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  • trans-1,4-Dichloro-2-butene CAS 110-57-6 (E)-1,4-Dichloro-2-butene IN Stock Dichloro(trans-1,4-)-2-Butene CAS 110-57-6

    Cas No: 110-57-6

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110-57-6 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 110-57-6 differently. You can refer to the following data:
1. clear colorless to light yellow liquid
2. The 1,4-dichloro-2-butenes are colorless liquids. Some have a distinct odor. (cis-isomer)

Uses

1,4-Dichloro-2-butene is used in the synthesis of anthraquinones used in the asymmetric dihydroxylation of olefins. Also used to prepare arylcarboxamides used as novel dopamine receptor antagonists.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 2118, 1951 DOI: 10.1021/ja01149a061The Journal of Organic Chemistry, 36, p. 2088, 1971 DOI: 10.1021/jo00814a013

General Description

Colorless liquid with a distinct odor. An intermediate for hexamethylenediamine and chloroprene.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

trans-1,4-Dichloro-2-butene will burn, though trans-1,4-Dichloro-2-butene may require some effort to ignite. Fire produces irritating and poisonous gases. When heated to decomposition, trans-1,4-Dichloro-2-butene emits toxic fumes of chlorine-containing compounds. [EPA, 1998].

Health Hazard

(Non-Specific -- Dichlorobutene) Liquid and vapors from the material are highly corrosive and may damage skin, eyes, lungs, and internal organs.

Fire Hazard

The material will burn, though trans-1,4-Dichloro-2-butene may require some effort to ignite. Fire produces irritating and poisonous gases. When heated to decomposition, trans-1,4-Dichloro-2-butene emits toxic fumes of chlorine-containing compounds.

Potential Exposure

DC occurs as a by-product in chloroprene manufacture and may be used as a chemical intermediate

Shipping

UN3384 Toxic by inhalation liquid, flammable, n. o.s. with an LC50 ≦ 1000 ml/m3 and saturated vapor concentration ≧to 10 LC50, Hazard class: 6.1; Labels: 6.1-Poisonous materials, 3-Flammable liquid, Technical Name Required, Inhalation Hazard Zone B. UN2920 Corrosive liquids, flammable, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid. The code “D” identifies proper shipping names which are appropriate for describing materials for domestic transportation but may be inappropriate for international transportation under the provisions of international regulations, e.g., IMO, ICAO). An alternate proper shipping name may be selected when either domestic or international transportation is involved

Incompatibilities

Vapors may form explosive mixture with air. 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, and epoxides. (cis-isomer): Reacts slowly with water forming hydrogen chloride. Attacks metals and may form other, more dangerous materials; attacks some plastics.

Waste Disposal

High-temperature incineration with hydrochloric acid scrubbing. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 110-57-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 110-57:
(5*1)+(4*1)+(3*0)+(2*5)+(1*7)=26
26 % 10 = 6
So 110-57-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H6Cl2/c5-3-1-2-4-6/h1,3H,2,4H2

110-57-6SDS

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 trans-1,4-Dichloro-2-butene

1.2 Other means of identification

Product number -
Other names trans 1,4-dichloro-2-butene

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:110-57-6 SDS

110-57-6Synthetic route

3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

Conditions
ConditionsYield
With poly(tetrafluoroethylene); iron oxide nanoparticles; oxygen at 100℃; for 0.5h;67%
With copper(l) chloride at 175℃;
With aluminium trichloride; iron(III) chloride at -10 - -5℃;
buta-1,3-diene
106-99-0

buta-1,3-diene

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

Conditions
ConditionsYield
With tetrachloromethane; chlorine at -80℃; unter Lichtausschluss;
With pyridine; tetrachloromethane; chlorine at -80℃; unter Lichtausschluss;
buta-1,3-diene
106-99-0

buta-1,3-diene

A

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

B

3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

Conditions
ConditionsYield
With chlorine at 60 - 75℃; in der Dampfphase;
With chlorine at 60 - 75℃; in verschiedenen Loesungsmitteln unter Kuehlung;
at 25℃; electrolysis; anolyte=CoCl2-MeCN, catholyte=NH4Cl-H2O;
buta-1,3-diene
106-99-0

buta-1,3-diene

A

Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

B

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

C

3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

Conditions
ConditionsYield
With iodine; copper dichloride In benzene at 70℃; for 2h;
With copper dichloride In acetonitrile at 60℃; for 2h;
1,4-dichloro-2-butene
764-41-0

