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928-95-0

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928-95-0 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 928-95-0 differently. You can refer to the following data:
1. colourless liquid
2. (E)-2-Hexen-1-ol occurs in many fruits and has a fruity, green odor, which is sweeter than that of the isomeric (Z)-3- hexen-1-ol and is, therefore, preferred in aroma compositions.

Uses

trans-2-Hexen-1-ol was used to evaluate the quality of protected designation of virgin olive oils by headspace solid-phase microextraction-gas chromatography using flame ionization detection and multivariate analysis. It was also used in encapsulation of vanadium catalysts in inorganic and hybrid matrices using sol-gel method.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 2792, 1971 DOI: 10.1021/ja00740a040Tetrahedron Letters, 24, p. 3413, 1983 DOI: 10.1016/S0040-4039(00)86286-3

General Description

trans-2-Hexen-1-ol undergoes allylic epoxidation to yield (2R,3R)-(+)-3-propyloxiranemethanol in high pressure carbon dioxide.

Biochem/physiol Actions

Taste at 2.0-9.0 ppm

Check Digit Verification of cas no

The CAS Registry Mumber 928-95-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 8 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 928-95:
(5*9)+(4*2)+(3*8)+(2*9)+(1*5)=100
100 % 10 = 0
So 928-95-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O/c1-2-3-4-5-6-7/h4-5,7H,2-3,6H2,1H3/b5-4+

928-95-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name trans-2-Hexen-1-ol

1.2 Other means of identification

Product number -
Other names (E)-2-hexen-1-ol

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:928-95-0 SDS

928-95-0Synthetic route

trans-tert-butyl(hex-2-en-1-yloxy)dimethylsilane
113997-32-3

trans-tert-butyl(hex-2-en-1-yloxy)dimethylsilane

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With phosphomolybdic acid hydrate; silica gel In tetrahydrofuran at 20℃; for 0.5h;97%
With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 1h;96%
(E)-1-(methoxymethoxy)hex-2-ene
88738-36-7

(E)-1-(methoxymethoxy)hex-2-ene

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In butanone for 10h; Heating;94%
(E)-1-(2-Methoxy-ethoxymethoxy)-hex-2-ene
88738-35-6

(E)-1-(2-Methoxy-ethoxymethoxy)-hex-2-ene

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In butanone for 11h; Heating;94%
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With bis(cyclopentadienyl)dihydrozirconium In isopropyl alcohol at 130℃; for 8h;93%
With phosphotungstic acid; sodium tetrahydroborate In methanol93%
With isopropyl alcohol; zirconium(IV) oxide for 6h; Rate constant; Heating;92%
hex-2-yn-1-ol
764-60-3

hex-2-yn-1-ol

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Heating;90%
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Heating;90.5%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating;87%
ethyl (E)-hex-2-enoate
27829-72-7

ethyl (E)-hex-2-enoate

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride at 0 - 20℃;85%
With diisobutylaluminium hydride In dichloromethane; toluene at -78 - 20℃; Inert atmosphere;79%
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 3h; Heating;55%
3-Methylselanyl-hex-1-ene
88088-14-6

3-Methylselanyl-hex-1-ene

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With dihydrogen peroxide In pyridine; dichloromethane at 20℃;85%
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

C12H22O2

C12H22O2

Conditions
ConditionsYield
With acetic acid; zinc In water at 20℃; for 0.333333h; Green chemistry;A 21%
B 79%
1-hexene-3-ol
4798-44-1

1-hexene-3-ol

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With methanesulfonic acid In tetrahydrofuran; water at 20℃; for 12h;76%
(2S*,3S*)-1-Acetoxy-2,3-epoxyhexane
170209-06-0

(2S*,3S*)-1-Acetoxy-2,3-epoxyhexane

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With tellurium; lithium triethylborohydride In tetrahydrofuran at 0℃; for 0.2h;70%
(E)-1-bromo-2-hexene
73881-10-4

(E)-1-bromo-2-hexene

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With potassium hydroxide; tetrafluoroboric acid; sodium hydrogencarbonate; mercury(II) oxide In 1,4-dioxane 1.) room temp., 2 h;65%
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With Beauveria sulfurescens In dimethyl sulfoxide at 20℃; for 48h;A 37%
B 63%
With hydrogen In hexane at 50℃; under 30003 Torr; for 18h; Reagent/catalyst; Autoclave; chemoselective reaction;
(E)-tert-butyl(hex-2-en-1-yloxy)diphenylsilane
11997-33-4

