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593-60-2

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593-60-2 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 593-60-2 differently. You can refer to the following data:
1. colourless liquid
2. Vinyl bromide is a colorless gas or liquid at low ambient temperature. Pleasant odor. Shipped as a liquefied compressed gas with 0.1% phenol added to prevent polymerization.

Uses

Different sources of media describe the Uses of 593-60-2 differently. You can refer to the following data:
1. Vinyl bromide is used as a fire retardant inplastics.
2. Production of flame-resistant plastics or thermoplastic resins.

Production Methods

VB can be produced by the catalytic addition of hydrogen bromide to acetylene in the presence of mercury and copper halide catalysts or by partial dehydrobromination of ethylene dibromide with alcoholic potassium hydroxide.

General Description

Boiling point 60°F. Liquid at low ambient temperatures. Specific gravity 1.51. A suspected carcinogen. Under exposure to fire or heat containers may rupture violently and rocket.

Air & Water Reactions

Highly flammable, with air forms peroxides

Reactivity Profile

VINYL BROMIDE is a light sensitive, peroxidizable monomer may initiate exothermic polymerization of the bulk material [Handling Chemicals Safely 1980.. p. 958]. Vinyl bromide will react violently with oxidants.

Health Hazard

Different sources of media describe the Health Hazard of 593-60-2 differently. You can refer to the following data:
1. Vapors may cause dizziness or asphyxiation without warning. Some may be toxic if inhaled at high concentrations. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating and/or toxic gases.
2. Inhalation of this gas at high concentrationscan produce anesthesia and kidney damage.Exposure to 2.5% concentration in air pro duced anesthetic effects in rats. A 15-minuteexposure to 10% concentration was fatal torats (ACGIH 1986). Kidney injury occurredat a 5% exposure level. Human toxicity datafor this compound are not available. The liq uid is mild to moderately irritating to theeyes.Vinyl bromide manifested carcinogenicproperties in laboratory animals. It producedliver and blood tumors in rats and mice.Its cancer-causing effects in humans arenot known. However, on the basis of itssimilarity to vinyl chloride, it is suspectedto be a human carcinogen.

Fire Hazard

EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Silane will ignite spontaneously in air. May polymerize explosively when heated or involved in a fire. Vapors from liquefied gas are initially heavier than air and spread along ground. Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Moderately toxic by ingestion. Mutation data reported. A very dangerous fire hazard when exposed to heat or flame. Can react violently with oxidzing materials. May polymerize in sunlight. To fight fire, use CO2, dry chemical, or water spray. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES and VINYL CHLORIDE.

Potential Exposure

Vinyl bromide is used as an intermediate in organic synthesis and for the preparation of plastics by polymerization and copolymerization; as a comonomer with acrylonitrile and other vinyl monomers in modacrylic fibers; in the production of flame-retardant synthetic fibers.

Carcinogenicity

Vinyl bromide is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Shipping

UN1085 Vinyl bromide, stabilized, Hazard Class: 2.1; Labels: 2.1-Flammable gas. Cylinders must be transported in a secure upright position, in a well-ventilated truck. Protect cylinder and labels from physical damage. The owner of the compressed gas cylinder is the only entity allowed by federal law (49CFR) to transport and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express written permission of the owner.

Incompatibilities

Vinyl bromide is a dangerous chemically unstable compound that may polymerize spontaneously in heat, sunlight and possibly exposure to UV. Dangerously reactive with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, acetylene, strong acids, strong bases, copper compounds. Add 0.1% phenol to gas to prevent polymerization.

Check Digit Verification of cas no

The CAS Registry Mumber 593-60-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 3 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 593-60:
(5*5)+(4*9)+(3*3)+(2*6)+(1*0)=82
82 % 10 = 2
So 593-60-2 is a valid CAS Registry Number.
InChI:InChI=1/C2H3Br/c1-2-3/h2H,1H2

593-60-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (V0127)  Vinyl Bromide (ca. 12% in Tetrahydrofuran, ca. 1.0mol/L)  

