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26260-02-6

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26260-02-6 Usage

Chemical Properties

white to light beige low melting crystalline

Uses

Different sources of media describe the Uses of 26260-02-6 differently. You can refer to the following data:
1. 2-Iodo-benzaldehyde is a very useful synthetic intermediate. It is halogenated Benzaldehyde (B119740) which is mainly used as a precursor to other organic compounds, such as pharmaceuticals, and plastic additives.
2. 2-Iodobenzaldehyde may be used as a reactant in the synthesis of the following heterocycles:2,3-diaryl-1-indenonesindolo[1,2-a]quinazolinesBaylis-Hillman (BH) adductsIt may also be used in preparing:5-phenylindazolo[3,2-b]quinazolin-7(5H)-one4-(3-iodophenyl)-2,2:6,2-terpyridinefluoren-9-one2-formyl-3′-methoxybiphenyl

General Description

2-Iodobenzaldehyde (o-iodobenzaldehyde) is a 2-halobenzaldehyde derivative. Its crystals belong to the orthorhombic crystal system and P212121 space group.

Check Digit Verification of cas no

The CAS Registry Mumber 26260-02-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,2,6 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 26260-02:
(7*2)+(6*6)+(5*2)+(4*6)+(3*0)+(2*0)+(1*2)=86
86 % 10 = 6
So 26260-02-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H5IO/c8-7-4-2-1-3-6(7)5-9/h1-5H

26260-02-6 Well-known Company Product Price

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  • Alfa Aesar

  • (L17446)  2-Iodobenzaldehyde, 98%   

  • 26260-02-6

  • 1g

  • 1066.0CNY

  • Detail
  • Alfa Aesar

  • (L17446)  2-Iodobenzaldehyde, 98%   

  • 26260-02-6

  • 5g

  • 4285.0CNY

  • Detail

26260-02-6SDS

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 2-Iodobenzaldehyde

1.2 Other means of identification

Product number -
Other names iodobenzaldehyde

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:26260-02-6 SDS

26260-02-6Synthetic route

2-iodobenzyl alcohol
5159-41-1

2-iodobenzyl alcohol

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform at 20℃; for 70h;99%
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 1h;98%
With silica gel; pyridinium chlorochromate In dichloromethane at 20℃; Inert atmosphere;98%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; Trimethylenediamine; sodium iodide In 1,4-dioxane for 24h; Finkelstein Reaction; Reflux; Inert atmosphere;99%
Multi-step reaction with 3 steps
1: 83 percent / TsOH / 5 h / Heating
2: 1.) Grignard reagent, 2.) I2 / 1.), 2.) THF
3: 83 percent / aq. HCl / tetrahydrofuran / 20 h / Ambient temperature
View Scheme
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; under 1500.15 Torr; for 24h; Reagent/catalyst; Finkelstein Reaction; Autoclave; Inert atmosphere; Schlenk technique;
(2-iodophenyl)methyl acetate
80953-51-1

(2-iodophenyl)methyl acetate

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 14h;98%
Multi-step reaction with 2 steps
1: aqueous KOH
2: AgNO3; Na2S2O8; water
View Scheme
2-bromobenzaldehyde diethyl acetal
35822-58-3

2-bromobenzaldehyde diethyl acetal

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
Stage #1: 2-bromobenzaldehyde diethyl acetal With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; for 1.41667h;
Stage #2: With iodine In tetrahydrofuran; hexane at -78 - 20℃; for 12.6667h;
98%
2-[diethyl(hydroxy)silyl]benzaldehyde

2-[diethyl(hydroxy)silyl]benzaldehyde

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;94%
2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide; borane-THF Inert atmosphere;90%
Multi-step reaction with 2 steps
1: 40 percent / HCl / 30 h / Heating
2: 34 percent / diisobutylaluminum hydride / toluene / 2 h / -60 °C
View Scheme
Multi-step reaction with 2 steps
1: 67 percent / SOCl2, DMF / 2 h / Heating
2: tert-butyl alcohol, LiAlH4 / bis-(2-methoxy-ethyl) ether / -78 - 20 °C
View Scheme
2-Iodo-N-methyl-N-phenylbenzamide
7022-46-0

