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6117-80-2

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6117-80-2 Usage

Chemical Properties

clear liquid

Uses

cis-2-Butene-1, 4-diol is used as a probe for studying isomerization versus hydrogenation and hydrogenolysis reactions. (DPCB-OMe) efficiently catalyzes cyclodehydration of cis-2-butene-1,4-diol with active methylene compounds to give 2-vinyl-2,3-dihydrofurans in good to high yields. Grubbs's cross metathesis of eugenol with cis-2-butene-1, 4-diol to make a natural product, an organometallic experiment.

Check Digit Verification of cas no

The CAS Registry Mumber 6117-80-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,1 and 7 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6117-80:
(6*6)+(5*1)+(4*1)+(3*7)+(2*8)+(1*0)=82
82 % 10 = 2
So 6117-80-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O2/c5-3-1-2-4-6/h1-2,5-6H,3-4H2/b2-1-

6117-80-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Butene-1,4-diol

1.2 Other means of identification

Product number -
Other names 2-(3,4-dihydroxybenzylidene)-4,6-dihydroxy-1-benzofuran-3(2H)-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:6117-80-2 SDS

6117-80-2Synthetic route

1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With quinoline; hydrogen; Lindlar's catalyst In methanol at 0℃;100%
With borane-ammonia complex; Cu2O In ethanol at 50℃; for 0.75h; Sealed tube; Green chemistry; stereoselective reaction;100%
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760.051 Torr;99%
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A n/a
B 99%
With LaNi5 hydride In tetrahydrofuran; methanol at 0℃; for 6h;A 10%
B 67%
cis-2-butene-1,4-diol bis-trifluoroacetate

cis-2-butene-1,4-diol bis-trifluoroacetate

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With silica gel; triethylamine In diethyl ether; Petroleum ether Substitution; Detrifluoroacetylation;95%
cis-1,4-bis-(O-trityl)but-2-ene
125274-08-0

cis-1,4-bis-(O-trityl)but-2-ene

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With Nafion-H In methanol at 20℃; for 18h;91%
1-tert-butyldimethylsilyloxy-4-triethylsilyloxy-2-butene

1-tert-butyldimethylsilyloxy-4-triethylsilyloxy-2-butene

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol
91202-69-6, 134297-05-5, 113123-37-8

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

Conditions
ConditionsYield
With MCM-41 In methanol for 8h; Ambient temperature;A 3%
B 90%
With mesoporous silica MCM-41 In methanol at 20℃; for 8h;A 3%
B 90%
(Ζ)-4-(triphenylmethoxy)-2-buten-1-ol
126027-87-0

(Ζ)-4-(triphenylmethoxy)-2-buten-1-ol

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With Nafion-H In methanol at 20℃; for 16h;90%
cis-1,4-bis(acetyloxy)but-2-ene
25260-60-0

cis-1,4-bis(acetyloxy)but-2-ene

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 0.5h;83%
bis(2-butenoxy)methylphenylsilane
141412-50-2

bis(2-butenoxy)methylphenylsilane

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With Mo(CHCMe2Ph)2 In benzene at 20℃; for 2h;71%
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With hydrogen; Montmorillonite-Ph2PPd(II) In tetrahydrofuran at 25℃; under 760 Torr; for 2h; Product distribution; other catalysts (5percent Pd-C, Lindlar catalyst), other solvents (ethyl acetate);
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With hydrogen; ruthenium palladium In propan-1-ol at 89.9℃; Rate constant;
With hydrogen; copper(II) sulfate; nickel In ammonium hydroxide; water at 40℃; under 5250.4 Torr; Title compound not separated from byproducts;
With hydrogen In isopropyl alcohol at 30℃; under 7500.75 Torr; for 1h; Autoclave; optical yield given as %de; stereoselective reaction;
Formic acid (2S,3R)-4-formyloxy-2,3-dihydroxy-butyl ester

