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111-71-7

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111-71-7 Usage

General Description

Heptanal, also known as heptanaldehyde, is a chemical compound with the molecular formula C7H14O. It is a colorless liquid with a strong, pungent odor and is classified as an aldehyde. Heptanal is commonly used as a flavoring agent in the food industry, particularly in the production of fruit and nut flavors. It is also used in the manufacture of perfumes and fragrances due to its pleasant fruity aroma. Heptanal can be produced synthetically or extracted from natural sources such as plants and fruits. It is considered to be relatively safe for use in food and fragrance products when used in accordance with regulations and guidelines.

Check Digit Verification of cas no

The CAS Registry Mumber 111-71-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 111-71:
(5*1)+(4*1)+(3*1)+(2*7)+(1*1)=27
27 % 10 = 7
So 111-71-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3

111-71-7 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (H0025)  Heptanal  >95.0%(GC)

  • 111-71-7

  • 25mL

  • 105.00CNY

  • Detail
  • TCI America

  • (H0025)  Heptanal  >95.0%(GC)

  • 111-71-7

  • 500mL

  • 620.00CNY

  • Detail
  • Alfa Aesar

  • (B23830)  Heptanal, 97%   

  • 111-71-7

  • 100ml

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (B23830)  Heptanal, 97%   

  • 111-71-7

  • 250ml

  • 296.0CNY

  • Detail
  • Alfa Aesar

  • (B23830)  Heptanal, 97%   

  • 111-71-7

  • 500ml

  • 331.0CNY

  • Detail
  • Alfa Aesar

  • (B23830)  Heptanal, 97%   

  • 111-71-7

  • 1000ml

  • 562.0CNY

  • Detail
  • Sigma-Aldrich

  • (61696)  Heptaldehyde  analytical standard

  • 111-71-7

  • 61696-1ML

  • 458.64CNY

  • Detail

111-71-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Heptaldehyde

1.2 Other means of identification

Product number -
Other names Heptanal

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:111-71-7 SDS

111-71-7Synthetic route

1-hexene
592-41-6

1-hexene

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With carbon monoxide; rhodium(I) acetylacetonate; hydrogen; triphenylphosphine In toluene at 100℃; under 10343.2 Torr; for 2h; Autoclave;81%
n-heptan1ol
111-70-6

n-heptan1ol

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With pyridine chromium peroxide In dichloromethane for 1.25h; Ambient temperature;99%
With polymeric complex of oxodiperoxochromium(VI) compound and pyrazine (Pyz-CrO5)n In dichloromethane for 1.5h; Ambient temperature;99%
With pyridine chromium peroxide In dichloromethane for 1.25h; Product distribution; Ambient temperature; effect of various chromium(VI) based oxidants;99%
2-hexyl-1,3-dithiolane
6008-84-0

2-hexyl-1,3-dithiolane

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide In methanol; dichloromethane at 20℃; for 0.1h;97%
With iodosylbenzene In dichloromethane at 20℃; for 0.416667h;95%
With silica gel In neat (no solvent) at 20℃; for 0.0833333h;93%
With Clayan for 0.05h; Irradiation; microwave irradiation;81%
formaldehyd
50-00-0

formaldehyd

1-hexene
592-41-6

1-hexene

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With synthesis gas; dicarbonylacetylacetonato rhodium (I); C44H33BrN2P2 In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; under 7500.75 - 30003 Torr; for 3h; Autoclave; Inert atmosphere;96.3%
hexan-1-ol
111-27-3

hexan-1-ol

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With oxidase In water at 40℃; for 1.5h; Reformatsky Reaction;100%
With oxygen In neat (no solvent) at 45℃; for 7h; Solvent; Temperature;50 %Chromat.
oenanthic acid
111-14-8

oenanthic acid

A

1-hexene
592-41-6

1-hexene

B

heptanal
111-71-7

heptanal

C

tridecan-7-one
462-18-0

tridecan-7-one

Conditions
ConditionsYield
With hydrogen In octane at 400℃; under 760.051 Torr; for 6h; Reagent/catalyst;A 36.6%
B 15.3%
C 7.6%
oct-1-ene
111-66-0

oct-1-ene

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With sodium periodate; [η5-C5H5Ru(CO)2NH2C6H11]BF4 In water; acetonitrile at 60℃; for 3h; Catalytic behavior; Schlenk technique; Inert atmosphere;98%
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;98%
With sodium periodate; C18H14Cl3N2Ru(1+)*F6P(1-) In water; tert-butyl alcohol at 60℃; for 1h; Catalytic behavior; Inert atmosphere; Schlenk technique;91%
n-heptan1ol
111-70-6

n-heptan1ol

A

heptanal
111-71-7

heptanal

B

heptyl heptanoate
624-09-9

heptyl heptanoate

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In hexane; water at 20℃; for 24h;A 9%
B 91%
With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 25℃; for 3h;A 12.9%
B 87.1%
With chloro-tris-(2-methoxy-phenyl)-methane In dichloromethane for 9h; Ambient temperature;A 28%
B 57%
With chromium(VI) oxide; aluminum oxide In hexane for 15h; Ambient temperature;A 47%
B 48%
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; iodine; sodium hydrogencarbonate In dichloromethane; water at 20 - 22℃; for 3h;A 36 %Chromat.
B 22 %Chromat.
1,1-diacetoxy-heptane
56438-09-6

1,1-diacetoxy-heptane

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.25h;96%
With tetra-N-butylammonium tribromide In methanol at 20℃; for 0.25h;95%
With carbon tetrabromide In acetonitrile for 3h; Heating;87%
n-heptan1ol
111-70-6

n-heptan1ol

A

heptanal
111-71-7

heptanal

B

oenanthic acid
111-14-8

oenanthic acid

Conditions
ConditionsYield
With dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tungstate In tert-butyl alcohol at 90℃;A 11%
B 89%
With 1-methyl-3-(2-oxo-2-(2,2,6,6-tetramethyl-1-ylooxy-4-piperidoxyl)ethyl)imidazolium chloride; 1-(carboxymethyl)-3-methylimidazolium chloride; oxygen; sodium nitrite In water at 59.84℃; under 7500.75 Torr; for 12h; Inert atmosphere;A 76%
B 12%
With C30H24N2O7W; dihydrogen peroxide In water; acetonitrile for 17h; Reflux;A 72%
B 17%
1-penten
109-67-1

1-penten

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

2-methylhexanal
925-54-2

2-methylhexanal

Conditions
ConditionsYield
With hydrogen; rhodium (III) acetate; trisodium tris(3-sulfophenyl)phosphine In water at 125℃; under 18751.9 - 22502.3 Torr; for 3h;
With 18-crown-6 ether; hydrogen; rhodium (III) acetate; trisodium tris(3-sulfophenyl)phosphine In water at 125℃; under 18751.9 - 37503.8 Torr; for 3h;
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

R-(-)-2-methylhexanal
132151-88-3

R-(-)-2-methylhexanal

C

S-(+)-2-methylhexanal
66875-71-6

S-(+)-2-methylhexanal

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene under 76000 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;A 76%
B n/a
C n/a
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene under 76000 Torr; Yields of byproduct given;A 76%
B n/a
C n/a
With hydrogen; Rh(acac)<(S)-(5,5'-dichloro-2-diphenylphosphino-4,4',6,6'-tetramethylbiphenyl-2'-yl)(R)-1,1'-binaphthalen-2,2'-diyl)phosphite> In benzene at 30℃; under 76000 Torr; for 40h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
1-benzenesulfonyl-1-nitronon-2-ene