(E)-tert-butyl(hex-2-en-1-yloxy)diphenylsilane

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.75h;53%
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

(4E,8E)-dodeca-4,8-diene-6,7-diol
114612-53-2

(4E,8E)-dodeca-4,8-diene-6,7-diol

Conditions
ConditionsYield
With zinc In water at 70℃; for 2h; Green chemistry;A 10%
B n/a
C n/a
With acetic acid; zinc In ethanol at 20℃; Flow reactor;
epoxybutene
930-22-3

epoxybutene

diethyl ether
60-29-7

diethyl ether

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

5-hexen-3-ol
688-99-3

5-hexen-3-ol

C

2-ethylbut-3-en-1-ol
53045-70-8

2-ethylbut-3-en-1-ol

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

ethanol
64-17-5

ethanol

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
at 350℃; ueber Lebedew-Katalysator;
(E)-2-Hexenoic acid
13419-69-7

(E)-2-Hexenoic acid

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
ethanol
64-17-5

ethanol

butyraldehyde
123-72-8

butyraldehyde

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
at 350℃; ueber Lebedew-Katalysator;
bromoethyl acetate
927-68-4

bromoethyl acetate

butyraldehyde
123-72-8

butyraldehyde

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With tetrahydrofuran; magnesium; mercury dichloride Erwaermen des Reaktionsgemisches mit wss.Kalilauge;
2,3-butadien-1-ol
18913-31-0

2,3-butadien-1-ol

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With copper(l) iodide In diethyl ether
2-methyl-4,7-dihydro-1,3-dioxepine
7045-86-5

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

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

A

trans-4-Octene
14850-23-8

trans-4-Octene

B

(Z)-2-hexen-1-ol
928-94-9

(Z)-2-hexen-1-ol

C

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

D

iso-butanol
78-92-2, 15892-23-6

iso-butanol

Conditions
ConditionsYield
1,2-bis(diphenylphosphino)ethane nickel(II) chloride for 5h; Product distribution; Ambient temperature; regio- and stereoselectivity of Ni-catalyzed alkylation; various Grignard reagents;A 47 % Chromat.
B n/a
C n/a
D n/a
1,2-bis(diphenylphosphino)ethane nickel(II) chloride for 5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

hexanal
66-25-1

hexanal

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 60h;A 52 % Chromat.
B 2 % Chromat.
(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

hexanal
66-25-1

hexanal

C

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
ConditionsYield
With copper(l) iodide; lithium aluminium tetrahydride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -78℃; for 60h;A 12 % Chromat.
B 63 % Chromat.
C 1 % Chromat.
methyl (E)-hex-2-enoate
13894-63-8

methyl (E)-hex-2-enoate

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride In diethyl ether at -78℃;
With diisobutylaluminium hydride In tetrahydrofuran at -78 - 20℃;
1-hexene
592-41-6

1-hexene

A

(Z)-2-hexen-1-ol
928-94-9

(Z)-2-hexen-1-ol

B

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
With oxygen; rose bengal; triphenylphosphine Product distribution; multistep reaction: 1.) EtOH, 25 deg C, irradiation; other temperature (50 deg C); photosensitised oxidation of olefins, reduction of the hydroperoxides formed;
1-hexene
592-41-6

1-hexene

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

1-hexene-3-ol
4798-44-1

1-hexene-3-ol

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; triphenylphosphine Product distribution; multistep reaction: 1.) 25 deg C; other temperature (50 deg C); other catalysts; autooxidation of olefins, reduction of the hydroperoxides formed;
trans-2-hexene
4050-45-7

trans-2-hexene

A

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

B

(E)-hex-4-en-3-ol
4798-58-7, 29478-27-1

(E)-hex-4-en-3-ol

C

1-hexene-3-ol
4798-44-1

1-hexene-3-ol

D

(S,R)-trans-3-hexen-2-ol
29478-26-0

(S,R)-trans-3-hexen-2-ol

E

cis-3-hexen-2-one
29478-31-7

cis-3-hexen-2-one

Conditions
ConditionsYield
With oxygen; cobalt(II) acetate; triphenylphosphine Product distribution; multistep reaction: 1.) 25 deg C; other temperature (50 deg C); other catalysts; autooxidation of olefins, reduction of the hydroperoxides formed;
1-hexene-3-ol
4798-44-1

