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4-Chlorobenzaldehyde
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4-Chlorobenzaldehyde CAS 104-88-1 PCAD IN Stock p-Chlorobenzenecarboxaldehyde 104-88-1
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p-Chlorobenzaldehyde
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CAS No104-88-1, 4-chlorobenzaldehyde
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104-88-1 Usage

General Description

Colorless to yellow powder or white crystalline solid. Pungent odor.

Production method

The preparation methods commonly used are the following.
Light Reaction
Throw p-chlorotoluene into the reactor equipped with a UV lamp and put through chlorine gas at a reaction temperature of 60~100 ℃ for reaction. The molar ratio between the p-chlorotoluene amount and chlorine gas amount should be 1: 1.5. You can control the chlorine depth through GC approach. The reaction product contains chlorobenzyl chloride, p-chlorobenzal dichloride and 4-α, α, α-tetrachloro toluene. In case of large chlorine-depth, there is less amount of p-chlorobenzyl chloride while the amount of 4-α, α, α-tetrachloride toluene is about 8% with all the above three-component separated by distillation.
The mixture of 4-chlorobenzal dichloride and 4-α, α, α-tetrachloro-toluene can have hydrolysis reaction in the presence of catalysts such as FeCl3, ZnCl2, SnCl4, and metal oxides with the reaction temperature being 110~140 ℃. Add water for 4 hour of reaction, use GC approach for controlling the end of the reaction, and then go through vacuum distillation, under the protection of nitrogen gas, collect the fraction of 124 ℃/5.4kPa that is the product of p-chlorobenzaldehyde with the purity being over 99% and the yield being over 93% (calculated from 4-chlorobenzal dichloride).
The catalytic chlorination of Azobisisobutyronitrile:
Add p-chlorotoluene to the reactor and heated to 160 ℃, add azobisisobutyronitrile as the catalyst and put through chlorine gas for starting the reaction. Use GC approach for controlling the end point of the reaction. Take care that avoid generating 4-α, α, α-tetrachloride toluene and then apply vacuum distillation, collect the fraction of 116~126 ℃/3kPa with yield being 87%. The first fraction of p-chlorotoluene and p-chloro-benzyl chloride can be recycled for further application.
Add the 4-chlorobenzal dichloride obtained above into a reactor. Then add SnCl2 and adequate water for reaction upon reflux for 4h with the white crystal obtained after treatment being the product and the purity being 96% and the yield being 94%.
Methenamine hydrolysis approach
Add methenamine, water to the reactor, add the light chlorination reaction product of p-chlorotoluene, chlorobenzyl chloride and 4-chloro-benzal dichloride to the reaction flask and have reaction at 60~100 ℃ for 30~60min. The end point of the reaction is reached when the hydrolysis conversion ratio of benzyl chloride is 99%. After the post-treatment, we can obtain p-chlorobenzaldehyde with the purity being 99% and the yield of being 93.82%.
Manganese dioxide oxidation
Take p-chlorotoluene as raw materials, in the presence of sulfuric acid, take manganese dioxide as oxidizing agent for oxidation and then have steam distillation to obtain p-chlorobenzene formaldehyde which is the method of laboratory.
In addition to these methods, there are also some other methods including electrochemical synthesis and catalytic oxidation method. These methods are more difficult to be applied for industrialization. Some technology is not yet mature, pending further study. Regarding to hydrolysis of the 4-chlorobenzal chloride, we can also use 65% nitric acid for hydrolysis reaction at 90°C. The product purity is high and is up to 99% with the yield being 80%. In addition, in the presence of phosphorus trichloride, using chlorine gas for chlorination and further have hydrolysis reaction in the presence of sulfuric acid can also generate chlorobenzaldehyde but with lower yield and the older technology. For this reason, for the optimum technology for producing p-chlorobenzaldehyde, you can choose: use p-chlorotoluene as raw materials, have light chlorination, control the depth of chloride, then apply methenamine hydrolysis reaction. Through doing this, you need small investment; easy operation and can get high products quality and high yield.