2-Iodo-N-methyl-N-phenylbenzamide

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.116667h; Inert atmosphere;90%
C12H18O2Si

C12H18O2Si

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;90%
Multi-step reaction with 2 steps
1: acetonitrile / 10 h / 20 °C / pH 5
2: Iodine monochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere
View Scheme
2-(hydroxydiisopropylsilyl)benzaldehyde

2-(hydroxydiisopropylsilyl)benzaldehyde

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;89%
C14H22O2Si

C14H22O2Si

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;85%
Multi-step reaction with 2 steps
1: acetonitrile / 10 h / 20 °C / pH 5
2: Iodine monochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere
View Scheme
2-iodobenzaldehyde ethylene glycol ketal
152302-84-6

2-iodobenzaldehyde ethylene glycol ketal

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 20h; Ambient temperature;83%
2-formylbenzene boronic acid
40138-16-7

2-formylbenzene boronic acid

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24h;83%
2-iodo-N-methoxy-N-methyl-benzamide
294190-47-9

2-iodo-N-methoxy-N-methyl-benzamide

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;77%
C13H20IN
76464-87-4

C13H20IN

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate In chloroform at 60℃; for 2h; Polonovski type reaction;75%
2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
380151-85-9

2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With copper(I) oxide; 1,10-Phenanthroline; potassium iodide In methanol; water at 80℃; for 1h; High pressure;70%
With copper(I) oxide; 1,10-Phenanthroline; potassium iodide In methanol; water at 80℃; for 1h; Sealed tube;65%
o-iodo-methyl-benzoic acid
610-97-9

o-iodo-methyl-benzoic acid

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -60℃; for 2h;34%
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With sulfuric acid bei der elektrolytischen Oxydation;
Multi-step reaction with 4 steps
1: tetrachloromethane; dibenzoyl peroxide; N-bromo-succinimide
2: acetic acid
3: aqueous KOH
4: AgNO3; Na2S2O8; water
View Scheme
2-iodobenzonitrile
4387-36-4

2-iodobenzonitrile

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether; tin(ll) chloride anschl. mit H2O;
2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With chloroform; hexamethylenetetramine Erhitzen des Reaktionsprodukts mit wss. Essigsaeure;
Multi-step reaction with 3 steps
1: acetic acid
2: aqueous KOH
3: AgNO3; Na2S2O8; water
View Scheme
benodanil
15310-01-7

benodanil

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With phosphorus pentachloride; toluene at 100℃; Erwaermen des Reaktionsprodukts mit SnCl2 und aether. HCl und anschliessendes Behandeln mit Wasser;
2-Iodobenzoyl chloride
609-67-6

2-Iodobenzoyl chloride

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With tetrahydrogenoboratebis(triphenylphosphine)copper(I); triphenylphosphine In acetone for 1h;17.2 g
Multi-step reaction with 2 steps
1: 98 percent / sodium borohydride / dioxane / 1 h / steam-bath
2: 76.4 percent / pyridinium dichromate / CH2Cl2 / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
2: toluene; PCl5 / 100 °C / Erwaermen des Reaktionsprodukts mit SnCl2 und aether. HCl und anschliessendes Behandeln mit Wasser
View Scheme
2-iodobenzylamine
39959-51-8

2-iodobenzylamine

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With N-bromoacetamide In water at 14.9 - 34.9℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.);
C7H7IO*C5H5N*Br3H

C7H7IO*C5H5N*Br3H

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
In acetic acid at 19.9℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.), var. temp.;
2-Iodobenzoyl chloride
609-67-6

2-Iodobenzoyl chloride

A

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

B

2-iodobenzyl alcohol
5159-41-1

2-iodobenzyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; tert-butyl alcohol In diethylene glycol dimethyl ether at -78 - 20℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

sulfuric acid
7664-93-9

sulfuric acid

lead dioxide anode

lead dioxide anode

A

2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

B

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
bei der elektrolytischen Oxydation;
diazotized o-amino-benzaldehyde

diazotized o-amino-benzaldehyde

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With potassium iodide
With potassium iodide
o-iodo-cinnamic acid

o-iodo-cinnamic acid

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
With potassium permanganate
(2-iodo-benzylidene)-malonic acid
121263-09-0