  • 593-60-2

  • 100mL

  • 780.00CNY

  • Detail
  • Aldrich

  • (434191)  Vinylbromidesolution  1.0 M in THF

  • 593-60-2

  • 434191-100ML

  • 873.99CNY

  • Detail
  • Aldrich

  • (434191)  Vinylbromidesolution  1.0 M in THF

  • 593-60-2

  • 434191-800ML

  • 3,763.89CNY

  • Detail

593-60-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name bromoethene

1.2 Other means of identification

Product number -
Other names Vinyl bromide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Vinyl bromide is primarily used in the manufacture of flame retardant synthetic fibers. Its copolymer with vinyl chloride is also used for preparing films, for laminating fibers, and as rubber substitutes.
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:593-60-2 SDS

593-60-2Synthetic route

ethylene dibromide
106-93-4

ethylene dibromide

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 40℃; for 1h;70%
With potassium hydroxide In ethanol Heating;56%
With potassium hydroxide at 60℃;
acrylic acid
79-10-7

acrylic acid

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
With N,N-dimethyl-formamide; potassium bromide; trichlorophosphate In acetonitrile at 20℃; Reagent/catalyst; Sonication;60%
1,2,2,4,5,5-hexamethyl-piperazine
99178-24-2

1,2,2,4,5,5-hexamethyl-piperazine

ethylene dibromide
106-93-4

ethylene dibromide

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1,2,2,4,5,5-hexamethyl-piperazine; dihydrobromide

1,2,2,4,5,5-hexamethyl-piperazine; dihydrobromide

diethyl ether
60-29-7

diethyl ether

1,1,2-tribromoethane
78-74-0

1,1,2-tribromoethane

phenylmagnesium bromide

phenylmagnesium bromide

A

bromobenzene
108-86-1

bromobenzene

B

Vinyl bromide
593-60-2

Vinyl bromide

C

biphenyl
92-52-4

biphenyl

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
Zersetzen des Reaktionsproduktes mit Wasser;
1,1-Dibromoethane
557-91-5

1,1-Dibromoethane

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

A

Vinyl bromide
593-60-2

Vinyl bromide

B

acetylene
74-86-2

acetylene

1,1-Dibromoethane
557-91-5

1,1-Dibromoethane

Vinyl bromide
593-60-2

Vinyl bromide

1,1,2-tribromoethane
78-74-0

1,1,2-tribromoethane

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
With diethyl ether; phenylmagnesium bromide und Zers. des Reaktionsproduktes mit Wasser;
1,4-dibenzyl-2,2,5,5-tetramethyl-piperazine
856929-61-8

1,4-dibenzyl-2,2,5,5-tetramethyl-piperazine

ethylene dibromide
106-93-4

ethylene dibromide

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1,4-dibenzyl-2,2,5,5-tetramethyl-piperazine; dihydrobromide

1,4-dibenzyl-2,2,5,5-tetramethyl-piperazine; dihydrobromide

1,1-Dibromoethane
557-91-5

1,1-Dibromoethane

aniline
62-53-3

aniline

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
at 120 - 125℃;
acetylene
74-86-2

acetylene

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
With hydrogen bromide; copper(I) bromide at 60℃;
With pyridine-base; hydrogen bromide; cadmium(II) bromide at 215 - 230℃;
With BaBr2-charcoal; hydrogen bromide at 200℃;
acetylene
74-86-2

acetylene

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1,1-Dibromoethane
557-91-5

1,1-Dibromoethane

Conditions
ConditionsYield
With mercury bromide; hydrogen bromide at 200℃;
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

vinyl cation
14604-48-9

vinyl cation

A

ethyl bromide
74-96-4

ethyl bromide

B

Vinyl bromide
593-60-2

Vinyl bromide

C

ethene
74-85-1

ethene

D

acetylene
74-86-2

acetylene

Conditions
ConditionsYield
With hydrogen at 100℃; under 60 - 600 Torr; Product distribution; Kinetics; Thermodynamic data; labelled with tritium; -ΔH;
ethyl bromide
74-96-4

ethyl bromide

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1,1-Dibromoethane
557-91-5

1,1-Dibromoethane

C

ethane
74-84-0

ethane

D

ethene
74-85-1

ethene

E

n-butane
106-97-8

n-butane

Conditions
ConditionsYield
at 24.9℃; Quantum yield; Irradiation; dependence of the product quantum yields on ethyl bromide pressure, photolysios time and additives (as N2, CF4, NO).;
1-bromo-1-chloroethane
593-96-4