1-hexene-3-ol

A

(Z)-2-hexen-1-ol
928-94-9

(Z)-2-hexen-1-ol

B

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
triphenylsilyl perrhenate In dichloromethane at 0 - 30℃; Thermodynamic data; Product distribution; Rate constant; ΔH(excit.), ΔS(excit.);
tetrahydrofuran
109-99-9

tetrahydrofuran

bromoethyl acetate
927-68-4

bromoethyl acetate

butyraldehyde
123-72-8

butyraldehyde

magnesium

magnesium

mercury (II)-chloride

mercury (II)-chloride

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Conditions
ConditionsYield
Erhitzen des Reaktionsprodukts mit wss.Kalilauge;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

<(E)-hex-2-enyl>triphenylphosphonium bromide
88517-93-5

<(E)-hex-2-enyl>triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 10h; Heating;100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

(E)-2-Hexenal
6728-26-3

(E)-2-Hexenal

Conditions
ConditionsYield
With oxygen; 2,2,6,6-tetramethyl-piperidine-N-oxyl; copper(l) chloride In N,N-dimethyl-formamide at 25℃; for 1.75h;100%
With manganese(IV) oxide; 3-mercapto-2-(mercaptomethyl)-ethyl propanoate; 4 A molecular sieve In dichloromethane Heating;100%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 16h; Inert atmosphere;99%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

2,3-epoxyhexanol
106498-75-3

2,3-epoxyhexanol

Conditions
ConditionsYield
With tert.-butylhydroperoxide In chloroform for 4h; Catalytic behavior; Reflux;100%
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h; Catalytic behavior; Reagent/catalyst;100%
With tributyl-n-octylphosphonium peroxotantalate; dihydrogen peroxide In water at 0℃; Reagent/catalyst; Schlenk technique; chemoselective reaction;100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

trans-2-hexenyl mesylate
99704-81-1

trans-2-hexenyl mesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;100%
With triethylamine In dichloromethane at -15℃; for 1.5h;100%
With triethylamine In tetrahydrofuran at 0℃; for 3h;99%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

trans-2-hexenyl tosylate
205882-94-6

trans-2-hexenyl tosylate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 48h;100%
With n-butyllithium 1) hexane, THF, -78 deg C, 2) -78 deg C, 72 h; Multistep reaction;
With potassium hydroxide
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

anti-2,3-dichloro-1-hexanol

anti-2,3-dichloro-1-hexanol

Conditions
ConditionsYield
With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; tetraethylammonium trichloride In dichloromethane Ambient temperature;100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

pivaloyl chloride
3282-30-2

pivaloyl chloride

(E)-hex-2-enyl pivalate
1194667-13-4

(E)-hex-2-enyl pivalate

Conditions
ConditionsYield
at 20℃; for 0.0833333h; Neat (no solvent);100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

(E)-hex-2enyl N-phenylbenzimidate
188122-37-4

(E)-hex-2enyl N-phenylbenzimidate

Conditions
ConditionsYield
Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 30℃; for 1.25h;
Stage #2: N-phenyl-benzimidoyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h;
100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

N-benzyl-2,4-dinitro-benzenesulfonamide

N-benzyl-2,4-dinitro-benzenesulfonamide

(E)-N-benzyl-N-(hex-2-enyl)-2',4'-dinitrobenzenesulfonamide
1391485-27-0

(E)-N-benzyl-N-(hex-2-enyl)-2',4'-dinitrobenzenesulfonamide

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 19h;100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

A

trans-4-Octene
14850-23-8

trans-4-Octene

B

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

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

Conditions
ConditionsYield
With C37H40Cl2N2ORuS2 In tetrahydrofuran-d8 at 45℃; for 1h; Inert atmosphere;A 100%
B 100%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

acetic anhydride
108-24-7

acetic anhydride

(E)-2-hexen-1-yl acetate
2497-18-9

(E)-2-hexen-1-yl acetate

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In acetonitrile for 0.0833333h;99%
With dmap In diethyl ether at 20℃; for 16h; Inert atmosphere;89%
With triethylamine; dmap In dichloromethane at 20℃;88%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

(E)-2,2,2-trichloroacetimidic acid hex-2-enyl ester
51479-70-0

(E)-2,2,2-trichloroacetimidic acid hex-2-enyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h;99%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at -15 - 25℃; for 1h;95%
With sodium hydride 1.) THF, 0 deg C, 1 h, 2.) THF, 1.5 h, RT; Yield given. Multistep reaction;
With sodium hydride 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 1.5 h; Multistep reaction;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 4℃; for 0.1h;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

cyclohexanone O-acetyl oxime
19689-92-0

cyclohexanone O-acetyl oxime

(E)-2-hexen-1-yl acetate
2497-18-9

(E)-2-hexen-1-yl acetate

Conditions
ConditionsYield
With Cp*2Sm(THF)2 In toluene for 0.1h; Ambient temperature;99%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

trans-tert-butyl(hex-2-en-1-yloxy)dimethylsilane
113997-32-3

trans-tert-butyl(hex-2-en-1-yloxy)dimethylsilane

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere;99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
Wittig Reaction;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Bromoform
75-25-2