Reactivity Profile

4-Chlorobenzaldehyde is sensitive to exposure to air. 4-Chlorobenzaldehyde is also sensitive to light. REACTIVITY: 4-Chlorobenzaldehyde is incompatible with strong bases, strong oxidizers and strong reducing agents.

4-Chlorobenzaldehyde

p-Chlorobenzaldehyde is also known as 4-chlorobenzaldehyde. It is colorless flake crystalline to pale yellow powder. The molecular weight is 140.57. Melting point is 47.5 ℃. Boiling point is 213~214 ℃. The relative density is 1.196 (61/4 ℃). The refractive index is 1.5552 (61 ℃). The flash point is 87 ℃. It is insoluble in water, easily soluble in alcohol, ether and benzene and soluble in acetone. It can be evaporated together with the steam. It can be used as the intermediates of medicine and dyes, for the manufacturing of chlormezanone, dapsone aminobutyric acid and so on. It can be obtained through the chlorination and hydrolysis of the chlorotoluene. It may also be produced through the oxidation of the p-chlorotoluene manganese dioxide oxidation. Furthermore, it can also be made by the air oxidation of the p-chlorotoluene.
It can be used for producing the plant growth regulator paclobutrazol: take p-dichlorobenzene formaldehyde and 2,2-dimethyl-3-butanone as raw material, have them react with each other in the solution of sodium hydroxide and tert-butanol, generating 1-(2,2-dimethyl-3-ketone-4-penten) p-chlorophenyl. In the ethyl acetate solution, take nickel as catalyst and have hydrogenation reaction at a high temperature to yield 1-(2,2-dimethyl-3-pentanone) chlorobenzene; have bromination reaction at carbon tetrachloride solution to generate 1-(2,2-dimethyl-4-bromo-3-pentanone) p-chlorophenyl, and further put into acetone solution to have reaction with 2,4-triazole, and finally generate paclobutrazol in the methanol solution of sodium boron hydride.
Baclofen can be used as the skeletal muscle relaxants and antispasmodic agent of spine. It is produced through the following process: first p-Chlorobenzaldehyde has condensation reaction with ethyl acetoacetate to generate chlorobenzene methylene-bis-ethyl acetoacetate. Then heat and hydrolyze to obtain p-chlorophenyl glutaric acid. Further use acetic anhydride for dehydration and cyclization to obtain p-chlorophenyl glutaric anhydride. Then use concentrated aqueous ammonia for amination to generate chlorophenyl glutaric acid imide, and finally have ring opening reaction and degradation to get it.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Chemical Properties

colourless to light yellow crystalline powder

Air & Water Reactions

4-Chlorobenzaldehyde is sensitive to exposure to air. Insoluble in water.

Uses

p-Chlorobenzaldehyde is not only the intermediate of tebuconazole fungicides, plant growth regulators uniconazole but also the intermediate of insecticide chlorfenapyr. In medicine it can be used as the intermediate of chlormezanone and dapsone aminobutyric acid and dye intermediates.
It can be used for the manufacturing of sedative chlormezanone and dye Acid Brilliant Blue 6B, etc.
In pesticide field, it can be used for the manufacturing of chlorine cinnamic aldehyde and weeding agent.
It can be applied to organic synthesis for making triphenylmethane and dye related intermediate.

Flammability and hazard properties

thermal decomposition can release toxic nitrogen oxides and chlorides fume.

Category

toxic substances

Extinguishing media

water, carbon dioxide, foam, powder

Purification Methods

Crystallise it from EtOH/water (3:1), then sublime it twice at ~50o/2mm. [Beilstein 7 H 235, 7 IV 568.]

Acute toxicity

oral-rat LD50: 1575 mg/kg; Oral-Mouse LD50: 1400 mg/kg

Toxicity grading

poisoning

Fire Hazard

4-Chlorobenzaldehyde is combustible.

Chemical Properties

p-Chlorobenzaldehyde is a white solid with m.p. of 46~47 ℃, b.p. of 213~214 ℃ and n20D 1.5640, It is soluble in benzene, toluene and other solvents but insoluble in water.

