Conditions | Yield |
---|---|
With air; poly-alkylated (nitrosyl)Ru(salen) In toluene at 20℃; for 24h; Irradiation; | 100% |
With dmap; tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N'-di-tert-butylethylenediamine; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 3h; Schlenk technique; Molecular sieve; Sealed tube; | 99% |
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction; | 99% |
methyl 4-(diethoxymethyl)benzenecarboxylate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 3h; | 100% |
Conditions | Yield |
---|---|
In methanol | 100% |
In dichloromethane | |
In dichloromethane | |
Multi-step reaction with 2 steps 1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 2: copper(II) bis(trifluoromethanesulfonate) / 16 h / 20 °C View Scheme |
4-(hydroxyiminomethyl)benzoic acid methyl ester
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With hydrogenchloride In water; toluene at 20℃; for 4h; Reflux; Large scale; | 98% |
methyl 4-(dimethoxymethyl)benzoate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone at 20℃; for 20h; | 98% |
methyl 4-[2-(methylthio)-1,3-dithian-2-yl]benzoate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 3h; Ambient temperature; | 97% |
With p-benzoquinone; sodium iodide In water; acetonitrile at 100℃; for 31h; | 86 %Spectr. |
Conditions | Yield |
---|---|
magnesium(II) perchlorate In nitromethane at 40℃; for 16h; | 97% |
di(p-tolyl) sulfoxide
4-(methoxycarbonyl)benzyl alcohol
A
di-(p-tolyl)sulfane
B
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With per-rhenic acid In toluene for 24h; Reflux; | A 97% B 85% |
Conditions | Yield |
---|---|
With acetyl chloride at 0 - 20℃; | 96% |
With thionyl chloride Ambient temperature; | 95% |
With thionyl chloride at 0 - 20℃; | 93% |
4-quinolynylmethyl 4-formylbenzoate
methyl iodide
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
Stage #1: 4-quinolynylmethyl 4-formylbenzoate With ammonium formate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 50℃; for 12h; Reduction; Deprotection; Stage #2: methyl iodide With sodium carbonate In water; dimethyl sulfoxide at 20℃; for 12h; Methylation; | 96% |
methanol
dicobalt octacarbonyl
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 96% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.05h; Microwave irradiation; | 95% |
With pyridine N-oxide; silver(l) oxide In acetonitrile at 25℃; | 81% |
With ethanol; sodium 2-nitropropane | |
With methanol; hexamethylenetetramine | |
With 4-methylmorpholine N-oxide In acetonitrile at 0℃; Inert atmosphere; Molecular sieve; |
(4-(methoxycarbonyl)phenyl)methylene diacetate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With potassium tert-butylate; 3-Dimethylaminophenol In tetrahydrofuran for 0.0833333h; | 92% |
With zirconium(IV) chloride In methanol at 20℃; for 0.1h; | 89% |
4-(diethylaminocarbonyl)benzoic acid methyl ester
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.416667h; Inert atmosphere; | 92% |
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.5h; | 73% |
methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate
A
1,2,3,4,5-pentamethylcyclopentadiene
B
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With trichloroacetic acid In dichloromethane at 28℃; for 1.5h; | A n/a B 91% |
methanol
4-formyl-N,N-bis(pyridin-2-ylmethyl)benzamide
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) at 20℃; for 16h; | 91% |
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube; | 91% |
Stage #1: formic acid; methyl 4-iodobenzoate 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; | 79% |
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube; | 71% |
dicobalt octacarbonyl
4-methoxycarbonylphenyl bromide
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 60℃; for 16h; Schlenk technique; Inert atmosphere; | 91% |
dicobalt octacarbonyl