1-benzenesulfonyl-1-nitronon-2-ene

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With ozone In dichloromethane at -78℃; for 0.166667h;73%
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With dicarbonylacetylacetonato rhodium (I); C41H26F4O8P2; hydrogen In toluene at 90℃; under 3750.38 - 7500.75 Torr; for 3h; Reagent/catalyst; regioselective reaction;98.8%
With dicarbonylacetylacetonato rhodium (I); C64H46O12P4; hydrogen In dichloromethane at 80℃; for 2h; Catalytic behavior; regioselective reaction;98.9%
With hydrogen; triethylamine; di(rhodium)tetracarbonyl dichloride; triphenylphosphine at 80℃; under 15001.2 Torr; for 0.333333h;71%
carbon monoxide
201230-82-2

carbon monoxide

hex-1-yne
693-02-7

hex-1-yne

A

heptanal
111-71-7

heptanal

B

2-methylhexanal
925-54-2

2-methylhexanal

Conditions
ConditionsYield
With dicarbonyl(acetylacotonato)rhodium(I); hydrogen; triphenylphosphine In water at 100℃; under 12001.2 Torr; Autoclave; Inert atmosphere; regioselective reaction;
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

2-methylhexanal
925-54-2

2-methylhexanal

Conditions
ConditionsYield
With dicarbonylacetylacetonato rhodium (I); C44H34O8P2; hydrogen In toluene at 90℃; under 3750.38 - 7500.75 Torr; for 3h; regioselective reaction;A 91.9%
B n/a
With hydrogen; 1-octyl-3-methyl-imidazolium bromide In water at 100℃; under 15001.5 Torr; for 3h; Product distribution; Further Variations:; Reagents;A 90.2%
B 8.95%
With acetylacetonatodicarbonylrhodium(l); hydrogen; triphenylphosphine In neat (no solvent) at 80℃; under 7500.75 Torr; for 1h; Catalytic behavior; Pressure; Autoclave;A 81%
B 11%
1,1-dimethoxyheptane
10032-05-0

1,1-dimethoxyheptane

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With erbium(III) triflate In nitromethane at 20℃; for 1h;90%
With (trimethylsilyl)bis(fluorosulfuryl)imide In dichloromethane at -78℃; for 12h;83%
1-Heptyne
628-71-7

1-Heptyne

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With (2-(diphenylphosphino)-6-(2,4,6-triisopropylphenyl)pyridine); water; (η5-cyclopentadienyl) (η6-naphthalene)ruthenium hexafluorophosphate In acetone at 60℃; for 6.5h;91%
1-heptanal oxime
629-31-2

1-heptanal oxime

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With poly[4-vinyl-N,N-dichlorobenzenesulfonamide] In tetrachloromethane at 40℃; for 5h;90%
With CuCl*Kieselghur; oxygen In dichloromethane at 20℃; for 0.416667h;89%
With iron(III) chloride In N,N-dimethyl-formamide at 25℃; for 0.2h; sonication;86%
1-Heptene
592-76-7

1-Heptene

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With dicarbonyl(acetylacotonato)rhodium(I); carbon monoxide; hydrogen; C60H60N6P2 In toluene at 100℃; under 7500.75 Torr; for 12h; Sealed tube;
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

2-methylhexanal
925-54-2

2-methylhexanal

C

n-heptan1ol
111-70-6

n-heptan1ol

Conditions
ConditionsYield
With hydrogen; and zeolite X In ethanol; toluene at 120℃; under 38000 Torr; for 17h; Yields of byproduct given;A n/a
B n/a
C 52%
1,2-octandiol
1117-86-8

1,2-octandiol

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With tert-butylhypochlorite; lead acetate; dibenzoyl peroxide In toluene at 20℃; for 0.25h;90%
With oxygen; palladium diacetate; toluene-4-sulfonic acid In water at 100℃; under 6080.41 Torr; for 24h;89%
With cerium(III) chloride heptahydrate; tetrabutyl-ammonium chloride In [D3]acetonitrile at 20℃; for 18h; Reagent/catalyst; Molecular sieve; Sealed tube; Irradiation;87 %Spectr.
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

5-methylhexanal
1860-39-5

5-methylhexanal

C

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen In toluene at 129.84℃; under 37503.8 Torr; for 1h; Reagent/catalyst; Autoclave;
heptanol trimethylsilyl ether
18132-93-9

heptanol trimethylsilyl ether

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;93%
With ammonium cerium(IV) nitrate; HZSM-5 zeolite In water for 0.0833333h; microwave irradiation;92%
With quinolinium monofluorochromate(VI) In acetonitrile at 25℃; for 1.6h;86%
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

2-methylhexanal
925-54-2

2-methylhexanal

C

2-ethylpentanal
22092-54-2

2-ethylpentanal

D

hexane
110-54-3

hexane

Conditions
ConditionsYield
With hydrogen; N-dodecyl-N-(2-hydroxyethyl)-N,N-dimethylammonium bromide; {Rh(cod)[μ-S(CH2)3Si(OMe)3]}2; triphenylphosphine In water; butan-1-ol at 80℃; under 20701.7 Torr; for 14h; microemulsion/sol-gel;A 52%
B 23.9%
C 3.8%
D 0.6%
With hydrogen In 1-methyl-pyrrolidin-2-one at 149.84℃; under 37503.8 Torr; for 17h; Autoclave;
With hydrogen at 70℃; under 37503.8 Torr; for 1h;
carbon monoxide
201230-82-2

carbon monoxide

hex-1-yne
693-02-7

hex-1-yne

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With dicarbonyl(acetylacotonato)rhodium(I); hydrogen; triphenylphosphine at 80℃; under 7500.75 Torr; Autoclave; Inert atmosphere; regioselective reaction;
1-hexene
592-41-6

1-hexene

carbon monoxide
201230-82-2

carbon monoxide

A

heptanal
111-71-7

heptanal

B

2-methylhexanal
925-54-2

2-methylhexanal

C

2-ethylpentanal
22092-54-2

2-ethylpentanal

Conditions
ConditionsYield
With dicobalt octacarbonyl; hydrogen; silica gel In acetonitrile at 79.9℃; under 90007.2 - 105008 Torr; for 100h; Product distribution; other catalyst and support systems;
With dodecacarbonyltetrarhodium(0); hydrogen; di(3-natriumsulfonato-4-fluorophenyl)(4-fluorophenyl)phosphine; C18H9F3O9PS3(3-)*3Na(1+) In water at 120℃; under 37503 Torr; for 2h; Product distribution; other substituted triphenylphosphines-Rh4(CO)12 two-phase catalytic system;
With hydrogen; C10H3Co3O12Si In toluene at 120℃; under 52504.2 Torr; for 8h; Product distribution; further cobalt catalysts, various pressure, time, solvents;
2-hexyl-1,3-dioxolane
1708-34-5

2-hexyl-1,3-dioxolane

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With polyaniline-sulfate salt; water for 0.5h; Heating;96%
potassium ferrate(VI); montmorillonite K-10 In dichloromethane for 0.25h; Heating;91%
With ammonium nitrate; Montmorillonite-K10 for 0.05h; deprotection; microwave irradiation;90%
2-(heptyloxy)tetrahydro-2H-pyran
132336-04-0