Storage characteristics

warehouse: low-temperature, dry, ventilation
InChI:InChI=1/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H

104-88-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A12757)  4-Chlorobenzaldehyde, 98%    104-88-1 5000g 4923.0CNY Detail
Alfa Aesar (A12757)  4-Chlorobenzaldehyde, 98%    104-88-1 1000g 1203.0CNY Detail
Alfa Aesar (A12757)  4-Chlorobenzaldehyde, 98%    104-88-1 250g 368.0CNY Detail
TCI America (C0125)  4-Chlorobenzaldehyde  >97.0%(GC) 104-88-1 500g 590.00CNY Detail
TCI America (C0125)  4-Chlorobenzaldehyde  >97.0%(GC) 104-88-1 100g 290.00CNY Detail
TCI America (C0125)  4-Chlorobenzaldehyde  >97.0%(GC) 104-88-1 25g 120.00CNY Detail

104-88-1SDS

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 4-Chlorobenzaldehyde

1.2 Other means of identification

Product number -
Other names AMMONIUM STANDARD

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:104-88-1 SDS

104-88-1Synthetic route

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 1h; Oxidation;100%
With n-butyltriphenylphosphonium permanganate In acetonitrile at 20℃; for 0.25h;100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.75h; Heating;100%
2-(4-chlorophenyl)-1,3-benzodithiole
62102-59-4

2-(4-chlorophenyl)-1,3-benzodithiole

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran for 0.25h; Ambient temperature;100%
Sodium; 6-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

Sodium; 6-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
(acetyloxy)(4-chlorophenyl)methyl acetate
13086-93-6

(acetyloxy)(4-chlorophenyl)methyl acetate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;100%
With poly(4-vinylpyridine)-supported sulfuric acid In acetonitrile at 50℃; for 0.75h; Green chemistry;100%
With bismuth(III) chloride In chloroform for 0.416667h; deprotection; Heating;99%
4-chlorobenzyltrimethylsilyl ether
14856-74-7

4-chlorobenzyltrimethylsilyl ether

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With nitrogen dioxide at 20℃; for 0.0833333h;100%
With trichloroisocyanuric acid In acetonitrile for 0.166667h; Reflux;100%
With NTPPPODS In acetonitrile for 0.0666667h; Reflux;99%
2-(4-chlorobenzyloxy)tetrahydro-2H-pyran
18484-03-2

2-(4-chlorobenzyloxy)tetrahydro-2H-pyran

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; benzyltriphenylphosphonium chlorate In acetonitrile at 20℃; for 1h;100%
With allyltriphenylphopsphonium peroxodisulfate In acetonitrile for 0.333333h; Heating;99%
With N-Bromosuccinimide; β‐cyclodextrin In acetone at 20℃; for 0.5h;95%
(E)-2-(4-chlorobenzylidene)hydrazine carboxamide

(E)-2-(4-chlorobenzylidene)hydrazine carboxamide

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 0.133333h; Heating;100%
ethyl 4-chlorobenzoate
7335-27-5

ethyl 4-chlorobenzoate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
Stage #1: ethyl 4-chlorobenzoate With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;
99%
With phenylsilane; cobalt(II) diacetate tetrahydrate; sodium triethylborohydride In 1,2-dimethoxyethane; toluene at 25℃; for 15h; Inert atmosphere; Schlenk technique;84%
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;83%
4-chlorobenzamide
619-56-7

4-chlorobenzamide

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature;99%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;99%
With sodium periodate; C22H23ClIN2Os(1+)*F6P(1-) In water; tert-butyl alcohol at 60℃; for 1h; Schlenk technique; Inert atmosphere;99%
With sodium periodate; C18H15ClFN2Ru(1+)*Cl(1-) In water; tert-butyl alcohol at 60℃; for 1h; Catalytic behavior; Schlenk technique; Inert atmosphere;99%
N,N-dimethyl-4-chlorobenzamide
14062-80-7