(2-iodo-benzylidene)-malonic acid

water
7732-18-5

water

A

malonic acid
141-82-2

malonic acid

B

carbon dioxide
124-38-9

carbon dioxide

C

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

D

(E)-3-(2-Iodophenyl)propenoic acid
90276-19-0

(E)-3-(2-Iodophenyl)propenoic acid

2-(2-bromophenyl)-1,3-dioxolan
34824-58-3

2-(2-bromophenyl)-1,3-dioxolan

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Grignard reagent, 2.) I2 / 1.), 2.) THF
2: 83 percent / aq. HCl / tetrahydrofuran / 20 h / Ambient temperature
View Scheme
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

[2-(3,4-dimethoxy-phenyl)-ethyl]-(2-iodo-benzylidene)amine

[2-(3,4-dimethoxy-phenyl)-ethyl]-(2-iodo-benzylidene)amine

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

phenylhydrazine
100-63-0

phenylhydrazine

2-iodo-benzaldehyde phenylhydrazone
35713-98-5

2-iodo-benzaldehyde phenylhydrazone

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 160℃; for 0.166667h; microwave irradiation;100%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

N-methylhydroxyamine hydrochloride
4229-44-1

N-methylhydroxyamine hydrochloride

(Z)-N-(2-iodobenzylidene)methylamine N-oxide
1037396-94-3

(Z)-N-(2-iodobenzylidene)methylamine N-oxide

Conditions
ConditionsYield
With sodium hydrogencarbonate at 20℃; for 2h;100%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

methyl 2-[N-(2-iodobenzyl)amino]acetate
1245604-64-1

methyl 2-[N-(2-iodobenzyl)amino]acetate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid; triethylamine In dichloromethane at 20℃; for 19h; Inert atmosphere;100%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

ethyl 2-[N-(2-iodobenzyl)amino]acetate

ethyl 2-[N-(2-iodobenzyl)amino]acetate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid; triethylamine In dichloromethane at 20℃; for 19h; Inert atmosphere;100%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

methoxymethyltriphenylphosphonium bromide
33670-32-5

methoxymethyltriphenylphosphonium bromide

(E)-1-iodo-2-(2-methoxyvinyl)benzene

(E)-1-iodo-2-(2-methoxyvinyl)benzene

Conditions
ConditionsYield
Stage #1: methoxymethyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
100%
2-Methoxypropene
116-11-0

2-Methoxypropene

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

1-Iodo-2-[3-methoxy-1-(1-methoxy-1-methyl-ethoxy)-but-3-enyl]-benzene

1-Iodo-2-[3-methoxy-1-(1-methoxy-1-methyl-ethoxy)-but-3-enyl]-benzene

Conditions
ConditionsYield
With silica gel; acetic acid; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium In dichloromethane at 25℃; Addition;99%
With tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; silica gel; acetic acid at 25℃;97%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid

Conditions
ConditionsYield
With potassium permanganate; tetrabutylammomium bromide; water In dichloromethane; acetone at 20℃; for 24h;99%
With perchloric acid; N-Chlorourethan; acetic acid In water at 29.9℃; for 10h; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.);
With perchloric acid; mercury(II) diacetate; N-bromoacetamide In acetic acid at 24.9℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔG(excit.), ΔH(excit.), ΔS(excit.);
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

phenylboronic acid
98-80-6

phenylboronic acid

2-Phenylbenzaldehyde
1203-68-5

2-Phenylbenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 0.5h; Suzuki-Miyaura Coupling;99%
With potassium carbonate In ethanol; water at 20℃; for 1h; Suzuki-Miyaura Coupling; Green chemistry;94%
With potassium phosphate In 1,4-dioxane at 70℃; for 1.5h; Suzuki-Miyaura Coupling;93%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

acetic acid
64-19-7

acetic acid

N-butylamine
109-73-9

N-butylamine

2-(acetyl-butyl-amino)-N-cyclohexyl-2-(2-iodo-phenyl)-acetamide

2-(acetyl-butyl-amino)-N-cyclohexyl-2-(2-iodo-phenyl)-acetamide

Conditions
ConditionsYield
In methanol at 20℃; Ugi reaction;99%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

isocyanoacetic acid methyl ester
39687-95-1

isocyanoacetic acid methyl ester

acetic acid
64-19-7

acetic acid

GlyOEt*HCl
459-73-4

GlyOEt*HCl

{acetyl-[(2-iodo-phenyl)-(methoxycarbonylmethyl-carbamoyl)-methyl]-amino}-acetic acid ethyl ester