Formic acid (2S,3R)-4-formyloxy-2,3-dihydroxy-butyl ester

A

3,4-butenediol
497-06-3

3,4-butenediol

B

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature; Yield given;
dl-2,3-dibromo-1,4-butanediol
1947-58-6

dl-2,3-dibromo-1,4-butanediol

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With samarium In methanol for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

aqueous KOH-solution

aqueous KOH-solution

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
durch elektrochemische Reduktion an einer mit Silber beschichteten Kupfer-Kathode;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

cobalt

cobalt

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
unter Druck.Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

copper

copper

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
unter Druck.Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

iron

iron

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
unter Druck.Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

nickel

nickel

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
unter Druck.Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

methanol
67-56-1

methanol

palladium-calcium carbonate

palladium-calcium carbonate

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

ethanol
64-17-5

ethanol

palladium/charcoal

palladium/charcoal

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

platinum

platinum

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
unter Druck.Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

ethanol
64-17-5

ethanol

Raney nickel

Raney nickel

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

palladium/charcoal

palladium/charcoal

ethanolic NaOH-solution

ethanolic NaOH-solution

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
Hydrogenation;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

ethanol
64-17-5

ethanol

Raney nickel

Raney nickel

A

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

1,4-butenediol
6117-80-2

1,4-butenediol

D

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
Produkt5: But-2ξ-en-1-ol.Hydrogenation;
cis-1,4-dibromo-2-butene
18866-73-4

cis-1,4-dibromo-2-butene

diluted natrium carbonate

diluted natrium carbonate

A

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

B

3,4-butenediol
497-06-3

3,4-butenediol

C

1,4-butenediol
6117-80-2

1,4-butenediol

D

crotonaldehyde
123-73-9

crotonaldehyde

Conditions
ConditionsYield
at 90 - 95℃; Hydrolysis;
tert-butyl-dimethyl-[4-(tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-silane
222713-57-7

tert-butyl-dimethyl-[4-(tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-silane

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With Nafion-H(R); sodium iodide In methanol at 20℃; for 1h;
allyl alcohol
107-18-6

allyl alcohol

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With Ru metathesis catalyst In water at 45℃; for 12h; Title compound not separated from byproducts;
With Hoveyda-Grubbs catalyst second generation; 5,11,17,23-tetrakis(trimethylammoniomethyl)-25,26,27,28-tetrapropoxycalix<4>arene tetrachloride In water at 45℃; for 24h; optical yield given as %de;
With C39H58Cl2N4ORu(1+)*Cl(1-) In water-d2 at 25℃; for 24h; Catalytic behavior; Reagent/catalyst; Time;A n/a
B n/a
With C106H182Cl2N2O34Ru In water at 20℃; for 24h; Overall yield = 93 %Spectr.;A n/a
B n/a
With C106H182Cl2N2O34Ru In water-d2 at 20℃; for 24h; Overall yield = 94 percent;A n/a
B n/a
3-hexyn-1-ol
1002-28-4

3-hexyn-1-ol

A

Butane-1,4-diol
110-63-4

Butane-1,4-diol

B

1,4-butenediol
6117-80-2

1,4-butenediol

C

(E)-2-butene-1,4-diol
821-11-4

(E)-2-butene-1,4-diol

Conditions
ConditionsYield
With 5% Pd(II)/C(eggshell); hydrogen In isopropyl alcohol at 30℃; under 7500.75 Torr; for 1h; Autoclave; optical yield given as %de;
meso-erythritol
909878-64-4

meso-erythritol

A

1,4-butenediol
6117-80-2

1,4-butenediol

B

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

buta-1,3-diene

Conditions
ConditionsYield
With 1,2,4-tri(tert-butyl)cyclopentadienyl tricarbonyl rhenium; triphenylphosphine In chlorobenzene at 140℃; for 26h;A 5.8 %Chromat.
B 18 %Chromat.
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

pentanal
110-62-3

pentanal

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

1,4-butenediol
6117-80-2

1,4-butenediol

D

butan-1-ol
71-36-3

butan-1-ol

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; under 150.015 - 900.09 Torr; for 0.005h; Inert atmosphere; Schlenk technique; Green chemistry;A n/a
B n/a
C n/a
D n/a
1,4-butenediol
6117-80-2