N,N-dimethyl-4-chlorobenzamide

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h;99%
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction;71%
With bis-(1,2-dimethylpropyl)borane In tetrahydrofuran; dodecane at 25℃;70 % Chromat.
With C11H25AlNO4(1-)*Na(1+) In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h;> 99 %Chromat.
copper(I) chloride
7758-89-6

copper(I) chloride

1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

Å molecular sieves

Å molecular sieves

di(tert-butyl) diazodicarboxylate

di(tert-butyl) diazodicarboxylate

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
In diethyl ether; toluene99%
di(p-tolyl) sulfoxide
1774-35-2

di(p-tolyl) sulfoxide

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

A

di-(p-tolyl)sulfane
620-94-0

di-(p-tolyl)sulfane

B

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With per-rhenic acid In toluene for 17h; Reflux;A 99%
B 70%
4-chlorobenzyl acetate
5406-33-7

4-chlorobenzyl acetate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 24h;99%
With lithium perchlorate In methanol at 0℃; Inert atmosphere; Sealed tube; Electrochemical reaction; Cooling with ice;68%
4-chlorobenzaldoxime
3848-36-0

4-chlorobenzaldoxime

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.25h; Oxidation; Heating;98%
With benzyltriphenylphosphonium dichromate; silica gel for 0.0833333h;98%
With tribromo-isocyanuric acid In acetonitrile at 20℃; for 1h;98%
2-(4-chlorophenyl)-1,3-dithiane
10359-09-8

2-(4-chlorophenyl)-1,3-dithiane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate at 20℃; for 0.166667h;98%
With bromine; dimethyl sulfoxide In chloroform at 20℃; for 0.25h;97%
With bromine; silica gel In dichloromethane at 20℃; for 0.166667h;97%
α-(3-oxobutyl)-4,4'-dichlorobenzoin
174869-08-0

α-(3-oxobutyl)-4,4'-dichlorobenzoin

A

1-(p-chlorophenyl)-1,4-pentanedione
53842-12-9

1-(p-chlorophenyl)-1,4-pentanedione

B

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide for 0.5h; Ambient temperature;A 98%
B n/a
α-(2-ethoxycarbonylethyl)-4,4'-dichlorobenzoin
174869-05-7

α-(2-ethoxycarbonylethyl)-4,4'-dichlorobenzoin

A

ethyl 4-(4-chlorophenyl)-4-oxobutanoate
53503-49-4

ethyl 4-(4-chlorophenyl)-4-oxobutanoate

B

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide at 80℃; for 0.25h;A 98%
B n/a
2-(4-chlorophenyl)-1,3-dioxolane
2403-54-5

2-(4-chlorophenyl)-1,3-dioxolane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With cerium triflate In nitromethane; water at 20℃; for 2h;98%
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate for 0.0111111h;97%
With erbium(III) triflate In nitromethane at 20℃; for 8h;97%
N-(4-chlorobenzylidene)-N'-phenylhydrazine
2829-26-7

N-(4-chlorobenzylidene)-N'-phenylhydrazine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With quinolinium dichromate(VI) In acetonitrile for 1h; Heating;98%
With water; silica gel; bis(trimethylsilyl)chromate In chloroform for 0.166667h; Heating;98%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.1h; Heating;96%
formic acid
64-18-6

formic acid

1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
Stage #1: 1-Chloro-4-iodobenzene With iodine; triethylamine; triphenylphosphine In dichloromethane; toluene at 20℃; for 0.0833333h; Sealed tube; Green chemistry;
Stage #2: formic acid In dichloromethane; toluene at 70℃; for 1.5h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Time; Sealed tube; Green chemistry;
98%
Stage #1: formic acid; 1-Chloro-4-iodobenzene With palladium diacetate; acetic anhydride; tricyclohexylphosphine In N,N-dimethyl-formamide at 30℃; for 1h; Inert atmosphere; Green chemistry;
Stage #2: With triethylamine In N,N-dimethyl-formamide at 80℃; for 6h; Inert atmosphere; Green chemistry;
95%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;92%
α-(2-cyano-1-methylethyl)-4,4'-dichlorobenzoin
174869-06-8