1-bromo-1-chloroethane

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
copper and nickel chlorides at 170℃; Equilibrium constant; Thermodynamic data; 200 - 250 deg C, ΔH(excit.), ΔS(excit.);
Bromocyclobutane
4399-47-7

Bromocyclobutane

A

Vinyl bromide
593-60-2

Vinyl bromide

B

ethene
74-85-1

ethene

C

buta-1,3-diene
106-99-0

buta-1,3-diene

Conditions
ConditionsYield
With sulphur hexafluoride In gaseous matrix Rate constant; Thermodynamic data; Irradiation; effect of laser fluence, effect of partial pressure of SF6, energy distribution, activation energy;
vinyl radical
2669-89-8

vinyl radical

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
With bromine at 23.9 - 258.9℃; Kinetics; Irradiation; carrier gas, He, the role of resonance stabilization;
N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

ethylene dibromide
106-93-4

ethylene dibromide

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1,2-bisethane
6141-70-4

1,2-bisethane

C

1--2-bromoethane

1--2-bromoethane

Conditions
ConditionsYield
With sodium hydride 1.) Et2O, -78 deg C, 0.5 h, 2.) diglyme, 50 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;
(6-iodohex-1-yn-1-yl)benzene
57718-12-4

(6-iodohex-1-yn-1-yl)benzene

allyl bromide
106-95-6

allyl bromide

A

Vinyl bromide
593-60-2

Vinyl bromide

B

(1-cyclopentylidene-3-butenyl)benzene
57718-21-5

(1-cyclopentylidene-3-butenyl)benzene

Conditions
ConditionsYield
With tert.-butyl lithium 1.) pentane, Et2O, from -78 deg C to RT, 1 h, 2.) pentane, Et2O, -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;
2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

3-bromo-3-methyldiazirine
4222-23-5

3-bromo-3-methyldiazirine

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1-Bromo-1,2,2,3,3-pentamethyl-cyclopropane
96335-77-2

1-Bromo-1,2,2,3,3-pentamethyl-cyclopropane

Conditions
ConditionsYield
In n-heptane Product distribution; Quantum yield; Mechanism; Irradiation; energy data: ΔH;
In n-heptane at 80℃; Product distribution; Mechanism; Thermodynamic data; ΔH;
acetylene
74-86-2

acetylene

A

Vinyl bromide
593-60-2

Vinyl bromide

B

bromoethyne
593-61-3

bromoethyne

C

bromodiacetylene
6088-90-0

bromodiacetylene

Conditions
ConditionsYield
With hydrogen bromide at -261.2℃; for 5.03333h; Product distribution; Irradiation;
ethene
74-85-1

ethene

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
With bromine In methanol at 25℃; Mechanism; deuterium kinetic isotope effect; also deuterated ethylenes; other solvent;
methane
34557-54-5

methane

Bromotrifluoromethane
75-63-8

Bromotrifluoromethane

A

methyl bromide
74-83-9

methyl bromide

B

Vinyl bromide
593-60-2

Vinyl bromide

C

bromofluoromethane
373-52-4

bromofluoromethane

D

trifluoromethan
75-46-7

trifluoromethan

E

Vinylidene fluoride
75-38-7

Vinylidene fluoride

F

1,1-dibromomethane
74-95-3

1,1-dibromomethane

Conditions
ConditionsYield
Mn exchaged zeolite ZSM-5 at 599.85℃; Product distribution; other catalysts, temp.;
ethylene dibromide
106-93-4

ethylene dibromide

alkali

alkali

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
Kinetics; Bromwasserstoffabspaltung;
ethylene dibromide
106-93-4