1,4-butenediol

acetic anhydride
108-24-7

acetic anhydride

cis-1,4-bis(acetyloxy)but-2-ene
25260-60-0

cis-1,4-bis(acetyloxy)but-2-ene

Conditions
ConditionsYield
With pyridine for 14h; Ambient temperature;100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; Acetylation;97%
With pyridine91%
1,4-butenediol
6117-80-2

1,4-butenediol

Δ5-1,3-dioxa-2-thialepin-2-oxide
6214-15-9

Δ5-1,3-dioxa-2-thialepin-2-oxide

Conditions
ConditionsYield
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Cyclization;100%
With thionyl chloride; triethylamine In ethyl acetate at -10℃; for 0.166667h;87%
With dimethylsulfite
With dimethylsulfite at 110 - 120℃;
With 1H-imidazole; thionyl chloride In dichloromethane for 1h;
1,4-butenediol
6117-80-2

1,4-butenediol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(Z)-but-2-ene-1,4-diyl dimethanesulfonate
1953-56-6, 70886-56-5, 2303-47-1

(Z)-but-2-ene-1,4-diyl dimethanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 0.5h;100%
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice;96%
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice;96%
1,4-butenediol
6117-80-2

1,4-butenediol

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With 5 wt% Pd nanoparticles loaded on phosphate anion exchanged [Mg6Al2(OH)16]CO3*xH2O; air at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Irradiation;100%
With acetone; dihydridotetrakis(triphenylphosphine)ruthenium In toluene at 180℃; for 3h;88 % Chromat.
1,4-butenediol
6117-80-2

1,4-butenediol

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With 5 wt% Pd nanoparticles loaded on phosphate anion exchanged [Mg6Al2(OH)16]CO3*xH2O; air at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Irradiation;100%
With Celite; silver carbonate In benzene for 2h; Heating;78%
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium In toluene for 6h; Heating;77%
at 30℃; for 24h; Nocardia corallina B-276;50%
With sodium hydrogencarbonate; sodium carbonate at 20℃; for 3h; anodic oxidation on PbO2;
1,4-butenediol
6117-80-2

1,4-butenediol

benzyl chloride
100-44-7

benzyl chloride

(Z)-1,4-dibenzyloxy-2-butene
68972-96-3

(Z)-1,4-dibenzyloxy-2-butene

Conditions
ConditionsYield
With potassium hydroxide; triethylbenzyl ammonium bromide In dichloromethane for 2.5h; Ambient temperature;100%
With sodium hydroxide; tetrabutylammomium bromide In water at 60 - 95℃; for 2h;100%
With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran at 66℃; Etherification;99%
With sodium hydride In tetrahydrofuran Alkylation; Heating;99%
1,4-butenediol
6117-80-2

1,4-butenediol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene
132835-15-5

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene

Conditions
ConditionsYield
With triethylamine100%
With dmap In dichloromethane at 0 - 20℃;100%
Stage #1: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane for 0.166667h;
Stage #2: 1,4-butenediol In dichloromethane at 20℃; for 16h;
98%
1,4-butenediol
6117-80-2

1,4-butenediol

methyl chloroformate
79-22-1

methyl chloroformate

carbonic acid (Z)-4-methoxycarbonyloxy-but-2-enyl ester methyl ester
5332-81-0, 99260-79-4

carbonic acid (Z)-4-methoxycarbonyloxy-but-2-enyl ester methyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃;100%
With pyridine In dichloromethane at 0 - 20℃;98%
With pyridine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;96%
1,4-butenediol
6117-80-2

1,4-butenediol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(Z)-2,2,11,11-tetramethyl-3,3,10,10-tetraphenyl-4,9-dioxa-3,10-disiladodec-6-ene
145365-08-8

(Z)-2,2,11,11-tetramethyl-3,3,10,10-tetraphenyl-4,9-dioxa-3,10-disiladodec-6-ene

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;100%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 2.83333h;99%
With dmap; triethylamine In dichloromethane at 0 - 20℃;97%
1,4-butenediol
6117-80-2

1,4-butenediol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene
1026530-53-9

1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h; Inert atmosphere;100%
In tetrahydrofuran for 24h; Ambient temperature;85%
In dichloromethane at 20℃; Inert atmosphere;84.7%
1,4-butenediol
6117-80-2