α-(2-cyano-1-methylethyl)-4,4'-dichlorobenzoin

A

4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile
53012-96-7

4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile

B

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide for 0.5h; Ambient temperature;A 97%
B n/a
2-(4-chlorophenyl)-1,3-oxathiolane
22391-05-5

2-(4-chlorophenyl)-1,3-oxathiolane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
Stage #1: 2-(4-chlorophenyl)-1,3-oxathiolane In ethanol at 20℃;
Stage #2: With water In ethanol at 20℃;
97%
With Iron(III) nitrate nonahydrate at 90℃; for 0.1h;92%
With N-Bromosuccinimide; water In acetone at 20℃; for 0.25h; Hydrolysis;91%
2-(4-chloro-phenyl)-[1,3]dioxane
6413-52-1

2-(4-chloro-phenyl)-[1,3]dioxane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With iron(III) p-toluenesulfonate hexahydrate In water for 1h; Reflux;97%
With N-Bromosuccinimide In water; acetone at 20℃; for 18h; Ring cleavage;21 % Chromat.
N-(4-chlorobenzylidene)-4-chlorobenzylamine
31264-06-9

N-(4-chlorobenzylidene)-4-chlorobenzylamine

A

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

B

4-chlorobenzamide
619-56-7

4-chlorobenzamide

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane at 40℃; under 760.051 Torr; for 24h; Molecular sieve;A 97%
B 95%
4-chlorophenylacetic Acid
1878-66-6

4-chlorophenylacetic Acid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation;96%
With 1H-imidazole; sodium periodate In water; acetonitrile at 20℃; for 30h;94%
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.233333h; Microwave irradiation;94%
4-chlorobenzaldehyde dimethyl acetal
3395-81-1

4-chlorobenzaldehyde dimethyl acetal

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
indium(III) chloride In methanol; water for 1.08333h; Heating;96%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 1h; Ambient temperature;92%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 1h; Product distribution; Ambient temperature; other protected acetals; var. solvents and reaction times;92%
1-(4-Chloro-phenyl)-2-methylsulfanyl-2-(toluene-4-sulfonyl)-ethanol

1-(4-Chloro-phenyl)-2-methylsulfanyl-2-(toluene-4-sulfonyl)-ethanol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In isopropyl alcohol for 1.5h; Ambient temperature; stirred;96%
(4-Chloro-phenyl)-phenylamino-methanesulfonic acid; compound with methylamine
114021-96-4

(4-Chloro-phenyl)-phenylamino-methanesulfonic acid; compound with methylamine

A

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

B

(4-Chloro-phenyl)-phenylamino-methanesulfonic acid; compound with phenylamine
66349-00-6

(4-Chloro-phenyl)-phenylamino-methanesulfonic acid; compound with phenylamine

Conditions
ConditionsYield
With hydrogenchloride for 24h;A n/a
B 96%
Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With sodium tris(diethylamino)aluminum hydride In tetrahydrofuran; dodecane at -78℃; for 12h;96%
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran at -78℃; for 3h; Reduction;90%
Multi-step reaction with 2 steps
1: chlorobis(cyclooctene)-iridium(I) dimer / dichloromethane / 1 h / 50 °C / Inert atmosphere
2: hydrogenchloride / diethyl ether; water / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
2: pyridinium chlorochromate / dichloromethane
View Scheme
3-Methyl-2-thioxo-thiazolidin-4-on
4807-55-0

3-Methyl-2-thioxo-thiazolidin-4-on

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine
23517-83-1

5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine

Conditions
ConditionsYield
With sodium acetate In methanol for 0.416667h; Heating;100%
With acetic acid; triethylamine In ethyl acetate at 85℃; for 3h;96%
With aluminum oxide; potassium fluoride In solid for 0.0666667h; microwaves (350 W);94%
Nitroethane
79-24-3

Nitroethane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-chloro-4-(2-nitropropenyl)benzene
710-20-3

