16588-34-4

Basic information

• Product Name: 4-Chloro-3-nitrobenzaldehyde
• Synonyms: 4-chloro-3-nitro-benzaldehyd;Benzaldehyde, 4-chloro-3-nitro-;TIMTEC-BB SBB007674;ASISCHEM R36965;AKOS BBS-00003244;3-NITRO-4-CHLOROBENZALDEHYDE;4-CHLORO-3-NITROBENZALDEHYDE;4-Chloro-3-Nitrobenzaldehyde 3-Nitro-4-Chlorobenzaldehyde
• CAS NO: 16588-34-4
• Molecular Formula: C₇H₄ClNO₃
• Molecular Weight: 185.56
• EINECS: 240-645-7
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C7;Carbonyl Compounds
• Mol File: 16588-34-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 61-63 °C(lit.)
• Boiling Point: 276.5°C (rough estimate)
• Flash Point: 135.1 °C
• Appearance: Off-white to light yellow to light green/Powder
• Density: 1.4791 (rough estimate)
• Vapor Pressure: 0.00117mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 4g/l
• Water Solubility: 4 g/L (98 ºC)
• Sensitive: Air Sensitive
• BRN: 778323
• CAS DataBase Reference: 4-Chloro-3-nitrobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-nitrobenzaldehyde(16588-34-4)
• EPA Substance Registry System: 4-Chloro-3-nitrobenzaldehyde(16588-34-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37-36/37/39-22-36
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 16588-34-4(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

4-Chloro-3-nitrobenzaldehyde is a potent inhibitor of VCAM-1 expression and a potential drug candidate for autoimmune and allergic inflammatory diseases.

InChI:InChI=1/C7H4ClNO3/c8-6-2-1-5(4-10)3-7(6)9(11)12/h1-4H

Synthetic route

4-chloro-3-nitrobenzyl alcohol (55912-20-4) → 4-chloro-3-nitro-benzaldehyde (16588-34-4)

Conditions	Yield
With 4-methyl-morpholine; chromium(VI) oxide; hydrogenchloride In diethyl ether; chloroform at 65℃; for 0.116667h; microwave irradiation;	98%
With oxygen; sodium carbonate In water for 1.5h; Reflux;	91%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; oxygen; potassium nitrite at 80℃; for 15h;	60 % Spectr.
With galactose oxidase M3-5 from Fusarium; dihydrogen peroxide; copper(II) sulfate; catalase; horseradish peroxidase In aq. phosphate buffer; dimethyl sulfoxide at 20℃; under 2068.65 Torr; pH=7.4; Flow reactor; Enzymatic reaction;

4-chlorobenzaldehyde (104-88-1) → 4-chloro-3-nitro-benzaldehyde (16588-34-4)

Conditions	Yield
With sulfuric acid; nitric acid for 2h; Cooling;	97%
With sulfuric acid; nitric acid at 0 - 20℃; for 0.5h; Inert atmosphere;	94%
With magnesium(II) nitrate hexahydrate; AMA at 20℃; for 4h; Neat (no solvent);	87%

2-chloro-5-hydroxyiminomethylnitrobenzene (66399-01-7) → 4-chloro-3-nitro-benzaldehyde (16588-34-4)

Conditions	Yield
With water; 2-nitro-4,5-dichloropyridazin-3(2H)-one In methanol at 130℃; under 10336 Torr; for 0.166667h; Microwave irradiation;	94%

2-(4'-chloro-3'-nitrophenyl)-1,3-oxathiolane (662165-72-2) → 4-chloro-3-nitro-benzaldehyde (16588-34-4)

Conditions	Yield
With Montmorillonite K10 In benzene for 5h; Heating;	76%

4-chloro-3-nitrobenzaldehyde hydrate (85152-60-9) → 4-chloro-3-nitro-benzaldehyde (16588-34-4)

Conditions	Yield
In water at 25℃; Rate constant; base and acid catalysis;

diazotized 3-nitro-4-amino-benzaldehyde → 4-chloro-3-nitro-benzaldehyde (16588-34-4)

Conditions	Yield
With hydrogenchloride; copper(l) chloride
With hydrogenchloride; copper chloride

isoniazid (54-85-3) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → isonicotinic acid N2-(4-chloro-3-nitrobenzylidene)hydrazide (99513-84-5)

Conditions	Yield
In ethanol Reflux;	100%
With ethanol

dibromodifluoromethane (75-61-6) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 3-nitro-4-(trifluoromethyl)benzaldehyde (102844-90-6)

Conditions	Yield
With ISOPROPYLAMIDE; copper at 100℃; for 8h;	100%
With copper In N,N-dimethyl acetamide at 100℃; for 7h;	60%

