10203-08-4

Basic information

• Product Name: 3,5-Dichlorobenzaldehyde
• Synonyms: 3,5-Dichlorobenzaldehyde,97%;3,5-Dichlorobenzaldehyde, Tech.;3,5-Dichlorobenzalde;3,5- twochlorobenzeneforMaldehyde;RARECHEM AQ A2 0002;3,5-dichloro-benzaldehyd;Benzaldehyde, 3,5-dichloro-;3,5-DICHLOROBENZALDEHYDE
• CAS NO: 10203-08-4
• Molecular Formula: C₇H₄Cl₂O
• Molecular Weight: 175.01
• EINECS: 233-499-0
• Product Categories: Aldehydes;C7;Carbonyl Compounds;Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde
• Mol File: 10203-08-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 63.5-65.5 °C(lit.)
• Boiling Point: 235-240°C
• Flash Point: 235-240°C
• Appearance: white to slightly yellow fluffy powder
• Density: 1.3456 (rough estimate)
• Vapor Pressure: 0.0365mmHg at 25°C
• Refractive Index: 1.5756 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 2040553
• CAS DataBase Reference: 3,5-Dichlorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dichlorobenzaldehyde(10203-08-4)
• EPA Substance Registry System: 3,5-Dichlorobenzaldehyde(10203-08-4)

Safety Data

• Hazard Codes: C,Xi,Xn
• Statements: 34-36/37/38-22
• Safety Statements: 26-36/37/39-45-22-37/39
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 10203-08-4(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly yellow fluffy powder

Uses

3,5-Dichlorobenzaldehyde was used as starting reagent during synthesis of β-aryl-β-amino acid enantiomers. It was used in the synthesis of dichlorophenylpyruvic acid.

InChI:InChI=1/C7H4Cl2O/c8-6-1-5(4-10)2-7(9)3-6/h1-4H

Synthetic route

3,5-dichloro-N,N-diethylbenzamide (35515-07-2) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.5h;	82%

3,5-dichlorobenzaldehyde oxime (93033-57-9) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; acetic acid In water at 40 - 45℃; for 3.5h;	80%

3,5-dichlorotoluene (25186-47-4) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With sodium molybdate; dihydrogen peroxide; cobalt(II) acetate; acetic acid; sodium bromide at 105℃; for 0.166667h; Temperature;	39.2%

3,5-dichlorobenzyl alcohol (60211-57-6) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; (trifluoromethyl)trimethylsilane; Selectfluor In ethyl acetate at 20℃; for 12h; Glovebox; Inert atmosphere;

3,5-dichlorobenzoyl chloride (2905-62-6) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With lithium tri-t-butoxyaluminum hydride In diethylene glycol dimethyl ether
Multi-step reaction with 2 steps 1: dichloromethane / 0.5 h / 20 °C / Cooling with ice 2: Schwartz's reagent / tetrahydrofuran / 0.5 h / 20 °C View Scheme

sulfuric acid (7664-93-9) + 1,3-dichloro-5-dichloromethyl-benzene (56961-85-4) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
at 0℃;

3.5-dichloro-benzylidene dibromide → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With sulfuric acid at 80 - 85℃;

3.5-dichloro-benzylidene dichloride → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With sulfuric acid at 0℃;

formaldoxime (75-17-2) + diazotized.3,5-dichloro-aniline → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
anschliessenden Erhitzen mit wss.HCl;

diazotized.4-amino-3,5-dichloro-benzaldehyde → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With hydrogenchloride

water (7732-18-5) + (3,5-dichloro-phenyl)-hydroxy-methanesulfonic acid ; sodium-salt → 3,5-dichlorobenzaldehyde (10203-08-4)

3,5-dichlorobenzoic acid (51-36-5) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 2: Li / bis-(2-methoxy-ethyl) ether View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / toluene / 4 h / Reflux 1.2: 6.5 h / 0 - 20 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / -20 - -10 °C View Scheme

2,4-dichlorobenzoyl chloride (89-75-8) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; (Z)-N,N-diisopropyl-2-styrylbenzamide In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; chemoselective reaction;