2-(heptyloxy)tetrahydro-2H-pyran

heptanal
111-71-7

heptanal

Conditions
ConditionsYield
With NTPPPODS In acetonitrile for 0.5h; Reflux;87%
With HMTAB; silica gel for 0.0333333h; microwave irradiation;82%
With potassium permanganate; tetrachlorosilane In acetonitrile at 20℃; for 0.5h;75%
With aluminum oxide; [bis(acetoxy)iodo]benzene In acetonitrile for 0.833333h; Oxidation; Heating;70%
With aluminium trichloride; silver bromate In acetonitrile for 1.5h; Heating; Yield given;
1,2-octandiol
1117-86-8

1,2-octandiol

A

heptanal
111-71-7

heptanal

B

2,4-dihexyl-1,3-dioxolane

2,4-dihexyl-1,3-dioxolane

Conditions
ConditionsYield
With methanesulfonic acid; oxygen; [(n-Bu)4N]3H2[IMo6O24] In acetonitrile at 80℃; under 1520.1 Torr; for 15h;A 17%
B 83%
With oxygen; aluminum oxide; ruthenium In toluene at 99.84℃; for 24h;
With oxygen; Ru(PPh3)3Cl2/CW In various solvent(s) at 60℃; under 760.051 Torr; for 15h; Product distribution; Further Variations:; Catalysts;
heptanal
111-71-7

heptanal

1-heptanal oxime
629-31-2

1-heptanal oxime

Conditions
ConditionsYield
With acetic acid; acetone oxime at 110℃; for 1.5h;100%
With acetylhydroxamic acid; boron trifluoride diethyl etherate In methanol for 0.1h; Microwave irradiation; Sealed tube;82%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 0 - 20℃;76%
heptanal
111-71-7

heptanal

n-heptan1ol
111-70-6

n-heptan1ol

Conditions
ConditionsYield
With Triethoxysilane; potassium fluoride at 25℃; for 20h;100%
With Triethoxysilane; 1,3-Diphenylpropanone; potassium fluoride at 25℃; for 7h;100%
With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 25℃; for 6h; Inert atmosphere; Glovebox; Sealed tube;98%
heptanal
111-71-7

heptanal

allyl bromide
106-95-6

allyl bromide

dec-1-en-4-ol
36971-14-9

dec-1-en-4-ol

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran for 1h; Ambient temperature;100%
With silica gel; ammonium chloride; zinc for 16h; Product distribution; Mechanism; Ambient temperature; other carbonyl compounds; other allyl halides; var. solid or liquid phases; var. reaction time;98%
With chloro-trimethyl-silane; Piperonyl butoxide; tetrabutylammomium bromide In N,N-dimethyl-formamide for 2h; Ambient temperature;98%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

heptanal
111-71-7

heptanal

ethyl 2-nonenoate
17463-01-3

ethyl 2-nonenoate

Conditions
ConditionsYield
With triethylamine; magnesium bromide In tetrahydrofuran at 25℃; for 12h;100%
(i) NaH, Et2O, (ii) /BRN= 1560236/; Multistep reaction;
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

heptanal
111-71-7

heptanal

1-Benzotriazol-1-yl-heptan-1-ol
111507-84-7

1-Benzotriazol-1-yl-heptan-1-ol

Conditions
ConditionsYield
at 25℃;100%
heptanal
111-71-7

heptanal

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2-(trimethylsiloxy)octanenitrile
93554-94-0

2-(trimethylsiloxy)octanenitrile

Conditions
ConditionsYield
With [Sc3(3,5-disulfobenzoic acid)2(μ-O2H3)(μ-OH)2(H2O)2] In neat (no solvent) at 40℃; for 2h; Catalytic behavior; Schlenk technique; Inert atmosphere;100%
With 2Zn(2+)*10H2O*3C10H8N2*2H(1+)*Co2Mo10H4O38(6-) In neat (no solvent) at 25℃; for 7h; Reagent/catalyst; Inert atmosphere;100%
With tin-tungsten mixed oxide, Sn/W molar ratio = 2, calcined at 800 °C In 1,2-dichloro-ethane at 22 - 23℃; for 0.5h; Inert atmosphere;99%
heptanal
111-71-7

heptanal

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

non-1-en-3-ol
21964-44-3

non-1-en-3-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;100%
85%
In tetrahydrofuran for 1h;82%
heptanal
111-71-7

heptanal

(dichloro-fluoro-methyl)-tris-dimethylamino-phosphonium; chloride
70393-08-7

(dichloro-fluoro-methyl)-tris-dimethylamino-phosphonium; chloride

1-chloro-1-fluoro-oct-1-ene
64258-20-4, 64288-23-9

1-chloro-1-fluoro-oct-1-ene

Conditions
ConditionsYield
With zinc copper In tetrahydrofuran100%
heptanal
111-71-7

heptanal

sodium cyanide
143-33-9

sodium cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Carbonic acid 1-cyano-heptyl ester ethyl ester

Carbonic acid 1-cyano-heptyl ester ethyl ester

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride In dichloromethane; water Ambient temperature;100%
heptanal
111-71-7

heptanal

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-hexyl-[1,3]oxathiolane
6712-27-2

2-hexyl-[1,3]oxathiolane

Conditions
ConditionsYield
With iodine In water; butanone at 20℃; for 0.5h;100%
With poly(ethyleneglycol) linked dicationic sulfonic acid ionic liquid In toluene at 20 - 80℃; for 0.133333h;90%
TiCl4 on montmorillonite In dichloromethane for 1h; Heating;89%
heptanal
111-71-7

heptanal

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

rac-1-(trimethylsilyl)-1-nonyn-3-ol
135501-86-9

rac-1-(trimethylsilyl)-1-nonyn-3-ol

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
Stage #2: heptanal In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
100%
With n-butyllithium 1.) THF, -78 deg C, 1 h, 2.) THF, room temp., 1 h; Multistep reaction;
With n-butyllithium 1) THF, -78 deg C, 1 h, 2) THF, r. t., 1 h; Yield given. Multistep reaction;
heptanal
111-71-7

heptanal

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(R)-(+)-2-hydroxy-octanenitrile
116214-06-3

(R)-(+)-2-hydroxy-octanenitrile

Conditions
ConditionsYield
With Tributylphosphine oxide; (R)-3,3'-bis(diphenylphosphinoylmethyl)-1,1'-binaphthalene-2,2'-dioxyaluminium chloride In dichloromethane at -40℃; for 58h;100%
heptanal
111-71-7

heptanal

C21H32BNO3

C21H32BNO3

(2R,3S)-3-hydroxy-2-methylnonanoic acid
247579-05-1

(2R,3S)-3-hydroxy-2-methylnonanoic acid

Conditions
ConditionsYield
Stage #1: heptanal; C21H32BNO3 Addition;
Stage #2: With lithium hydroperoxide; dihydrogen peroxide In water Hydrolysis;
100%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

heptanal
111-71-7

heptanal

tri-n-butyllithium magnesate complex

tri-n-butyllithium magnesate complex

1-(4-methoxyphenyl)-1-heptanol

1-(4-methoxyphenyl)-1-heptanol

Conditions
ConditionsYield
Stage #1: 1-bromo-4-methoxy-benzene; tri-n-butyllithium magnesate complex In tetrahydrofuran; hexane at 0℃; for 0.5h;
Stage #2: heptanal In tetrahydrofuran; hexane at -78℃; for 0.5h; Further stages.;
100%
heptanal
111-71-7

heptanal

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

5-hydroxy-3-oxo-undecanoic acid methyl ester
869211-56-3

5-hydroxy-3-oxo-undecanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h;
Stage #3: heptanal In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h;
100%
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃;
Stage #2: With n-butyllithium In tetrahydrofuran at -78℃;
Stage #3: heptanal In tetrahydrofuran Further stages.;
heptanal
111-71-7

heptanal

2-bromo-3,3,3-trifluoropropene
1514-82-5

2-bromo-3,3,3-trifluoropropene

1,1,1-trifluoro-2-decyn-4-ol
94792-94-6

1,1,1-trifluoro-2-decyn-4-ol

Conditions
ConditionsYield
Stage #1: 2-bromo-3,3,3-trifluoropropene With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: heptanal In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
100%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;90%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3h;
pyrrolidine
123-75-1

pyrrolidine

heptanal
111-71-7

heptanal

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2-(pyrrolidin-1-yl)octanenitrile