{acetyl-[(2-iodo-phenyl)-(methoxycarbonylmethyl-carbamoyl)-methyl]-amino}-acetic acid ethyl ester

Conditions
ConditionsYield
In methanol at 20℃; Ugi reaction;99%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

(2-iodobenzyl)triphenylphosphonium bromide
62680-65-3

(2-iodobenzyl)triphenylphosphonium bromide

C14H10I2

C14H10I2

Conditions
ConditionsYield
Stage #1: (2-iodobenzyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃;
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran at 20℃; Wittig reaction; Further stages.;
99%
With potassium hydroxide In chloroform; water at 20℃; for 2.5h; Reflux;92%
4-Octyne
1942-45-6

4-Octyne

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

1-amino-naphthalene
134-32-7

1-amino-naphthalene

N-(2,3-dipropyl-1H-inden-1-yl)naphthalen-1-amine
1099616-13-3

N-(2,3-dipropyl-1H-inden-1-yl)naphthalen-1-amine

Conditions
ConditionsYield
With Co(dppe)Cl2; zinc In tetrahydrofuran; acetonitrile at 120℃; for 12h; Inert atmosphere; regioselective reaction;99%
4-Octyne
1942-45-6

4-Octyne

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

p-toluidine
106-49-0

p-toluidine

2,3-dipropyl-N-p-tolyl-1H-inden-1-amine
1099615-80-1

2,3-dipropyl-N-p-tolyl-1H-inden-1-amine

Conditions
ConditionsYield
With Co(dppe)Cl2; zinc In tetrahydrofuran; acetonitrile at 120℃; for 12h; Inert atmosphere; regioselective reaction;99%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

1-(2-iodophenyl)-4,4-dimethylpent-2-yn-1-ol

1-(2-iodophenyl)-4,4-dimethylpent-2-yn-1-ol

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran at 20℃; for 3h;
99%
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran; hexane at 20℃; for 4h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(2-iodophenyl)(phenyl)methanol
134456-76-1

(2-iodophenyl)(phenyl)methanol

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;99%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

ethyl 3-(2-iodophenyl)acrylate
412272-54-9

ethyl 3-(2-iodophenyl)acrylate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 2h;
99%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere;
85%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

ethyl (E)-3-(2-iodophenyl)-2-propenoate
378759-67-2

ethyl (E)-3-(2-iodophenyl)-2-propenoate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In dichloromethane at 0℃; for 0.0833333h; Wittig-Horner reaction;
Stage #2: 2-iodobenzaldehyde In dichloromethane at 0℃; for 0.5h; Wittig-Horner reaction; Further stages.;
98.7%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran
Stage #2: 2-iodobenzaldehyde In tetrahydrofuran at 20℃;
92%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In dichloromethane; mineral oil at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-iodobenzaldehyde In dichloromethane; mineral oil at 0℃; for 2h; Inert atmosphere;
89%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

Biphenyl-2,2'-dicarbaldehyde
1210-05-5

Biphenyl-2,2'-dicarbaldehyde

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; copper In dimethyl sulfoxide at 65℃; Ullmann Condensation;98%
With indium; palladium 10% on activated carbon; tetrabutylammomium bromide; lithium chloride In water at 90℃; for 24h; Green chemistry;75%
With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;64%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

1-(2-iodophenyl)prop-2-yn-1-ol
81758-22-7

1-(2-iodophenyl)prop-2-yn-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Sealed tube;98%
In tetrahydrofuran for 2h; Ambient temperature;95%
In tetrahydrofuran at -60℃; for 14h;86%
In tetrahydrofuran at 0℃; Inert atmosphere;
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

N-tosyl-N-allylpropargylamine
133886-40-5

N-tosyl-N-allylpropargylamine

N-allyl-N-(3-(2-formylphenyl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide
857026-45-0