1,4-dichloro-2-butene

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

methanol
67-56-1

methanol

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

buta-1,3-diene

A

4-Chlor-3-methoxy-but-1-en
7795-90-6

4-Chlor-3-methoxy-but-1-en

B

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

C

3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

D

1-chloro-4-methoxy-2-butene
57513-14-1

1-chloro-4-methoxy-2-butene

Conditions
ConditionsYield
With tert-butylhypochlorite at 0 - 5℃; Further byproducts given;
With tert-butylhypochlorite at -5 - 0℃; Further byproducts given. Title compound not separated from byproducts;
trans-1-bromo-4-chloro-2-butene
102776-00-1

trans-1-bromo-4-chloro-2-butene

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

Conditions
ConditionsYield
With (C4H9)N(1+)*Cl(1-) In dichloromethane at 0℃; for 24h; Title compound not separated from byproducts;95 % Chromat.
3,4-dichlorobut-1-ene
310447-99-5, 310448-01-2

3,4-dichlorobut-1-ene

A

Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

B

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

Conditions
ConditionsYield
With poly(p-xylylene); palladium In toluene at 99.85℃; Product distribution;
With oxygen at 100℃;
Z-1,4-dichlorobutene
1476-11-5

Z-1,4-dichlorobutene

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

Conditions
ConditionsYield
With maleic anhydride In acetone for 4h; Irradiation; Inert atmosphere;
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

tributylphosphine
998-40-3

tributylphosphine

(E)-but-2-ene-1,4-diylbis(tributylphosphonium) dichloride
36288-32-1, 134839-26-2

(E)-but-2-ene-1,4-diylbis(tributylphosphonium) dichloride

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 18h; Inert atmosphere; Reflux;100%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

iminodicarboxylic acid di-tert-butyl ester
51779-32-9

iminodicarboxylic acid di-tert-butyl ester

C14H24ClNO4
121030-31-7

C14H24ClNO4

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 3h;98%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

triethyl phosphite
122-52-1

triethyl phosphite

tetraethyl (E)-2-butene-1,4-diphosphonate
1112-96-5, 16626-80-5, 56727-14-1

tetraethyl (E)-2-butene-1,4-diphosphonate

Conditions
ConditionsYield
at 150 - 193℃; for 1h; Arbuzov reaction;97%
at 140℃; for 12h; Inert atmosphere;97%
at 134 - 144℃; for 33.5h;94.1%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

trimethylamine
75-50-3

trimethylamine

trans-1-chloro-4-methylammonio-2-butene chloride
60347-24-2

trans-1-chloro-4-methylammonio-2-butene chloride

Conditions
ConditionsYield
In tetrahydrofuran for 6h; Ambient temperature;95%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

triethyl phosphite
122-52-1

triethyl phosphite

tetraethyl trans-2-butenyl-1,4-bisphosphonate
211677-08-6

tetraethyl trans-2-butenyl-1,4-bisphosphonate

Conditions
ConditionsYield
at 133 - 144℃; for 2.16667h; Inert atmosphere;94.1%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

anthracene
120-12-7

anthracene

11,12-bis(chloromethyl)-9,10-dihydro-9,10-ethanoanthracene

11,12-bis(chloromethyl)-9,10-dihydro-9,10-ethanoanthracene

Conditions
ConditionsYield
at 200℃; for 48h; Sealed tube;91%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

1,4-dichloro-2,3-butanediol
2419-73-0

1,4-dichloro-2,3-butanediol

Conditions
ConditionsYield
With tetraethylammonium acetate; 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 In water; acetone; acetonitrile at 20℃;90%
With potassium permanganate; magnesium sulfate at -15℃;
With potassium permanganate; acetone at -35℃;
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

2-[5-(tetrahydropyran-2-yloxy)pent-3-ynyl]malonic acid dimethyl ester
111036-27-2

2-[5-(tetrahydropyran-2-yloxy)pent-3-ynyl]malonic acid dimethyl ester

methyl 2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptynoate
111014-17-6

methyl 2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptynoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) reflux, 30 min; 2.) 25 deg C, then reflux, 30 min;90%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

N-(tert-butyloxycarbonyl)(2,4,6-triisopropylphenyl)sulfonamide
335004-12-1

N-(tert-butyloxycarbonyl)(2,4,6-triisopropylphenyl)sulfonamide

N-[(E)-4-chloro-2-buten-1-yl]-N-(tert-butoxycarbonyl)-(2,4,6-triisopropyl)phenylsulfonamide
918401-82-8