2-(pyrrolidin-1-yl)octanenitrile

Conditions
ConditionsYield
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 0.5h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;100%
heptanal
111-71-7

heptanal

cyclohexylamine
108-91-8

cyclohexylamine

Oenanthaldehyd-cyclohexylimid
56037-76-4

Oenanthaldehyd-cyclohexylimid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃;100%
heptanal
111-71-7

heptanal

benzylamine
100-46-9

benzylamine

(E)-N-heptylidene-1-phenylmethanamine

(E)-N-heptylidene-1-phenylmethanamine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;100%
heptanal
111-71-7

heptanal

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

1-heptanoyl-1,2-hydrazinedicarboxylic acid 1,2-diisopropyl ester
1340546-37-3

1-heptanoyl-1,2-hydrazinedicarboxylic acid 1,2-diisopropyl ester

Conditions
ConditionsYield
With Graphite In acetonitrile at 20℃; for 2h; Reagent/catalyst; Solvent; Irradiation;100%
With copper(II) acetate monohydrate In ethyl acetate at 20℃; for 8h;98%
With zinc(II) acetate dihydrate In acetonitrile at 20℃; for 16h;88%
nitroacetic acid ethyl ester
626-35-7

nitroacetic acid ethyl ester

heptanal
111-71-7

heptanal

C11H19NO4

C11H19NO4

Conditions
ConditionsYield
With [Zr6(μ3-O)4(μ3-OH)4(1,4-benzenedicarboxylate)6][(S)-6-((hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methyl)picolinaldehyde]-NH2 In toluene at 100℃; for 24h; Reagent/catalyst; Knoevenagel Condensation;100%
heptanal
111-71-7

heptanal

danishefsky's diene
54125-02-9

danishefsky's diene

(+)-2-hexyl-2,3-dihydro-4H-pyran-4-one

(+)-2-hexyl-2,3-dihydro-4H-pyran-4-one

Conditions
ConditionsYield
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclo-hexanediaminato(2-)]Mn(II)sulfophenyl-L-sodum lactose templated helical silica supported In dichloromethane at 0℃; for 6h; Reagent/catalyst; Diels-Alder Cycloaddition; Ionic liquid; Molecular sieve; enantioselective reaction;100%
heptanal
111-71-7

heptanal

tert-butyl 1-(2-bromobenzyl)hydrazine-1-carboxylate

tert-butyl 1-(2-bromobenzyl)hydrazine-1-carboxylate

C19H29BrN2O2

C19H29BrN2O2

Conditions
ConditionsYield
In ethanol at 20℃;100%
heptanal
111-71-7

heptanal

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

C11H23NSi

C11H23NSi

Conditions
ConditionsYield
With K[(H2O)4(3-picolinic acid)2Ce][(H2O)5(3-picolinic acid)2Ce][PW10Ti2O40]·11H2O at 49.84℃; for 4h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;99.8%
heptanal
111-71-7

heptanal

nitromethane
75-52-5

nitromethane

1-nitro-2-octanol
2224-39-7

1-nitro-2-octanol

Conditions
ConditionsYield
With P(i-PrNCH2CH2)3N; magnesium sulfate for 0.666667h; Ambient temperature;99%
With triethylamine; lithium bromide at 80℃; for 0.05h; Henry reaction; microwave irradiation;96%
With acrylic acid methyl ester; triphenylphosphine In ethanol at 20℃; for 2h; Henry reaction;96%
heptanal
111-71-7

heptanal

2-nitropropane
79-46-9

2-nitropropane

2-methyl-2-nitro-3-nonanol
80379-17-5

2-methyl-2-nitro-3-nonanol

Conditions
ConditionsYield
With P(i-PrNCH2CH2)3N; magnesium sulfate for 1.5h; Ambient temperature;99%
With tetrabutyl ammonium fluoride; tert-butyldimethylsilyl chloride; triethylamine In tetrahydrofuran for 0.0833333h;91%
With Amberlyst A-21 for 7h;80%
With methanol; sodium hydroxide
heptanal
111-71-7

heptanal

oenanthic acid
111-14-8

oenanthic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With water; oxygen at 100℃; for 24h;98%
With periodic acid; pyridinium chlorochromate In acetonitrile for 1.5h;97%

111-71-7Related news

The aldol condensation of acetaldehyde and Heptanal (cas 111-71-7) on hydrotalcite-type catalysts08/27/2019

The aldol condensation of acetaldehyde and heptanal has been carried out in the liquid phase between 353 and 413 K using different types of solid base catalysts: MgO with strong Lewis basic sites, Mg(Al)O mixed oxides with acid–base pairs of the Lewis type obtained from hydrotalcite precursor, ...detailed

Crystal growth study of K-F nanozeolite and its catalytic behavior in Aldol condensation of benzaldehyde and Heptanal (cas 111-71-7) enhanced by microwave heating08/24/2019

An investigation of nanosized potassium aluminosilicate F-type zeolite (K-F, structure code EDI) converted from rice husk ash (RHA) is reported. The crystallization process was studied in an organic template-free system under microwave radiation at 100 °C and the evolution was followed by spect...detailed

Determination of hexanal and Heptanal (cas 111-71-7) in human urine using magnetic solid phase extraction coupled with in-situ derivatization by high performance liquid chromatography08/22/2019

In this study, magnetic solid phase extraction coupled with in-situ derivatization (MSPE-ISD) was established for the determination of hexanal and heptanal in human urine. 2,4-Dinitrophenylhydrazine (DNPH) was used as the derivatization reagent that was adsorbed onto the surface of magnetite/sil...detailed

Upgrading castor oil: From Heptanal (cas 111-71-7) to non-isocyanate poly(amide-hydroxyurethane)s08/21/2019

Intensive research has recently been carried out to synthesize non-isocyanate polyurethanes (NIPUs) from five-membered cyclic carbonates and amines as a sustainable route to industrial relevant polyurethanes. Herein, an activated disubstituted cyclic carbonate and methyl ester containing monomer...detailed

Hydrogenation of Heptanal (cas 111-71-7) over heterogeneous catalysts08/20/2019

Among the series of heterogeneous catalysts tested in hydrogenation of heptanal, Ni–Cr–O composition possessed excellent stability and showed the best performance with the heptanol selectivity approaching 100%.detailed

111-71-7Relevant articles and documents

Preparation and catalytic properties of resin bound binuclear rhodium tetracarboxylate complexes

Andersen, Jo-Ann M.,Karodia, Nazira,Miller, David J.,Stones, Duane,Gani, David

, p. 7815 - 7818 (1998)

4-(4'-Polystyryimethyloxy)-3-carboxylatomethyloxy-1-phenylacetate bis- μ-coordinated rhodium(II) diacetate complex, a resin-bound analogue of dirhodium tetraacetate in which two adjacent μ-bridging acetate moleties are covalently linked, serves as an efficient, stable and re-useable immobilised alkene hydrofomylation and hydrogenation catalyst.

