Product Name

  • Name

    (Z)-3-Methylpent-2-en-4-yn-1-ol

  • EINECS 228-168-2
  • CAS No. 6153-05-5
  • Article Data18
  • CAS DataBase
  • Density 0.940
  • Solubility
  • Melting Point
  • Formula C6H8 O
  • Boiling Point 171 ºC
  • Molecular Weight 96.1289
  • Flash Point 65 ºC
  • Transport Information UN 1760
  • Appearance
  • Safety S26;S37/39
  • Risk Codes R22;R36/37/38   
  • Molecular Structure Molecular Structure of 6153-05-5 ((Z)-3-Methylpent-2-en-4-yn-1-ol)
  • Hazard Symbols
  • Synonyms 2-Penten-4-yn-1-ol,3-methyl-, (Z)- (8CI); (2Z)-3-Methyl-2-penten-4-yn-1-ol;(Z)-3-Methylpent-2-en-4-yn-1-ol; Z-3-Methyl-2-penten-4-yn-1-ol;cis-3-Methyl-2-penten-4-yn-1-ol; cis-3-Methyl-2-pentene-4-yn-1-ol
  • PSA 20.23000
  • LogP 0.55820

Synthetic route

3-methyl-1-penten-4-yn-3-ol
3230-69-1

3-methyl-1-penten-4-yn-3-ol

A

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

B

(E)-3-methylpent-2-en-4-yn-1-ol
6153-06-6

(E)-3-methylpent-2-en-4-yn-1-ol

Conditions
ConditionsYield
acid Allylic Rearrangement;A 85%
B 15%
With sulphurous acid at 50℃; for 2h; Isomerization;A 81%
B n/a
With sulfuric acid; hydroquinone In di-isopropyl ether at 50 - 52℃; for 2h;A 73.7%
B 14.1%
3-methyl-1-penten-4-yn-3-ol
3230-69-1

3-methyl-1-penten-4-yn-3-ol

A

(E)-1-bromo-3-methylpent-2-en-4-yne
69371-58-0

(E)-1-bromo-3-methylpent-2-en-4-yne

B

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

Conditions
ConditionsYield
With hydrogen bromide; hydroquinone In di-isopropyl ether at 50 - 52℃; for 8h;A 59.6%
B 19.3%
(Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol
121635-19-6

(Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

Conditions
ConditionsYield
With methanol; potassium carbonate at 20℃;58%
With potassium carbonate In methanol
3-methyl-1-penten-4-yn-3-ol
3230-69-1

3-methyl-1-penten-4-yn-3-ol

A

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

B

cis-3-methyl-5-nitroxy-3-penten-1-yne

cis-3-methyl-5-nitroxy-3-penten-1-yne

C

trans-3-methyl-5-nitroxy-3-penten-1-yne

trans-3-methyl-5-nitroxy-3-penten-1-yne

Conditions
ConditionsYield
With nitric acid; hydroquinone In di-isopropyl ether at 50 - 52℃; for 7h;A 16.1%
B 56.4%
C 13%
...Expand
3-methyl-1-penten-4-yn-3-ol
3230-69-1

3-methyl-1-penten-4-yn-3-ol

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

Conditions
ConditionsYield
With sulfuric acid; water at 20℃; for 48h;56%
With water at 70℃;13%
With sulfuric acid for 20h;
5-Trimethylsilyl-3-methyl-pent-1-en-4-in-3-ol
50516-66-0

5-Trimethylsilyl-3-methyl-pent-1-en-4-in-3-ol

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3, MeOH
2: H2O, H2SO4
View Scheme
Multi-step reaction with 2 steps
1: K2CO3 / methanol
2: 10percent H2SO4
View Scheme
(E)-3-methylpent-2-en-4-yn-1-ol
6153-06-6

(E)-3-methylpent-2-en-4-yn-1-ol

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

Conditions
ConditionsYield
With benzophenone In acetonitrile for 0.333333 - 4h; Product distribution / selectivity; UV-irradiation; Microwave irradiation;
With bis(p-dimethylaminophenyl)methanone In acetonitrile for 0.333333 - 2h; Product distribution / selectivity; UV-irradiation; Microwave irradiation;
With benzophenone In acetonitrile at 25℃; for 1h; Product distribution / selectivity; UV-irradiation;
With iodine In acetonitrile at 200℃; under 15001.5 Torr; for 1.01667h; Product distribution / selectivity; UV-irradiation; Microwave irradiation;
3-methyl-2-penten-4-yn-1-al
53635-18-0

