

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558-13-4 Usage

Description

Carbon tetrabromide is considered a highly toxic chemical, may be fatal if inhaled, swallowed, or absorbed through skin. It is metabolized in vitro to produce carbon monoxide but the in vivo significance has not been established. Under anaerobic reducing conditions it forms complexes with ferrous cytochrome P450. Carbon monoxide is detected as a metabolic product of the interaction. Carbon tetrabromide’s production and use in organic syntheses may result in its release to the environment through various waste streams. Carbon tetrabromide has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii. It was detected in water from treated chlorinated seawater used for drinking at oil platforms. Occupational exposure to carbon tetrabromide may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. The general population may be exposed to carbon tetrabromide via ingestion of drinking water. Acute exposures to high concentrations may cause upper respiratory tract irritation and injury to lungs, liver (hepatotoxicity) and kidneys (nephrotoxicity). Chronic exposure effects at very low levels will be almost entirely limited to liver injury. It is a potent lachrymator even at low exposure concentrations. Although carbon tetrabromide may release bromine ions during metabolism, clinical bromism is not expected to occur.

Chemical Properties

Different sources of media describe the Chemical Properties of 558-13-4 differently. You can refer to the following data:
1. Crystalline colorless
2. Carbon tetrabromide, is a colorless powder, white crystalline solid, or yellow-brown crystals. Slight odor

Uses

Different sources of media describe the Uses of 558-13-4 differently. You can refer to the following data:
1. Carbon tetrabromide is used to a limited extent as a chemical intermediate. It has been isolated from red algae, Asparagopsis toxiformis, found in the ocean near Hawaii.
2. Used to a limited extent as an intermediate in organic synthesis
3. Organic synthesis.

Definition

ChEBI: A one-carbon compound substituted by 4 bromo groups.

General Description

A colorless crystalline solid. Much more dense than water and insoluble in water. Toxic by ingestion. Vapors are narcotic in high concentration. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Carbon tetrabromide is incompatible with the following: Strong oxidizers, hexacyclohexyldilead, lithium .

Hazard

A poison; narcotic in high concentration. Liver damage, eye, skin, and upper respiratory tract irritant.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

Safety Profile

Poison by subcutaneous and intravenous routes. Narcotic in high concentration. Mixture with Li particles is an impact-sensitive explosive. Explodes on contact with hexacyclohexylddead. When heated to decomposition it emits toxic fumes of Br-. See also CHLORINATED HYDROCARBONS, ALIPHATIC.

Potential Exposure

CBr4 is used in organic synthesis.

Environmental Fate

Carbon tetrabromide inhibits protein synthesis and causes lipid peroxidation, both of which may be involved in cell injury or death mediated by free radicals.

Shipping

UN2516 Carbon tetrabromide, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Reactive bromide is removed from CBr4 by refluxing with dilute aqueous Na2CO3, then steam distilling, crystallising from EtOH, and drying in the dark under vacuum. [Sharpe & Walker J Chem Soc 157 1962.] It can be sublimed at 70o and low pressure. [Beilstein 1 IV 85.]

Toxicity evaluation

Carbon tetrabromide is a colorless nonflammable solid at room temperature. It is insoluble in water, but soluble in several organic solvents such as alcohol, ether, and chloroform. Its specific gravity is 3.42, melting point is 90°C, boiling point is 189°C, and vapor pressure is 0.72 torr at 25°C. Production and use of carbon tetrabromide may result in its release in the environment through various hazardous waste streams. Carbon tetrabromide is expected to have very high mobility in soil and volatilizes slowly from dry soil surface. Its biodegradation is expected to be slow and to exist solely as a vapor in the ambient atmosphere. It is not expected to adsorb to suspended solids and sediment in the water column. Its potential for bioconcentration in aquatic organisms is moderate.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, lithium and hexacyclohexyldiilead, since violent reactions may occur.

Waste Disposal

Purify by distillation and return to suppliers.