Low pressure catalytic hydroformylation of 1-hexene by the carbonylhydrido-tris(triphenylphosphine)rhodium(I), RhH(CO)(PPh3)3, in association with phosphinomethylzirconium complexes

Choukroun, R.,Gervais, D.,Kalck, P.,Senocq, F.

, p. C9 - C12 (1987)

Low pressure catalytic hydroformylation of 1-hexene was performed in the presence of RhH(CO)(PPh3)3 in association with diphenylphosphinomethylzirconium complexes such as Cp2Zr(CH2PPh2)2 and 2O or in the presence of bis(diphenylphosphine)butane.An isolated rhodium-zirconium complex, formulated as , was found to be catalytically active.

Sulphur-containing Dinuclear Rhodium Complexes as Catalyst Precursors for the Selective Hydroformylation of Alkenes

Kalck, Philippe,Frances, Jean-Marc,Pfister, Pierre-Marie,Southern, Timothy G.,Thorez, Alain

, p. 510 - 511 (1983)

Dinuclear thiolato bridged complexes, particularly 2>, catalyse the hydroformylation of hex-1-ene at low pressure and temperature to afford selectively and with high turnover rates the corresponding aldehydes.

Study of reaction and kinetics in pyrolysis of methyl ricinoleate

Guobin, Han,Zuyu, Liu,Suling, Yao,Rufeng, Yan

, p. 1109 - 1112 (1996)

The effects of pyrolysis temperature, space-velocity, and dilution ratio of starting materials on the reaction have been studied in the pyrolysis of methyl ricinoleate. The reaction parameters were optimized to obtain yield ranges of 25.8-26.7% for heptaldehyde and 45.7-46.5% for methyl undecenoate. The kinetic study showed that pyrolysis of methyl ricinoleate is a first-order reaction at 828-878 K, and the activation energy is 1.729 × 105 J/mol.

Hydroformylation in perfluorinated solvents; improved selectivity, catalyst retention and product separation

Foster, Douglas F,Gudmunsen, David,Adams, Dave J,Stuart, Alison M,Hope, Eric G,Cole-Hamilton, David J,Schwarz, Gary P,Pogorzelec, Peter

, p. 3901 - 3910 (2002)

The hydroformylation of linear terminal alkenes using rhodium based catalysts under fluorous biphasic conditions in the presence and absence of toluene is reported. Using fluorinated ponytails to modify triarylphosphites and triarylphosphines, good selectivities and reactivities can be obtained, along with good retention of the catalyst and ligand within the fluorous phase. Using P(O-4-C6H4C6F13)3 (P/Rh=3:1) as the ligand in toluene/perfluoro-1,3-dimethylcyclohexane, good results are obtained at 60°C, but decomposition of the catalyst and/or ligand occurs on increasing the temperature. More impressive results are obtained by omitting the toluene, with higher rates, better l/b ratios, and better retention of the catalyst and the phosphite within the perfluorocarbon solvent. Competing isomerisation restricts linear aldehyde selectivities to 6H4C6F13)3 is used as the ligand in the absence of toluene, even more impressive results can be obtained, with linear aldehyde selectivities up to 80.9%, high rates, and the retention of up to 99.95% of the rhodium and up to 96.7% of the phosphine within the fluorous phase. These results are compared with those of commercial systems for propene hydroformylation and with those previously reported in the literature for hydroformylation under fluorous biphasic conditions. Phase behaviour studies show that 1-octene is completely miscible with the fluorous solvent under the conditions used for the hydroformylation experiments, but that the product nonanal, phase separates.

Selective Hydroformylation with a Recoverable Dirhodium μ-Thiolato Complex

Bayon, J. C.,Real, J.,Claver, C.,Polo, A.,Ruiz, A.

, p. 1056 - 1057 (1989)

The dimeric precursor complex 2(cod)2>, (cod=cyclo-octa-1,5-diene), with PPh3 catalyses the hydroformylation of hex-1-ene, under mild conditions, into heptanals with high yields and selectivities; owing to the presence of the amine group the rhodium catalyst can be quantitatively recovered from the reaction mixture by adding dilute H2SO4, and reused without loss of activity.

Hydroformylation of olefins catalysed with bimetallic systems: HRh{P(OPh) 3}4 + cp2ZrH(CH2PPh2) and HRh(CO) {P(OPh) 3}3 + cp2ZrH(CH2PPh2)

Trzeciak, Anna M.,Ziotkowski, Jozef J.,Choukroun, Robert

, p. 145 - 149 (1996)

The catalytic activity of bimetallic systems containing the rhodium complex HRh{P(OPh)3}4 or HRh(CO){P(OPh)3}3 and the Zr(IV) complex cp2ZrH(CH2PPh2) was tested in the hydroformylation reaction of 1-hexene and E-,Z-2-hexene. An increase in n/iso ratio (from 2.2 to 3.5 in the case of HRh{P(OPh)3}4 and from 0.4 to 3.7 in the case of HRh(CO){P(OPh)3}3) was observed in 1-hexene hydroformylation in the presence of cp2ZrH(CH2PPh2).

Manninen,Krieger

, p. 2071 (1967)

Describing the Reaction of the Hydrocarboxylation of 1-Hexene, Catalyzed by Co2(CO)8, in Marcelin–de Donde Kinetics

Vigranenko, Yu. T.,de Vekki,Krylova,Koluzhnikova

, (2020)

Abstract: An equation is derived for calculating the rate coefficient of the 1-hexene hydrocarboxylation reaction in Marcelin–de Donde kinetics. The equation correctly describes experimental data in the range of concentrations of an unsaturated substrate,

Biphase hydroformylation catalyzed by rhodium in combination with a water-soluble pyridyl-triazole ligand

Scrivanti, Alberto,Beghetto, Valentina,Alam, Md. Mahbubul,Paganelli, Stefano,Canton, Patrizia,Bertoldini, Matteo,Amadio, Emanuele

, p. 613 - 617 (2017)

[RhCl(COD)]2in combination with a water soluble sulphonated pyridyl-triazolyl N,N-bidentate ligand efficiently catalyzes styrene and 1-hexene hydroformylation in water/organic solvent biphasic systems. The catalyst displays a good activity affording mixtures of linear and branched aldehydes with complete chemoselectivity. The aqueous catalytic phase may be recycled four times giving complete substrate conversion by 18 h. Mercury-poisoning experiments and transmission electron microscopy indicate that, after the first catalytic run, rhodium is present in the aqueous phase in nanoparticle form.

THE SYNTHESIS OF PGF1α BY RE-STRUCTURING OF CASTOR OIL

Ranganathan, D.,Ranganathan, S.,Mehrotra, M. M.

, p. 1869 - 1876 (1980)

Castor oil has been transformed - via methyl ricinoleate - to PGF1α by strategy wherein 16 of the 18 carbons of the castor oil backbone are incorporated in the C-20 PGF1α, involving, inter alia, a novel procedure for the regiospecific functionalisation of terminal olefins, a novel degradation of aldehyde to lower acid and strategies useful for the generation of the highly functionalised prostanoid system, which specially illustrate the utility of MEM protecting group in diverse types of chemical transformations.Additionally, this work describes the preparation of synthons having potential utility and the synthesis of novel homo-PGF1α.