4-carbomethoxyphenyl triflate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 25℃; for 16h; Schlenk technique; Inert atmosphere; | 91% |
carbon monoxide
methyl 4-iodobenzoate
A
benzoic acid methyl ester
B
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; under 2280 Torr; | A 8% B 90% |
With hydrogen; potassium carbonate In 1,4-dioxane at 120 - 140℃; under 30003 Torr; for 20h; Autoclave; | A 45% B 8% |
Conditions | Yield |
---|---|
With sodium formate In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 4h; | 90% |
With sodium formate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h; | 89% |
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 24h; | 83% |
With poly-γ-(p-diphenylphosphinophenyl)propylsiloxane Pd; sodium acetate In N,N-dimethyl-formamide at 90℃; for 8h; | 81% |
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
Stage #1: N-cyclohexyl-4-(methoxycarbonyl)benzamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; Inert atmosphere; Stage #2: With triethylsilane In dichloromethane at 0 - 25℃; Inert atmosphere; Stage #3: With citric acid In tetrahydrofuran; dichloromethane; water at 45℃; for 2h; chemoselective reaction; | 90% |
methyl 4-(isopropylcarbamoyl)benzoate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
Stage #1: methyl 4-(isopropylcarbamoyl)benzoate With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 0 - 20℃; for 6.16667h; Inert atmosphere; Stage #3: With hydrogenchloride In dichloromethane; water at 20℃; Inert atmosphere; | 90% |
Multi-step reaction with 3 steps 1: phosphorus pentachloride / dichloromethane / 20 °C / Schlenk technique 2: Dimethylphenylsilane; CpRu(PiPr3)(CH3CN)2PF6; tert-butyl isocyanide / dichloromethane-d2 / 0.5 h / 20 °C / Schlenk technique 3: hydrogenchloride; water / hexane View Scheme |
methyl 4-(aminomethyl)benzoate
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With copper(I) 2-hydroxy-3-methylbenzoate; oxygen; ascorbic acid In N,N-dimethyl acetamide at 40℃; for 2h; chemoselective reaction; | 89% |
With N-chloro-succinimide In water at 24.9℃; Kinetics; Thermodynamic data; pH 10.6; ΔH(excit.), ΔS(excit.); | |
With N-bromoacetamide In water at 14.9 - 34.9℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.); |
Conditions | Yield |
---|---|
With P(p-CH3OC6H4)3; methylphenylsilane; 2,2-dimethylpropanoic anhydride; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 20h; Schlenk technique; Inert atmosphere; | 89% |
With bis-triphenylphosphine-palladium(II) chloride; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; Dimethylphenylsilane In toluene at 80℃; for 7h; Inert atmosphere; Sealed tube; | 89% |
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere; | 80% |
4-Carboxybenzaldehyde
carbonic acid dimethyl ester
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry; | 89% |
4-Carboxybenzaldehyde
methyl salicylate
A
salicylic acid
B
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
Stage #1: 4-Carboxybenzaldehyde With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl salicylate at 110℃; for 24h; | A n/a B 89% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 1h; | 88% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 2h; | 71% |
With potassium carbonate In N-methyl-acetamide; water | 4.7 g (84%) |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Darkness; |
methanol
dicobalt octacarbonyl
4-(trifluormethanesulfonyloxy)benzaldehyde
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 88% |
Conditions | Yield |
---|---|
With phosphate-buffered silica gel supported KMnO4 In cyclohexane at 65℃; | 100% |
With chromium(VI) oxide; sulfuric acid In water; acetone at 0℃; Jones Oxidation; | 97% |
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 5h; Heating; | 95% |
2,2-Dimethyl-1,3-propanediol
methyl 4-formylbenzoate