3,5-dichloro-N-methoxy-N-methylbenzamide (259796-12-8) → 3,5-dichlorobenzaldehyde (10203-08-4)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at -20 - -10℃; for 1h; Temperature;

3,5-dichlorobenzaldehyde (10203-08-4) + 2,2-dimethoxyethylamine (22483-09-6) → [1-(3,5-Dichloro-phenyl)-meth-(Z)-ylidene]-(2,2-dimethoxy-ethyl)-amine

Conditions	Yield
In benzene Heating;	100%

3,5-dichlorobenzaldehyde (10203-08-4) + 2,2-diethoxy-ethanamine (645-36-3) → (3,5-dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine (1000210-73-0)

Conditions	Yield
In toluene for 2.5h; Reflux;	100%
In ethanol at 20 - 78℃; for 2h;	94%
In ethanol at 20℃; for 8h;	70.68%
In ethanol at 75℃; for 3h; Temperature;	125 g

3,5-dimethyl-4-nitroisoxazole (1123-49-5) + 3,5-dichlorobenzaldehyde (10203-08-4) → 5-[(E)-2-(3,5-Dichloro-phenyl)-vinyl]-3-methyl-4-nitro-isoxazole

Conditions	Yield
With pyrrolidine In neat (no solvent) at 20℃; for 0.05h; Aldol Condensation;	100%
With piperidine In acetonitrile for 4h; Knoevenagel condensation; Reflux;

5,6-dihydro-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepine + 3,5-dichlorobenzaldehyde (10203-08-4) → C17H14Cl2N4 (1358787-23-1)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane	100%

3,5-dichlorobenzaldehyde (10203-08-4) → C7H5Cl2NO

Conditions	Yield
Stage #1: 3,5-dichlorobenzaldehyde With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 4 - 20℃; for 3h; Stage #2: pH=6; Acidic aqueous solution;	99%

3,5-dichlorobenzaldehyde (10203-08-4) → 3,5-dichlorobenzaldehyde oxime (93033-57-9)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 2.5h;	98%

3,5-dichlorobenzaldehyde (10203-08-4) + 2,6-dichloro-p-phenylenediamine (609-20-1) → 2,6-Dichloro-N'-[1-(3,5-dichloro-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine (84562-37-8)

Conditions	Yield
In ethanol for 1.5h; Heating;	98%

tert-butyl (2S)-2-[(isobutylamino)methyl]pyrrolidine-1-carboxylate (871499-96-6) + 3,5-dichlorobenzaldehyde (10203-08-4) → tert-butyl (2S)-2-{[(3,5-dichlorobenzyl)(isobutyl)amino]methyl}pyrrolidine-1-carboxylate (871499-97-7)

Conditions	Yield
With sodium tris(acetoxy)borohydride In DMF (N,N-dimethyl-formamide); 1,2-dichloro-ethane for 16h;	98%

