34046-43-0

Basic information

• Product Name: 2-Formylbenzoic acid ethyl ester
• Synonyms: 2-formylbenzoic acid ethyl ester;Ethyl 2-formylbenzoate;ethyl phthalaldehydate
• CAS NO: 34046-43-0
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.1846
• Product Categories: Organic acids
• Mol File: 34046-43-0.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 294°C
• Flash Point: 128°C
• Appearance: /
• Density: 1.145
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 2-Formylbenzoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Formylbenzoic acid ethyl ester(34046-43-0)
• EPA Substance Registry System: 2-Formylbenzoic acid ethyl ester(34046-43-0)

Safety Data

• Hazardous Substances Data: 34046-43-0(Hazardous Substances Data)

Usage

General Description

2-Formylbenzoic acid ethyl ester, also known as ethyl 2-formylbenzoate, is a chemical compound with the molecular formula C10H10O3. It is a derivative of benzoic acid and has a white crystalline appearance. 2-Formylbenzoic acid ethyl ester is often used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. It is also commonly used as a flavoring agent in the food industry. Its chemical properties make it an important reagent in organic chemistry, particularly in the production of esters, aldehydes, and carboxylic acids. Its versatility and relatively stable nature make it a valuable component in the manufacturing of various products.

InChI:InChI=1/C10H10O3/c1-2-13-10(12)9-6-4-3-5-8(9)7-11/h3-7H,2H2,1H3

Synthetic route

ethyl iodide (75-03-6) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	98%
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	79%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	68%

ethanol (64-17-5) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 12h;	85%

ethanol (64-17-5) + o-phthalic dicarboxaldehyde (643-79-8) → 3-ethoxy-3H-isobenzofuran-1-one (16824-02-5) + ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate at 60℃;	A 78% B 8%

ethyl 2-(2-hydroxybenzylidine)-hydrazine carboxylate (88674-90-2) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane for 2h; Ambient temperature;	72%
With lead(IV) acetate In tetrahydrofuran for 2h; Ambient temperature;	60%

ethyl cyclohepta-2,4,6-trienecarboxylate (27332-37-2) → ethyl 2-formylbenzoate (34046-43-0) + (1R,2S,3R,4R,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carboxylic acid ethyl ester + C10H12O4

Conditions	Yield
With hematoporphyrin In acetone Irradiation;	A 6% B 70% C 8%

ethyl 2-methylbenzoate (87-24-1) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With dipotassium peroxodisulfate; cobalt(II) diacetate tetrahydrate; trifluoroacetic acid; trifluoroacetic anhydride at 80℃; chemoselective reaction;	69%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + ethanol (64-17-5) + ortho-bromobenzaldehyde (6630-33-7) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With dmap; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 0.5h; Microwave irradiation;	65%

triethyloxonium fluoroborate (368-39-8) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With triethylamine In dichloromethane for 2h; Ambient temperature;	60%

ethyl cyclohepta-2,4,6-trienecarboxylate (27332-37-2) → ethyl 2-formylbenzoate (34046-43-0) + benzoic acid ethyl ester (93-89-0) + p-ethoxycarbonylbenzaldehyde (6287-86-1) + Ethyl 2-phenylethanoate (101-97-3) + Diethyl maleate (141-05-9)

Conditions	Yield
With sodium acetate; palladium diacetate In acetic acid at 80℃; for 4h; Product distribution; Mechanism; also 7-cyano-1,3,5-cycloheptatriene, var. solvents and reaction conditions;	A 11 % Spectr. B 8% C 9 % Spectr. D 3% E 4%

o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With thionyl chloride Behandeln des Reaktionsprodukts mit Alkohol;

(2-Ethoxycarbonyl-phenylmethylidyne)-isopropyl-ammonium → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With triethylsilane; water 1) CH2Cl2, reflux, 2) heating; Yield given. Multistep reaction;

4-Ethoxy-1,4-dihydro-2,3-benzodioxin-1-ol (70760-53-1) → ethyl 2-formylbenzoate (34046-43-0) + o-carboxybenzaldehyde (119-67-5)

Conditions	Yield
With water In acetonitrile at 29.6℃; Rate constant; Mechanism; variation of water-content, other solvents without water; addition of dimethylpyrroline N-oxide (formation of OH* adduct), also with D2O;

diethyl sulfate (64-67-5) + o-carboxybenzaldehyde (119-67-5) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
With potassium hydroxide; Aliquat 336 1.) 60 deg C, 0.1 Torr, 6 h, 2.) room temp., 18 h; Yield given. Multistep reaction;
With potassium hydroxide; Aliquat 336
With triethylamine In dichloromethane