N-allyl-N-(3-(2-formylphenyl)prop-2-yn-1-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
Stage #1: 2-iodobenzaldehyde With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine for 0.166667h; Inert atmosphere;
Stage #2: N-tosyl-N-allylpropargylamine Inert atmosphere;
98%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In tetrahydrofuran at 50℃; for 6h; Sonogashira coupling;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Inert atmosphere;
4-Octyne
1942-45-6

4-Octyne

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

3,5-difluoroaniline
372-39-4

3,5-difluoroaniline

N-(3,5-difluorophenyl)-2,3-dipropyl-1H-inden-1-amine
1099616-26-8

N-(3,5-difluorophenyl)-2,3-dipropyl-1H-inden-1-amine

Conditions
ConditionsYield
With Co(dppe)Cl2; zinc In tetrahydrofuran; acetonitrile at 120℃; for 12h; Inert atmosphere; regioselective reaction;98%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone
36646-78-3

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

9-(4,4-dimethyl-6-oxo-2-(p-tolylamino)cyclohex-1-enyl)-3,3-dimethyl-10-(p-tolyl)-3,4,9,10-tetrahydroacridin-1(2H)-one
1196957-90-0

9-(4,4-dimethyl-6-oxo-2-(p-tolylamino)cyclohex-1-enyl)-3,3-dimethyl-10-(p-tolyl)-3,4,9,10-tetrahydroacridin-1(2H)-one

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; caesium carbonate In toluene at 110℃; for 12h;98%
With caesium carbonate In toluene at 110℃; for 24h; Inert atmosphere;86%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

tri(naphthalen-1-yl)bismuth
33397-22-7

tri(naphthalen-1-yl)bismuth

2-(naphthalene-1-yl)benzaldehyde
142598-69-4

2-(naphthalene-1-yl)benzaldehyde

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 3h;98%
2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

3-(4-methylphenyl)acrylaldehyde
1504-75-2

3-(4-methylphenyl)acrylaldehyde

C17H14OS

C17H14OS

Conditions
ConditionsYield
With silver(I) acetate; copper diacetate; ethoxy(potassiosulfanyl)methanethione In N,N-dimethyl-formamide at 100℃; for 5h;98%
1-ethynyl-4-fluorobenzene
766-98-3

1-ethynyl-4-fluorobenzene

2-iodobenzaldehyde
26260-02-6

2-iodobenzaldehyde

3-(4-fluorophenyl)isoquinoline
1383549-86-7

3-(4-fluorophenyl)isoquinoline

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; triethylamine In acetonitrile at 20℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;98%

26260-02-6Relevant articles and documents

Reconciling Electrostatic and n→π* Orbital Contributions in Carbonyl Interactions

Adam, Catherine,Borsley, Stefan,Cockroft, Scott L.,Ling, Kenneth B.,Mati, Ioulia K.,Muchowska, Kamila B.,Nichol, Gary S.,Pascoe, Dominic J.,Smolyar, Ivan V.

, p. 14602 - 14608 (2020)

Interactions between carbonyl groups are prevalent in protein structures. Earlier investigations identified dominant electrostatic dipolar interactions, while others implicated lone pair n→π* orbital delocalisation. Here these observations are reconciled.

Diversity-oriented synthesis of intensively blue emissive 3-hydroxyisoquinolines by sequential Ugi four-component reaction/reductive heck cyclization

Moni, Lisa,Valentini, Gianluca,Riva, Renata,Deniβen, Melanie,Müller, Thomas J. J.

, p. 753 - 762 (2015)

A convergent approach to highly functionalized 3-hydroxyisoquinolines is reported. The key steps are an Ugi multicomponent reaction and a subsequent intramolecular reductive Heck reaction; these can also be performed as a one-pot procedure. The structures

V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls

Upadhyay, Rahul,Kumar, Shashi,Maurya, Sushil K.

, p. 3594 - 3600 (2021/07/02)

The versatile application of different functional groups such as alcohols (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, we report a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions. The method was successfully applied for the alcohol oxidation, oxidative scission of styrenes, and benzylic C?H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30 % aq.), TBHP (70 % aq.), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

-

Paragraph 0071; 0077, (2021/07/10)

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

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