4-(5,5-Dimethyl-[1,3]dioxan-2-yl)-benzoic acid methyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 2h; Heating; | 100% |
With toluene-4-sulfonic acid In toluene for 24h; Reflux; | 66% |
trimethylsilyl cyanide
methyl 4-formylbenzoate
methyl 4-(cyano(trimethylsilyloxy)methyl)benzoate
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 1h; | 100% |
With Al(3+)*C36H48NO3(3-) In acetonitrile at 20℃; for 9.5h; Inert atmosphere; Schlenk techniques; | 92% |
With iodine In dichloromethane at 20℃; for 0.05h; | 90% |
benzyl 2-bromopropionate
methyl 4-formylbenzoate
benzyl 2-methyl-3-hydroxy-p-carbomethoxyhydrocinnamate
Conditions | Yield |
---|---|
With iodine; zinc In benzene for 18h; Heating; | 100% |
2-bromobutyric acid benzyl ester
methyl 4-formylbenzoate
4-(2-Benzyloxycarbonyl-1-hydroxy-butyl)-benzoic acid methyl ester
Conditions | Yield |
---|---|
With iodine; zinc In benzene Heating; | 100% |
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With TiCl4*Et2O In dichloromethane at -78℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 5℃; for 0.5h; | 100% |
With zirconium dioxide hydrate; isopropyl alcohol at 60℃; for 0.133333h; Meerwein-Ponndorf-Verley Reduction; | 100% |
Stage #1: methyl 4-formylbenzoate With polymethylhydrosiloxane; iron(II) acetate; tricyclohexylphosphine In tetrahydrofuran at 65℃; for 16h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; methanol at 0 - 20℃; Further stages.; | 99% |
malonic acid
methyl 4-formylbenzoate
4-(2-carboxyvinyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With piperidine; pyridine at 120℃; for 12h; | 100% |
With piperidine In pyridine at 100 - 120℃; for 19h; | 99.39% |
With piperidine; pyridine at 80 - 100℃; for 4h; | 91.6% |
With piperidine; pyridine at 110℃; for 2h; | 75% |
With piperidine; pyridine for 5h; Reflux; | 36% |
3-acetyl-2,4-dihydroxyquinoline
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
100% |
benzylamine
methyl 4-formylbenzoate
N-benzyl-(4-methoxycarbonylphenyl)methanimine
Conditions | Yield |
---|---|
In toluene for 15.5h; Heating; | 100% |
With 4 A molecular sieve In methanol for 4h; Heating; | 96% |
In methanol |
methyl 4-formylbenzoate
methyl 4-[(1E)-(hydroxyimino)methyl]benzoate
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux; | 100% |
With hydroxylamine hydrochloride; sodium acetate In methanol; water for 0.5h; Reflux; | 79% |
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol at 20℃; for 4h; | 60% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 10h; | 100% |
1,6-Hexanediamine
methyl 4-formylbenzoate
1,6-bis(4-methoxycarbonylbenzylidene)hexanediamine
Conditions | Yield |
---|---|
In toluene for 0.5h; Condensation; Heating; | 100% |
In toluene for 1h; Reflux; Dean-Stark trap; | 100% |
Conditions | Yield |
---|---|
Stage #1: 1H-indene-1,3(2H)-dione; methyl 4-formylbenzoate With L-proline In methanol at 20℃; for 0.5h; organocatalytic Knoevenagel condensation; Stage #2: (E)-benzalacetone In methanol at 25℃; for 96h; Diels-Alder/epimerization reaction; | 100% |
(E)-3-methyl-4-methoxy-2-[(trimethylsilyl)oxy]-1,3-butadiene
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
Stage #1: (E)-3-methyl-4-methoxy-2-[(trimethylsilyl)oxy]-1,3-butadiene; methyl 4-formylbenzoate With lithium methanolate In N,N-dimethyl-formamide at 0℃; Mukaiyama aldol addition; Stage #2: With trifluoroacetic acid In N,N-dimethyl-formamide at 0℃; | 100% |
(1H,1H,2H,2H-perfluorooctyl)triphenylphosphonium iodide
methyl 4-formylbenzoate
C17H11F13O2
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane; water Wittig reaction; Heating; | 100% |
2-(5-fluoro-2-methoxyphenyl)ethanamine
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
In ethanol for 2h; Heating / reflux; | 100% |
p-Trifluoromethylbenzylamine
methyl 4-formylbenzoate
N-(4-(methylcarboxy)benzylidene)-p-trifluoromethylbenzylamine
Conditions | Yield |
---|---|