2-cyano-benzoic acid ethyl ester (6525-45-7) → ethyl 2-formylbenzoate (34046-43-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: FeCl3 / CH2Cl2 / Heating 2: 1) Et3SiH, 2) H2O / 1) CH2Cl2, reflux, 2) heating View Scheme

ethyl 2-formylbenzoate (34046-43-0) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) → ethyl 2-(oxazol-5-yl)benzoate (1186127-15-0)

Conditions	Yield
With triethylamine; β‐cyclodextrin In water at 50℃; for 2h; Green chemistry;	94%

ethyl 2-formylbenzoate (34046-43-0) + allyl bromide (106-95-6) → 3-allyl-3H-isobenzofuran-1-one (24282-29-9, 148761-98-2)

Conditions	Yield
With tin In tetrahydrofuran at 80℃; for 8h;	94%

ethyl 2-formylbenzoate (34046-43-0) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (S)-ethyl 2-(((tert-butylsulfinyl)imino)methyl) benzoate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 8h;	90%

ethyl 2-formylbenzoate (34046-43-0) + allyl bromide (106-95-6) → (S)-3-allylisobenzofuran-1(3H)-one (24282-29-9)

Conditions

Yield

Stage #1: ethyl 2-formylbenzoate; allyl bromide With chromium chloride; manganese; chloro-trimethyl-silane; (10,10-dimethyl-5-(pyridin-2-yl)-6-azatricyclo[7.1.1.02,7]undeca-2(7),3,5-trien-8-yl)diphenylmethanol; triethylamine In tetrahydrofuran at 0℃; for 48h; Nozaki-Hiyama-Kishi Reaction; Molecular sieve; Inert atmosphere; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran Molecular sieve; Inert atmosphere; Stage #3: With toluene-4-sulfonic acid In tetrahydrofuran Molecular sieve; Inert atmosphere; enantioselective reaction;

86%

ethyl 2-formylbenzoate (34046-43-0) + triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide (56013-01-5) → 2-[(E)-2-(2,6,6-Trimethyl-cyclohex-1-enyl)-vinyl]-benzoic acid ethyl ester (223742-36-7)

Conditions	Yield
With n-butyllithium at 0℃;	85%

ethyl 2-formylbenzoate (34046-43-0) + malonic acid (141-82-2) → 3-(2-ethoxycarbonylphenyl)acrylic acid (188545-22-4)

Conditions	Yield
With piperidine; pyridine for 2h; Reflux;	82%

ethyl 2-formylbenzoate (34046-43-0) + (trifluoromethyl)trimethylsilane (81290-20-2) → 3-(trifluoromethyl)-1(3H)-isobenzofuranone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Concentration; Solvent;	82%

ethyl 2-formylbenzoate (34046-43-0) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;	81%

2-(2-methyl-1,3-dioxolane-2-yl)ethan-1-amine (62240-37-3) + ethyl 2-formylbenzoate (34046-43-0) → 1',3',4',10b'-tetrahydro-6'H-spiro[1,3-dioxolane-2,2'-pyrido[2,1-a]isoindol]-6'-one (817554-52-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Dean-Stark apparatus; Reflux;	77%

ethyl 2-formylbenzoate (34046-43-0) + 2,4-difluorophenylamine (367-25-9) → 2-(2,4-difluorophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (1375015-42-1)

Conditions	Yield
Stage #1: 2,4-difluorophenylamine With TurboGrignard In tetrahydrofuran at 20℃; for 0.1h; Microreactor; Stage #2: ethyl 2-formylbenzoate In tetrahydrofuran at 20℃; for 0.233333h; Bodroux reaction; Microreactor;	70%

ethyl 2-formylbenzoate (34046-43-0) + (2-nitrobenzyl)triphenylphosphonium bromide (23308-83-0) → ethyl 2-(2-nitrostyryl)benzoate (90011-52-2)

Conditions	Yield
With sodium ethanolate In dichloromethane at 20℃; Wittig reaction;	60%

ethyl 2-formylbenzoate (34046-43-0) + allyltrimethoxysilane (2551-83-9) → (R)-3-allylisobenzofuran-1(3H)-one + (S)-3-allylisobenzofuran-1(3H)-one (24282-29-9)

