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2548-87-0 Usage

Chemical Properties

Colorless liquid

Uses

trans-2-Octenal is one of the probable major contributors to the Californian long-grain cooked rice odor.

Definition

ChEBI: The (E)-isomer of oct-2-enal.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2607, 1986 DOI: 10.1021/jo00363a043Journal of the American Chemical Society, 93, p. 1724, 1971 DOI: 10.1021/ja00736a027Tetrahedron, 39, p. 3207, 1983 DOI: 10.1016/S0040-4020(01)91568-6

General Description

The rate constant for the gas-phase reaction of the NO(3) radical with trans-2-octenal was studied using absolute rate method. The fungal volatile organic compound trans-2-octenal, caused locomotory defects and changes in green fluorescent protein (GFP) and antigen-labeled dopaminergic neurons in adult Drosophila melanogaster.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Check Digit Verification of cas no

The CAS Registry Mumber 2548-87-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,4 and 8 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2548-87:
(6*2)+(5*5)+(4*4)+(3*8)+(2*8)+(1*7)=100
100 % 10 = 0
So 2548-87-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O/c1-2-3-4-5-6-7-8-9/h6-8H,2-5H2,1H3/b7-6+

2548-87-0 Well-known Company Product Price

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  • Detail
  • TCI America

  • (O0176)  trans-2-Octenal  >96.0%(GC)

  • 2548-87-0

  • 10mL

  • 520.00CNY

  • Detail
  • TCI America

  • (O0176)  trans-2-Octenal  >96.0%(GC)

  • 2548-87-0

  • 25mL

  • 900.00CNY

  • Detail
  • Alfa Aesar

  • (A18830)  trans-2-Octenal, 95%   

  • 2548-87-0

  • 5g

  • 301.0CNY

  • Detail
  • Alfa Aesar

  • (A18830)  trans-2-Octenal, 95%   

  • 2548-87-0

  • 25g

  • 1167.0CNY

  • Detail
  • Sigma-Aldrich

  • (52464)  trans-2-Octenal  analytical reference material

  • 2548-87-0

  • 52464-1ML

  • 553.41CNY

  • Detail
  • Sigma-Aldrich

  • (52464)  trans-2-Octenal  analytical reference material

  • 2548-87-0

  • 52464-5ML

  • 2,196.09CNY

  • Detail

2548-87-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-oct-2-enal

1.2 Other means of identification

Product number -
Other names trans-oct-2-enal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:2548-87-0 SDS

2548-87-0Synthetic route

(E)-oct-2-en-1-ol
18409-17-1

(E)-oct-2-en-1-ol

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With dmap; tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N'-di-tert-butylethylenediamine; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 1h; Schlenk technique; Molecular sieve; Sealed tube;99%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; TPGS-750-M; copper(I) bromide In water at 20℃; for 9h;93%
With potassium osmate(VI) dihydrate; potassium carbonate; potassium hexacyanoferrate(III) In water; acetonitrile at 60℃; for 14h; chemoselective reaction;88%
cis-2-octene
7642-04-8

cis-2-octene

trans-2-Octene
13389-42-9

trans-2-Octene

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

cis-2-octene oxide
20664-46-4

cis-2-octene oxide

Conditions
ConditionsYield
With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; 3-chloro-benzenecarboperoxoic acid In water; acetonitrile at 20℃; for 0.166667h; Reagent/catalyst; Concentration; Solvent; Inert atmosphere;A 7%
B 91%
1,1-Diethoxy 2(E)-octene
20052-00-0

1,1-Diethoxy 2(E)-octene

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With water for 0.133333h; Microwave irradiation;84%
2-octyn-1-ol
20739-58-6

2-octyn-1-ol

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

cis-2-octene oxide
20664-46-4

cis-2-octene oxide

Conditions
ConditionsYield
tris(triphenylphosphine)ruthenium(II) chloride; tris(1-methylethyl)phosphine In toluene for 36h; Heating;A 82%
B n/a
triphenylarsonium salt of bromoacetaldehyde
103698-50-6

triphenylarsonium salt of bromoacetaldehyde

hexanal
66-25-1

hexanal

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With water; potassium carbonate In tetrahydrofuran; diethyl ether for 17h; Ambient temperature;81%
With potassium carbonate In tetrahydrofuran; diethyl ether; water at 25℃;81%
2-<(E)heptenyl>-1,3-dioxolane

