6153-05-5

Basic information

• Product Name: (Z)-3-Methylpent-2-en-4-yn-1-ol
• Synonyms: cis-3-methyl-2-pentene-4-yn-1-ol;(z)-3-methylpent-2-en-4-yn-1-ol;CIS-3-METHYL-2-PENTEN-4-YN-1-OL;Hexacarbinal;(E)-3-METHYL-2-PENTENE-4-YN-1-OL;(2Z)-3-Methyl-2-penten-4-yn-1-ol;(Z)-3-Methyl-2-penten-4-yn-1-ol;(Z)-3-Methyl-3-penten-1-yn-5-ol
• CAS NO: 6153-05-5
• Molecular Formula: C₆H₈O
• Molecular Weight: 96.13
• EINECS: 228-168-2
• Mol File: 6153-05-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 171°C
• Flash Point: 65°C
• Appearance: /
• Density: 0.940
• Vapor Pressure: 0.46mmHg at 25°C
• Refractive Index: 1.4445-1.4465
• Storage Temp.: 2-8°C
• PKA: 13.80±0.10(Predicted)
• CAS DataBase Reference: (Z)-3-Methylpent-2-en-4-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-Methylpent-2-en-4-yn-1-ol(6153-05-5)
• EPA Substance Registry System: (Z)-3-Methylpent-2-en-4-yn-1-ol(6153-05-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 1760
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6153-05-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H8O/c1-3-6(2)4-5-7/h1,4,7H,5H2,2H3/b6-4-

Synthetic route

3-methyl-1-penten-4-yn-3-ol (3230-69-1) → (Z)-3-methylpent-2-en-4-ynol (6153-05-5) + (E)-3-methylpent-2-en-4-yn-1-ol (6153-06-6)

Conditions	Yield
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) → (E)-1-bromo-3-methylpent-2-en-4-yne (69371-58-0) + (Z)-3-methylpent-2-en-4-ynol (6153-05-5)

Conditions	Yield
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-methylpent-2-en-4-ynol (6153-05-5)

Conditions	Yield
With methanol; potassium carbonate at 20℃;	58%
With potassium carbonate In methanol

3-methyl-1-penten-4-yn-3-ol (3230-69-1) → (Z)-3-methylpent-2-en-4-ynol (6153-05-5) + cis-3-methyl-5-nitroxy-3-penten-1-yne + trans-3-methyl-5-nitroxy-3-penten-1-yne

Conditions	Yield
With nitric acid; hydroquinone In di-isopropyl ether at 50 - 52℃; for 7h;	A 16.1% B 56.4% C 13%

3-methyl-1-penten-4-yn-3-ol (3230-69-1) → (Z)-3-methylpent-2-en-4-ynol (6153-05-5)

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

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

Conditions	Yield
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) → (Z)-3-methylpent-2-en-4-ynol (6153-05-5) + (E)-3-methylpent-2-en-4-yn-1-ol (6153-06-6)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 25℃; for 3h; Overall yield = 95 %;

(Z)-3-methylpent-2-en-4-ynol (6153-05-5) → 2,3-dimethylfuran (14920-89-9)

Conditions	Yield
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*2H2O	98%
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) → 3-methyl-1-penten-4-yn-3-ol (3230-69-1)

Conditions	Yield
With sulfuric acid; hydroquinone; mercury dichloride In di-isopropyl ether at 50 - 52℃; for 0.166667h; Product distribution;	100%

vinyl acetate (108-05-4) + (Z)-3-methylpent-2-en-4-ynol (6153-05-5) → (Z)-3-Methyl-2-penten-4-in-1-ylacetat (35272-87-8)

Conditions	Yield
With hexamethyltriamido-N-benzylimidophosphate In tetrahydrofuran at 20℃; for 15h; Acylation;	99%

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

Conditions	Yield
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) + (Z)-3-methylpent-2-en-4-ynol (6153-05-5) → (Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether (41967-81-1)

Conditions	Yield
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) + 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

Conditions	Yield
With diethylamine; potassium bromide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ambient temperature;	97%

heptanal (111-71-7) + (Z)-3-methylpent-2-en-4-ynol (6153-05-5) → (Z)-3-Methyl-2-dodecen-4-yne-1,6-diol

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane	97%

(Z)-3-methylpent-2-en-4-ynol (6153-05-5) + trimethyl orthoformate (149-73-5) → (Z)-5-Dimethoxymethoxy-3-methyl-pent-3-en-1-yne (118328-41-9)