N-[(E)-4-chloro-2-buten-1-yl]-N-(tert-butoxycarbonyl)-(2,4,6-triisopropyl)phenylsulfonamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 16h; Heating;90%
1,3-dihydro-3,3,7-trimethyl-2H-indol-2-one
19501-89-4

1,3-dihydro-3,3,7-trimethyl-2H-indol-2-one

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

4-(1-(trans-4-chloro-2-butenyl)oxy)-2,3-dihydro-3,3,7-trimethyl-1H-indol-2-one
170683-22-4

4-(1-(trans-4-chloro-2-butenyl)oxy)-2,3-dihydro-3,3,7-trimethyl-1H-indol-2-one

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide90%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

Methyl phenyl sulfone
3112-85-4

Methyl phenyl sulfone

(E)-1-chloro-5-(phenylsulfonyl)pent-2-ene
1187312-40-8

(E)-1-chloro-5-(phenylsulfonyl)pent-2-ene

Conditions
ConditionsYield
Stage #1: methylphenylsulfonate With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.0833333h;
Stage #2: With copper(l) iodide In tetrahydrofuran; hexane; N,N-dimethyl-formamide at -40 - 0℃; for 1h;
Stage #3: trans-1,4-dichlorobut-2-ene In tetrahydrofuran; hexane; N,N-dimethyl-formamide at 0℃; for 1h;
90%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

phenylacetylene
536-74-3

phenylacetylene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(S,E)-2-(3-(chloromethyl)-2-phenylpenta-1,4-dien-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(S,E)-2-(3-(chloromethyl)-2-phenylpenta-1,4-dien-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: bis(pinacol)diborane With (C6H5)2C3N2H3((CH3)3C6H2)C6H4SO3; copper(l) chloride; sodium t-butanolate In toluene Inert atmosphere; Schlenk technique;
Stage #2: trans-1,4-dichlorobut-2-ene; phenylacetylene In toluene at 30℃; for 16h; Inert atmosphere; Schlenk technique; enantioselective reaction;
90%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

11-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-butadiene

11-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-butadiene

Conditions
ConditionsYield
Stage #1: trans-1,4-dichlorobut-2-ene With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -90℃; for 0.25h;
Stage #2: bis(pinacol)diborane In tetrahydrofuran at -90 - 20℃;
89%
Stage #1: trans-1,4-dichlorobut-2-ene With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -90℃;
Stage #2: bis(pinacol)diborane In tetrahydrofuran at -90 - 20℃;
89%
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -90°C, 15 min;89%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione
14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

N-(4-Chloro-2-trans-butenyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide
105981-25-7

N-(4-Chloro-2-trans-butenyl)bicyclo<2.2.1>heptane-2,3-di-exo-carboximide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 2h;88.7%
N,N'-dimethylbenzylamine
103-83-3

N,N'-dimethylbenzylamine

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

C22H32N2(2+)*2Cl(1-)
100186-77-4

C22H32N2(2+)*2Cl(1-)

Conditions
ConditionsYield
In acetonitrile for 0.5h; Ambient temperature; Heating;87%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

1-chloro-1,3-bis(2,4,6-trichlorophenyl)triazene
187464-05-7

1-chloro-1,3-bis(2,4,6-trichlorophenyl)triazene

A

(Z)-4,5-bis(chloromethyl)-1,3-bis(2,4,6-trichlorophenyl)-1,2,3-triazolium hexachloroantimonate

(Z)-4,5-bis(chloromethyl)-1,3-bis(2,4,6-trichlorophenyl)-1,2,3-triazolium hexachloroantimonate

(E)-4,5-bis(chloromethyl)-1,3-bis(2,4,6-trichlorophenyl)-1,2,3-triazolium hexachloroantimonate

(E)-4,5-bis(chloromethyl)-1,3-bis(2,4,6-trichlorophenyl)-1,2,3-triazolium hexachloroantimonate

Conditions
ConditionsYield
With antimonypentachloride In dichloromethane at -60 - 23℃; for 1.75h;A 14 % Spectr.
B 87%
With antimonypentachloride In dichloromethane at -60 - 23℃; for 1.75h;A 14 % Spectr.
B 80%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

salicylaldehyde
90-02-8

salicylaldehyde

2,2'-[but-2-ene-1,4-diylbis(oxy)]dibenzaldehyde
918655-71-7

2,2'-[but-2-ene-1,4-diylbis(oxy)]dibenzaldehyde

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide for 0.25h; Heating;87%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