2-hydroxyethanethiol (60-24-2) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 2-(4'-chloro-3'-nitrophenyl)-1,3-oxathiolane (662165-72-2)

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 3h; Heating;	100%

p-cresol (106-44-5) + tert-butyl methyl ether (1634-04-4) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 6,6-((4-chloro-3-nitrophenyl)methylene)bis(2-(tert-butyl)4-methylphenol)

Conditions	Yield
With sulfonated multi-walled carbon nanotubes In neat (no solvent) at 100℃; for 3.5h; Catalytic behavior; regiospecific reaction;	100%

4-chloro-3-nitro-benzaldehyde (16588-34-4) → 4-azido-3-nitrobenzaldehyde (19155-93-2)

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 75℃; for 1h;	99%
With sodium azide In dimethyl sulfoxide at 75℃; for 1h;	99%
With sodium azide; benzyl tri-n-butylammonium bromide In 1,2-dichloro-ethane at 29℃; for 6h;	96%

triphenyl-(pyridin-3-yl-methyl)-phosphonium chloride (79296-92-7) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 3-[2-(4-chloro-3-nitrophenyl)vinyl]pyridine (388594-38-5)

Conditions	Yield
Stage #1: triphenyl-(pyridin-3-yl-methyl)-phosphonium chloride With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-chloro-3-nitro-benzaldehyde In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	99%

3,5-dimethyl-4H-1,2,4-triazol-4-amine (3530-15-2) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → (N-(4-chloro-3-nitrobenzylidene)-4H-3,5-Dimethyl-1,2,4-triazole-4-amine) hydrochloride

Conditions	Yield
With hydrogenchloride In acetonitrile for 3h; Reflux;	98%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 5-(4-chloro-3-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	97%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.166667h; Irradiation; Green chemistry;	95%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 6-Amino-1,3-dimethylbarbituric acid (6642-31-5) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 6-Amino-5-((4-chloro-3-nitrophenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With 2-(3-phenylthioureido)ethylprolinamide In water for 0.333333h; Reflux;	98%

2-Hydroxy-1,4-naphthoquinone (83-72-7) + malononitrile (109-77-3) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 2-amino-4-(4-chloro-3-nitrophenyl)-5,10-dihydro-5,10-dioxo-4H-benzo[g]chromene-3-carbonitrile

Conditions	Yield
In neat (no solvent) at 80℃; for 0.133333h; Green chemistry;	98%

4‐hydroxycoumarin (22105-09-5) + 6-Amino-1,3-dimethylbarbituric acid (6642-31-5) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → R-6-amino-5-((4-chloro-3-nitrophenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 20℃; for 1.5h; Sonication;	98%

orthoformic acid triethyl ester (122-51-0) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 4-chloro-3-nitrobenzaldehyde diethyl acetal (129011-62-7)

Conditions	Yield
With ammonium chloride In ethanol for 30h; Ambient temperature;	97%

acrylonitrile (107-13-1) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 3-hydroxy-2-methylene-3-(4-chloro-3-nitrophenyl)propanenitrile

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; choline chloride; glycerol In water at 20℃; for 0.833333h; Morita-Baylis-Hillman Alkylation; Green chemistry;	97%
N-methylcyclohexylamine In 1,4-dioxane; water at 20℃; for 20h; Morita-Baylis-Hillman reaction;	83%
With hexamethylenetetramine; N-butylpyridinium tetrafluoroborate at 20℃; for 8h; Baylis-Hillman reaction;	82%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 3,3'-((4-chloro-3-nitrophenyl)methylene)bis(2-hydroxy-4H-chromen-4-one)

Conditions	Yield
With 2-(3-phenylthioureido)ethylprolinamide In water for 0.25h; Reflux;	97%
With copper chromite nanoparticles In water at 20℃; for 0.0333333h; Green chemistry;	96%
With nanoparticles of the immobilized Ni(II) species on thiourea functionalized copper ferrite (CuFe2O4SiO2PTMSTuNi(II)) In neat (no solvent) at 70℃; for 0.416667h;	95%

methyl (triphenylphosphoranylidene)acetate (21204-67-1) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 3-(4-chloro-3-nitrophenyl)acrylic acid methyl ester (877065-30-0)

Conditions	Yield
Stage #1: methyl (triphenylphosphoranylidene)acetate; 4-chloro-3-nitro-benzaldehyde In toluene for 1.5h; Wittig Reaction; Heating / reflux; Stage #2: With water In toluene	97%

β-naphthol (135-19-3) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 14-(4-chloro-3-nitrophenly)-14H-dibenxo[a,j]xanthene (68828-13-7)