Check Digit Verification of cas no

The CAS Registry Mumber 558-13-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 8 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 558-13:
(5*5)+(4*5)+(3*8)+(2*1)+(1*3)=74
74 % 10 = 4
So 558-13-4 is a valid CAS Registry Number.
InChI:InChI=1/CBr4/c2-1(3,4)5

558-13-4 Well-known Company Product Price

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  • Detail
  • TCI America

  • (T0038)  Carbon Tetrabromide  >99.0%(GC)

  • 558-13-4

  • 25g

  • 245.00CNY

  • Detail
  • TCI America

  • (T0038)  Carbon Tetrabromide  >99.0%(GC)

  • 558-13-4

  • 100g

  • 595.00CNY

  • Detail
  • TCI America

  • (T0038)  Carbon Tetrabromide  >99.0%(GC)

  • 558-13-4

  • 500g

  • 1,520.00CNY

  • Detail
  • Alfa Aesar

  • (L00821)  Carbon tetrabromide, 98% (dry wt.), may cont. up to ca 6% water   

  • 558-13-4

  • 25g

  • 240.0CNY

  • Detail
  • Alfa Aesar

  • (L00821)  Carbon tetrabromide, 98% (dry wt.), may cont. up to ca 6% water   

  • 558-13-4

  • 100g

  • 398.0CNY

  • Detail
  • Alfa Aesar

  • (L00821)  Carbon tetrabromide, 98% (dry wt.), may cont. up to ca 6% water   

  • 558-13-4

  • 500g

  • 1532.0CNY

  • Detail
  • Aldrich

  • (C11081)  Tetrabromomethane  ReagentPlus®, 99%

  • 558-13-4

  • C11081-5G

  • 355.68CNY

  • Detail
  • Aldrich

  • (C11081)  Tetrabromomethane  ReagentPlus®, 99%

  • 558-13-4

  • C11081-100G

  • 463.32CNY

  • Detail
  • Aldrich

  • (C11081)  Tetrabromomethane  ReagentPlus®, 99%

  • 558-13-4

  • C11081-500G

  • 2,763.54CNY

  • Detail

558-13-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tetrabromomethane

1.2 Other means of identification

Product number -
Other names Methane, tetrabromo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:558-13-4 SDS

558-13-4Synthetic route

2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

dibromodifluoromethane
75-61-6

dibromodifluoromethane

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

1,1-difluoro-2,2,3,3-tetramethylcyclopropane
823-25-6

1,1-difluoro-2,2,3,3-tetramethylcyclopropane

Conditions
ConditionsYield
With potassium hydroxide; 1,2-dibromomethane; tetra(n-butyl)ammonium hydrogensulfate at 18 - 20℃; for 27h; Product distribution; Mechanism; other alkenes;A n/a
B 70%
Vinyl bromide
593-60-2

Vinyl bromide

Bromoform
75-25-2

Bromoform

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

1,1,2-tribromocyclopropane
178425-55-3

1,1,2-tribromocyclopropane

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 0℃;A 5%
B 30%
Bromoform
75-25-2

Bromoform

A

dibromoiodomethane
593-94-2

dibromoiodomethane

B

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether; sodium iodide In dichloromethane; water at 0℃; for 48h; Iodination; substitution; Title compound not separated from byproducts;A 20%
B 7%
methane
34557-54-5

methane

A

methyl bromide
74-83-9

methyl bromide

B

Bromoform
75-25-2

Bromoform

C

carbon tetrabromide
558-13-4

carbon tetrabromide

D

1,2-dibromomethane
74-95-3

1,2-dibromomethane

Conditions
ConditionsYield
With bromine at 500℃; Product distribution; Further Variations:; Temperatures; Bromination;A 17.4%
B 0.48%
C 2.5%
D 5%
carbon disulfide
75-15-0

carbon disulfide

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine at 180 - 200℃;
With bromine; iodine(I) bromide at 150℃;
With bromine; antimony(III) bromide at 150℃; an Stelle von Antimontribromid koennen auch andere Bromide z.B. des Wismuts,Arsens,Goldes verwendet werden;
With aluminium trichloride; bromine
tetrachloromethane
56-23-5