1,4-butenediol

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

(Z)-but-2-ene-1,4-diyl bis-(4-methoxybenzoate)
422268-02-8

(Z)-but-2-ene-1,4-diyl bis-(4-methoxybenzoate)

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;100%
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;97%
With pyridine In dichloromethane at 5 - 20℃; for 4h; Inert atmosphere;86%
1,4-butenediol
6117-80-2

1,4-butenediol

isopropyl chloroformate
108-23-6

isopropyl chloroformate

(Z)-1,4-bis(i-propoxycarbonyloxy)-2-butene
783368-59-2

(Z)-1,4-bis(i-propoxycarbonyloxy)-2-butene

Conditions
ConditionsYield
With pyridine In dichloromethane at 5 - 20℃; for 4h; Inert atmosphere;100%
1,4-butenediol
6117-80-2

1,4-butenediol

Diisopropylsilyl dichloride
7751-38-4

Diisopropylsilyl dichloride

2,2-Diisopropyl-4,7-dihydro-[1,3,2]dioxasilepine
85272-44-2

2,2-Diisopropyl-4,7-dihydro-[1,3,2]dioxasilepine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide100%
1,4-butenediol
6117-80-2

1,4-butenediol

benzyl bromide
100-39-0

benzyl bromide

(Z)-1,4-dibenzyloxy-2-butene
68972-96-3

(Z)-1,4-dibenzyloxy-2-butene

Conditions
ConditionsYield
Stage #1: 1,4-butenediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h;
99%
Stage #1: 1,4-butenediol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;
Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h;
99%
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran; mineral oil for 2h; Inert atmosphere; Reflux;
Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere; Reflux;
98%
1,4-butenediol
6117-80-2

1,4-butenediol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol
87770-83-0

(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 25℃; for 6h;99%
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran at 20℃; for 1h; Further stages.;
99%
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
99%
1,4-butenediol
6117-80-2

1,4-butenediol

benzoyl chloride
98-88-4

benzoyl chloride

cis-1,4-dibenzoyloxybut-2-ene
55759-12-1

cis-1,4-dibenzoyloxybut-2-ene

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;99%
With pyridine at 0 - 20℃; Inert atmosphere;99%
With pyridine In dichloromethane at 0 - 20℃; for 4.25h;99%
1,4-butenediol
6117-80-2

1,4-butenediol

1-Iodododecane
4292-19-7

1-Iodododecane

cis-2-butenyl-1,4-didodecyl ether
479404-45-0

cis-2-butenyl-1,4-didodecyl ether

Conditions
ConditionsYield
Stage #1: 1,4-butenediol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 1-Iodododecane In N,N-dimethyl-formamide at 20℃; for 1h; Further stages.;
99%
Stage #1: 1,4-butenediol With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere;
Stage #2: 1-Iodododecane In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;
82%
1,4-butenediol
6117-80-2

1,4-butenediol

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

(Z)-but-2-ene-1,4-bis(ethylcarbonate)
219838-95-6

(Z)-but-2-ene-1,4-bis(ethylcarbonate)

Conditions
ConditionsYield
With pyridine In dichloromethane at 5 - 20℃; for 4h; Inert atmosphere;99%
1,4-butenediol
6117-80-2

1,4-butenediol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-butenyl 1,4-dimesylate
70886-56-5

2-butenyl 1,4-dimesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -10 - 0℃; for 1h;99%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

1,4-butenediol
6117-80-2

1,4-butenediol

cis-1,4-bis(acetyloxy)but-2-ene
25260-60-0

cis-1,4-bis(acetyloxy)but-2-ene

Conditions
ConditionsYield
With tetraethylammonium bicarbonate at 60℃; for 2h;99%
1,4-butenediol
6117-80-2

1,4-butenediol

pivaloyl chloride
3282-30-2

pivaloyl chloride

cis 2-butene-1,4-diol mono pivalate
132329-48-7

cis 2-butene-1,4-diol mono pivalate

Conditions
ConditionsYield
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.916667h; Inert atmosphere;
Stage #2: pivaloyl chloride In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;
99%
1,4-butenediol
6117-80-2