4-Trifluoromethylbenzaldehyde (455-19-6) + 4-hydroxy-3,5-diiodobenzaldehyde (1948-40-9) + 3,5-dibromo-4-hydroxybenzaldehyde (2973-77-5) + O-phenylhydroxylamine (4846-21-3) + 3,5-dichlorobenzaldehyde (10203-08-4) + 2-Trifluoromethylbenzaldehyde (447-61-0) + m-formylphenyl benzoic acid (619-21-6) + 3-Trifluoromethylbenzaldehyde (454-89-7) + O-(3-(trifluoromethyl)phenyl)hydroxylamine (99907-98-9) + 3,5-difluorobenzaldehyde (32085-88-4) + 2,6-dichlorobenzaldehyde (83-38-5) + benzaldehyde (100-52-7) + 4-Carboxybenzaldehyde (619-66-9) + O-(2-trifluoromethylphenyl)hydroxylamine (160725-42-8) + o-carboxybenzaldehyde (119-67-5) + O-(3,5-difluorophenyl)hydroxylamine (197588-25-3) + O-(3,5-dichlorophenyl)hydroxylamine (99907-90-1) → E-O-phenylbenzaldoxime (75735-31-8) + 3-(phenoxyimino-methyl)-benzoic acid + 2-(phenoxyimino-methyl)-benzoic acid + 4-(phenoxyimino-methyl)-benzoic acid + 3,5-dibromo-4-hydroxy-benzaldehyde O-phenyl-oxime + 3,5-difluoro-benzaldehyde O-(3,5-difluoro-phenyl)-oxime + 3,5-dichloro-benzaldehyde O-(3,5-difluoro-phenyl)-oxime + 4-[(3,5-dichloro-phenoxyimino)-methyl]-benzoic acid + 3-[(3,5-dichloro-phenoxyimino)-methyl]-benzoic acid + 2-trifluoromethyl-benzaldehyde O-(3,5-dichloro-phenyl)-oxime + 3-trifluoromethyl-benzaldehyde O-(3,5-dichloro-phenyl)-oxime + 3-[(3-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid + 3-trifluoromethyl-benzaldehyde O-(3,5-difluoro-phenyl)-oxime + 2-trifluoromethyl-benzaldehyde O-(3,5-difluoro-phenyl)-oxime + 4-trifluoromethyl-benzaldehyde O-(3,5-difluoro-phenyl)-oxime + 4-[(3-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid + 3-[(2-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid + 4-trifluoromethyl-benzaldehyde O-(2-trifluoromethyl-phenyl)-oxime + 3-trifluoromethyl-benzaldehyde O-(2-trifluoromethyl-phenyl)-oxime + 2-trifluoromethyl-benzaldehyde O-(2-trifluoromethyl-phenyl)-oxime + 2-[(2-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid + 3,5-dibromo-4-hydroxy-benzaldehyde O-(3,5-dichloro-phenyl)-oxime + 2-trifluoromethyl-benzaldehyde O-(3-trifluoromethyl-phenyl)-oxime + 3,5-dibromo-4-hydroxy-benzaldehyde O-(3-trifluoromethyl-phenyl)-oxime + 4-hydroxy-3,5-diiodo-benzaldehyde O-(3-trifluoromethyl-phenyl)-oxime

Conditions	Yield
With acetic acid In water; dimethyl sulfoxide at 20℃; for 24h; Combinatorial reaction / High throughput screening (HTS);	A 98% B 98% C 98% D 98% E 98% F 98% G 98% H 98% I 98% J 98% K 98% L 98% M 98% N 98% O 98% P 98% Q 98% R 98% S 98% T 98% U 98% V 98% W 98% X 98% Y 98%

...Expand

3,5-dichlorobenzaldehyde (10203-08-4) + 8-bromo-5,6-dihydro-4H-benzo[f][1,2,3]triazolo[1,5-a][1,4]diazepine (1266452-21-4) → C17H13BrCl2N4 (1358787-29-7)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane	98%

3,5-dichlorobenzaldehyde (10203-08-4) → 3,5-dichlorobenzaldehyde oxime

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol; dichloromethane; water	98%

5-hydroxy-2,3-dihydro-1H-indene-1-one (3470-49-3) + 3,5-dichlorobenzaldehyde (10203-08-4) → (E)-2-(3,5-dichlorobenzylidene)-5-hydroxy-2,3-dihydro-1H-inden-1-one

Conditions	Yield
With sodium hydroxide In methanol at 20℃;	98%

3,5-dichlorobenzaldehyde (10203-08-4) + ethylenediamine (107-15-3) → N,N'-(ethane-1,2-diyl)bis(1-(3,5-dichlorophenyl)methanimine)

Conditions	Yield
In ethanol at 20℃; for 6h;	96%

3,5-dichlorobenzaldehyde (10203-08-4) + cyclohexylamine (108-91-8) → cychlohexyl(3,5-dichlorobenzyl)amine

Conditions	Yield
Stage #1: 3,5-dichlorobenzaldehyde; cyclohexylamine In methanol at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In methanol at 20℃;	95.4%

3,5-dichlorobenzaldehyde (10203-08-4) + ethyl acetoacetate (141-97-9) → diethyl 4-(3,5-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (897627-79-1)