Conditions	Yield
With magnesium chloride In dichloromethane at 25℃; for 2h;	96%

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

Conditions	Yield
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) + (Z)-3-methylpent-2-en-4-ynol (6153-05-5) → (Z)-3-methyl-5-phenyl-2-penten-4-yn-1-ol (148802-08-8)

Conditions	Yield
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) + benzoyl chloride (98-88-4) → Benzoic acid (Z)-3-methyl-pent-2-en-4-ynyl ester (210236-01-4)

Conditions	Yield
With pyridine In dichloromethane 1.) 0 deg C, 2 h, 2.) room temperature, 16 h;	95%
With triethylamine	91%

(Z)-3-methylpent-2-en-4-ynol (6153-05-5) → 3-methyl-2-methylene-2, 5-dihydrofuran

Conditions	Yield
With silver carbonate In benzene-d6 at 20℃; for 2h; Cyclization;	95%

(Z)-3-methylpent-2-en-4-ynol (6153-05-5) + chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → (Z)-[(2,3-dimethyl-2-butyl)dimethylsilyloxy]-3-methylpent-2-en-4-yne (196600-08-5)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0℃; for 18h;	93%

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

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

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

Conditions	Yield
With propylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0)	92%

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

Conditions	Yield
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) + 4-methoxy-benzoyl chloride (100-07-2) → (Z)-3-methylpent-2-en-4-yn-1-yl 4-methoxybenzoate

Conditions	Yield
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) + tert-butylchlorodiphenylsilane (58479-61-1) → (2Z)-1-tert-butyldiphenylsilyloxy-3-methylpent-2-en-4-yne

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	92%

(Z)-3-methylpent-2-en-4-ynol (6153-05-5) → cis-2,3-epoxy-3-methylpent-4-ynol

Conditions	Yield
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) + acetylenedicarboxylic acid diethyl ester (762-21-0) → 1,6-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid diethyl ester (1261167-88-7)

Conditions	Yield
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) + (Z)-3-methylpent-2-en-4-ynol (6153-05-5) + propargyl bromide (106-96-7) → (Z)-3-methylocta-2-en-4,7-diyn-1-ol

Conditions	Yield
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%

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

Conditions	Yield
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) + 6,6-dimethyl-5,6-dihydrobenzofuran-4,7-dione → C16H18O4

Conditions	Yield
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) + 4-methoxy-phenol (150-76-5) → (Z)-(4-methoxyphenoxy)-3-methylpent-2-en-4-yne (196600-09-6)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine for 4h; Ambient temperature;	89%

(Z)-3-methylpent-2-en-4-ynol (6153-05-5) + dimethyl acetylenedicarboxylate (762-42-5) → 1,6-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester (63098-21-5)

Conditions	Yield
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) + 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

Conditions	Yield
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%

Upstream product

• 121635-19-6 (Z)-3-methyl-5-trimethylsilylpent-2-en-4-yn-1-ol 
• 53635-18-0 3-methyl-2-penten-4-yn-1-al 
• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 50516-66-0 5-Trimethylsilyl-3-methyl-pent-1-en-4-in-3-ol 
• 3230-69-1 3-methyl-1-penten-4-yn-3-ol 

Downstream Products

• 6153-06-6 (E)-3-methylpent-2-en-4-yn-1-ol 
• 62030-09-5 (4-chloro-benzoylamino)-phenyl-acetic acid (Z)-3-methyl-pent-2-en-4-ynyl ester 
• 148802-08-8 (Z)-3-methyl-5-phenyl-2-penten-4-yn-1-ol 
• 25428-56-2 11,12-Didehydro-[7t,9t,13c]retinol 
• 71869-05-1 Triphenyl<(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-4-ynyl>phosphonium Bromide 
• 661492-81-5 (2Z,4E)-5-(6,6-dimethylcyclohex-1-en-1-yl)-3,4-dimethylpenta-2,4-dienal 
• 661492-73-5 (2Z,4E)-5-(6,6-dimethylcyclohex-1-en-1-yl)-3,4-dimethylpenta-2,4-dien-1-ol 
• 661492-82-6 (2Z,4E)-3,4-dimethyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienal 
• 661492-76-8 (2Z,4E)-3,4-dimethyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dien-1-ol 
• 405113-03-3 ethyl (2E,4E,6Z,8E)-9-(6,6-dimethylcyclohex-1-en-1-yl)-3,7,8-trimethylnona-2,4,6,8-tetraenoate 
• 661492-83-7 ethyl (2E,4E,6Z,8E)-3,7,8-trimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 
• 79204-33-4 benzoic acid 3-methyl-furan-2-ylmethyl ester 
• 632-16-6 2,3-dimethylthiophene 
• 36602-31-0 (Z)-β-ocimene 

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