1,4-butenediol

benzyl bromide
100-39-0

benzyl bromide

(Z)-4-benzyloxy-but-2-en-1-ol
81028-03-7

(Z)-4-benzyloxy-but-2-en-1-ol

Conditions
ConditionsYield
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; mineral oil for 1h; Inert atmosphere; Reflux;
98%
Stage #1: 1,4-butenediol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 2h;
95%
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; dimethyl sulfoxide at 60℃;
92%
1,4-butenediol
6117-80-2

1,4-butenediol

acetaldehyde
75-07-0

acetaldehyde

2-methyl-4,7-dihydro-1,3-dioxepine
7045-86-5

2-methyl-4,7-dihydro-1,3-dioxepine

Conditions
ConditionsYield
With magnesium sulfate; toluene-4-sulfonic acid In tetrahydrofuran; dichloromethane at 20℃;98%
With magnesium sulfate; toluene-4-sulfonic acid In tetrahydrofuran; dichloromethane at 20℃;80%
With toluene-4-sulfonic acid In benzene Heating;77%
With toluene-4-sulfonic acid In benzene for 3h; Heating;40%
With toluene-4-sulfonic acid In benzene Heating;
1,4-butenediol
6117-80-2

1,4-butenediol

tridecanal
10486-19-8

tridecanal

4,7-Dihydro-2-dodecyl-1,3-dioxepine
188883-49-0

4,7-Dihydro-2-dodecyl-1,3-dioxepine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 5h; Heating;98%
1,4-butenediol
6117-80-2

1,4-butenediol

chlorodimethyl(1,1,2-trimethylpropyl)silane
67373-56-2

chlorodimethyl(1,1,2-trimethylpropyl)silane

(Z)-1,4-bis-(dimethyl(1,1,2-trimethylpropyl)silyloxy)-2-butene
220496-84-4

(Z)-1,4-bis-(dimethyl(1,1,2-trimethylpropyl)silyloxy)-2-butene

Conditions
ConditionsYield
In N,N-dimethyl-formamide silylation;98%
With 1H-imidazole In N,N-dimethyl-formamide at 5 - 20℃; for 18h; silylation;97%
1,4-butenediol
6117-80-2

1,4-butenediol

cis-1,2,3,6-tetrahydrophthalic anhydride
935-79-5

cis-1,2,3,6-tetrahydrophthalic anhydride

C20H24O8
888485-45-8

C20H24O8

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 9h;98%
1,4-butenediol
6117-80-2

1,4-butenediol

(4R/S,5R/S)-(2-benzylisoxazolidine-4,5-diyl)dimethanol

(4R/S,5R/S)-(2-benzylisoxazolidine-4,5-diyl)dimethanol

Conditions
ConditionsYield
Stage #1: N-benzylhydroxylamine hydrochloride With sodium acetate In ethanol at 20℃; for 0.25h;
Stage #2: formaldehyd In ethanol; water for 0.5h;
Stage #3: 1,4-butenediol In ethanol; water for 16h; Heating / reflux;
98%
Stage #1: N-benzylhydroxylamine hydrochloride With sodium acetate In ethanol at 20℃; for 0.25h;
Stage #2: formaldehyd In ethanol; water for 0.5h;
Stage #3: 1,4-butenediol In ethanol; water for 16h; Heating / reflux;
98%
1,4-butenediol
6117-80-2

1,4-butenediol

p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

(Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene
179548-99-3

(Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene

Conditions
ConditionsYield
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
Stage #2: p-Methoxybenzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
98%
Stage #1: 1,4-butenediol With sodium hydride In tetrahydrofuran; nujol at 0℃; for 0.25h;
Stage #2: p-Methoxybenzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; nujol at 0 - 20℃; for 4h;
96%
Stage #1: 1,4-butenediol With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; nujol at 0 - 20℃; for 0.25h; Inert atmosphere;
Stage #2: p-Methoxybenzyl bromide In tetrahydrofuran; nujol at 0℃; for 1h; Inert atmosphere;
78%