2-<(E)heptenyl>-1,3-dioxolane

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane for 140h; Ambient temperature;80%
With water; toluene-4-sulfonic acid for 4h; Ambient temperature;
cis-2-octene oxide
20664-46-4

cis-2-octene oxide

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With toluene-4-sulfonic acid In chloroform Heating;75%
1,1-diethoxy-3-octanol
94704-96-8

1,1-diethoxy-3-octanol

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water for 4h; Heating;75%
(Z)-1-tert-Butylsulfanyl-oct-1-en-3-ol
86254-73-1

(Z)-1-tert-Butylsulfanyl-oct-1-en-3-ol

A

di-tert-butyl disulfide
110-06-5

di-tert-butyl disulfide

B

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With copper(II) oxide In water; acetone for 1h; Ambient temperature;A 33%
B 74%
(Z)-oct-2-en-1-ol
26001-58-1

(Z)-oct-2-en-1-ol

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 3h; low temperature;66%
1,1-dimethoxy-oct-2t-ene
18286-98-1

1,1-dimethoxy-oct-2t-ene

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

(E)-oct-2-enoic acid
1871-67-6

(E)-oct-2-enoic acid

Conditions
ConditionsYield
With chromium (VI) oxide; air In chloroform for 4h; Hydrolysis; Oxidation; Heating;A 60%
B 40%
triphenylarsonium salt of bromoacetaldehyde
103698-50-6

triphenylarsonium salt of bromoacetaldehyde

hexanal
66-25-1

hexanal

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

2,4-trans,trans-decadienal
25152-84-5

2,4-trans,trans-decadienal

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; diethyl ether; water at 40℃; for 17h;A 48%
B 46%
oct-1-ene
111-66-0

oct-1-ene

A

oct-1-en-3-one
4312-99-6

oct-1-en-3-one

B

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

C

hexyl-methyl-ketone
111-13-7

hexyl-methyl-ketone

Conditions
ConditionsYield
With oxygen; palladium(II) trifluoroacetate In acetonitrile for 22h; Irradiation; Yields of byproduct given;A n/a
B n/a
C 10%
With oxygen; palladium(II) trifluoroacetate In acetonitrile for 22h; Irradiation; Yield given. Yields of byproduct given;A n/a
B n/a
C 10%
With oxygen; palladium(II) trifluoroacetate In acetonitrile Irradiation;
1,1-diethoxy-oct-2c-ene
16387-56-7

1,1-diethoxy-oct-2c-ene

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With sulfuric acid
Multi-step reaction with 2 steps
1: p-C6H4-SO3H / acetone; H2O / 0.25 h / 0 °C
2: 75 percent / p-CH3-C6H4-SO3H / CHCl3 / Heating
View Scheme
1,1-dimethoxy-octan-3-one

1,1-dimethoxy-octan-3-one

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether und Behandeln des Reaktionsprodukts mit wss.Schwefelsaeure;
methoxyethene
107-25-5

methoxyethene

hexanal
66-25-1

hexanal

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With boron fluoride ether und Erhitzen des Reaktionsprodukts mit wss.Essigsaeure;
hept-1-en-t-yl-trimethyl-silane
64997-06-4

hept-1-en-t-yl-trimethyl-silane

Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
(i) TiCl4, CH2Cl2, (ii) aq. MeOH; Multistep reaction;
1t-phenylsulfanyl-oct-1-en-3-ol
56561-13-8

1t-phenylsulfanyl-oct-1-en-3-ol

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With mercury dichloride In water; acetonitrile
dimethyl-dithiocarbamic acid oct-2t-enyl ester
55161-31-4

dimethyl-dithiocarbamic acid oct-2t-enyl ester

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
(i) LDA, (ii) Me2S2, (iii) Hg2+, aq. MeCN; Multistep reaction;
acetaldehydedimethylhydrazone
7422-90-4

acetaldehydedimethylhydrazone

hexanal
66-25-1

hexanal

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
Multistep reaction;
1t,3-bis-methylsulfanyl-oct-1-ene
31924-94-4

