(+)1,2-Epoxyhex-5-ene supplier

Name
(+)-1,2-epoxyhex-5-ene
EINECS
CAS No. 137688-20-1
Article Data14
CAS DataBase
Density 0.892 g/cm³
Solubility
Melting Point
Formula C₆H₁₀O
Boiling Point 120 °C at 760 mmHg
Molecular Weight 98.1448
Flash Point 15.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-(3-Buten-1-yl)oxirane;
PSA 12.53000
LogP 1.35140

Synthetic route

: 10353-53-4
1,2-epoxy-5-hexene

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
With (R,R) Co(salen); water Jacobsen kinetic racemate resolution;	86%
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); acetic acid In tetrahydrofuran; water at 0 - 20℃; for 23h; Inert atmosphere;	49%
With (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) In water at 20℃; Jacobsen Asymmetric Epoxidation;	40%

: 10353-53-4
1,2-epoxy-5-hexene

A: 127102-61-8
(S)-hex-5-ene-1,2-diol

B: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

C: 137688-21-2
(-)-(S)-2-(but-3-enyl)oxirane

Conditions

Conditions	Yield
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A 44% B n/a C n/a

...Expand

: 10353-53-4
1,2-epoxy-5-hexene

A: 133494-68-5
(R)-1,2-dihydroxy-5-hexene

B: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

C: 137688-21-2
(-)-(S)-2-(but-3-enyl)oxirane

Conditions

Conditions	Yield
With [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃;	A 44% B n/a C n/a

...Expand

: 10353-53-4
1,2-epoxy-5-hexene

A: 127102-61-8
(S)-hex-5-ene-1,2-diol

B: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid In tetrahydrofuran at 0 - 20℃; for 10h;	A 44% B n/a
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid In tetrahydrofuran at 20℃; for 16h;	A n/a B 43%

: 10353-53-4
1,2-epoxy-5-hexene

A: 127102-61-8
(S)-hex-5-ene-1,2-diol

B: 133494-68-5
(R)-1,2-dihydroxy-5-hexene

C: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); air; acetic acid In tetrahydrofuran at 20℃; for 16h;	A n/a B n/a C 43.1%

...Expand

: 10353-53-4
1,2-epoxy-5-hexene

A poly((S)-5,6-epoxy-1-hexene): poly((S)-5,6-epoxy-1-hexene)

B: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

C: 137688-21-2
(-)-(S)-2-(but-3-enyl)oxirane

Conditions

Conditions	Yield
C64H74Cl2Co2N4O4; bis(triphenylphosphoranylidene)-ammonium acetate In toluene at 0℃; for 0.183333h; Product distribution / selectivity;	A 35% B n/a C n/a

...Expand

: 10353-53-4
1,2-epoxy-5-hexene

A: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

B: 137688-21-2
(-)-(S)-2-(but-3-enyl)oxirane

Conditions

Conditions	Yield
With Rhodotorula glutinis CIMW 147 cells In phosphate buffer at 30℃; pH=7.5; kinetic resolution; Title compound not separated from byproducts;

: Carbonic acid (R)-1-bromomethyl-pent-4-enyl ester methyl ester

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
With methanol; potassium carbonate In diethyl ether Cyclization;

: 592-42-7
1,5-Hexadien

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: AD-mix-β 2: PPTS 3: CH3COBr; Et3N 4: K2CO3; MeOH / diethyl ether View Scheme

: 133494-68-5
(R)-1,2-dihydroxy-5-hexene

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: PPTS 2: CH3COBr; Et3N 3: K2CO3; MeOH / diethyl ether View Scheme

: (R)-4-But-3-enyl-2-methoxy-[1,3]dioxolane

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH3COBr; Et3N 2: K2CO3; MeOH / diethyl ether View Scheme

: 1,2-epoxyhex-5-ene

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

Conditions

Conditions	Yield
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate In diethyl ether; water at 0 - 20℃;	672 mg

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 82065-64-3
methyl (R)-(-)-3-hydroxyhepr-6-enoate

Conditions

Conditions	Yield
With 3-HYDROXYPYRIDINE; dicobalt octacarbonyl In tetrahydrofuran at 60℃; under 31028.9 Torr; for 9h;	95%