6117-80-2Relevant articles and documents

One-step synthesis of Pt@ZIF-8 catalyst for the selective hydrogenation of 1,4-butynediol to 1,4-butenediol

Li, Chuang,Zhang, Mingming,Di, Xin,Yin, Dongdong,Li, Wenzhen,Liang, Changhai

, p. 1555 - 1561 (2016)

A catalyst consisting of platinum nanoparticles on a ZIF-8 support (Pt@ZIF-8) was synthesized in a straightforward one-step procedure, by adding a nanostructured platinum sol during the formation of ZIF-8 at room temperature. Pt@ZIF-8 was highly porous an

PVP-Pd@ZIF-8 as highly efficient and stable catalysts for selective hydrogenation of 1,4-butynediol

Zhang, Mingming,Yang, Yuebin,Li, Chuang,Liu, Qian,Williams, Christopher T.,Liang, Changhai

, p. 329 - 332 (2014)

Cubic Pd nanoparticles were rapidly encapsulated in ZIF-8 through a PVP-assisted synthetic method at room temperature. The obtained PVP-Pd@ZIF-8 exhibited high activity and stability for hydrogenation of 1,4-butynediol, with excellent selectivity to 1,4-b

Highly selective semi-hydrogenation of alkynes with a Pd nanocatalyst modified with sulfide-based solid-phase ligands

Huang, Lingqi,Hu, Kecheng,Ye, Ganggang,Ye, Zhibin

, (2021/03/30)

Soluble small molecular/polymeric ligands are often used in Pd-catalyzed semi-hydrogenation of alkynes as an efficient strategy to improve the selectivity of targeted alkene products. The use of soluble ligands requires their thorough removal from the reaction products, which adds significant extra costs. In the paper, commercially available, inexpensive, metallic sulfide-based solid-phase ligands (SPL8-4 and SPL8-6) are demonstrated as simple yet high-performance insoluble ligands for a heterogeneous Pd nanocatalyst (Pd@CaCO3) toward the semi-hydrogenation of alkynes. Based on the reactions with a range of terminal and internal alkyne substrates, the use of the solid-phase ligands has been shown to markedly enhance the selectivity of the desired alkene products by efficiently suppressing over-hydrogenation and isomerization side reactions, even during the long extension of the reactions following full substrate conversion. A proper increase in the dosage or a reduction in the average size of the solid-phase ligands enhances such effects. With their insoluble nature, the solid-phase ligands have the distinct advantage in their simple, convenient recycling and reuse while without contaminating the products. A ten-cycle reusability test with the SPL8-4/Pd@CaCO3 catalyst system confirms its well-maintained activity and selectivity over repeated uses. A mechanistic study with x-ray photoelectron spectroscopy indicates that the solid-phase ligands have electronic interactions with Pd in the supported catalyst, contributing to inhibit the binding and further reaction of the alkene products. This is the first demonstration of solid-phase ligands for highly selective semi-hydrogenation of alkynes, which show strong promise for commercial applications.

Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**

Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry

supporting information, p. 19685 - 19690 (2021/08/06)

The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.

Fourth subgroup metal complex with rigid annular bridging structure and application of fourth subgroup metal complex

-

Paragraph 0058; 0061; 0066, (2021/06/23)

The invention belongs to the technical field of olefin polymerization catalysts, and particularly relates to a fourth subgroup metal complex with a rigid annular bridging structure and an application of the fourth subgroup metal complex. The fourth subgroup metal complex provided by the invention has a structure represented by a formula (A) or a formula (B), X is halogen or alkyl; and M is titanium, zirconium or hafnium. On the basis of a non-metallocene catalyst, a bridging structure in catalyst molecules is improved and upgraded, and a brand-new metal complex with excellent catalytic performance and good high-temperature tolerance is designed; when the fourth subgroup metal complex is used as a main catalyst to catalyze olefin polymerization reaction, under the activation action of a small amount of mixed cocatalyst, the fourth subgroup metal complex can efficiently catalyze the copolymerization reaction of ethylene and alpha-olefin to obtain polyolefin with high molecular weight and high comonomer insertion rate.

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