1t,3-bis-methylsulfanyl-oct-1-ene

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With mercury dichloride In tetrahydrofuran; acetonitrile
1-dimethylcarbamoylsulfanyl-1-methylsulfanyl-oct-2-ene
65367-45-5

1-dimethylcarbamoylsulfanyl-1-methylsulfanyl-oct-2-ene

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With water; calcium carbonate; mercury dichloride
trans-2-benzenesulfinyl-3-hexyl-oxirane
64190-30-3

trans-2-benzenesulfinyl-3-hexyl-oxirane

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
In xylene Heating;
1,1-diethoxy-oct-2c-ene
16387-56-7

1,1-diethoxy-oct-2c-ene

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

cis-2-octene oxide
20664-46-4

cis-2-octene oxide

Conditions
ConditionsYield
With p-C6H4-SO3H In water; acetone at 0℃; for 0.25h; Yield given. Title compound not separated from byproducts;
oct-1-ene
111-66-0

oct-1-ene

A

oct-1-en-3-one
4312-99-6

oct-1-en-3-one

B

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

C

(E)-oct-2-en-1-ol
18409-17-1

(E)-oct-2-en-1-ol

D

1-octen-3-ol
3391-86-4

1-octen-3-ol

E

1,2-Epoxyoctane
2984-50-1

1,2-Epoxyoctane

Conditions
ConditionsYield
With oxygen; bis(acetylacetonato)dioxidomolybdenum(VI); cobalt(III) acetylacetonate In 1,2-dichloro-benzene at 110℃; for 5.3h; Product distribution; other temperatures, catalysts, times, olefins;A n/a
B n/a
C n/a
D n/a
E 61 % Chromat.
1,1-diethoxy-oct-2-ene
54306-01-3

1,1-diethoxy-oct-2-ene

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

cis-2-octene oxide
20664-46-4

cis-2-octene oxide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; acetone at 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
cis-2-(1'-hexyl)-1-(trimethylsilyl)oxirane
62427-11-6

cis-2-(1'-hexyl)-1-(trimethylsilyl)oxirane

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With trimethyl ester of coenzyme PQQ; oxygen; palladium diacetate In N,N-dimethyl-formamide at 70℃; for 7h;
With palladium diacetate In N,N-dimethyl-formamide at 60℃; for 7h;80 % Chromat.
C8H15O(1-)*Br(1-)*Mg(2+)

C8H15O(1-)*Br(1-)*Mg(2+)

A

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

B

(E)-oct-2-en-1-ol
18409-17-1

(E)-oct-2-en-1-ol

Conditions
ConditionsYield
With benzaldehyde In diethyl ether for 5h; Yield given. Yields of byproduct given;
With benzaldehyde In diethyl ether for 5h; Product distribution;
α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine
127896-07-5

α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine

hexanal
66-25-1

hexanal

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With zinc(II) chloride; zinc dibromide 1) THF, RT, 6 h, 2) ether, water, RT, 1 h; Yield given. Multistep reaction;
1,1-dimethoxy-oct-2t-ene
18286-98-1

1,1-dimethoxy-oct-2t-ene

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Conditions
ConditionsYield
With water; toluene-4-sulfonic acid for 4h; Ambient temperature;
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

hydrogen cyanide
74-90-8

hydrogen cyanide

(E)-(S)-2-Hydroxy-non-3-enenitrile
186087-75-2

(E)-(S)-2-Hydroxy-non-3-enenitrile

Conditions
ConditionsYield
With (S)-hydroxynitrile lyase from Hevea brasiliensis Addition; Enzymatic reaction;100%
With hydroxynitrile lyase from Hevea brasiliensis In water at 15℃; for 0.25h; pH 5.5;96%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(E)-2-trimethylsilyloxy-3-nonenenitrile