tetrachloromethane

A

chlorotribromomethane
594-15-0

chlorotribromomethane

B

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With aluminum tri-bromide at 0℃;
tetrachloromethane
56-23-5

tetrachloromethane

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With ethyl bromide; aluminum tri-bromide
With aluminum tri-bromide at 100℃;
With aluminium trichloride; hydrogen bromide
With ethyl bromide; aluminum tri-bromide
ethanol
64-17-5

ethanol

A

bromal
115-17-3

bromal

B

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine
i-Amyl alcohol
123-51-3

i-Amyl alcohol

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine
Bromoform
75-25-2

Bromoform

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With hypobromite
With potassium hydroxide; bromine und Stehenlassen an der Sonne;
With bromine; iodine(I) bromide at 150 - 160℃;
With bromine; antimony(III) bromide at 150 - 160℃;
With sodium hydroxide; bromine
carbon tetraiodide
507-25-5

carbon tetraiodide

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine
bromopicrin
464-10-8

bromopicrin

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine; antimony(III) bromide
bis-tribromomethyl trisulfide
116277-70-4

bis-tribromomethyl trisulfide

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
ueber den Schmelzpunkt;
1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

2,4,6-trimethyl-3-tribromoacetyl-benzoic acid
859192-95-3

2,4,6-trimethyl-3-tribromoacetyl-benzoic acid

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

2,4,6-trimethyl-isophthalic acid
85190-53-0

2,4,6-trimethyl-isophthalic acid

C

3-dibromoacetyl-2,4,6-trimethyl-benzoic acid

3-dibromoacetyl-2,4,6-trimethyl-benzoic acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

bromopicrin
464-10-8

bromopicrin

Conditions
ConditionsYield
With water; bromine am Sonnenlicht;
With bromine; sodium carbonate am Sonnenlicht;
acetone
67-64-1

acetone

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With hypobromite
With sodium hydroxide; water; bromine
With sodium hydroxide; bromine
phenol
108-95-2

phenol

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With bromine statt Phenole auch mit Zuckerarten,ungesaettigte Saeuren,Alkaloiden usw.;
tetrachloromethane
56-23-5

tetrachloromethane

A

Bromotrichloromethane
75-62-7

Bromotrichloromethane

B

dibromodichloromethane
594-18-3

dibromodichloromethane

C

chlorotribromomethane
594-15-0

chlorotribromomethane

D

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With Bromoform; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Mechanism; Ambient temperature; equilibrium; products determined by GC-MS;
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

CH2Br2*Br
150714-78-6

CH2Br2*Br

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

C9H12O3(1+)*Br(1-)

C9H12O3(1+)*Br(1-)

Conditions
ConditionsYield
In neat (no solvent) at 22℃; Rate constant; Irradiation;
1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

CBr4*Br
144616-69-3

CBr4*Br

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

C9H12O3(1+)*Br(1-)

C9H12O3(1+)*Br(1-)

Conditions
ConditionsYield
In cyclohexane at 22℃; Rate constant; Irradiation;
Bromotrichloromethane
75-62-7

Bromotrichloromethane

A

tetrachloromethane
56-23-5

tetrachloromethane

B

dibromodichloromethane
594-18-3

dibromodichloromethane

C

chlorotribromomethane
594-15-0

chlorotribromomethane

D

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With chloroform; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Mechanism; Ambient temperature; without CHCl3 but add of acidic acceptor; equilibrium; products determined by GC-MS;
dibromodichloromethane
594-18-3

dibromodichloromethane

A

tetrachloromethane
56-23-5

tetrachloromethane

B

Bromotrichloromethane
75-62-7

Bromotrichloromethane

C

chlorotribromomethane
594-15-0

chlorotribromomethane

D

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With acidic acceptor; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Mechanism; Ambient temperature; equilibrium; products determined by GC-MS;
chlorotribromomethane
594-15-0

chlorotribromomethane

A

tetrachloromethane
56-23-5

tetrachloromethane

B

Bromotrichloromethane
75-62-7

Bromotrichloromethane

C

dibromodichloromethane
594-18-3

dibromodichloromethane

D

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
With acidic acceptor; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Mechanism; Ambient temperature; equilibrium; products determined by GC-MS;
Hexamethylbenzene
87-85-4