Conditions	Yield
With polyethylene glycol-supported sulfonic acid catalyst at 60 - 65℃; for 0.333333h; Neat (no solvent);	97%
With sulfonic acid functionalized diatomite In neat (no solvent) at 90℃; for 0.05h; Catalytic behavior; Green chemistry;	96%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate In ethanol for 0.0583333h; Microwave irradiation; Green chemistry;	95%

3-aminoethyl-2-[(p-trifluoromethoxy)anilino]quinazolin-4(3H)-one (1275601-94-9) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → C24H17ClF3N5O4 (1461736-79-7)

Conditions	Yield
In ethanol at 75℃; for 1.5h;	97%

dimedone (126-81-8) + malononitrile (109-77-3) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 2-amino-4-(4-chloro-3-nitrophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (303012-46-6)

Conditions	Yield
With 1-carboxymethyl-3-methyl-3H-imidazolium bromide at 110℃; for 0.0166667h;	97%
With Fe3O4 supported on SiO2-imidazole-H3PMo12O40 magnetic nanoparticles In water at 20℃; for 0.0833333h; Temperature; Sonication; Green chemistry;	96%
With magnetic core shell titanium dioxide nanoparticle In neat (no solvent) at 95℃; for 0.0666667h; Knoevenagel Condensation;	96%

phthalic anhydride (85-44-9) + ethyl 2-cyanoacetate (105-56-6) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → C20H15ClN4O6

Conditions	Yield
With hydrazine hydrate In neat (no solvent) at 80℃; for 0.333333h;	97%

O-benzyl carbamate (621-84-1) + β-naphthol (135-19-3) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → C25H19ClN2O5

Conditions	Yield
With {Fe3O4(at)SiO2(at)(CH2)3-NHNHC(O)NH-SO3H*HCl} In neat (no solvent) at 70℃; for 0.0833333h; Green chemistry;	97%

Upstream product

• 66399-01-7 2-chloro-5-hydroxyiminomethylnitrobenzene 
• 55912-20-4 4-chloro-3-nitrobenzyl alcohol 
• 662165-72-2 2-(4'-chloro-3'-nitrophenyl)-1,3-oxathiolane 
• 85152-60-9 4-chloro-3-nitrobenzaldehyde hydrate 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 101439-37-6 quinoline-2-carboxylic acid-(4-chloro-3-nitro-benzylidenehydrazide) 
• 92498-33-4 4-(4-formyl-2-methoxyphenoxy)-3-nitrobenzaldehyde 
• 256925-04-9 (4-chloro-3-nitro-phenyl)-bis-(4-dimethylamino-phenyl)-methane 
• 15962-63-7 3-Nitro-4-(4'-methoxy-phenoxy)-benzaldehyd 
• 3306-87-4 3-(4-chloro-3-nitro-phenyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 
• 51234-91-4 2-[2-(4-chloro-3-nitro-phenyl)-benzooxazol-5-yl]-propionic acid 
• 30932-47-9 [5c-(4-chloro-3-nitro-phenyl)-3-cyclohexyl-2t-(4-nitro-phenyl)-oxazolidin-4r-yl]-phenyl-methanone 
• 30932-47-9 [5t-(4-chloro-3-nitro-phenyl)-3-cyclohexyl-2t-(4-nitro-phenyl)-oxazolidin-4r-yl]-phenyl-methanone 
• 64501-66-2 trans-4-Chlor-3,4'-dinitro-stilben 
• 40923-55-5 [(4-Chloro-3-nitro-phenyl)-(diethoxy-phosphorylamino)-methyl]-phosphoramidic acid diethyl ester 
• 64501-67-3 trans-4-Chlor-3-nitro-stilben 
• 30932-46-8 [5t-(4-chloro-3-nitro-phenyl)-3-isopropyl-2t-(3-nitro-phenyl)-oxazolidin-4r-yl]-phenyl-methanone 
• 30932-46-8 [5c-(4-chloro-3-nitro-phenyl)-3-isopropyl-2t-(3-nitro-phenyl)-oxazolidin-4r-yl]-phenyl-methanone 
• 38921-00-5 trans-4,2',5'-Trichlor-3-nitro-stilben 

Related news

FT-IR, FT-Raman spectra, NBO, HOMO–LUMO and thermodynamic functions of 4-Chloro-3-nitrobenzaldehyde (cas 16588-34-4) based on ab initio HF and DFT calculations08/11/2019

FT-IR (4000–400 cm–1) and FT-Raman (3500–100 cm−1) spectral measurements of 4-chloro-3-nitrobenzaldehyde have been done. Ab initio (HF/6-311+G(d,p)) and DFT (B3LYP/6-311+G(d,p)) calculations have been performed giving energies, optimized structures, harmonic vibrational frequencies, infrared ...detailed

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