(E)-2-trimethylsilyloxy-3-nonenenitrile

Conditions
ConditionsYield
With lithium chloride In tetrahydrofuran at 22℃; for 22h;98%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2E)-1-phenyloct-2-en-1-ol
181229-27-6

(2E)-1-phenyloct-2-en-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 17h;98%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

ethanethiol
75-08-1

ethanethiol

3-(ethylthio)octanal
1258408-40-0

3-(ethylthio)octanal

Conditions
ConditionsYield
With triethylamine In chloroform at 110℃; for 1h; Michael Addition; Inert atmosphere; Microwave irradiation;98%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

1-ethoxyacetylene
927-80-0

1-ethoxyacetylene

ethyl 2E,4E-decadienoate
7328-34-9

ethyl 2E,4E-decadienoate

Conditions
ConditionsYield
Stage #1: (E)-2-Octenal With boron trifluoride diethyl etherate In diethyl ether at -30℃; for 0.5h; Inert atmosphere;
Stage #2: 1-ethoxyacetylene In diethyl ether; hexane at -30℃; for 1.5h; Inert atmosphere;
98%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

1-Heptyne
628-71-7

1-Heptyne

(E)-6-pentadecen-9-yn-8-ol
754226-60-3

(E)-6-pentadecen-9-yn-8-ol

Conditions
ConditionsYield
Stage #1: 1-Heptyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h;
Stage #2: (E)-2-Octenal In tetrahydrofuran; hexane at -78℃; for 30h;
97%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

3-butyl-phthalic acid dimethyl ester

3-butyl-phthalic acid dimethyl ester

Conditions
ConditionsYield
With acetamide; toluene-4-sulfonic acid for 0.166667h; Beller reaction; microwave irradiation;96%
potassium cyanide

potassium cyanide

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

(E)-2-hydroxynon-3-enenitrile
1092455-54-3

(E)-2-hydroxynon-3-enenitrile

Conditions
ConditionsYield
Stage #1: potassium cyanide; (E)-2-Octenal In diethyl ether; water at -10℃; for 0.166667h;
Stage #2: With hydrogenchloride In diethyl ether; water at -10 - 20℃;
96%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

(E)-oct-2-en-1-ol
18409-17-1

(E)-oct-2-en-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol for 3h;95%
With sodium bis(2-methoxyethoxy)aluminium dihydride In diethyl ether at 0 - 20℃; for 3.5h;84.4%
With formic acid; 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; sodium formate In water at 80℃; for 6h; pH=4.5; Inert atmosphere; chemoselective reaction;78%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

L-Phenylalaninol
3182-95-4

L-Phenylalaninol

(S,2E)-2-((E)-oct-2-enylideneamino)-3-phenylpropan-1-ol
1246300-53-7

(S,2E)-2-((E)-oct-2-enylideneamino)-3-phenylpropan-1-ol

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 0.333333h;95%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

allyl bromide
106-95-6

allyl bromide

C11H20O

C11H20O

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran; water at 0 - 25℃; for 4h; Barbier Coupling Reaction;95%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

A

octanol
111-87-5

octanol

B

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With phosphate buffer; D-glucose; Synechococcus sp. PCC 7942; Triton X-100 In water at 25℃; for 72h; pH=7.0; Irradiation;A 94%
B 5%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

(E)-oct-3-en-2-ol
57648-55-2

(E)-oct-3-en-2-ol

Conditions
ConditionsYield
With 1-Phenylethanol In toluene at 120℃; for 12h; Inert atmosphere; chemoselective reaction;94%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

dimethyl 2-oxoheptylphosphonate
36969-89-8

dimethyl 2-oxoheptylphosphonate

trans-2-octenal

trans-2-octenal

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium chloride In acetonitrile for 3h; Inert atmosphere;91%
3-oxopentanedioic acid dimethyl ester
1830-54-2

3-oxopentanedioic acid dimethyl ester

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

7-pentyl-2,4,8,9-tetramethoxycarbonylbicyclo<3.3.1>-3-nonene-1,3-diol

7-pentyl-2,4,8,9-tetramethoxycarbonylbicyclo<3.3.1>-3-nonene-1,3-diol

Conditions
ConditionsYield
With piperidine In tetrahydrofuran for 144h; Ambient temperature;90%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