A

(1Z)-1-chloro-1,3-butadiene
10033-99-5

(1Z)-1-chloro-1,3-butadiene

B

1-chloro-1E,3-butadiene
16503-25-6

1-chloro-1E,3-butadiene

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In water at 50 - 60℃; under 10 Torr; Dehydrochlorination; Title compound not separated from byproducts;A 86%
B n/a
With potassium hydroxide In various solvent(s) at 85℃; Title compound not separated from byproducts.;
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl 2-vinylcyclopropane-1,1-dicarboxylate
17447-60-8

dimethyl 2-vinylcyclopropane-1,1-dicarboxylate

Conditions
ConditionsYield
With sodium methylate In methanol 1.) RT, 45 min; 2.) 50 deg C, 3 h;85%
With methanol; sodium In methanol at 55℃; for 3h;58%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

4-bromo-4'-hydroxybiphenyl
29558-77-8

4-bromo-4'-hydroxybiphenyl

(E)-4-(4'-Bromo-biphenyl-4-yloxy)-but-2-en-1-ol

(E)-4-(4'-Bromo-biphenyl-4-yloxy)-but-2-en-1-ol

Conditions
ConditionsYield
Stage #1: trans-1,4-dichlorobut-2-ene; 4-bromo-4'-hydroxybiphenyl With potassium carbonate at 20℃; for 96h;
Stage #2: With tetrabutylammonium acetate In acetone Heating;
Stage #3: With methanol; sodium hydroxide at 20℃; for 12h;
85%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

N-(tert-butyloxycarbonyl)-4-fluorobenzenesulfonamide
501682-72-0

N-(tert-butyloxycarbonyl)-4-fluorobenzenesulfonamide

N-[(E)-4-chloro-2-buten-1-yl]-N-(tert-butoxycarbonyl)-(4-fluorophenyl)sulfonamide
918401-81-7

N-[(E)-4-chloro-2-buten-1-yl]-N-(tert-butoxycarbonyl)-(4-fluorophenyl)sulfonamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 16h; Heating;85%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

methyl 2-carbomethoxy-10-<(tetrahydro-2H-pyran-2-yl)oxy>-8-decynoate
114952-70-4

methyl 2-carbomethoxy-10-<(tetrahydro-2H-pyran-2-yl)oxy>-8-decynoate

2-((E)-4-Chloro-but-2-enyl)-2-[8-(tetrahydro-pyran-2-yloxy)-oct-6-ynyl]-malonic acid dimethyl ester
114939-17-2

2-((E)-4-Chloro-but-2-enyl)-2-[8-(tetrahydro-pyran-2-yloxy)-oct-6-ynyl]-malonic acid dimethyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 0.666667h; Heating;84%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

methyl (E)-2-carbomethoxy-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenoate
111013-96-8

methyl (E)-2-carbomethoxy-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenoate

methyl (E)-2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenoate
111014-08-5

methyl (E)-2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-7-<(tetrahydro-2H-pyran-2-yl)oxy>-5-heptenoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) reflux, 30 min; 2.) 25 deg C, then reflux, 30 min;84%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

(2R,3R)-1,4-dichloro-2,3-dihydroxybutane
221467-90-9

(2R,3R)-1,4-dichloro-2,3-dihydroxybutane

Conditions
ConditionsYield
With Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃;84%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

2-((Z)-6-Chloro-3-methyl-5-triisopropylsilanyloxy-hex-3-enyl)-malonic acid dimethyl ester
244262-62-2

2-((Z)-6-Chloro-3-methyl-5-triisopropylsilanyloxy-hex-3-enyl)-malonic acid dimethyl ester

2-((E)-4-Chloro-but-2-enyl)-2-((Z)-6-chloro-3-methyl-5-triisopropylsilanyloxy-hex-3-enyl)-malonic acid dimethyl ester
244262-65-5

2-((E)-4-Chloro-but-2-enyl)-2-((Z)-6-chloro-3-methyl-5-triisopropylsilanyloxy-hex-3-enyl)-malonic acid dimethyl ester

Conditions
ConditionsYield
Stage #1: 2-((Z)-6-Chloro-3-methyl-5-triisopropylsilanyloxy-hex-3-enyl)-malonic acid dimethyl ester With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; Metallation;
Stage #2: trans-1,4-dichlorobut-2-ene In tetrahydrofuran; N,N-dimethyl-formamide at 75℃; Alkylation;
83%
1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