1-chloro-4-(2-nitropropenyl)benzene

Conditions
ConditionsYield
With ammonium acetate at 110℃; for 96h;100%
With ammonium acetate Henry reaction; Reflux;92%
With (2-hydroxyethyl)ammonium formate at 20℃; for 2.1h; Knoevenagel condensation; Ionic liquid;90%
nitromethane
75-52-5

nitromethane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-chloro-4-(2-nitrovinyl)benzene
706-07-0

1-chloro-4-(2-nitrovinyl)benzene

Conditions
ConditionsYield
With copper(II) ferrite In dimethyl sulfoxide at 120℃; for 0.0333333h; Microwave irradiation;100%
With bridged diamino-functionalized periodic mesoporous organosilicas with high nitrogen contents at 90℃; for 5h; Henry Nitro Aldol Condensation;99%
With acetic acid; benzylamine at 78 - 80℃; for 3.5h; Product distribution / selectivity;97.1%
nitromethane
75-52-5

nitromethane

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-(4-chlorophenyl)-2-nitroethanol
89979-04-4

1-(4-chlorophenyl)-2-nitroethanol

Conditions
ConditionsYield
With polymer supported 4-DMAP at 20℃; for 0.416667h; Reagent/catalyst; Henry Nitro Aldol Condensation;100%
With triethylamine at 80℃; for 0.0166667h; Henry reaction; microwave irradiation;99%
With Musca acuminata (banana) peel ash In neat (no solvent) at 20℃; for 0.333333h; Henry Nitro Aldol Condensation; Green chemistry;98%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-methoxy-aniline
104-94-9

4-methoxy-aniline

N-(4-chlorobenzylidene)-4-methoxyaniline
1749-03-7

N-(4-chlorobenzylidene)-4-methoxyaniline

Conditions
ConditionsYield
for 6h; Ambient temperature;100%
In ethanol for 1h; Sonication;100%
at 20℃; for 14h; Molecular sieve;99%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

aniline
62-53-3

aniline

N-(4-chlorobenzylidene)aniline
2362-79-0

N-(4-chlorobenzylidene)aniline

Conditions
ConditionsYield
With acetic acid In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;100%
With formic acid In ethanol; water at 20℃; for 0.0166667h; Green chemistry;99%
at 20℃; for 14h; Molecular sieve;98%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-(4-chlorophenyl)benzimidazole
1019-85-8

2-(4-chlorophenyl)benzimidazole

Conditions
ConditionsYield
With sodium hydrogensulfite In N,N-dimethyl acetamide at 100℃; for 2h;100%
With copper(II) particles immobilized on nanosilica thiolated dendritic polymer In ethyl acetate at 50℃; for 0.25h; Catalytic behavior; Solvent; Temperature; Time; Reagent/catalyst;100%
With sodium metabisulfite In N,N-dimethyl-formamide at 80℃; for 0.1h; Microwave irradiation;99%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

benzylamine
100-46-9

benzylamine

N-(4-chlorobenzylidene)benzylamine
130517-96-3, 13540-93-7

N-(4-chlorobenzylidene)benzylamine

Conditions
ConditionsYield
for 6h; Molecular sieve; Reflux;100%
In ethanol at 20℃;94%
In dichloromethane at 20℃; for 16h; Molecular sieve;92%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-(4-chlorophenyl)-1,3-oxathiolane
22391-05-5

2-(4-chlorophenyl)-1,3-oxathiolane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 3h; Heating;100%
With zirconium(IV) chloride In dichloromethane at 20℃; for 0.333333h; Cyclization; Condensation; Monothioacetalization;97%
TiCl4 on montmorillonite In dichloromethane for 0.5h; Heating;97%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

malononitrile
109-77-3

malononitrile

4-chlorobenzylidenemalonodinitrile
1867-38-5

4-chlorobenzylidenemalonodinitrile

Conditions
ConditionsYield
at 150℃; for 1h; Knoevenagel condensation;100%
hydrotalcite structure integrating fluoride ions In DMF (N,N-dimethyl-formamide) at 25℃; for 0.25h; Conversion of starting material; Knoevenagel Condensation;100%
With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In water at 20℃; for 0.0333333h; Knoevenagel condensation;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