7-chlorobicyclo<2.2.1>hepta-2,5-diene
1609-39-8

7-chlorobicyclo<2.2.1>hepta-2,5-diene

7-(1'-hydroxyoct-2'-enyl)bicyclo[2.2.1]hepta-2,5-diene
612500-53-5

7-(1'-hydroxyoct-2'-enyl)bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
Stage #1: 7-chlorobicyclo<2.2.1>hepta-2,5-diene With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: (E)-2-Octenal In tetrahydrofuran at -78 - 20℃; for 1h;
90%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Acetic acid 2-methoxy-4-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-phenyl ester
162794-22-1

Acetic acid 2-methoxy-4-[3-oxo-4-(triphenyl-λ5-phosphanylidene)-butyl]-phenyl ester

Acetic acid 2-methoxy-4-((4E,6E)-3-oxo-dodeca-4,6-dienyl)-phenyl ester

Acetic acid 2-methoxy-4-((4E,6E)-3-oxo-dodeca-4,6-dienyl)-phenyl ester

Conditions
ConditionsYield
In benzene Heating;89%
methanol
67-56-1

methanol

(E)-2-Octenal
2548-87-0

(E)-2-Octenal

1,1-dimethoxy-oct-2t-ene
18286-98-1

1,1-dimethoxy-oct-2t-ene

Conditions
ConditionsYield
With samarium(III) trifluoromethanesulfonate at 20℃; for 0.0833333h; Etherification;89%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

2,3-epoxyoctanal
42134-50-9

2,3-epoxyoctanal

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide In water for 2h; pH=8 - 8.5;88%
With dihydrogen peroxide; sodium carbonate; alpha cyclodextrin In water at 0℃; for 3h;76 % Turnov.
With oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate In water; acetonitrile for 3h;
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

dihydroxyacetone
96-26-4

dihydroxyacetone

(3aR,6S,6aS)-6-Pentyl-dihydro-furo[3,4-c]furan-1,3a-diol

(3aR,6S,6aS)-6-Pentyl-dihydro-furo[3,4-c]furan-1,3a-diol

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 0℃; for 21h;88%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

Chloroiodomethane
593-71-5

Chloroiodomethane

(+/-)-(3E)-1-chloro-oct-3-en-2-ol
399513-58-7

(+/-)-(3E)-1-chloro-oct-3-en-2-ol

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃; for 1h;88%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

L-proline tert-butyl ester hydrochloride
5497-76-7

L-proline tert-butyl ester hydrochloride

tert-butyl (E)-oct-2-en-1-yl-L-prolinate

tert-butyl (E)-oct-2-en-1-yl-L-prolinate

Conditions
ConditionsYield
Stage #1: (E)-2-Octenal; L-proline tert-butyl ester hydrochloride In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 3h; Inert atmosphere;
88%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

(carbethoxyethylidene)triphenylphosphorane
21382-82-1

(carbethoxyethylidene)triphenylphosphorane

(2E,4E)-2-Methyl-deca-2,4-dienoic acid ethyl ester

(2E,4E)-2-Methyl-deca-2,4-dienoic acid ethyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 18h;87%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

N-benzyl-N-trimethylsilanylethynyl-4-methylbenzenesulphonamide
205885-29-6

N-benzyl-N-trimethylsilanylethynyl-4-methylbenzenesulphonamide

(Z)-1-[benzyl(p-toluenesulfonyl)amino]-2-(trimethylsilyl)-1,4-decadien-3-ol

(Z)-1-[benzyl(p-toluenesulfonyl)amino]-2-(trimethylsilyl)-1,4-decadien-3-ol

Conditions
ConditionsYield
Stage #1: N-benzyl-N-trimethylsilanylethynyl-4-methylbenzenesulphonamide With titanium(IV) isopropylate; isopropylmagnesium chloride
Stage #2: (E)-2-Octenal
Stage #3: With hydrogen cation Acid hydrolysis; Further stages.;
87%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