(E)-1,4-Bis-(1'-azonia-4'-azobicyclo[2.2.2]octyl)but-2-ene dichloride

(E)-1,4-Bis-(1'-azonia-4'-azobicyclo[2.2.2]octyl)but-2-ene dichloride

Conditions
ConditionsYield
In acetonitrile for 24h; Alkylation; Heating;82%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

3-tert-butyl-2-cyclopenten-1-one
5682-70-2

3-tert-butyl-2-cyclopenten-1-one

5-tert-butyl-6,7-bis(chloromethyl)bicyclo[3.2.0]heptan-2-one
767565-08-2

5-tert-butyl-6,7-bis(chloromethyl)bicyclo[3.2.0]heptan-2-one

Conditions
ConditionsYield
In dichloromethane at 12℃; for 10h; Irradiation;82%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

methyl (Z)-2-carbomethoxy-8-<(tetrahydro-2H-pyran-2-yl)oxy>-6-octenoate
111013-93-5

methyl (Z)-2-carbomethoxy-8-<(tetrahydro-2H-pyran-2-yl)oxy>-6-octenoate

methyl (Z)-2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-8-<(tetrahydro-2H-pyran-2-yl)oxy>-6-octenoate
111014-32-5

methyl (Z)-2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-8-<(tetrahydro-2H-pyran-2-yl)oxy>-6-octenoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran 1.) reflux, 30 min; 2.) 25 deg C, then reflux, 30 min;81%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

N-(4-(3-chloro-4-fluorophenyl))-7-(2-(3-methyl-3-aza-bicyclo[3.1.0]-6-hexyl)-ethoxy)quinazolin-4,6-diamine
1363359-89-0

N-(4-(3-chloro-4-fluorophenyl))-7-(2-(3-methyl-3-aza-bicyclo[3.1.0]-6-hexyl)-ethoxy)quinazolin-4,6-diamine

(E)-N-[4-(3-chloro-4-fluorophenylamino)-7-((2-(3-methyl-3-aza-bicyclo[3.1.0]-6-hexyl)-ethoxy)-quinazolin-6-yl-4-chloro)]-crotonamide
1363569-81-6

(E)-N-[4-(3-chloro-4-fluorophenylamino)-7-((2-(3-methyl-3-aza-bicyclo[3.1.0]-6-hexyl)-ethoxy)-quinazolin-6-yl-4-chloro)]-crotonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice;81%
trans-1,4-dichlorobut-2-ene
110-57-6

trans-1,4-dichlorobut-2-ene

2-[(E)-4-(Tetrahydro-pyran-2-yloxy)-but-2-enyl]-malonic acid dimethyl ester
93915-02-7

2-[(E)-4-(Tetrahydro-pyran-2-yloxy)-but-2-enyl]-malonic acid dimethyl ester

2-((E)-4-Chloro-but-2-enyl)-2-[(E)-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-malonic acid dimethyl ester
112181-18-7

2-((E)-4-Chloro-but-2-enyl)-2-[(E)-4-(tetrahydro-pyran-2-yloxy)-but-2-enyl]-malonic acid dimethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 90℃; for 12h; Inert atmosphere;80%
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide for 13h; Heating;45%

110-57-6Relevant articles and documents

[2+2] Photocycloaddition of symmetrically disubstituted alkenes to 2(5H)-furanones: Diastereoselective entry to 1,2,3,4-tetrasubstituted cyclobutanes

Pares, Sonia,De March, Pedro,Font, Josep,Alibes, Ramon,Figueredo, Marta

, p. 3888 - 3895 (2011)

A study on the [2+2] photochemical cycloaddition of 1,4-difunctionalized 2-butenes to 2(5H)-furanones is presented. These reactions deliver 1,2,3,4-tetrasubstituted cyclobutanes with suitable functionalization in the four side chains for further synthetic elaboration. The effects of the substituents in both the lactone and the 2-butene on the stereoselectivity of the photochemical reaction have been evaluated. Starting from (Z)-2-butenes, under photosensitized conditions, a competitive cis/trans isomerization of the olefin inhibits the cycloaddition process. It was found that the presence of a cis double bond confined within a medium-size ring does not prevent bond rotation in the intermediate 1,4-biradicals. Copyright

Catalytic conversions of chloroolefins over iron oxide nanoparticles: 1. Isomerization of dichlorobutenes in the presence of iron oxide nanopaticles immobilized on silicas with different structures

Rostovshchikova,Smirnov,Tsodikov,Bukhtenko,Maksimov,Kiseleva,Pankratov

, p. 1418 - 1424 (2005)

The influence of the support nature and electronic state of iron oxide nanoclusters on the catalytic properties of supported systems was studied for dichlorobutene isomerization. A sample with a Fe content of 2.5 wt.% on the activated silica matrix containing FeIII and FeII ions in the paramagnetic state exhibits the highest activity. The activity of iron on silica gel enhances with the appearance of magnetically ordered nanoclusters of γ-iron oxide formed at the iron content on the catalyst as high as 15 wt.%. An increase in the catalyst activity is favored by the formation of two states of iron (FeIII and FeII) that occurs under the synthesis conditions or during the action of a reactant.