ethylene dibromide

concentrated alcoholic KOH-solution

concentrated alcoholic KOH-solution

Vinyl bromide
593-60-2

Vinyl bromide

ethylene dibromide
106-93-4

ethylene dibromide

mercury (I)-fluoride

mercury (I)-fluoride

Vinyl bromide
593-60-2

Vinyl bromide

Conditions
ConditionsYield
at 120 - 140℃;
water
7732-18-5

water

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

acetylene
74-86-2

acetylene

mercury (II)-bromide

mercury (II)-bromide

A

Vinyl bromide
593-60-2

Vinyl bromide

B

1,1-Dibromoethane
557-91-5

1,1-Dibromoethane

Conditions
ConditionsYield
at 100℃; under 80 - 240 Torr; Kinetics;
ethylene dibromide
106-93-4

ethylene dibromide

KF

KF

A

Vinyl bromide
593-60-2

Vinyl bromide

B

2-fluoroethyl bromide
762-49-2

2-fluoroethyl bromide

Conditions
ConditionsYield
at 200℃;
ethylene glycol
107-21-1

ethylene glycol

ethylene dibromide
106-93-4

ethylene dibromide

KF

KF

A

Vinyl bromide
593-60-2

Vinyl bromide

B

2-fluoroethyl bromide
762-49-2

2-fluoroethyl bromide

Conditions
ConditionsYield
at 150℃;
Vinyl bromide
593-60-2

Vinyl bromide

1-phenylethylmagnesium chloride
60779-09-1

1-phenylethylmagnesium chloride

3-phenylbut-1-ene
934-10-1

3-phenylbut-1-ene

Conditions
ConditionsYield
With (2R,3R)-2,3-(2,5,8,11-tetrathiadodecamethylene)-1,4-dioxaspiro<4.5>decane; nickel dichloride In diethyl ether at -10 - 0℃; for 24h; Product distribution; var. of ligand, temp., ratio, time; asymmetric induction;100%
all-(S) 4-Me2N-cis-decaline[3,2-b](1-Ph2P-ferrocene)*PdCl2 In diethyl ether at 0℃; for 24h;96%
Vinyl bromide
593-60-2

Vinyl bromide

(R)-Citronellal
2385-77-5

(R)-Citronellal

(5R)-5,9-dimethyl-1,8-decadien-3-ol
1037496-91-5

(5R)-5,9-dimethyl-1,8-decadien-3-ol

Conditions
ConditionsYield
Stage #1: Vinyl bromide With magnesium In tetrahydrofuran at 20℃; for 2h;
Stage #2: (R)-Citronellal In tetrahydrofuran at 20℃; for 3h; Further stages.;
100%
Vinyl bromide
593-60-2

Vinyl bromide

1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one
132563-81-6

1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one

(3S,4R)-3-(2,4-Difluorophenyl)-4-(2-tetrahydropyranyloxy)-1-penten-3-ol
126945-39-9

(3S,4R)-3-(2,4-Difluorophenyl)-4-(2-tetrahydropyranyloxy)-1-penten-3-ol

Conditions
ConditionsYield
With sodium chloride; ammonium chloride; magnesium In tetrahydrofuran; acetone100%
4,4-dimethyl-1,3-oxazolidin-2-one
26654-39-7

4,4-dimethyl-1,3-oxazolidin-2-one

Vinyl bromide
593-60-2

Vinyl bromide

4,4-dimethyl-3-vinyloxazolidin-2-one
929554-28-9

4,4-dimethyl-3-vinyloxazolidin-2-one

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 113℃; for 16h;100%
Vinyl bromide
593-60-2

Vinyl bromide

N-(2-(cyclohex-1-en-1-yl)ethyl)-4-methylbenzenesulfonamide
389079-71-4

N-(2-(cyclohex-1-en-1-yl)ethyl)-4-methylbenzenesulfonamide

C17H23NO2S
1180843-91-7

C17H23NO2S

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In tetrahydrofuran at 80℃; Inert atmosphere;100%
4-bromo-1-ethynylbenzene
766-96-1

4-bromo-1-ethynylbenzene

Vinyl bromide
593-60-2

Vinyl bromide

1-bromo-4-(but-3-en-1-yn-1-yl)benzene

1-bromo-4-(but-3-en-1-yn-1-yl)benzene

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 20 - 50℃; Sonogashira Cross-Coupling; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 24℃; for 4h; Inert atmosphere; Alkaline conditions;96%
Stage #1: Vinyl bromide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Sonogashira Cross-Coupling; Inert atmosphere;
Stage #2: 4-bromo-1-ethynylbenzene In tetrahydrofuran at 20℃; Inert atmosphere;
79.1%
Vinyl bromide
593-60-2