New glycosphingolipids from the fungus Catathelasma ventricosa

Zhan, Zha-Jun,Yue, Jian-Min

, p. 1013 - 1016 (2003)

Three new glycosphingolipids with a cis-Δ17-fatty acyl moiety, namely, catacerebrosides A-C (1-3), along with two known glycosphingolipids, cerebrosides B and D, six known ergostane-type sterols, and tyrosamine were isolated from the fungus Catathelasma ventricosa. The structures of 1-3 were elucidated on the basis of spectroscopic analysis and chemical methods.

Impact of structured catalysts in amine oxidation under mild conditions

Santos, Jose Luis,Navarro, Pablo,Odriozola, Jose Antonio,Centeno, Miguel Angel,Pavel, Octavian D.,Jurca, Bogdan,Parvulescu, Vasile I.

, p. 266 - 272 (2016)

A structured graphene/graphite catalyst grown on a commercial austenitic stainless steel sheet providing a micromonolith was obtained by submitting the nude stainless steel structure to a carbon-rich atmosphere (first 300 mL/min of a reductive H2/N2 (1:1) flow, then to 180 mL/min of a CH4/H2 (1:5)) at high temperature (900 °C) for 2 h. The preparation procedure resulted in a homogenous surface coated with a carbon-rich film as observed by EDX and SEM images. Further characterizations by Raman spectroscopy revealed characteristic Raman lines of graphene and crystalline graphite disposed in a hierarchical organization. The disposal of the obtained surface layers was also confirmed by grazing incidence X-ray diffraction. Besides this, XRD indicated the overlapping diffraction lines of graphite, cementite and M7C3 carbides. The graphene nature of the outermost layer was also confirmed by XPS. The catalytic behavior of the structured graphene/graphite catalyst was evaluated in the selective oxidation of heptylamine. At 200 °C it afforded a total conversion with a combined selectivity in heptanonitrile and N-heptylidene-heptylamine of 67% (10% heptanonitrile) that corresponds indeed to a very efficient system in the absence of any metal. Kinetic experiments with the scope to calculate the activation energies were also performed.

MCM-41 supported water-soluble TPPTS-Rh complex in ionic liquids: A new robust catalyst for olefin hydroformylation

Yang, Yong,Lin, Haiqiang,Deng, Changxi,She, Jiarong,Yuan, Youzhu

, p. 220 - 221 (2005)

MCM-41 mesoporous silicas-supported water-soluble TPPTS-Rh complex in the ionic liquid TMGL exhibited high performance and stability for the hydroformylation of 1-hexene, and the catalyst system could be reused many times without reducing the activity and selectivity. Copyright

Rh/Cu2O nanoparticles: Synthesis, characterization and catalytic application as a heterogeneous catalyst in hydroformylation reaction

Jagtap, Samadhan A.,Bhosale, Manohar A.,Sasaki, Takehiko,Bhanage, Bhalchandra M.

, p. 162 - 168 (2016)

In this work, we report a rapid protocol for the synthesis of Rh/Cu2O nanoparticles (Rh/Cu2O NPs) in aqueous medium using microwave route. The microwave energy acts as driving force in synthesis which makes the process economical. The obtained nanoparticles were characterized with the help of FEG-SEM, TEM, HRTEM, EDS, XRD, FT-IR and ICP-AES techniques. The prepared Rh/Cu2O nanoparticles gave 100% yield of uniform spherical morphology. This is a simple, inexpensive and time saving protocol for synthesis of Rh/Cu2O nanoparticles than conventional methods. Furthermore, we showed the catalytic application of Rh/Cu2O nanoparticles in hydroformylation reaction for the conversion of 1-hexene to 1-hexanal at mild reaction conditions such as Rh/Cu2O NPs (10 mg), 35 bar pressure of H2/CO at 360 K. The reaction provides 99% conversion and high selectivity (>90%) toward aldehydes with branched aldehyde is a major product. Notably the reaction does not require the any phosphine ligand source, low catalyst loading, low temperature with major advantage of catalyst recyclability.

Synthesis, Structural Characterization, and Hydroformylation Activity of Rhodium(I) Complexes with a Polar Phosphinoferrocene Sulfonate Ligand

Zábransky, Martin,Císa?ová, Ivana,Trzeciak, Anna M.,Alsalahi, Waleed,?těpni?ka, Petr

, p. 479 - 488 (2019)

1′-(Diphenylphosphino)ferrocene-1-sulfonic acid (HL), isolated from the salt (Et3NH)L on an ion exchanger, reacts with Rh(I) complexes [Rh(acac)(CO)(PR3)] (acac = acetylacetonato-κ2O,O′) to give complexes of the type [Rh(CO)(PR3)(Ph2PfcSO3-κ2O,P)] (1a-d; R = Ph (a), Cy (b), 2-furyl (c), and OMe (d); fc = ferrocene-1,1′-diyl). In an analogous reaction with [Rh(acac)(nbd)] (nbd = n 2: n 2-norbornadiene), HL produces [Rh(nbd)(Ph2PfcSO3-κ2O,P)] (2). Adding (Et3NH)L (2 equiv per Rh) to [Rh(μ-Cl)(CO)2]2 and [Rh(acac)(CO)2] gives rise to the cationic complexes trans-(Et3NH)2[RhCl(CO)(Ph2PfcSO3-κP)2] (3) and (Et3NH)[Rh(CO)(Ph2PfcSO3-κ2O,P)(Ph2PfcSO3-κP)] (4), respectively. In complex 4, resulting from the simultaneous substitution of a CO ligand and acid-base replacement of the acac ligand, the P-monodentate and O,P-chelating phosphinoferrocene sulfonate ligands rapidly interconvert (in a solution). All compounds were characterized by spectroscopic methods and by elemental analysis, and the crystal structures of 1a·Me2CO, solvated 1b, 2, and 4·H2O were determined. Furthermore, the catalytic activity of all Rh(I) complexes was assessed in hydroformylation of vinyl acetate under solvent-free conditions at 80 °C and at 20 bar of synthesis gas (H2/CO = 1:1). High conversion with good selectivity to iso-aldehyde was observed for 1a·1/2H2O and 4·1/2H2O. When applied to "on-water" hydroformylation of 1-hexene (80 °C/10 bar), the complexes mainly promoted 1-hexene isomerization to 2-hexene. However, two of them, 1a·1/2H2O and 1c, exhibited reasonable selectivity to aldehydes and preferentially produced the linear product (n/iso ratios up to 3).