3-methyl-2-penten-4-yn-1-al

A

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

B

(E)-3-methylpent-2-en-4-yn-1-ol
6153-06-6

(E)-3-methylpent-2-en-4-yn-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 25℃; for 3h; Overall yield = 95 %;
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

2,3-dimethylfuran
14920-89-9

2,3-dimethylfuran

Conditions
ConditionsYield
With [Au2Cl2(μ-1,1′-bis(ditert-butylphosphino)ferrocene)] In chloroform-d1; 1,2-dichloro-ethane at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;100%
With CuCl2*2H2O98%
With trimethyl-4,6,9 hexaza-1,3,4,6,7,9 phospha-5 tricyclo<3.3.1.13,7>decane; [{IrCl(μ-Cl)(η4-cod)}2] In water at 80℃; for 1h;96%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

3-methyl-1-penten-4-yn-3-ol
3230-69-1

3-methyl-1-penten-4-yn-3-ol

Conditions
ConditionsYield
With sulfuric acid; hydroquinone; mercury dichloride In di-isopropyl ether at 50 - 52℃; for 0.166667h; Product distribution;100%
vinyl acetate
108-05-4

vinyl acetate

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

(Z)-3-Methyl-2-penten-4-in-1-ylacetat
35272-87-8

(Z)-3-Methyl-2-penten-4-in-1-ylacetat

Conditions
ConditionsYield
With hexamethyltriamido-N-benzylimidophosphate In tetrahydrofuran at 20℃; for 15h; Acylation;99%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

6-iodo-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

6-iodo-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

(Z)-1-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)-6-iodo-2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

(Z)-1-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)-6-iodo-2,2-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran at -80℃; for 0.75h;
Stage #2: 6-iodo-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one In tetrahydrofuran at -80 - 20℃; for 1.16667h;		99%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

(Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether
41967-81-1

(Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 0℃; for 3h;98%
With pyridinium p-toluenesulfonate In dichloromethane for 2h; Ambient temperature;96%
With toluene-4-sulfonic acid In diethyl ether at 20℃;87%
With toluene-4-sulfonic acid at 20℃; for 0.75h;
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

4-Hex-1-ynyl-4,5,5-trimethyl-[1,3]dioxolan-2-one

4-Hex-1-ynyl-4,5,5-trimethyl-[1,3]dioxolan-2-one

(Z)-6-Butyl-3,8,9-trimethyl-deca-2,6,7-trien-4-yne-1,9-diol

(Z)-6-Butyl-3,8,9-trimethyl-deca-2,6,7-trien-4-yne-1,9-diol

Conditions
ConditionsYield
With diethylamine; potassium bromide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ambient temperature;97%
heptanal
111-71-7

heptanal

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

(Z)-3-Methyl-2-dodecen-4-yne-1,6-diol

(Z)-3-Methyl-2-dodecen-4-yne-1,6-diol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane97%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

trimethyl orthoformate
149-73-5

trimethyl orthoformate

(Z)-5-Dimethoxymethoxy-3-methyl-pent-3-en-1-yne
118328-41-9

(Z)-5-Dimethoxymethoxy-3-methyl-pent-3-en-1-yne

Conditions
ConditionsYield
With magnesium chloride In dichloromethane at 25℃; for 2h;96%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

7,7-dimethyl-2-phenyl-6,7-dihydroquinoline-5,8-dione

7,7-dimethyl-2-phenyl-6,7-dihydroquinoline-5,8-dione

(Z)-5-hydroxy-5-(5′-hydroxy-3-methylpent-3′-en-1′-yn-1′-yl)-7,7-dimethyl-2-phenyl-6,7-dihydroquinolin-8(5H)-one

(Z)-5-hydroxy-5-(5′-hydroxy-3-methylpent-3′-en-1′-yn-1′-yl)-7,7-dimethyl-2-phenyl-6,7-dihydroquinolin-8(5H)-one

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 7,7-dimethyl-2-phenyl-6,7-dihydroquinoline-5,8-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;		96%
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 7,7-dimethyl-2-phenyl-6,7-dihydroquinoline-5,8-dione In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere; regioselective reaction;		79%
iodobenzene
591-50-4

iodobenzene

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

(Z)-3-methyl-5-phenyl-2-penten-4-yn-1-ol
148802-08-8

(Z)-3-methyl-5-phenyl-2-penten-4-yn-1-ol

Conditions
ConditionsYield
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In various solvent(s) 15 min, 0 deg C; 30 min, RT;95%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide for 2h; Ambient temperature;93%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

benzoyl chloride
98-88-4

benzoyl chloride

Benzoic acid (Z)-3-methyl-pent-2-en-4-ynyl ester
210236-01-4

Benzoic acid (Z)-3-methyl-pent-2-en-4-ynyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane 1.) 0 deg C, 2 h, 2.) room temperature, 16 h;95%
With triethylamine91%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