Vinyl bromide

1,6-dibromodiamantane
32401-10-8

1,6-dibromodiamantane

1,6-bis(2,2-dibromoethyl)diamantane

1,6-bis(2,2-dibromoethyl)diamantane

Conditions
ConditionsYield
With aluminium bromide at -50℃; for 1h;100%
Vinyl bromide
593-60-2

Vinyl bromide

tert-butyldimethylsilyl hex-5-yn-1-yl ether
73448-13-2

tert-butyldimethylsilyl hex-5-yn-1-yl ether

8-<(tert-butyldimethylsilyl)oxy>-1-octen-3-yne
138059-76-4

8-<(tert-butyldimethylsilyl)oxy>-1-octen-3-yne

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine for 2h; Ambient temperature;99%
Vinyl bromide
593-60-2

Vinyl bromide

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
6141-72-6

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)

1-bromo-2-<-1->ethane

1-bromo-2-<-1->ethane

Conditions
ConditionsYield
for 1h; Ambient temperature; in vacuo;99%
Vinyl bromide
593-60-2

Vinyl bromide

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

1-(but-3-en-1-yn-1-yl)-4-methoxybenzene
55088-86-3

1-(but-3-en-1-yn-1-yl)-4-methoxybenzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;99%
Stage #1: Vinyl bromide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Sonogashira Cross-Coupling; Inert atmosphere;
Stage #2: 4-methoxyphenylacetylen In tetrahydrofuran at 20℃; Inert atmosphere;
92.5%
C21H17NO4
943151-35-7

C21H17NO4

Vinyl bromide
593-60-2

Vinyl bromide

C23H21NO4
943151-36-8

C23H21NO4

Conditions
ConditionsYield
Stage #1: Vinyl bromide With tert.-butyl lithium In diethyl ether at -78℃; for 0.25h;
Stage #2: C21H17NO4 In tetrahydrofuran; diethyl ether at 0℃; for 0.166667h; Further stages.;
99%
Vinyl bromide
593-60-2

Vinyl bromide

[(4'-(4-t-butylphenyl)-2,2':6',2''-terpyridine)Rh(Br)]
654085-09-3

[(4'-(4-t-butylphenyl)-2,2':6',2''-terpyridine)Rh(Br)]

Rh(III)Br2(ethenyl)(4'-(4-tertbutylphenyl)-2,2':6',2''-terpyridine)
654085-21-9

Rh(III)Br2(ethenyl)(4'-(4-tertbutylphenyl)-2,2':6',2''-terpyridine)

Conditions
ConditionsYield
In ethanol Ar; adding 100 equiv. of bromoethene to a mixt. of Rh complex with ethanol at room temp.; pouring the mixt. into pentane after 5 min, decantation, washing the solid with pentane, drying under reduced pressure;99%
1-decyne
764-93-2

1-decyne

Vinyl bromide
593-60-2

Vinyl bromide

1-dodecene-3-yne
74744-36-8

1-dodecene-3-yne

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;95%
Vinyl bromide
593-60-2

Vinyl bromide

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

1-(but-3-en-1-yn-1-yl)-4-methylbenzene
30011-66-6

1-(but-3-en-1-yn-1-yl)-4-methylbenzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; Sealed tube; Inert atmosphere;95%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;84%
Vinyl bromide
593-60-2

Vinyl bromide

1-Ethynyl-1-cyclohexanol
78-27-3

1-Ethynyl-1-cyclohexanol

1-vinylethynyl-1-cyclohexanol
2696-22-2

1-vinylethynyl-1-cyclohexanol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 0 - 20℃; for 6.5h;98%
Vinyl bromide
593-60-2

Vinyl bromide

1-Phenyl-2-propyn-1-ol
4187-87-5

1-Phenyl-2-propyn-1-ol

1-phenylpent-4-en-2-yn-1-ol
2720-52-7

1-phenylpent-4-en-2-yn-1-ol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;88%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 0 - 20℃; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;76%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 0 - 25℃; Inert atmosphere;45.9%
Vinyl bromide
593-60-2