Reactions of stabilized Criegee intermediates from the gas-phase reactions of O3 with selected alkenes

Baker,Aschmann,Arey,Atkinson

, p. 73 - 85 (2002)

The gas-phase reactions of O3 with 1-octene, trans-7-tetradecene, 1,2-dimethyl-l-cyclohexene, and α-pinene have been studied in the presence of an OH radical scavenger, primarily using in situ atmospheric ionization tandem mass spectrometry (API-MS), to investigate the products formed from the reactions of the thermalized Criege intermediates in the presence of water vapor and 2-butanol (1-octene and trans-7-tetradecene forming the same Criege intermediate). With H3O+(H2O)n as the reagent ions, ion peaks at 149 u ([M + H]+) were observed in the API-MS analyses of the l-octene and trans-7-tetradecene reactions, which show a neutral loss of 34 u (H2O2) and are attributed to the α-hydroxyhydroperoxide CH3(CH2)5CH(OH)OOH, which must therefore have a lifetime with respect to decomposition of tens of minutes or more. No evidence for the presence of α-hydroxyhyroperoxides was obtained in the 1,2-dimethyl-1-cyclohexene or α-pinene reactions, although the smaller yields of thermalized Criegee intermediates in these reactions makes observation of α-hydroxyhydroperoxides from these reactions less likely than from the 1-octene and trans-7-tetradecene reactions. Quantifications of 2,7-octanedione from the 1,2-dimethyl-1-cyclohexene reactions and pinonaldehyde from the α-pinene reactions were made by gas chromatographic analyses during reactions with cyclohexane and with 2-butanol as the OH radical scavenger. The measured yields of 2,7-octanedione from 1,2-dimethyl-1-cyclohexene and of pinonaldehyde from α-pinene were 0.110 ± 0.020 and 0.164 ± 0.029, respectively, and were independent of the OH radical scavenger used. Reaction mechanisms are presented and discussed.

Anisole: A further step to sustainable hydroformylation

Delolo, Fábio G.,Dos Santos, Eduardo N.,Gusevskaya, Elena V.

, p. 1091 - 1098 (2019)

Hydroformylation, also known as the "oxo" process, is a major industrial process that employs rhodium or cobalt catalysts in solution; therefore the solvent of this process is a critical issue for its sustainability. Although several innovative solutions have been proposed recently, traditional fossil-derived solvents dominate the scenario for this reaction. In this paper, we studied a series of solvents considered more sustainable in recent ranks in the hydroformylation of a series of olefins. Anisole, a solvent with an impressive sustainability rank and very scarcely exploited in hydroformylation, proved to be an excellent alternative for this reaction.

High-pressure investigations under CO/H2 of rhodium complexes containing hemispherical diphosphites

Semeril, David,Matt, Dominique,Toupet, Loic,Oberhauser, Werner,Bianchini, Claudio

, p. 13843 - 13849 (2010)

The two rhodium complexes [Rh(acac)(LR)] (LR=(S,S)-5, 11,17,23-tetra-tert-butyl-25,27-di(OR)-26,28-bis(1,1'-binaphthyl-2, 2'-dioxyphosphanyloxy)calix[4]arene; 6: R=benzyl, 7: R=fluorenyl), each based on a hemispherical chelator forming a pocket about the metal centre upon chelation, are active in the hydroformylation of 1-octene and styrene. As expected for this family of diphosphanes, both complexes resulted in remarkably high selectivity towards the linear aldehyde in the hydroformylation of 1-octene (l/b≈15 for both complexes). Linear aldehyde selectivity was also observed when using styrene, but surprisingly only 6 displayed a marked preference for the linear product (l/b=12.4 (6) vs. 1.9 (7)). A detailed study of the structure of the complexes under CO or CO/H2 in toluene was performed by high-pressure NMR (HP NMR) and FT-IR (HP-IR) spectroscopies. The spectroscopic data revealed that treatment of 6 with CO gave [Rh(acac)(CO) (I·1-Lbenzyl)] (8), in which the diphosphite behaves as a unidentate ligand. Subsequent addition of H2 to the solution resulted in a well-defined chelate complex with the formula [RhH(CO)2(Lbenzyl)] (9). Unlike 6, treatment of complex 7 with CO only led to ligand dissociation and concomitant formation of [Rh(acac)(CO)2], but upon addition of H2 a chelate complex analogous to 9 was formed quantitatively. In both [RhH(CO)2(L R)] complexes the diphosphite adopts the bis-equatorial coordination mode, a structural feature known to favour the formation of linear aldehydes. As revealed by variable-temperature NMR spectroscopy, these complexes show the typical fluxionality of trigonal bipyramidal [RhH(CO)2(diphosphane)] complexes. The lower linear selectivity of 7 versus 6 in the hydroformylation of styrene was assigned to steric effects, due to the pocket in which the catalysis takes place being less adapted to accommodate CO or larger olefins and, therefore, possibly leading to facile ligand decoordination. This interpretation was corroborated by an X-ray structure determination carried out for 7. Rhodium in confinement: As revealed by high-pressure NMR/IR spectroscopic studies, the reaction of rhodium complexes containing hemispherical diphosphites with CO/H2 leads to trigonal bipyramidal intermediates in which the phosphorus atoms exclusively occupy equatorial sites (see figure). The resulting metal confinement selectively drives olefin hydroformylation reactions to form aldehydes that best fit the cavity. Copyright

On rhodium complexes bearing H-spirophosphorane derived ligands: Synthesis, structural and catalytic properties

Skarzyńska, Anna,Mieczynska, Ewa,Siczek, Miosz

, p. 179 - 186 (2013)

We investigated the coordination properties of H-spirophosphoranes towards rhodium ion. Symmetrical phosphorus ligands: HP(OCH2CH 2NH)2 L1, HP(OCH2CM-2NH)2 L2, HP(OCMe2CMe 2O)2 L3, HP(OC6H4NH)2 L4, and unsymmetrical phosphorus ligands: HP(OCMe2CMe2O)(OCH2CM-2NH) L5, HP(OCMe2CMe2O)(OC6H4NH) L6 were found to coordinate to rhodium precursor [Rh(CO)2Cl]2 exclusively in protonated k2-P,E (E =N, O) bidentate fashion, yielding complexes [Rh(CO)ClL] 1-6. The complexes were characterised by spectroscopic methods. The molecular structures of the ligand L6 complexes 3, 5 and 6 were determined by single-crystal X-ray diffraction. The catalytic activity of the complexes was determined in hydroformylation reaction of 1-hexene. Complexes 1 and 2 appeared to be active in isomerisation reactions yielding 76 and 62% of 2-hexene. When used with six-fold excess of triphenylphosphite P(OPh)3 as a modified ligand, the most active catalyst 1 in hydroformylation reaction produced 66% of aldehydes and 22% of 2-hexene.

Tris(2-pyridyl)phosphine Complexes of Ruthenium(II) and Rhodium(I). Hydroformylation of Hex-1-ene by Rhodium Complexes

Kurtev, Kurti,Ribola, Dominique,Jones, Richard A.,Cole-Hamilton, David J.,Wilkinson, Geoffrey

, p. 55 - 58 (1980)

Complexes of ruthenium(II) and rhodium(I) containing tris(2-pyridyl)phosphine are described, examples being RuHCl3 and RhCl2.In certain cases, as in these, the nitrogen atom of one of the 2-pyridyl groups can act as a donor to give a P,N chelate ligand.In the presence of an excess of P(py)3 and at low CO + H2 (1 : 1) pressures, the complex RhH(CO)(PPh3)2 acts as a catalyst for the selective hydroformylation of hex-1-ene to n-heptanal.

Tri(3-pyridyl)phosphine as amphiphilic ligand in the rhodium-catalysed hydroformylation of 1-hexene

Meyer, Wolfgang H.,Bowen, Richard J.,Billing, David G.