3-methyl-2-methylene-2, 5-dihydrofuran

3-methyl-2-methylene-2, 5-dihydrofuran

Conditions
ConditionsYield
With silver carbonate In benzene-d6 at 20℃; for 2h; Cyclization;95%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

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

chlorodimethyl(1,1,2-trimethylpropyl)silane

(Z)-[(2,3-dimethyl-2-butyl)dimethylsilyloxy]-3-methylpent-2-en-4-yne
196600-08-5

(Z)-[(2,3-dimethyl-2-butyl)dimethylsilyloxy]-3-methylpent-2-en-4-yne

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0℃; for 18h;93%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

2,2-dimethyl-6-pentyl-3,4-dihydronaphthalen-1(2H)-one

2,2-dimethyl-6-pentyl-3,4-dihydronaphthalen-1(2H)-one

(Z)-1-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)-2,2-dimethyl-6-pentyl-1,2,3,4-tetrahydronaphthalen-1-ol

(Z)-1-(5-hydroxy-3-methylpent-3-en-1-yn-1-yl)-2,2-dimethyl-6-pentyl-1,2,3,4-tetrahydronaphthalen-1-ol

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran at -80℃; for 0.666667h; Inert atmosphere;
Stage #2: 2,2-dimethyl-6-pentyl-3,4-dihydronaphthalen-1(2H)-one In tetrahydrofuran at -80 - 20℃; for 0.666667h; Inert atmosphere;		93%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal
3155-71-3

2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal

2Z,7E-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,7-nonadiene-4-yne-1,6-diol
50895-68-6

2Z,7E-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,7-nonadiene-4-yne-1,6-diol

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With 2-Methoxypropene; toluene-4-sulfonic acid at 0℃; for 0.5h;
Stage #2: With triethylamine at 20℃;
Stage #3: 2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)-2-butenal Reagent/catalyst; Further stages;		92.2%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

{4-[2-Bromo-1-(2-methoxy-ethoxymethoxy)-cyclopent-2-enyl]-but-2-ynyloxy}-tert-butyl-dimethyl-silane
131318-35-9

{4-[2-Bromo-1-(2-methoxy-ethoxymethoxy)-cyclopent-2-enyl]-but-2-ynyloxy}-tert-butyl-dimethyl-silane

(Z)-5-[5-[4-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-5-(2-methoxy-ethoxymethoxy)-cyclopent-1-enyl]-3-methyl-pent-2-en-4-yn-1-ol
131318-37-1

(Z)-5-[5-[4-(tert-Butyl-dimethyl-silanyloxy)-but-2-ynyl]-5-(2-methoxy-ethoxymethoxy)-cyclopent-1-enyl]-3-methyl-pent-2-en-4-yn-1-ol

Conditions
ConditionsYield
With propylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0)92%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

4,4,5-Trimethyl-5-prop-1-ynyl-[1,3]dioxolan-2-one

4,4,5-Trimethyl-5-prop-1-ynyl-[1,3]dioxolan-2-one

(Z)-3,6,8,9-Tetramethyl-deca-2,6,7-trien-4-yne-1,9-diol

(Z)-3,6,8,9-Tetramethyl-deca-2,6,7-trien-4-yne-1,9-diol

Conditions
ConditionsYield
With diethylamine; potassium bromide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ambient temperature;92%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

(Z)-3-methylpent-2-en-4-yn-1-yl 4-methoxybenzoate

(Z)-3-methylpent-2-en-4-yn-1-yl 4-methoxybenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 14h; Inert atmosphere; Darkness;92%
With triethylamine In dichloromethane at 25℃; for 1h;89%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(2Z)-1-tert-butyldiphenylsilyloxy-3-methylpent-2-en-4-yne

(2Z)-1-tert-butyldiphenylsilyloxy-3-methylpent-2-en-4-yne

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;92%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

cis-2,3-epoxy-3-methylpent-4-ynol

cis-2,3-epoxy-3-methylpent-4-ynol

Conditions
ConditionsYield
With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h;91%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane 1.) 0 deg C, 30 min, 2.) room temperature, 13 h;62%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane Epoxidation;
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