Hexamethylbenzene

CBr4*Br
144616-69-3

CBr4*Br

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

pentamethylbenzyl radical
19121-64-3

pentamethylbenzyl radical

Conditions
ConditionsYield
In cyclohexane at 22℃; Rate constant; Irradiation;
N,N-diphenylaminobenzene
603-34-9

N,N-diphenylaminobenzene

CBr4*Br
144616-69-3

CBr4*Br

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

C18H15N(1+)*Br(1-)
52301-45-8

C18H15N(1+)*Br(1-)

Conditions
ConditionsYield
In cyclohexane at 22℃; Rate constant; Irradiation;
CBr4*Br
144616-69-3

CBr4*Br

4-methoxy-phenol
150-76-5

4-methoxy-phenol

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

C7H8O2(1+)*Br(1-)

C7H8O2(1+)*Br(1-)

Conditions
ConditionsYield
In cyclohexane at 22℃; Rate constant; Irradiation;
CBr4*Br
144616-69-3

CBr4*Br

cyclohexene
110-83-8

cyclohexene

A

carbon tetrabromide
558-13-4

carbon tetrabromide

B

cyclohexen-3-yl radical
7493-04-1

cyclohexen-3-yl radical

Conditions
ConditionsYield
In cyclohexane at 22℃; Rate constant; Irradiation;
1-methyl-octahydro-pyrano[3,4-c]pyridin-3-one

1-methyl-octahydro-pyrano[3,4-c]pyridin-3-one

alkaline sodium hypobromite solution

alkaline sodium hypobromite solution

carbon tetrabromide
558-13-4

carbon tetrabromide

bromine
7726-95-6

bromine

terpenylic acid
116-51-8, 26754-48-3

terpenylic acid

alkali

alkali

carbon tetrabromide
558-13-4

carbon tetrabromide

Conditions
ConditionsYield
inactive terpenylic acid;
carbon tetrabromide
558-13-4

carbon tetrabromide

4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde
128108-47-4

4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinecarboxaldehyde

1,1-Dibromo-2-(4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridin-3-yl)ethene
129122-41-4

1,1-Dibromo-2-(4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridin-3-yl)ethene

Conditions
ConditionsYield
With sodium hydrogencarbonate; triphenylphosphine; SiO2 In hexane; dichloromethane100%
With triphenylphosphine In dichloromethane for 0.416667h; Ambient temperature; Yield given;
With triphenylphosphine In dichloromethane13.0 g (68%)
carbon tetrabromide
558-13-4

carbon tetrabromide

(2R,3S,6S)-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxy-2-(tetrahydropyran-2-yloxy)heptanal
126394-04-5

(2R,3S,6S)-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxy-2-(tetrahydropyran-2-yloxy)heptanal

(3R,4S,7S)-1,1-dibromo-7-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-4,7-bismethoxymethoxy-3-(tetrahydropyran-2-yloxy)oct-1-ene
126394-05-6

(3R,4S,7S)-1,1-dibromo-7-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-4,7-bismethoxymethoxy-3-(tetrahydropyran-2-yloxy)oct-1-ene

Conditions
ConditionsYield
With triphenylphosphine; zinc In dichloromethane for 18h; Ambient temperature;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

1-(2,2-dibromovinyl)-4-methylbenzene
60512-56-3

1-(2,2-dibromovinyl)-4-methylbenzene

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4-methyl-benzaldehyde In dichloromethane at 0℃; for 2h; Inert atmosphere;
100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 4-methyl-benzaldehyde In dichloromethane at 0℃; for 2h; Inert atmosphere;
100%
With triphenylphosphine In dichloromethane at 0℃; for 0.5h;98%
carbon tetrabromide
558-13-4

carbon tetrabromide

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(2,2-dibromovinyl)-4-methoxybenzene
60512-57-4