, p. 339 - 345 (2007)

The molecular structure of carbonylchlorobis(tri(3-pyridyl)phosphine) rhodium, 1, has been determined by X-ray diffraction methods. The N-protonated trifluoromethanesulfonate (triflate) complex 3 was synthesised as a model compound for the extraction of a rhodium complex bearing amphiphilic ligands which can allow catalyst recycling in the hydroformylation of alkenes by using their distribution behavior in organic and aqueous solvents of different pH. The high water-solubility of the employed ligand renders the recycling method as only partly successful due to insufficient extraction from the water phase into the organic phase. In the hydroformylation of 1-hexene the production of rt-heptanal is slightly disfavoured when using the ligand tri(3-pyridyl) phosphine as compared to triphenylphosphine which can be ascribed to a higher amount of ligand-deficient active rhodium complexes of the less basic pyridyl phosphine ligand under CO pressure.

Benzoquinones from Embelia angustifolia

Lund, Anne-Kristine,Lemmich, John,Adsersen, Anne,Olsen, Carl E.

, p. 679 - 681 (1997)

Three new 2,5-dihydroxy-3-alkyl-1,4-benzoquinones, (Z)-2,5-dihydroxy-3- (pentadec-8-enyl)-1,4-benzoquinone, (Z,Z)-2,5-dihydroxy-3-(heptadeca-8,11- dienyl)-1,4-benzoquinone and (Z)-2,5-dihydroxy-3-(heptadec-8-enyl)-1,4- benzoquinone and the known 2,5-dihydroxy-3-pentadecyl-1,4-benzoquinone were isolated from the leaves of Embelia angustifolia. Their structures have been established on the basis of spectral analysis and by chemical methods.

Decreasing Side Products and Increasing Selectivity in the Tandem Hydroformylation/Acyloin Reaction

Ostrowski, Karoline A.,Fassbach, Thiemo A.,Vogelsang, Dennis,Vorholt, Andreas J.

, p. 2607 - 2613 (2015)

A highly selective catalyst system was developed for the recently discovered tandem hydroformylation/acyloin reaction by systematic investigations and changes of reaction conditions. This new catalyst system is characterized by an excellent selectivity of the desired reaction pathway with negligible amounts of side products. A successful application of the tandem hydroformylation/acyloin reaction to a variety of olefins is enabled with comparable excellent selectivities up to >99% for the first and second reaction step, therefore a general synthesis for the conversion of olefins into acyloins is found. Furthermore, very good to excellent yields for the intermediates and final acyloin products were observed within two catalysed reactions in one preparative step. The acyloin product was applied as a nonpolar precursor for surfactants. After attaching a polar head group to the acyloin and determination of tensiometric data, the molecule showed industrial relevant surface-active properties. Jointly successful: New catalyst systems for the tandem hydroformylation/acyloin reaction display excellent selectivities within two catalyzed reactions in one preparative step. A variety of olefins can be converted efficiently, and the acyloin product is applied successfully as a nonpolar precursor for surfactants.

Synthesis of electron-withdrawing butane- and arene-sulfonylamino phosphines and use in rhodium-catalyzed hydroformylation

Magee, Matthew P.,Li, Huan-Qiu,Morgan, Oma,Hersh, William H.

, p. 387 - 394 (2003)

Reaction of RSO2N(H)CH2CH2N(H)SO2R [R = Bu (1), 4-nitrobenzene (7), 1-naphthalene (9a), 2-naphthalene (9b)] with PhPCl2 or EtPCl2 gives monodentate phosphorus compounds 2 and 3 (R = Bu, PhP and EtP), and 8 (R = 4-nitrobenzene, PhP), and with Ph2PCl gives the corresponding bidentate phosphine ligands Ph2PN(SO2R)CH2CH2N(SO2R)P Ph2 [R = Bu (10), 4-nitrobenzene (11), 1- and 2-naphthalene (12a,b)]; similar reactions of N,N′-(1-butanesulfonyl)-2,2′-diaminobiphenyl (4) give monodentate 5 (PhP) and 6 (EtP) and N,N′-bis(diphenylphosphino)-N,N′-(1-butanesulfonyl)-2,2′-diami nobiphenyl (16). A monodentate analogue of 10 was also prepared, Ph2PN(Et)SO2Bu (14). Diphosphorus compounds with two butanesulfonylamino groups on phosphorus were also prepared from 1 and Cl2P(CH2)nPCl2 (n = 2, 4) to give 19 and 20. Details of the 13C NMR false AA′X systems are reported for 19 and 20. Rhodium-catalyzed hydroformylation reactions were run at 60 and 80 °C, at CO/H2 pressures from 4-11 atm, and in THF, toluene, CH2Cl2, and dioxane. Results show that the highest ratios of linear (n) to branched (iso) aldehydes were obtained with arenesulfonamides (n:iso > 10) while the bidentate alkanesulfonamide 10 gave a lower n:iso ratio of 7.2 but the highest rate [k1 = 1.98 h-1, turnover frequency = 1130 mol aldehyde (mol Rh)-1 h-1] in THF at 80 °C. Both the rate and n:iso ratio for 10 were found to increase with decreasing CO/H2 pressure in THF and in toluene, although the rate change was small for toluene. Both the rate and n:iso ratio for 10 also increased in CH2Cl2, but this was found not to be due to lower CO/H2 concentrations in solution, on the basis of solubility measurements in THF and CH2Cl2.

PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions

Du, Yunfei,Ouyang, Yaxin,Wang, Xi,Wang, Xiaofan,Yu, Zhenyang,Zhao, Bingyue,Zhao, Kang

, p. 48 - 65 (2021/06/16)

Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.

Directing Selectivity to Aldehydes, Alcohols, or Esters with Diphobane Ligands in Pd-Catalyzed Alkene Carbonylations

Aitipamula, Srinivasulu,Britovsek, George J. P.,Nobbs, James D.,Tay, Dillon W. P.,Van Meurs, Martin

, p. 1914 - 1925 (2021/06/28)

Phenylene-bridged diphobane ligands with different substituents (CF3, H, OMe, (OMe)2, tBu) have been synthesized and applied as ligands in palladium-catalyzed carbonylation reactions of various alkenes. The performance of these ligands in terms of selectivity in hydroformylation versus alkoxycarbonylation has been studied using 1-hexene, 1-octene, and methyl pentenoates as substrates, and the results have been compared with the ethylene-bridged diphobane ligand (BCOPE). Hydroformylation of 1-octene in the protic solvent 2-ethyl hexanol results in a competition between hydroformylation and alkoxycarbonylation, whereby the phenylene-bridged ligands, in particular, the trifluoromethylphenylene-bridged diphobane L1 with an electron-withdrawing substituent, lead to ester products via alkoxycarbonylation, whereas BCOPE gives predominantly alcohol products (n-nonanol and isomers) via reductive hydroformylation. The preference of BCOPE for reductive hydroformylation is also seen in the hydroformylation of 1-hexene in diglyme as the solvent, producing heptanol as the major product, whereas phenylene-bridged ligands show much lower activities in this case. The phenylene-bridged ligands show excellent performance in the methoxycarbonylation of 1-octene to methyl nonanoate, significantly better than BCOPE, the opposite trend seen in hydroformylation activity with these ligands. Studies on the hydroformylation of functionalized alkenes such as 4-methyl pentenoate with phenylene-bridged ligands versus BCOPE showed that also in this case, BCOPE directs product selectivity toward alcohols, while phenylene-bridge diphobane L2 favors aldehyde formation. In addition to ligand effects, product selectivities are also determined by the nature and the amount of the acid cocatalyst used, which can affect substrate and aldehyde hydrogenation as well as double bond isomerization.

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