• Name

  4-IODOBENZALDEHYDE

• EINECS 627-186-1
• CAS No. 15164-44-0
• Article Data124
• CAS DataBase
• Density 1.883 g/cm³
• Solubility Insoluble in water
• Melting Point 78-82 °C(lit.)
• Formula C7H5 I O
• Boiling Point 264.8 °C at 760 mmHg
• Molecular Weight 232.021
• Flash Point 114 °C
• Transport Information
• Appearance Yellow crystals
• Safety 26-36 37 39
• Risk Codes R36/37/38   
• Molecular Structure
• Hazard Symbols
• Synonyms Benzaldehyde,p-iodo- (6CI,7CI,8CI); 4-Formyl-1-iodobenzene; 4-Formyliodobenzene;4-Iodobenzaldehyde; NSC 84301; p-Formylphenyl iodide; p-Iodobenzaldehyde
• PSA 17.07000
• LogP 2.10370

Synthetic route

619-58-9

4-iodobenzoic acid

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
Stage #1: 4-iodobenzoic acid With borane-THF at 20℃; Inert atmosphere; Cooling with ice; Stage #2: With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3.5h;	100%
Stage #1: 4-iodobenzoic acid With borane-THF Stage #2: With pyridinium chlorochromate In chloroform	92%
Multi-step reaction with 2 steps 1: 99 percent / BH3*THF / tetrahydrofuran / 16 h / 20 °C 2: 99 percent / MnO2 / CHCl3 / 72 h / Heating View Scheme

18282-51-4

4-iodo-benzyl alcohol

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With manganese(IV) oxide In chloroform for 72h; Heating;	99%
With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In neat (no solvent) at 80℃; for 18h; Green chemistry;	99%
With Iron(III) nitrate nonahydrate; tempol; oxygen; sodium chloride In 1,2-dichloro-ethane at 25℃; for 5h; chemoselective reaction;	99%

A

620-94-0

di-(p-tolyl)sulfane

B

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With per-rhenic acid In toluene for 17h; Reflux;	A 99% B 88%

...Expand

87199-17-5

4-formylphenylboronic acid,

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 81℃; for 14h;	94%
With iodine; potassium carbonate In acetonitrile at 80℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;	92%
With copper(I) oxide; ammonium hydroxide; oxygen; potassium iodide In water at 25℃; for 24h;	82%

2-amino-4-iodobenzyl alcohol

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
Stage #1: 2-amino-4-iodobenzyl alcohol With sodium sulfate at 26℃; for 3.83333h; Stage #2: With palladium (II) nitrate; 5-methyl-dihydro-furan-2-one at 35℃; for 1.83333h; Temperature;	94%

1448723-27-0

C14H13IN2O3S

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
Stage #1: C14H13IN2O3S With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; McFadyen-Stevens Reaction; Stage #2: With citric acid In methanol at 20℃; McFadyen-Stevens Reaction;	93%
Stage #1: C14H13IN2O3S With 1H-imidazole; 1-(Trimethylsilyl)imidazole In toluene at 55℃; Inert atmosphere; Stage #2: With citric acid In toluene at 23℃; Inert atmosphere;	93%

201230-82-2

carbon monoxide

1514-50-7

4-iodobenzenediazonium tetrafluoroborate

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With palladium diacetate; polymethylhydrosiloxane In diethyl ether; acetonitrile under 7355.08 Torr; for 12h;	59%

133746-50-6

4-iodobenzaldiacetate

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With sulfuric acid In ethanol; water for 0.5h; Hydrolysis; Heating;	58%

556-18-3

4-aminobenzaldehyde

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
Stage #1: 4-aminobenzaldehyde With sulfuric acid; sodium nitrite Stage #2: With water; potassium iodide	46%
With nitrosylsulfuric acid; phosphoric acid at 0℃; Behandeln des Reaktionsgemisches mit kalter wss. KI-Loesung;
Stage #1: 4-aminobenzaldehyde With sodium nitrite In hydrogenchloride ice bath; Stage #2: With potassium iodide In hydrogenchloride at 20℃; Further stages.;

619-66-9

4-Carboxybenzaldehyde

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; iodine In tetrachloromethane for 30h; Heating; Irradiation;	40%

1122-91-4

4-bromo-benzaldehyde

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; potassium iodide at 200℃; for 23h; Inert atmosphere;	21%
Stage #1: 4-bromo-benzaldehyde With indium; chloro-trimethyl-silane; bathophenanthroline; ethylene dibromide; lithium chloride; cobalt(II) bromide In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;	75 %Chromat.
With copper(l) iodide; potassium iodide at 200℃; for 6h; Finkelstein reaction; Inert atmosphere;

201230-82-2

carbon monoxide

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With pyridine; 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In dimethyl sulfoxide at 120℃; under 15001.5 Torr; for 0.716667h; Flow reactor;	8%

3058-39-7

4-iodobenzonitrile

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride anschliessend Erhitzen mit Wasserdampf;
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 7 h / Inert atmosphere; Reflux 2: dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen / toluene / 5 h / 110 °C / 760.05 Torr / Sealed tube View Scheme

4-iodosyl-benzaldehyde

A

4-iodyl-benzaldehyde

B

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With water

624-31-7

4-tolyl iodide

108-24-7

acetic anhydride

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With chromium(VI) oxide; sulfuric acid; acetic acid anschl. mit wss.-aethanol. H2SO4;

555-16-8

4-nitrobenzaldehdye

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
Reaktion ueber mehrere Stufen;
Multi-step reaction with 5 steps 1: 94 percent / toluenesulfonic acid / toluene / Heating 2: 100 percent / hydrogen / platinum(IV) oxide / ethyl acetate / 4.5 h 3: nitrogen tetroxide / acetonitrile / 1.25 h / -20 °C 4: sodium iodide / acetonitrile / -20 - 20 °C 5: 92 percent / trifluoroacetic acid / CH2Cl2 / 23 h / 20 °C View Scheme

2591-86-8

N-Formylpiperidine

624-38-4

para-diiodobenzene

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With n-butyllithium 1) diethylether, hexane, -78 deg C, 3 h; 2) ether, to RT, 17 h; Yield given. Multistep reaction;

16004-15-2

1-bromomethyl-4-iodobenzene

934-56-5

trimethyl(phenyl)stannane

A

644-08-6

4-Methylbiphenyl

B

3218-36-8

4-Phenylbenzaldehyde

C

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
Product distribution; multistep reaction;

...Expand

anhydro-p-amino-benzaldehyde

anhydro-p-amino-benzaldehyde

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With potassium iodide Reaktion ueber mehrere Stufen;

p-iodo-benzyl bromide

p-iodo-benzyl bromide

15164-44-0

p-(iodophenyl)carboxaldehyde

Conditions

Conditions	Yield
With lead(II) nitrate; water in einer CO2-Atmosphaere;

4-Iodobenzaldehyde Chemical Properties

4-Iodobenzaldehyde Safety Profile

4-Iodobenzaldehyde Specification