1-(2,2-dibromovinyl)-4-methoxybenzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 3.25h;100%
With triphenylphosphine In dichloromethane at 0℃; for 0.666667h;100%
With triphenylphosphine In dichloromethane at 0℃; for 2.25h;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

1,1-dibromo-2-(3-methoxyphenyl)ethene
253684-23-0

1,1-dibromo-2-(3-methoxyphenyl)ethene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane100%
With triphenylphosphine In dichloromethane at 0℃; for 5.25h; Inert atmosphere;96%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 3-methoxy-benzaldehyde In dichloromethane at 0℃; for 1.08333h; Inert atmosphere;
94%
carbon tetrabromide
558-13-4

carbon tetrabromide

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
22323-80-4

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

(R)-(+)-4-(2,2-Dibromoethenyl)-2,2-dimethyl-1,3-dioxolane
56017-84-6

(R)-(+)-4-(2,2-Dibromoethenyl)-2,2-dimethyl-1,3-dioxolane

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.75h;
Stage #2: (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde In dichloromethane at 0 - 20℃;
100%
Stage #1: carbon tetrabromide With triphenylphosphine; zinc In dichloromethane at 0℃; for 48h; Corey-Fuchs reaction;
Stage #2: (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde In dichloromethane for 2h; Further stages.;
61%
With triphenylphosphine In dichloromethane 0 deg C to room temp.;
carbon tetrabromide
558-13-4

carbon tetrabromide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

1,1-dibromo-2-cyclohexylethene
60754-49-6

1,1-dibromo-2-cyclohexylethene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 1.5h;100%
With triphenylphosphine In dichloromethane for 16h; Heating;98%
With triphenylphosphine92%
carbon tetrabromide
558-13-4

carbon tetrabromide

1,5-bis-triisopropylsilanylpenta-1,4-diyn-3-one
142761-85-1

1,5-bis-triisopropylsilanylpenta-1,4-diyn-3-one

(3-(dibromomethylene)penta-1,4-diyne-1,5-diyl)bis(triisopropylsilane)
142761-86-2

(3-(dibromomethylene)penta-1,4-diyne-1,5-diyl)bis(triisopropylsilane)

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 25℃;100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 1,5-bis-triisopropylsilanylpenta-1,4-diyn-3-one In dichloromethane at 0 - 23℃; for 1h; Inert atmosphere;
84%
With triphenylphosphine 1.) CH2Cl2, 0 deg C, 40 min, 2.) CH2Cl2, 0 deg C, 2 h; Yield given. Multistep reaction;
carbon tetrabromide
558-13-4

carbon tetrabromide

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

1,1-dibromo-4-methyl-1,3-pentadiene
64305-70-0

1,1-dibromo-4-methyl-1,3-pentadiene

Conditions
ConditionsYield
With triphenylphosphine; zinc In dichloromethane at 20℃;100%
Stage #1: carbon tetrabromide With triphenylphosphine; zinc In dichloromethane at 0 - 20℃;
Stage #2: 3,3-dimethyl acrylaldehyde In dichloromethane at 20℃; for 2h;
100%
Stage #1: carbon tetrabromide With triphenylphosphine; zinc In dichloromethane at 20℃; for 24h;
Stage #2: 3,3-dimethyl acrylaldehyde In dichloromethane at 20℃; for 2h;
100%
carbon tetrabromide
558-13-4

carbon tetrabromide

3,5-dimethoxybenzaldehdye
7311-34-4

3,5-dimethoxybenzaldehdye

1-(2,2-dibromoethen-1-yl)-3,5-dimethoxybenzene
205746-51-6

1-(2,2-dibromoethen-1-yl)-3,5-dimethoxybenzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 2h; Inert atmosphere;100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: 3,5-dimethoxybenzaldehdye In dichloromethane Inert atmosphere; Schlenk technique;
97%
With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h;96.4%
carbon tetrabromide
558-13-4

carbon tetrabromide

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

1-bromo-2-(2,2-dibromovinyl)benzene
213599-19-0

1-bromo-2-(2,2-dibromovinyl)benzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere;100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Wittig reaction;
Stage #2: ortho-bromobenzaldehyde In dichloromethane at 0 - 20℃;
97%
With triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;97%
carbon tetrabromide
558-13-4

carbon tetrabromide

((Z)-(2S,3S,8R,9R)-8-Bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-acetaldehyde
239121-18-7