In toluene Reflux; | 100% |
Conditions | Yield |
---|---|
In ethanol at 20℃; | 100% |
2,4-Dimethoxybenzylamine
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; Inert atmosphere; | 100% |
trimethylsilyl cyanide
3-Phenylpropan-1-amine
methyl 4-formylbenzoate
methyl 4-[cyano(3-phenylpropylamino)methyl]benzoate
Conditions | Yield |
---|---|
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction; | 99.9% |
trimethylsilyl cyanide
phenethylamine
methyl 4-formylbenzoate
methyl 4-[cyano(phenethylamino)methyl]benzoate
Conditions | Yield |
---|---|
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction; | 99.9% |
trimethylsilyl cyanide
aniline
methyl 4-formylbenzoate
methyl 4-[cyano(phenylamino)methyl]benzoate
Conditions | Yield |
---|---|
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction; | 99.8% |
With polymer-supported gallium(III) bis(trifluoromethanesulfonate) In dichloromethane at 40℃; under 15001.5 Torr; for 1h; Strecker reaction; Microreactor; | 99.9% |
trimethylsilyl cyanide
benzylamine
methyl 4-formylbenzoate
methyl 4-((benzylamino)(cyano)methyl)benzoate
Conditions | Yield |
---|---|
With polymer-supported scandium(III) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 1h; Strecker reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction; | 99.9% |
Conditions | Yield |
---|---|
With piperazine In acetonitrile for 1h; Knoevenagel condensation; electroosmos; | 99.8% |
methyl 4-formylbenzoate
4-(hydroxyiminomethyl)benzoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: methyl 4-formylbenzoate With hydroxylamine hydrochloride In methanol; water at 25 - 35℃; for 2h; Stage #2: With sodium hydroxide In methanol; water pH=7.5 - 8; | 99.5% |
Stage #1: methyl 4-formylbenzoate With hydroxylamine hydrochloride; 5%-palladium/activated carbon In methanol; water at 25 - 35℃; for 2h; Stage #2: With sodium hydroxide In methanol; water pH=7.5 - 8; Product distribution / selectivity; | 99.5% |
With hydroxylamine hydrochloride In methanol; water at 20℃; for 6h; Large scale; | 95% |
methyl 4-formylbenzoate
trimethyl orthoformate
methyl 4-(dimethoxymethyl)benzoate
Conditions | Yield |
---|---|
With *OTf3 In methanol for 5h; Ambient temperature; | 99% |
With amberlyst-15 In acetonitrile for 1h; electroosmos; | 99.4% |
With amberlyst-15 In acetonitrile for 0.166667h; | 95.3% |
Empirical Formula: C9H8O3
Molecular Weight: 164.158 g/mol
Index of Refraction: 1.557
Density: 1.181 g/cm3
Flash Point: 122.5 °C
Water solubility: Insoluble
Sensitive: Air Sensitive
Melting point: 59-63 °C(lit.)
Enthalpy of Vaporization: 50.29 kJ/mol
Boiling Point: 265 °C at 760 mmHg
Vapour Pressure: 0.0094 mmHg at 25 °C
Solubility: Methanol : 0.1 g/mL, clear
Appearance: White crystalline powder
Structure of Methyl 4-formylbenzoate (CAS NO.1571-08-0):
IUPAC Name: Methyl 4-formylbenzoate
Product Category of Methyl 4-formylbenzoate (CAS NO.1571-08-0): Intermediates of Dyes and Pigments;Aromatic Aldehydes & Derivatives (substituted)
Methyl 4-formylbenzoate (CAS NO.1571-08-0) can be used as drugs' intermediate and fluorescent brighteners' intermediate.
Methyl 4-formylbenzoate (CAS NO.1571-08-0) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. And the toxicological properties have not been fully investigated.
Hazard Codes: Xn,Xi
Risk Statements: 36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
Methyl 4-formylbenzoate , its cas register number is 1571-08-0. It also can be called 4-Carbomethoxybenzaldehyde; p-Carbomethoxybenzaldehyde ; 4-(Methoxycarbonyl)benzaldehyde ; Methyl benzaldehyde-4-carboxylate ; Methyl terephthalaldehydate ; and 4-Carboxybenzaldehyde methyl ester . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, Methyl 4-formylbenzoate (CAS NO.1571-08-0) is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide.
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