Bromoform

C7H12Br2O

C7H12Br2O

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In water99%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

2-bromohexanoic acid
616-05-7

2-bromohexanoic acid

2-bromohexanoic acid (E)-2-hexenyl ester
1206535-33-2

2-bromohexanoic acid (E)-2-hexenyl ester

Conditions
ConditionsYield
Stage #1: 2-bromohexanoic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: (E)-2-Hexen-1-ol With dmap In tetrahydrofuran Inert atmosphere;
99%
Stage #1: 2-bromohexanoic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;
Stage #2: (E)-2-Hexen-1-ol With dmap In tetrahydrofuran at 20℃; Inert atmosphere;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Tosyl isocyanate
4083-64-1

Tosyl isocyanate

(E)-hex-2-en-1-yl tosylcarbamate
1437784-91-2

(E)-hex-2-en-1-yl tosylcarbamate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 2h;99%
In dichloromethane at 20℃; for 2h;99%
2-Hydroxybenzophenone
117-99-7

2-Hydroxybenzophenone

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

C19H20O2

C19H20O2

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃;99%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

2-[((E)-Hex-2-enyl)oxy]-tetrahydro-pyran
119771-54-9

2-[((E)-Hex-2-enyl)oxy]-tetrahydro-pyran

Conditions
ConditionsYield
With lanthanum(III) nitrate at 20℃; for 3h;98%
With ruthenium(III) acetate at 20℃; for 24h;95%
With molybdenyl acetylacetonate In chloroform for 4h; Heating;70%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 4h;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

2,3-epoxyhexan-1-ol
89395-00-6

2,3-epoxyhexan-1-ol

Conditions
ConditionsYield
With dihydrogen peroxide; K2[{W(O)(O2)2(H2O)}2(μ-O)]*2H2O In water at 31.84℃; for 5h;98%
With dihydrogen peroxide In acetonitrile at 50℃; for 4h;94%
With dihydrogen peroxide; tetraphenylphosphonium; sodium hydrogencarbonate; WO(O2)(QO)4 In acetonitrile at 25℃; for 0.5h;90%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

1-Bromo-1-phenylsulfanyl-3,3,3-trifluoroprop-1-ene
177272-50-3

1-Bromo-1-phenylsulfanyl-3,3,3-trifluoroprop-1-ene

{(E)-3,3,3-Trifluoro-2-[((E)-hex-2-enyl)oxy]-propenylsulfanyl}-benzene
177272-48-9

{(E)-3,3,3-Trifluoro-2-[((E)-hex-2-enyl)oxy]-propenylsulfanyl}-benzene

Conditions
ConditionsYield
With sodium hydride In diethyl ether for 1h; Ambient temperature;98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

(+/-)-1-(1-hexenyl)-1-(trimethylsilyl)methanol
265135-87-3

(+/-)-1-(1-hexenyl)-1-(trimethylsilyl)methanol

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃;
Stage #2: With tert.-butyl lithium In tetrahydrofuran; hexane; pentane at -78 - -30℃; anti-Brook rearrangement;
98%
Stage #1: (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran at -78℃; for 1h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 2.5h;
Stage #3: With sec.-butyllithium In tetrahydrofuran at -78℃; for 2h;
68%
Stage #1: (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane for 2.5h; Inert atmosphere;
Stage #3: With sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane for 2h; Inert atmosphere;
57%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(E)-tert-butyl hex-2-en-1-yl carbonate
872672-17-8

(E)-tert-butyl hex-2-en-1-yl carbonate

Conditions
ConditionsYield
With dmap Heating;98%
Stage #1: (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
95%
With tetra(n-butyl)ammonium hydrogensulfate
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water
In dichloromethane for 12h; Molecular sieve;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

benzyloxycarbonyl isocyanate
69032-16-2

benzyloxycarbonyl isocyanate

benzyl trans-hexa-2-enyl imidodicarbonate

benzyl trans-hexa-2-enyl imidodicarbonate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;98%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