((Z)-(2S,3S,8R,9R)-8-Bromo-3-chloro-9-ethyl-2,3,4,7,8,9-hexahydro-oxonin-2-yl)-acetaldehyde

(Z)-(2R,3R,8S,9S)-3-Bromo-8-chloro-9-(3,3-dibromo-allyl)-2-ethyl-2,3,4,7,8,9-hexahydro-oxonine

(Z)-(2R,3R,8S,9S)-3-Bromo-8-chloro-9-(3,3-dibromo-allyl)-2-ethyl-2,3,4,7,8,9-hexahydro-oxonine

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 0.5h; olefination;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

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

3,4,5-trimethoxy-benzaldehyde

1,1-Dibromo-2-(3',4',5'-trimethoxyphenyl)ethene
77295-62-6

1,1-Dibromo-2-(3',4',5'-trimethoxyphenyl)ethene

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.25h; Corey-Fuchs homologation;
Stage #2: 3,4,5-trimethoxy-benzaldehyde In dichloromethane at 0℃; for 0.0833333h; Corey-Fuchs homologation;
100%
With triphenylphosphine In dichloromethane at 25℃; for 16h;99%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: 3,4,5-trimethoxy-benzaldehyde In dichloromethane Inert atmosphere; Schlenk technique;
94%
carbon tetrabromide
558-13-4

carbon tetrabromide

O-isopropylisovanillin
34123-66-5

O-isopropylisovanillin

β,β-dibromo-3-isopropoxy-4-methoxystyrene
215715-43-8

β,β-dibromo-3-isopropoxy-4-methoxystyrene

Conditions
ConditionsYield
With triphenylphosphine; zinc In dichloromethane at 0 - 20℃; Inert atmosphere;100%
Stage #1: carbon tetrabromide With triphenylphosphine; zinc In dichloromethane at 18℃; for 22h; complexation;
Stage #2: O-isopropylisovanillin In dichloromethane at 18℃; for 1h; Corey-Fuchs olefination;
99%
With triphenylphosphine; zinc In dichloromethane at 20℃; for 4h;93%
With triphenylphosphine; zinc In dichloromethane
With triphenylphosphine; zinc In dichloromethane at 20℃; for 1h; Corey-Fuchs Alkyne Synthesis;
carbon tetrabromide
558-13-4

carbon tetrabromide

2,5-bis(octyloxy)-4-[(triisopropylsilyl)ethynyl]benzaldehyde
350230-73-8

2,5-bis(octyloxy)-4-[(triisopropylsilyl)ethynyl]benzaldehyde

{[4-(2,2-dibromoethenyl)-2,5-bis(octyloxy)phenyl]ethynyl}triisopropylsilane
350230-74-9

{[4-(2,2-dibromoethenyl)-2,5-bis(octyloxy)phenyl]ethynyl}triisopropylsilane

Conditions
ConditionsYield
With triphenylphosphine; zinc In dichloromethane at 0 - 20℃; for 13h;100%
With triphenylphosphine; zinc In dichloromethane at 0 - 20℃; for 12h; Corey-Fuchs reaction;99%
carbon tetrabromide
558-13-4

carbon tetrabromide

(1S,5R)-1-formylbicyclo[3.1.0]hexan-2-one
406457-39-4

(1S,5R)-1-formylbicyclo[3.1.0]hexan-2-one

(1S,5R)-1-(2',2'-dibromovinyl)bicyclo[3.1.0]hexan-2-one
406457-42-9

(1S,5R)-1-(2',2'-dibromovinyl)bicyclo[3.1.0]hexan-2-one

Conditions
ConditionsYield
With triphenylphosphine; zinc In dichloromethane at 0℃; for 1.5h;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