...Expand

: 3989-45-5
N-benzylmethanesulfonamide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 900143-68-2
N-benzyl-N-(2-hydroxy-hex-5-enyl)-methanesulfonamide

Conditions

Conditions	Yield
tetraethylammonium chloride; potassium carbonate In 1,4-dioxane at 100℃;	94%

: 109-72-8, 29786-93-4
n-butyllithium

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 1374332-11-2
(5S)-dec-1-en-5-ol

Conditions

Conditions	Yield
With copper(I) cyanide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	90%

: 207574-06-9
N-benzylpropane-1-sulfonamide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 900143-78-4
Propane-1-sulfonic acid benzyl-((R)-2-hydroxy-hex-5-enyl)-amide

Conditions

Conditions	Yield
tetraethylammonium chloride; potassium carbonate In 1,4-dioxane at 100℃;	87%

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 74-99-7
prop-1-yne

: 1493781-03-5
C9H14O

Conditions

Conditions	Yield
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Stage #2: (R)-2-(but-3-en-1-yl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 1h; Schlenk technique;	87%
Stage #1: prop-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 0.5h; Schlenk technique; Stage #3: (R)-2-(but-3-en-1-yl)oxirane In tetrahydrofuran; hexane at -78℃; for 1h; Schlenk technique;	87%

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 741676-78-8
(1R,2R,5S)-bicyclo[3.1.0]hexan-2-ol

Conditions

Conditions	Yield
Stage #1: (R)-2-(but-3-en-1-yl)oxirane With n-hexyllithium; 2,2,6,6-tetramethyl-piperidine In hexane; tert-butyl methyl ether at -5 - 0℃; for 8h; Stage #2: With hydrogenchloride In hexane; tert-butyl methyl ether; water at 0℃; Product distribution / selectivity;	86%
Stage #1: (R)-2-(but-3-en-1-yl)oxirane With 2,2,6,6-tetramethyl-piperidine; n-hexyllithium In hexanes; tert-butyl methyl ether at -5 - 0℃; for 4h; Stage #2: With hydrogenchloride In hexanes; tert-butyl methyl ether; water at 0℃;	86%
With 2,2,6,6-tetramethylpiperidinyl-lithium In hexane at 20℃; for 16h;	72%

: 351003-49-1
5-chloro-2-fluorobenzene-1-sulfonyl chloride

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 1215721-26-8
C19H20ClNO3S

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 100℃; for 72h;	84%

...Expand

: 13368-42-8
4-(trimethylsilyl)morpholine

: 201230-82-2
carbon monoxide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

A: (R)-1-Morpholin-4-yl-hex-5-en-2-ol

B: (R)-3-Hydroxy-1-morpholin-4-yl-hept-6-en-1-one

Conditions

Conditions	Yield
Stage #1: 4-(trimethylsilyl)morpholine; carbon monoxide; (R)-2-(but-3-en-1-yl)oxirane With dicobalt octacarbonyl In ethyl acetate at 25℃; under 760 Torr; for 24h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 0.166667h;	A n/a B 80%

...Expand

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 6921-34-2
benzylmagnesium chloride

: 1-phenylhept-6-en-1-ol

Conditions

Conditions	Yield
Stage #1: (R)-2-(but-3-en-1-yl)oxirane; benzylmagnesium chloride With copper(l) chloride In tetrahydrofuran at -10 - 0℃; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water at 0 - 10℃; for 1h; regioselective reaction;	80%

: 141337-26-0
4-chloro-2-fluorobenzenesulfonyl chloride

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 1215721-28-0
C19H20ClNO3S

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 100℃; for 72h;	76%

...Expand

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 4-bromo-2,5-difluorobenzenesulfonyl chloride

: 1215721-25-7
C19H19BrFNO3S

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 100℃; for 72h;	76%

...Expand

: 150406-34-1
(S)-3-(tert-butyldimethylsilyloxy)but-1-yne

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 907998-55-4
(5R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-dec-1-en-7-yn-5-ol

Conditions

Conditions	Yield
Stage #1: (S)-3-(tert-butyldimethylsilyloxy)but-1-yne With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Stage #2: (R)-2-(but-3-en-1-yl)oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78 - 20℃; for 1.16667h;	74%

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: (R)-3-methylenecyclopentan-1-ol