Conditions	Yield
With ammonium acetate; phenylboronic acid In ethanol for 4h; Hantzsch reaction; Heating;	95%
With cadmium(II) nitrate tetrhydrate; ammonium acetate In neat (no solvent) at 80℃; for 3h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	89%
With ammonium acetate; triphenylphosphine In ethanol for 4h; Hantzsch reaction; Reflux;	80%
With ammonium acetate; triethylamine at 80℃; for 2h; Hantzsch condensation; Neat (no solvent);	52%
With ammonia In ethanol; water at 20 - 95℃; for 4h;	28%

3,5-dichlorobenzaldehyde (10203-08-4) + 3,4,5-trimethoxybenzohydrazide (3291-03-0) → C17H16Cl2N2O4

Conditions	Yield
In ethanol for 0.5h; Heating;	94.7%

3,5-dichlorobenzaldehyde (10203-08-4) + methyl 2-naphthyl ketone (93-08-3) → (2E)-1-(2-naphthyl)-3-(3,5-dichlorophenyl)-2-propen-1-one (1352444-94-0)

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃; for 24h; Aldol condensation;	94%

3,5-dichlorobenzaldehyde (10203-08-4) + anthranilic acid amide (28144-70-9) → 2,3-dihydro-2-(2,4-dichlorophenyl)quinazolin-4(1H)-one (359430-31-2)

Conditions	Yield
With antimony(III) chloride In methanol at 20℃; for 0.233333h;	94%

3,5-dichlorobenzaldehyde (10203-08-4) + 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one (24155-32-6) → (E)-1-(4-Chloro-phenyl)-3-(3,5-dichloro-phenyl)-2-imidazol-1-yl-propenone

Conditions	Yield
With piperidine; acetic acid In benzene Heating;	93%

3,5-dichlorobenzaldehyde (10203-08-4) + phenylacetylene (536-74-3) → (-)-(1S)-1-(3,5-dichlorophenyl)-3-phenylprop-2-yn-1-ol

Conditions	Yield
Stage #1: phenylacetylene With (-)-N-methylephedrine; triethylamine; zinc trifluoromethanesulfonate In toluene for 0.25h; Stage #2: 3,5-dichlorobenzaldehyde In toluene Further stages.;	93%

3,5-dichlorobenzaldehyde (10203-08-4) + 4-hydroxy 2,6-dimethylpyrimidine (6622-92-0) → 2-[2-(3,5-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol

Conditions	Yield
In acetic anhydride	93%

3,5-dichlorobenzaldehyde (10203-08-4) + 1,1-dimethylhydrazine (57-14-7) → 3,5-dichlorobenzaldehyde N,N-dimethylhydrazone (1362849-52-2)

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;	93%

3,5-dichlorobenzaldehyde (10203-08-4) + (trimethylsilyl)methylmagnesium chloride (13170-43-9) → 1-(3,5-dichlorophenyl)-2-(trimethylsilyl)ethanol (136272-29-2)

Conditions	Yield
In diethyl ether Ambient temperature;	92%

3,5-dichlorobenzaldehyde (10203-08-4) + phenylacetylene (536-74-3) → (+)-(1R)-1-(3,5-dichlorophenyl)-3-phenylprop-2-yn-1-ol

Conditions	Yield
Stage #1: phenylacetylene With triethylamine; zinc trifluoromethanesulfonate In toluene for 0.25h; Stage #2: 3,5-dichlorobenzaldehyde In toluene Further stages.;	92%

3,5-dichlorobenzaldehyde (10203-08-4) + benzil (134-81-6) → 2-(3,5-dichlorophenyl)-4,5-diphenyl-1H-imidazole (1259065-14-9)

Conditions	Yield
With iron(III) phosphate; ammonium acetate In ethanol for 4h; Reflux;	92%

3,5-dichlorobenzaldehyde (10203-08-4) + 1,2-diamino-benzene (95-54-5) → 1-(3,5-dichlorobenzyl)-2-(3,5-dichlorophenyl)-1H-1,3-benzimidazole (1370018-48-6)