(trimethylsilyl)methylmagnesium chloride
13170-43-9

(trimethylsilyl)methylmagnesium chloride

(E)-1-Trimethylsilanyl-non-3-en-2-ol

(E)-1-Trimethylsilanyl-non-3-en-2-ol

Conditions
ConditionsYield
In diethyl ether for 2h; Ambient temperature;86%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

tris-iso-propylsilyl acetylene
89343-06-6

tris-iso-propylsilyl acetylene

C19H36OSi
1198837-41-0

C19H36OSi

Conditions
ConditionsYield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; [Rh(OAc)(C2H4)2]2 In methanol at 40℃; for 24h; optical yield given as %ee; enantioselective reaction;86%
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

methylmagnesium bromide
75-16-1

methylmagnesium bromide

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.133333h;85%
In tetrahydrofuran at 0 - 20℃; for 2.33h; Inert atmosphere;
(E)-2-Octenal
2548-87-0

(E)-2-Octenal

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate
90965-06-3

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate

malononitrile
109-77-3

malononitrile

(E)-dimethyl 3-cyano-4-(hept-1-enyl)-1H-pyrazol-5-ylphosphonate
1228955-60-9

(E)-dimethyl 3-cyano-4-(hept-1-enyl)-1H-pyrazol-5-ylphosphonate

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 1h; Molecular sieve; regioselective reaction;85%

2548-87-0Relevant articles and documents

Corey,Terashima

, p. 1815 (1972)

Pt-Catalyzed selective oxidation of alcohols to aldehydes with hydrogen peroxide using continuous flow reactors

Kon, Yoshihiro,Nakashima, Takuya,Yada, Akira,Fujitani, Tadahiro,Onozawa, Shun-Ya,Kobayashi, Shū,Sato, Kazuhiko

supporting information, p. 1115 - 1121 (2021/02/16)

The oxidation of alcohols to aldehydes is a powerful reaction pathway for obtaining valuable fine chemicals used in pharmaceuticals and biologically active compounds. Although many oxidants can oxidize alcohols, only a few hydrogen peroxide oxidations can be employed to continuously synthesize aldehydes in high yields using a liquid-liquid two-phase flow reactor, despite the possibility of the application toward a safe and rapid multi-step synthesis. We herein report the continuous flow synthesis of (E)-cinnamaldehyde from (E)-cinnamyl alcohol in 95%-98% yields with 99% selectivity for over 5 days by the selective oxidation of hydrogen peroxide using a catalyst column in which Pt is dispersed in SiO2. The active species for the developed selective oxidation is found to be zero-valent Pt(0) from the X-ray photoelectron spectroscopy measurements of the Pt surface before and after the oxidation. Using Pt black diluted with SiO2as a catalyst to retain the Pt(0) species with the optimal substrate and H2O2introduction rate not only enhances the catalytic activity but also maintains the activity during the flow reaction. Optimizing the contact time of the substrate with Pt and H2O2using a flow reactor is important to proceed with the selective oxidation to prevent the catalytic H2O2decomposition.

Iodine-catalyzed alcohol disproportionation method

-

Paragraph 0034-0035, (2021/06/13)

The invention relates to the technical field of catalysis, in particular to an iodine-catalyzed alcohol disproportionation method which comprises the following steps: sequentially adding alcohol, iodine and a solvent into a high-temperature and high-pressure reaction kettle, introducing a certain amount of nitrogen, conducting reacting for a certain time, collecting an organic phase after the reaction is ended, and conducting fractionating to obtain corresponding alkane and aldehyde/ketone. Alcohol disproportionation is efficient and atom-economical conversion without any additional oxidizing agent and reducing agent, and hydrocarbon and aldehyde/ketone molecules which are easy to separate can be formed at the same time. Meanwhile, the method has wide functional group tolerance, various substrate samples including aryl alcohol derivatives, heterocyclic alcohol derivatives, allyl alcohol derivatives and dihydric alcohol are tested, and the result shows that most of the substrate samples show good or extremely good yield.

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