diethyl malonate
105-53-3

diethyl malonate

diethyl 4-chlorobenzylidenemalonate
6827-40-3

diethyl 4-chlorobenzylidenemalonate

Conditions
ConditionsYield
With C16H14MnN2O2(1+)*[(Si3Mg5.5Li0.3)O20(OH)4](1-) In toluene at 120℃; for 72h; Knoevenagel Condensation; Inert atmosphere;100%
With 3-hydroxyethylammonium-n-propanesulfonate In water at 70℃; for 0.25h; Knoevenagel condensation;92%
With piperidine; acetic acid In ethanol at 110℃; for 48h; Knoevenagel Condensation;92%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With aluminium; potassium hydroxide In methanol at 0℃; for 1h; Inert atmosphere;100%
With tris(2,2’-bipyridine)ruthenium(II); sodium dodecyl-sulfate; ascorbate In water for 3h; pH=12.7; Irradiation;100%
With ZnIn2S4; triethylamine In water; acetonitrile for 0.5h; Sealed tube; Sonication; Irradiation; Inert atmosphere;99%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

Conditions
ConditionsYield
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 80℃; for 18h;100%
With [(2-di-tert-butylphosphino-3-methoxy-6-methyl-2,4,6-triisopropyl-1,1-biphenyl)-2-(2-aminobiphenyl)]palladium(II) methanesulfonate; caesium carbonate; Benzaldoxime In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;99%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;93%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;100%
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.133333h;100%
With zirconium dioxide hydrate; isopropyl alcohol at 60℃; for 0.133333h; Meerwein-Ponndorf-Verley Reduction;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

Conditions
ConditionsYield
With sodium perborate In acetic acid for 1.5h; steam bath;100%
With hydrogen bromide; oxygen In acetonitrile at 20℃; for 5h; UV-irradiation;100%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
4-amino-phenol
123-30-8

4-amino-phenol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-{[(4-chlorophenyl)methylidene]amino}phenol
1749-05-9

4-{[(4-chlorophenyl)methylidene]amino}phenol

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
With piperidine In ethanol Condensation; Heating;85%
With dodecatungstosilic acid; phosphorus pentoxide In neat (no solvent, solid phase) at 20℃;82%
methanol
67-56-1

methanol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-chlorobenzaldehyde dimethyl acetal
3395-81-1

4-chlorobenzaldehyde dimethyl acetal

Conditions
ConditionsYield
antimony(III) chloride; iron for 12h; Ambient temperature;100%
Ce(3+)-mont at 25℃; for 12h;99%
With 1-Benzyl-3,5-bis(methoxycarbonyl)pyridin-1-ium Bromide at 20℃; for 24h; Inert atmosphere;99%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

acrylonitrile
107-13-1

acrylonitrile

2-[(4-chlorophenyl)hydroxymethyl]acrylonitrile
22056-04-8

2-[(4-chlorophenyl)hydroxymethyl]acrylonitrile

Conditions
ConditionsYield
With octanol; 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 12h; Baylis-Hillman reaction;100%
With 1,4-diaza-bicyclo[2.2.2]octane; 1-methyl-3-butyl-1,2,3-triazolium hexafluorophosphate at 20℃; Baylis-Hillman reaction; Inert atmosphere; Ionic liquid;99%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 1.2h; Baylis-Hillman reaction; neat (no solvent);99%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl 1-hydroxy-1-(4-chlorophenyl)methylphosphonate
6329-48-2

dimethyl 1-hydroxy-1-(4-chlorophenyl)methylphosphonate

Conditions
ConditionsYield
With triethylamine at 50℃; Pudovik Reaction; Inert atmosphere; Sealed tube;100%
Stage #1: 4-chlorobenzaldehyde With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 20℃; for 0.25h; Kabachnik-Fields Reaction; Green chemistry;
Stage #2: Dimethyl phosphite In neat (no solvent) at 20℃; for 4h; Green chemistry;
96%
With potassium phosphate In neat (no solvent) at 20℃; for 0.0666667h; Green chemistry;93%
morpholine
110-91-8

morpholine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4,4'-((4-chlorophenyl)methylene)dimorpholine
16361-37-8