Conditions	Yield
With iron(III) phosphate at 20℃; for 0.666667h; Neat (no solvent);	92%

methyl (3,4,5-trimethoxyphenyl) ketone (1136-86-3) + 3,5-dichlorobenzaldehyde (10203-08-4) → (2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,5-dichlorophenyl)-2-propen-1-one (1442690-93-8)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 24h; Aldol Condensation;	92%

Upstream product

• 60211-57-6 3,5-dichlorobenzyl alcohol 
• 25186-47-4 3,5-dichlorotoluene 
• 259796-12-8 3,5-dichloro-N-methoxy-N-methylbenzamide 
• 35515-07-2 3,5-dichloro-N,N-diethylbenzamide 
• 89-75-8 2,4-dichlorobenzoyl chloride 
• 51-36-5 3,5-dichlorobenzoic acid 
• 7732-18-5 water 
• 75-17-2 formaldoxime 
• 7664-93-9 sulfuric acid 
• 56961-85-4 1,3-dichloro-5-dichloromethyl-benzene 
• 93033-57-9 3,5-dichlorobenzaldehyde oxime 
• 2905-62-6 3,5-dichlorobenzoyl chloride 

Downstream Products

• 20595-53-3 3-(3,5-dichlorophenyl)-2-propenoic acid 
• 68029-45-8 (Z)-2-Cyano-3-(3,5-dichloro-phenyl)-thioacrylamide 
• 65298-12-6 2r-(3,5-dichloro-phenyl)-5c-methyl-oxazolidin-4-one 
• 65298-12-6 2r-(3,5-dichloro-phenyl)-5t-methyl-oxazolidin-4-one 
• 4402-87-3 3-(3,5-dichloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid methyl ester 
• 75692-67-0 [1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-ethyl-amine 
• 342892-67-5 [1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-(2,2-dimethoxy-ethyl)-amine 
• 78933-00-3 [1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-[4-(4-p-tolyl-piperazin-1-yl)-phenyl]-amine 
• 71867-47-5 3,5-Dichloro-3',5'-dimethylstilben 
• 682763-23-1 1-(3,5-dichloro-phenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 

Relevant articles and documents

Side-chain oxidation of benzyltrimethylsilanes by iodosylbenzene in the presence of iron and manganese porphyrins

Benzyltrimethylsilanes react with iodosylbenzene in the presence of either iron(III) or magnanese(III) tetrakis(pentafluorophenyl)porphyrin (TFPPM, with M = Fe, Mn) to give α-hydroxybenzyltrimethylsilanes, which are then rapidly converted into the corresponding benzaldehydes in the reaction medium. In these reactions the active species is the metal-oxo complex. TFPPM(V) = O, formed by iodosylbenzene and TFPPM. A relative reactivity study for a series of ring substituted benzyltrimethylsilanes has shown that when M = Fe, the reaction is quite selective (ρ = -1.85), with the m-MeO substituent exhibiting a much higher reactivity than expected. When M = Mn, a lower ρ value (-1.15) is observed and no anomalous reactivity is found with the m-MeO group. These result suggest that the side-chain hydroxylation of benzyltrimethylsilane by TFPPMn(V) = O occurs by the well known hydrogen atom transfer mechanism. For the corresponding reactions induced by TFPPFe(V) = O a coupled proton/electron transfer mechanism, which might involve the formation of a charge-transfer complex, seems more likely.

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The invention provides a method of continuously oxidizing 3,5-dichlorotoluene for producing 3,5-dichlorobenzaldehyde and belongs to the technical field of organic synthesis process. In the method, 3,5-dichlorobenzaldehyde is used as a raw material, one or more metal ionic complexes of cobalt, molybdenum, bromine serve as a catalyst, H2O2 serves as an oxidant and acetic acid serves as a solvent, and then the 3,5-dichlorotoluene is continuously oxidized in a tubular reactor to prepare the 3,5-dichlorobenzaldehyde. The method has mild conditions, short reaction time and high raw material utilization rate, can achieve effective control during the reaction process, is safe and stable, allows continuous operation and has high production efficiency.

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