1,1-dibromo-2-(2-methylphenyl)ethene
104464-03-1

1,1-dibromo-2-(2-methylphenyl)ethene

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 1h; Inert atmosphere;
Stage #2: 2-methylphenyl aldehyde In dichloromethane at 0 - 20℃; Inert atmosphere;
100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2-methylphenyl aldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere;
98%
With triphenylphosphine In dichloromethane at 0℃; for 0.5h;91%
carbon tetrabromide
558-13-4

carbon tetrabromide

1-naphthaldehyde
66-77-3

1-naphthaldehyde

1-(2,2-dibromovinyl)naphthalene
77295-63-7

1-(2,2-dibromovinyl)naphthalene

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 1-naphthaldehyde In dichloromethane at 20℃; for 1h; Inert atmosphere;
100%
With triphenylphosphine In dichloromethane at 0℃; for 2h; Inert atmosphere;88%
With triphenylphosphine In dichloromethane at 0℃; Inert atmosphere;75%
3’,5'-dimethyl-[1,1’]-biphenyl-2-carbaldehyde
445262-63-5

3’,5'-dimethyl-[1,1’]-biphenyl-2-carbaldehyde

carbon tetrabromide
558-13-4

carbon tetrabromide

2-(2,2-dibromovinyl)-3',5'-dimethyl-1,1'-biphenyl
445262-66-8

2-(2,2-dibromovinyl)-3',5'-dimethyl-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.166667h;
Stage #2: 3’,5'-dimethyl-[1,1’]-biphenyl-2-carbaldehyde In dichloromethane at 0℃; for 1h;
100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.166667h;
Stage #2: 3’,5'-dimethyl-[1,1’]-biphenyl-2-carbaldehyde In dichloromethane at 0℃; for 1h; Further stages.;
100%
With triisopropyl phosphite In dichloromethane at 0℃; for 3.5h;97%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: 3’,5'-dimethyl-[1,1’]-biphenyl-2-carbaldehyde In dichloromethane at 0℃; Inert atmosphere;
88%
carbon tetrabromide
558-13-4

carbon tetrabromide

2,3,4-trimethoxybenzaldehyde
2103-57-3

2,3,4-trimethoxybenzaldehyde

1-(2,2-dibromovinyl)-2,3,4-trimethoxybenzene
849186-15-8

1-(2,2-dibromovinyl)-2,3,4-trimethoxybenzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane100%
C48H42O6
863647-14-7

C48H42O6

carbon tetrabromide
558-13-4

carbon tetrabromide

C54H42Br12

C54H42Br12

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine; zinc In dichloromethane at 25℃;
Stage #2: C48H42O6 In dichloromethane at 25℃; for 72h; Corey-Fuchs reaction;
100%
carbon tetrabromide
558-13-4

carbon tetrabromide

(M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbaldehyde

(M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbaldehyde

(M)-5,8-bis(2,2-dibromoethenyl)-1,12-dimethylbenzo[c]phenanthrene

(M)-5,8-bis(2,2-dibromoethenyl)-1,12-dimethylbenzo[c]phenanthrene

Conditions
ConditionsYield
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0℃; for 0.75h;
Stage #2: (M)-1,12-dimethylbenzo[c]phenanthrene-5,8-dicarbaldehyde In dichloromethane for 3.5h; Further stages.;
100%
1,16-bis(4-tert-butyl-2-formylphenyloxy)hexadecane
887369-02-0

1,16-bis(4-tert-butyl-2-formylphenyloxy)hexadecane

carbon tetrabromide
558-13-4

carbon tetrabromide

1,16-bis[4-tert-butyl-2-(2,2-dibromoethenyl)phenyloxy]hexadecane
887369-08-6

1,16-bis[4-tert-butyl-2-(2,2-dibromoethenyl)phenyloxy]hexadecane

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 0.333333h; Corey-Fuchs olefination;100%
(R)-2-((S)-3-Chloro-1-methyl-propyl)-pent-4-enal