(E)-hex-2-en-1-yl 1H-imidazole-1-carboxylate

(E)-hex-2-en-1-yl 1H-imidazole-1-carboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h;98%
In dichloromethane at 20℃; for 4h; Inert atmosphere;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

1-bromovinyl p-tolyl sulphone
89478-86-4

1-bromovinyl p-tolyl sulphone

1-{1-Bromo-2-[((E)-hex-2-enyl)oxy]-ethanesulfonyl}-4-methyl-benzene
89478-89-7

1-{1-Bromo-2-[((E)-hex-2-enyl)oxy]-ethanesulfonyl}-4-methyl-benzene

Conditions
ConditionsYield
With sodium hydride for 5h; Ambient temperature;97%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

chloroamine-T
127-65-1

chloroamine-T

((2S*,3R*)-3-propyl-1-tosylaziridin-2-yl)methanol

((2S*,3R*)-3-propyl-1-tosylaziridin-2-yl)methanol

Conditions
ConditionsYield
With phenyltrimethylammonium tribromide In acetonitrile at 25℃; for 12h;97%
With iodine; Aliquat 336 at 20℃; for 3h;79%
With iodine; silica gel; potassium carbonate In water at 20℃; for 3h;58%
With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 12h; Sharpless aziridination;
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl (E)-hex-2-en-1-yl carbonate
120989-95-9

ethyl (E)-hex-2-en-1-yl carbonate

Conditions
ConditionsYield
aluminum oxide; cesium fluoride at 129.85℃; for 0.333333h;97%
With MgLa mixed oxide at 125℃; for 2h;96%
(E)-2-Hexen-1-ol
928-95-0

(E)-2-Hexen-1-ol

(E)-1-bromo-2-hexene
73881-10-4

(E)-1-bromo-2-hexene

Conditions
ConditionsYield
With tetrabutylammomium bromide; (chloro-phenylthio-methylene)dimethylammonium chloride In dichloromethane at 20℃; Bromination;96%
With phosphorus tribromide In diethyl ether90%
With phosphorus tribromide In dichloromethane at 25℃; for 3h; Inert atmosphere;89%

928-95-0Relevant articles and documents

Peyton,Brown

, p. 579,580 (1977)

Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes

Huang, Jiaxin,Li, Jie,Yang, Wen,Zhang, Kezhuo,Zhao, Pei,Zhao, Wanxiang

supporting information, p. 302 - 305 (2022/01/03)

The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.

Selective, base-free hydrogenation of aldehydes catalyzed by IR complexes based on proton-responsive lutidine-derived CNP ligands

álvarez, Eleuterio,Hernández-Juárez, Martín,López-Serrano, Joaquín,Paneque, Margarita,Rendón, Nuria,Sánchez, Práxedes,Suárez, Andrés

, p. 1314 - 1327 (2021/05/31)

Metal catalysts based on ligands containing proton-responsive sites have found widespread applications in the hydrogenation of polar unsaturated substrates. In this contribution, Ir complexes incorporating lutidine-derived CNP (C = N-heterocyclic carbene, NHC; P = phosphine) pincer ligands with two nonequivalent Br?nsted acid/base sites have been examined in the hydrogenation of aldehydes. To this end, Ir(CNP)H2Cl complexes were synthesized in two steps from the CNP ligand precursors and Ir(acac)(COD). These derivatives react with an excess of NaH to yield the trihydride derivatives Ir(CNP)H3, which were assessed as catalyst precursors in the hydrogenation of a series of aldehydes. The catalytic reactions were performed using commercial-grade substrates under neutral, mild conditions (0.1 mol % Ir-CNP; 4 bar H2, room temperature) with high conversions and selectivities for the reduction of the carbonyl function in the presence of other readily reducible groups such as C=C, nitro, and halogens. Reaction of an Ir(CNP)H2Cl complex with base in the presence of an aromatic aldehyde produces the reversible formation of alkoxide Ir complexes in which the aldehyde is bound to the deprotonated pincer framework (CNP*) through the CH-NHC arm of the ligand. These species, along with a carboxylate complex resulting from the Ir mediated oxidation of the aldehyde by water, is observed in the reaction of Ir(CNP)H3 with benzaldehyde. Finally, investigation of the mechanism of the hydrogenation of aldehydes has been carried out by means of DFT calculations considering the involvement of each arm of the Ir-CNP/CNP* derivatives. Calculations support a mechanism in which the catalyst switches its metal?ligand cooperation sites to follow the lowest energy pathway for each step of the catalytic cycle.

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