Conditions	Yield
With silver fluoride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In methanol at -20℃; for 5h; Sakurai-Hosomi Allylation; enantioselective reaction;	A 58% B n/a

ethyl 2-formylbenzoate (34046-43-0) + 2-(2-(2-bromo-5-chlorophenyl)-1-iminoethyl)-5-chlorophenol → ethyl 2-(4-(2-bromo-5-chlorobenzyl)-7-chloro-2H-benzo-[e][1,3]oxazin-2-yl)benzoate

Conditions	Yield
With trifluorormethanesulfonic acid; C17H17NO3 In 2-methyltetrahydrofuran at 0 - 20℃; for 18h; Molecular sieve;	57%
Stage #1: ethyl 2-formylbenzoate; 2-(2-(2-bromo-5-chlorophenyl)-1-iminoethyl)-5-chlorophenol With C17H17NO3 In 2-methyltetrahydrofuran at 0 - 5℃; for 0.0333333h; Inert atmosphere; Molecular sieve; Stage #2: With trifluorormethanesulfonic acid In 2-methyltetrahydrofuran at 20℃; Inert atmosphere;	56.9%

ethyl 2-formylbenzoate (34046-43-0) + 4-(2-chlorophenyl)-2-hydrazinothiazole → (E)-4-(2-chlorophenyl)-2-(2-ethoxyformylbenzylidenehydrazino)thiazole

Conditions	Yield
In ethanol for 4h; Inert atmosphere;	57%

ethyl 2-formylbenzoate (34046-43-0) + 1-bromo-2-(2-chloro-ethyl)benzene (75534-18-8) → 3-[2-(2-chloroethyl)phenyl]-3H-isobenzofuran-1-one

Conditions	Yield
Stage #1: 1-bromo-2-(2-chloro-ethyl)benzene With n-butyllithium In tetrahydrofuran at -100℃; for 0.166667h; Stage #2: With ytterbium(III) triflate In tetrahydrofuran at -78℃; for 0.5h; Stage #3: ethyl 2-formylbenzoate In tetrahydrofuran at -78 - 20℃; Further stages.;	56%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + ethyl 2-formylbenzoate (34046-43-0) + N-phenacylpyridinium bromide (16883-69-5) → ethyl trans-2-(2-benzoyl-4-oxo-2,3-dihydro-4H-furo[3,2-c]chromen-3-yl)benzoate

Conditions	Yield
With triethylamine In ethanol; water for 3h; Reflux; diastereoselective reaction;	50%

Upstream product

• 119-67-5 o-carboxybenzaldehyde 
• 64-67-5 diethyl sulfate 
• 368-39-8 triethyloxonium fluoroborate 
• 64-17-5 ethanol 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 87-24-1 ethyl 2-methylbenzoate 
• 15226-74-1 dicobalt octacarbonyl 
• 6630-33-7 ortho-bromobenzaldehyde 
• 70760-53-1 4-Ethoxy-1,4-dihydro-2,3-benzodioxin-1-ol 
• 27332-37-2 ethyl cyclohepta-2,4,6-trienecarboxylate 
• 6525-45-7 2-cyano-benzoic acid ethyl ester 
• 75-03-6 ethyl iodide 
• 88674-90-2 ethyl 2-(2-hydroxybenzylidine)-hydrazine carboxylate 

Downstream Products

• 83465-27-4 (3-oxo-1,3-dihydro-isobenzofuran-1-yl)acetic acid ethyl ester 
• 87-41-2 2-benzofuran-1(3H)-one 
• 1375015-42-1 2-(2,4-difluorophenyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one 
• 19312-06-2 4,5-dihydro-4,4-dimethyl-2-phenoxazole 
• 1186127-15-0 ethyl 2-(oxazol-5-yl)benzoate 
• 188545-22-4 3-(2-ethoxycarbonylphenyl)acrylic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 16824-02-5 3-ethoxy-3H-isobenzofuran-1-one 
• 90011-52-2 ethyl 2-(2-nitrostyryl)benzoate 
• 377774-80-6 2-((E)-8-Hydroxy-oct-1-en-3-ynyl)-benzoic acid ethyl ester 
• 377774-81-7 2-((1E,3Z)-8-Hydroxy-octa-1,3-dienyl)-benzoic acid ethyl ester 
• 377774-82-8 2-((E)-8-Hydroxy-oct-1-en-3-ynyl)-benzoic acid 

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