Conditions

Conditions	Yield
With Co(dimethylglyoximate)2(py)iPr; potassium tert-butylate In methanol at 34℃; for 24h; Jacobsen Rearrangement; Inert atmosphere; Irradiation; regioselective reaction;	74%

: 25300-37-2
2-chloro-6-methylbenzenesulfonyl chloride

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 1215721-32-6
C20H24ClNO3S

Conditions

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 100℃; for 72h;	59%

...Expand

: 2905-21-7
2-fluorobenzenesulfonyl chloride

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 1215721-23-5
C19H21NO3S

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 100℃; for 72h;	58%

...Expand

: 4-bromo-2-chlorobenzene-1-sulfonyl chloride

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 1215721-29-1
C19H20BrNO3S

Conditions

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 100℃; for 72h;	48%

...Expand

: 34813-49-5
t-butylsulfonamide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 881840-66-0
2-Methyl-propane-2-sulfonic acid ((R)-2-hydroxy-hex-5-enyl)-amide

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 16h;	45%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 16h;	45%

: 100-46-9
benzylamine

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 2905-23-9
2-chlorophenylsulfonyl chloride

: 1215721-23-5
C19H21NO3S

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 72h;	25%

...Expand

: 201230-82-2
carbon monoxide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 504-63-2
trimethyleneglycol

A: (R)-1-[1,3]Dioxan-2-yl-hex-5-en-2-ol

B: 2-[1,3]dioxan-2-yl-hex-5-en-1-ol

Conditions

Conditions	Yield
With hydrogen; toluene-4-sulfonic acid; dicobalt octacarbonyl 1.) 1000 psi; Yield given; Multistep reaction. Yields of byproduct given;

...Expand

: 29601-98-7
N-benzylhydroxylamine hydrochloride

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: (R)-1-(benzyl(hydroxy)amino)hex-5-en-2-ol

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 0.25h; Ring cleavage;
With triethylamine In methanol at 20℃; for 96h; Inert atmosphere;
With triethylamine In methanol at 20℃; for 96h; Inert atmosphere;

: 30043-41-5
(hex-5-enyl)magnesium bromide

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 288270-22-4
(S)-5-hydroxydodeca-1,11-diene

Conditions

Conditions	Yield
With copper(l) iodide Ring cleavage;

: 64024-63-1
1-morpholino-2-trimethylsilyl acetylene

: 137688-20-1
(R)-2-(but-3-en-1-yl)oxirane

: 4-((R)-5-But-3-enyl-3-trimethylsilanyl-4,5-dihydro-furan-2-yl)-morpholine

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃; for 0.5h;

(+)1,2-Epoxyhex-5-ene Specification

The (+)1,2-Epoxyhex-5-ene, with the CAS registry number of 137688-20-1, is also known as 2-(3-Buten-1-yl)oxirane. This chemical's molecular formula is C₆H₁₀O. What's more, its systematic name is 2-(But-3-en-1-yl)oxirane.

Physical properties about the (+)1,2-Epoxyhex-5-ene are: (1)ACD/LogP: 1.40; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.4; (4)ACD/LogD (pH 7.4): 1.4; (5)ACD/BCF (pH 5.5): 6.84; (6)ACD/BCF (pH 7.4): 6.84; (7)ACD/KOC (pH 5.5): 137.89; (8)ACD/KOC (pH 7.4): 137.89; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 12.53 Å²; (13)Index of Refraction: 1.442; (14)Molar Refractivity: 29.14 cm³; (15)Molar Volume: 109.9 cm³; (16)Surface Tension: 30 dyne/cm; (17)Density: 0.892 g/cm³; (18)Flash Point: 15.6 °C; (19)Enthalpy of Vaporization: 34.33 kJ/mol; (20)Boiling Point: 120 °C at 760 mmHg; (21)Vapour Pressure: 18.6 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O1C(CC\C=C)C1
(2) InChI: InChI=1/C6H10O/c1-2-3-4-6-5-7-6/h2,6H,1,3-5H2
(3) InChIKey: MUUOUUYKIVSIAR-UHFFFAOYAD

Product Name

(+)-1,2-epoxyhex-5-ene

Synthetic route

(+)1,2-Epoxyhex-5-ene Specification

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