Catalytic conversions of chloroolefins over iron oxide nanoparticles 2. Isomerization of dichlorobutenes over iron oxide nanoparticles stabilized on the surface of ultradispersed poly(tetrafluoroethylene)

Rostovshchikova,Korobov,Pankratov,Yurkov,Gubin

, p. 1425 - 1432 (2005)

Nanosized iron oxides stabilized on the surface of ultradispersed poly(tetrafluoroethylene) (UPTFE) granules were synthesized by the thermal destruction of iron formate in boiling bed of UPTFE on the surface of heated mineral oil. The particle size of nanoparticles (~6 nm) containing 5, 10, and 16 wt.% Fe depends weakly on the temperature of synthesis and iron to polymer ratio. The metal state is determined by the synthesis conditions. The nanoparticles synthesized at 280°C consist mainly of the Fe 3O4 and Fe2O3 phases. The samples obtained at 320°C also contain iron(II) oxide. The catalytic properties of the obtained samples were tested in dichlorobutene isomerization. Unlike isomerization on the iron oxide nanoparticles supported on silica gel, reaction over the UPTFE supports proceeds without an induction period. The sample with 10 wt.% Fe containing magnetically ordered γ-Fe2O3 nanoparticles possesses the highest catalytic activity. Fast electron exchange between the iron ions in different oxidation states and high defectiveness of the nanoparticles contribute, most likely, to the catalytic activity.

Kinetics of inversion of dichlorobutene in the heterogeneous system

Langeroodi, N. Samadani

experimental part, p. 2772 - 2774 (2012/08/28)

The reaction kinetics of the isomerization of 3,4-dichlorobutene-1 to 1,4-dichlorobutene-2 was investigated by using gas-liquid chromatography in presence of Fe2O3/ZrO2 as solid catalyst. At the optimizing conditions, the catalytic activity, rate constants of reaction and activation energy have been evaluated using kinetic equations. The structure of the catalyst was investigated by using Mossbauer spectroscopy.

Catalytic conversions of chloroolefines over iron oxide nanoparticles 3. Electronic and magnetic properties of γ-Fe2O3 nanoparticles immobilized on different silicas

Rostovshchikova,Kiseleva,Smirnov,Maksimov,Suzdalev,Prusakov,Tsodikov,Ikorskii

, p. 1768 - 1774 (2008/02/05)

Catalytic properties of superparamagnetic γ-ferric oxide nanoclusters, which are uniform in terms of size and magnetic properties were studied. The catalysts were supported on the activated silica gel matrix (AGM) prepared from the KSK-2 silica gel of globular structure and on the activated silica matrix (ASM) prepared from layered natural vermiculite. The clusters are active in some reactions of chloroolefin conversions: isomerization of dichlorobutenes and alkylation of benzene with allyl chloride. Their activity in these reactions is many times higher that of usual supported catalysts based on α-ferric oxide. Analysis of the Moessbauer spectra of the 2.5 wt.% Fe/AGM and 2.5 wt.%Fe/ASM samples before and after the reaction at T = 3-300 K shows that during the reaction some FeIII ions arranged in ~2-3-nm γ-Fe2O3 nanoclusters magnetically ordered at 6 K are reduced to form a high-spin FeII complex in the paramagnetic state. According to the macroscopic magnetization data (SQUID) of the initial clusters, curves with hysteresis are observed at 2 K in the plots of forward and backward magnetization, while the 2.5 wt.%Fe/ASM catalyst after the reaction at T = 2 K demonstrates a linear field dependence of the magnetization passing through the coordinate origin. Analysis of the Moessbauer spectra and magnetic properties suggests that during the catalytic reaction the Fe III ions in the γ-Fe2O3 nanoclusters interact with chloroolefin with the allylic structure to be partially reduced to the FeII ions that are bound in a complex containing chloride ions and OII ion(s) of the silicate matrix as ligands. This is a reason, probably, for the high catalytic activity of γ-Fe2O3 nanoparticles.

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