Vinyl bromide

(2-fluorophenyl)acetylene
766-49-4

(2-fluorophenyl)acetylene

1-(but-3-en-1-yn-1-yl)-2-fluorobenzene

1-(but-3-en-1-yn-1-yl)-2-fluorobenzene

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethylamine at 0 - 20℃; Inert atmosphere;69%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique;29%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Glovebox;
Vinyl bromide
593-60-2

Vinyl bromide

4-trifluoromethylphenylacetylene
705-31-7

4-trifluoromethylphenylacetylene

1-(but-3-en-1-yn-1-yl)-4-(trifluoromethyl)benzene

1-(but-3-en-1-yn-1-yl)-4-(trifluoromethyl)benzene

Conditions
ConditionsYield
Stage #1: Vinyl bromide With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Sonogashira Cross-Coupling; Inert atmosphere;
Stage #2: 4-trifluoromethylphenylacetylene In tetrahydrofuran at 20℃; Inert atmosphere;
99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; Schlenk technique;89%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Sealed tube; Inert atmosphere;
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine at 20℃; Sonogashira Cross-Coupling; Inert atmosphere;
Vinyl bromide
593-60-2

Vinyl bromide

6-benzoyloxy-1-hexyne
216064-35-6

6-benzoyloxy-1-hexyne

oct-7-en-5-yn-1-yl benzoate

oct-7-en-5-yn-1-yl benzoate

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;99%
Vinyl bromide
593-60-2

Vinyl bromide

n-octyne
629-05-0

n-octyne

dec-1-en-3-yne
33622-26-3

dec-1-en-3-yne

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine In tetrahydrofuran at 50℃; for 2h; Sonogashira Cross-Coupling;98%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;90%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;90%
Vinyl bromide
593-60-2

Vinyl bromide

3-[1,3]Dioxolan-2-ylmethyl-4-methyl-pentanal
127643-19-0

3-[1,3]Dioxolan-2-ylmethyl-4-methyl-pentanal

5-[1,3]Dioxolan-2-ylmethyl-6-methyl-hept-1-en-3-ol
127600-26-4

5-[1,3]Dioxolan-2-ylmethyl-6-methyl-hept-1-en-3-ol

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran98%
Vinyl bromide
593-60-2

Vinyl bromide

acetylmercaptoacetonitrile

acetylmercaptoacetonitrile

3-amino-5-phenylthiophene-2-carbonitrile
83060-72-4

3-amino-5-phenylthiophene-2-carbonitrile

Conditions
ConditionsYield
With NaOCH3 In ethanol; chloroform98%
Vinyl bromide
593-60-2

Vinyl bromide

pent-4-ynyl 4-(trifluoromethyl)benzoate
1567325-02-3

pent-4-ynyl 4-(trifluoromethyl)benzoate

hept-6-en-4-yn-1-yl 4-(trifluoromethyl)benzoate

hept-6-en-4-yn-1-yl 4-(trifluoromethyl)benzoate

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 0 - 20℃; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;98%
Vinyl bromide
593-60-2

Vinyl bromide

1,1,2-tribromoethane
78-74-0

1,1,2-tribromoethane

Conditions
ConditionsYield
With bromine In dichloromethane at 0 - 22℃; for 2h; Inert atmosphere;97%
With bromine In chloroform at 20℃; for 12h; Bromination;87%
With bromine
Vinyl bromide
593-60-2

Vinyl bromide

2-(phenylselenenyl)-2-cyclopentenone
71996-27-5

2-(phenylselenenyl)-2-cyclopentenone

LiMe2Cu

LiMe2Cu

3-Methyl-2-phenylselanyl-2-vinyl-cyclopentanone

3-Methyl-2-phenylselanyl-2-vinyl-cyclopentanone

Conditions
ConditionsYield
97%
Vinyl bromide
593-60-2

Vinyl bromide

(2S)-di-tert-butyl 5-methoxypyrrolidine-1,2-dicarboxylate
228579-91-7

(2S)-di-tert-butyl 5-methoxypyrrolidine-1,2-dicarboxylate

L-N-(tert-butyloxycarbonyl)-5-vinylproline tert-butyl ester
1017802-73-1

L-N-(tert-butyloxycarbonyl)-5-vinylproline tert-butyl ester

Conditions
ConditionsYield
Stage #1: Vinyl bromide With iodine; magnesium In tetrahydrofuran for 0.5h;
Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -40℃; for 0.75h;
Stage #3: (2S)-di-tert-butyl 5-methoxypyrrolidine-1,2-dicarboxylate With boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 20℃; for 4.5h;
97%
Vinyl bromide
593-60-2