(R)-2-((S)-3-Chloro-1-methyl-propyl)-pent-4-enal

carbon tetrabromide
558-13-4

carbon tetrabromide

(4S,5R)-7-Chloro-4-(2,2-dibromo-vinyl)-5-methyl-hept-1-ene

(4S,5R)-7-Chloro-4-(2,2-dibromo-vinyl)-5-methyl-hept-1-ene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0℃; for 0.333333h;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

(R)-4,4',6,6'-tetra[(1H,1H,2H,2H-heptadecafluorodecyl)(dimethyl)silyl]-2,2'-bis(hydroxymethyl)-1,1'-binaphthyl

(R)-4,4',6,6'-tetra[(1H,1H,2H,2H-heptadecafluorodecyl)(dimethyl)silyl]-2,2'-bis(hydroxymethyl)-1,1'-binaphthyl

(R)-4,4',6,6'-tetra[(1H,1H,2H,2H-heptadecafluorodecyl)(dimethyl)silyl]-2,2'-bis(bromomethyl)-1,1'-binaphthyl

(R)-4,4',6,6'-tetra[(1H,1H,2H,2H-heptadecafluorodecyl)(dimethyl)silyl]-2,2'-bis(bromomethyl)-1,1'-binaphthyl

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran at 20℃; for 4h;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

tert-butyl 4-(dibromomethylidene)piperidine-1-carboxylate
305794-65-4

tert-butyl 4-(dibromomethylidene)piperidine-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere;100%
With triphenylphosphine In acetonitrile at 0 - 25℃; for 2.25h;56%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h;
Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at -78 - 20℃;
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃;
Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at -78 - 20℃;
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃;
Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at -78 - 20℃;
(Z)-3-(4-bromophenyl)-3-iodoprop-2-en-1-ol
452296-51-4

(Z)-3-(4-bromophenyl)-3-iodoprop-2-en-1-ol

carbon tetrabromide
558-13-4

carbon tetrabromide

1-bromo-4-((Z)-3-bromo-1-iodopropenyl)benzene
869209-22-3

1-bromo-4-((Z)-3-bromo-1-iodopropenyl)benzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 0 - 20℃;100%
carbon tetrabromide
558-13-4

carbon tetrabromide

3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

1-(2,2-Dibromo-vinyl)-3-fluoro-benzene
221148-37-4

1-(2,2-Dibromo-vinyl)-3-fluoro-benzene

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 10℃; for 1h;
Stage #2: 3-Fluorobenzaldehyde In dichloromethane at 0℃; for 1h;
100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 10℃; for 1.05h;
Stage #2: 3-Fluorobenzaldehyde In dichloromethane at 0℃; for 1h;
100%
carbon tetrabromide
558-13-4

carbon tetrabromide

2-(3-fluorophenyl)ethanol
52059-53-7

2-(3-fluorophenyl)ethanol

1-(2-bromoethyl)-3-fluorobenzene
25017-13-4

1-(2-bromoethyl)-3-fluorobenzene

Conditions
ConditionsYield
With triphenylphosphine In diethyl ether100%
carbon tetrabromide
558-13-4

carbon tetrabromide

4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

1-Bromo-4-phenylbutane
13633-25-5

1-Bromo-4-phenylbutane

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane; hexane-diethyl ether100%

558-13-4Relevant articles and documents

-

Woodward,Fuson

, p. 3472,3474 (1933)

-

-

Bolas,Groves

, p. 773 (1871)

-

-

Bolas,Groves

, (1870)

-

Goldhaber et al.

, p. 2271,2272 (1951)

Gas-phase radiosynthesis of [11C]methyl bromide: The new route to [11C]methyl triflate

Mock,Mulholland,Vavrek

, p. S135-S137 (2007/10/03)

-

Fluoride anion catalyzed halogen dance in polyhalomethanes

Sasson, Y.,Kitson, F.,Webster, O, W.

, p. 599 - 600 (2007/10/02)

Tetrabutylammonium fluoride catalyzes the exchange of halogens between tetrahalomethanes.The presence of small amounts of haloform is suspected to be a necessary co-catalyst.Key Words: tetrabutyl ammonium fluoride; tetrahalomethanes; halogen exchange in.

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