1,6-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid diethyl ester
1261167-88-7

1,6-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With C49H42Au2Cl2N2O4P4S2 In glycerol at 45℃; for 4h; Solvent; Green chemistry;91%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride at 20℃; for 4h; Inert atmosphere;81%
ethyl bromide
74-96-4

ethyl bromide

(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

propargyl bromide
106-96-7

propargyl bromide

(Z)-3-methylocta-2-en-4,7-diyn-1-ol

(Z)-3-methylocta-2-en-4,7-diyn-1-ol

Conditions
ConditionsYield
Stage #1: ethyl bromide With iodine; magnesium In tetrahydrofuran at 50℃; Inert atmosphere;
Stage #2: (Z)-3-methylpent-2-en-4-ynol In tetrahydrofuran at 50℃; Inert atmosphere;
Stage #3: propargyl bromide Further stages;		91%
...Expand
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

2,2,3,3-tetramethyl-2,3-dihydronaphthalene-1,4-dione

2,2,3,3-tetramethyl-2,3-dihydronaphthalene-1,4-dione

(Z)-(1′-hydroxy-2′,2′,3′,3′-tetramethyl-4′-oxo-tetrahydronaph-thalene-one-yl)-3-methylpentyl-2-en-4-yn-1-ol

(Z)-(1′-hydroxy-2′,2′,3′,3′-tetramethyl-4′-oxo-tetrahydronaph-thalene-one-yl)-3-methylpentyl-2-en-4-yn-1-ol

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,2,3,3-tetramethyl-2,3-dihydronaphthalene-1,4-dione In tetrahydrofuran; hexane at -78 - 20℃; for 16h;		91%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

6,6-dimethyl-5,6-dihydrobenzofuran-4,7-dione

6,6-dimethyl-5,6-dihydrobenzofuran-4,7-dione

C16H18O4

C16H18O4

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 6,6-dimethyl-5,6-dihydrobenzofuran-4,7-dione In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere; regioselective reaction;		90%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

4-methoxy-phenol
150-76-5

4-methoxy-phenol

(Z)-(4-methoxyphenoxy)-3-methylpent-2-en-4-yne
196600-09-6

(Z)-(4-methoxyphenoxy)-3-methylpent-2-en-4-yne

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine for 4h; Ambient temperature;89%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

1,6-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester
63098-21-5

1,6-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With C49H42Au2Cl2N2O4P4S2 In glycerol at 45℃; for 4h; Green chemistry;89%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride at 20℃; for 4h; Inert atmosphere;83%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

C12H11BrO2

C12H11BrO2

(Z)-7-bromo-4-hydroxy-4-(5′-hydroxy-3-methylpent-3′-en-1′-yn-1′-yl)-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

(Z)-7-bromo-4-hydroxy-4-(5′-hydroxy-3-methylpent-3′-en-1′-yn-1′-yl)-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: C12H11BrO2 In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;		89%
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: C12H11BrO2 In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere; regioselective reaction;		70%

(Z)-3-Methylpent-2-en-4-yn-1-ol Chemical Properties

Molecular Structure:

Molecular Formula: C6H8O
Molecular Weight: 96.1271
IUPAC Name: (Z)-3-Methylpent-2-en-4-yn-1-ol
Synonyms of (Z)-3-Methylpent-2-en-4-yn-1-ol (CAS NO.6153-05-5): cis-3-Methyl-2-pentene-4-yn-1-ol ; EINECS 228-168-2
CAS NO: 6153-05-5
Index of Refraction: 1.481
Molar Refractivity: 29.1 cm3
Molar Volume: 102.2 cm3 
Surface Tension: 35.7 dyne/cm
Density: 0.94 g/cm3
Flash Point: 65.6 °C
Enthalpy of Vaporization: 47.42 kJ/mol
Boiling Point: 170.9 °C at 760 mmHg
Vapour Pressure of (Z)-3-Methylpent-2-en-4-yn-1-ol (CAS NO.6153-05-5): 0.46 mmHg at 25°C

(Z)-3-Methylpent-2-en-4-yn-1-ol Safety Profile

Hazard Codes of (Z)-3-Methylpent-2-en-4-yn-1-ol (CAS NO.6153-05-5): HarmfulXn
Risk Statements: 22-36/37/38 
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39: Wear suitable gloves and eye/face protection.
RIDADR: UN 1760
HazardClass: 8
PackingGroup: III

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