Vinyl bromide

cycloocta-1,5-dienebis(triphenylphosphine)nickel(0)
12151-13-2

cycloocta-1,5-dienebis(triphenylphosphine)nickel(0)

A

Ni(P(C6H5)3)2(C2H3)Br

Ni(P(C6H5)3)2(C2H3)Br

B

1,5-dicyclooctadiene
5259-72-3, 10060-40-9, 111-78-4

1,5-dicyclooctadiene

Conditions
ConditionsYield
In hexane addn. of Ni-complex to soln. of vinyl bromide in hexane (stirring, -50-(-70)°C), after 30 min warming to -10°C, stirring 30 min; filtration, washing (cold hexane), drying (vac., -10°C);A 97%
B n/a
Vinyl bromide
593-60-2

Vinyl bromide

copper(I) bromide dimethylsulfide complex

copper(I) bromide dimethylsulfide complex

Li(Cr(CO)3(η6-C6H4OMe-2))
69786-76-1

Li(Cr(CO)3(η6-C6H4OMe-2))

η6-[(2-methoxy)vinylbenzene]tricarbonylchromium(0)
164577-77-9, 52456-48-1, 147127-36-4

η6-[(2-methoxy)vinylbenzene]tricarbonylchromium(0)

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran react. with 1 equiv. CuBr*SMe2 in THF at -78°C, then with 1 equiv. CH2=CHBr and Pd(PPh3)4, -78°C to room temp.;97%
Vinyl bromide
593-60-2

Vinyl bromide

4-Phenyl-1-butyne
16520-62-0

4-Phenyl-1-butyne

hex-5-en-3-yn-1-yl benzene

hex-5-en-3-yn-1-yl benzene

Conditions
ConditionsYield
Stage #1: Vinyl bromide With copper(l) iodide; triethylamine; palladium dichloride In tetrahydrofuran at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: 4-Phenyl-1-butyne In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;
97%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 24℃; for 13h; Inert atmosphere; Alkaline conditions;96%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In tetrahydrofuran at 24℃; for 14h; Inert atmosphere;95%
Vinyl bromide
593-60-2

Vinyl bromide

C29H56O2Si2
1255097-31-4

C29H56O2Si2

A

C31H60O2Si2
1255097-32-5

C31H60O2Si2

B

C31H60O2Si2

C31H60O2Si2

Conditions
ConditionsYield
Stage #1: C29H56O2Si2 With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 0 - 20℃; for 7h;
Stage #2: Vinyl bromide With tetrakis(triphenylphosphine) palladium(0); water; sodium hydroxide In tetrahydrofuran at 20℃; for 1.5h; optical yield given as %de;
A 97%
B n/a

593-60-2Relevant articles and documents

Radical Carbonyl Propargylation by Dual Catalysis

Huang, Huan-Ming,Bellotti, Peter,Daniliuc, Constantin G.,Glorius, Frank

supporting information, p. 2464 - 2471 (2020/12/07)

Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.

Compounds and methods for the reduction of halogenated hydrocarbons

-

Page/Page column 19, (2017/12/27)

The present application relates to methods for the reduction of halogenated hydrocarbons using compounds of Formula (I): wherein the reduction of the halogenated compounds is carried out, for example, under ambient conditions without the need for a transition metal containing co-factor. The present application also relates to methods of recovering precious metals using compounds of Formula (I) that are absorbed onto a support material.

Synthetic methods and intermediates for the preparation of xenicanes

-

Page/Page column, (2014/09/03)

The invention provides novel synthetic intermediates and synthetic methods that are useful for preparing compounds of the xenicane family. Certain compounds of the invention may also possess anti-cancer properties.

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