4,4'-((4-chlorophenyl)methylene)dimorpholine

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0333333h;100%
With boron trioxide In benzene at 50℃; for 2h;90%
With potassium carbonate In dichloromethane at 20℃;80%
In benzene Reflux;50%
In water; methyl cyclohexane
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

3,3'-(4-chlorophenylmethylene)-bis-4-hydroxycoumarin
4322-59-2

3,3'-(4-chlorophenylmethylene)-bis-4-hydroxycoumarin

Conditions
ConditionsYield
With glycerol-based carbon sulfonic acid In ethanol; water at 80℃; for 0.333333h; Solvent; Temperature; Concentration;100%
With silica-supported Preyssler acid nanoparticles In ethanol at 25℃; for 0.333333h;99%
With cholin hydroxide In water at 50℃; for 2h;99%
4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one
83-07-8

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-(4-chlorobenzylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one
61098-04-2

4-(4-chlorobenzylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one

Conditions
ConditionsYield
at 20℃; for 1h;100%
In ethanol Reflux;94.66%
In ethanol at 20℃; for 0.0111111h;92%
acetic anhydride
108-24-7

acetic anhydride

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(acetyloxy)(4-chlorophenyl)methyl acetate
13086-93-6

(acetyloxy)(4-chlorophenyl)methyl acetate

Conditions
ConditionsYield
With poly(4-vinylpyridine)-supported sulfuric acid In dichloromethane at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;100%
1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 20℃; for 0.7h;99%
copper(II) sulfate at 20℃; for 0.5h;99%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(4-chlorophenyl)-1,3-dithiane
10359-09-8

2-(4-chlorophenyl)-1,3-dithiane

Conditions
ConditionsYield
With lithium tetrafluoroborate at 25℃; for 3h;100%
With perchloric acid; silica gel at 25 - 30℃; for 0.0166667h;100%
With Lewis acid100%
biphenyl-4-acetaldehyde
92-91-1

biphenyl-4-acetaldehyde

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-Chloro-4'-phenylchalcone
13662-60-7

4-Chloro-4'-phenylchalcone

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 35 - 40℃; for 2.5h;100%
With sodium hydroxide In ethanol
With sodium hydroxide In ethanol; water for 0.5h; Heating;
allyl iodid
556-56-9

allyl iodid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-(4-chlorophenyl)but-3-en-1-ol
14506-33-3

1-(4-chlorophenyl)but-3-en-1-ol

Conditions
ConditionsYield
With antimony In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 15h; Heating;100%
With water; tin(ll) chloride at 50℃; for 12h; Barbier reaction;98%
With stannous fluoride In various solvent(s) for 1h; Ambient temperature;96%
n-pentyl methyl ketone
110-43-0

n-pentyl methyl ketone

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

(E)-1-(4-chlorophenyl)oct-1-en-3-one
100765-38-6

(E)-1-(4-chlorophenyl)oct-1-en-3-one

Conditions
ConditionsYield
Stage #1: n-pentyl methyl ketone With piperidine In ethanol at 20℃; for 2h;
Stage #2: 4-chlorobenzaldehyde In ethanol for 72h; Reflux;
100%
barium dihydroxide In ethanol for 1h; Heating;93%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

[(4-chloro-phenyl)-hydroxy-methyl]-phosphonic acid diisopropyl ester
20641-27-4

[(4-chloro-phenyl)-hydroxy-methyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
With triethylamine In neat (no solvent) at 20℃; for 24h; Pudovik Reaction; Inert atmosphere;100%
With triethylamine at 50℃; Pudovik Reaction; Inert atmosphere; Sealed tube;100%
With potassium phosphate In neat (no solvent) at 20℃; for 0.1h; Green chemistry;96%

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