643-79-8

Basic information

• Product Name: o-Phthalaldehyde
• Synonyms: The developMent of forMaldehyde;O-PHTHALDIALDEHYDE REAGENT SOLUTION*;1,2-Benzenedialdehyde;o-Phthaladehyde;phtalaldehydes;Phthalaldialdehyde;Phthalic aldehyde;Phthalic dialdehyde
• CAS NO: 643-79-8
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• EINECS: 211-402-2
• Product Categories: Carbonyl Compounds;Amino Group Labeling Reagents for Fluorescence HPLC;Amino Group Labeling Reagents for HPLC;Analytical Chemistry;Fluorescence Detection (HPLC Labeling Reagents);HPLC Labeling Reagents;UV Detection (HPLC Labeling Reagents);Amino Acid Analysis;Carbohydrate Labels;Carbohydrate Labels for Chromatography;Derivatization Reagents TLC;Detection Products for Amino Acid Analysis;Fluorescent Labels;Functional Group Reactive Label;Functional Group Reactive Labels;Aldehydes;Alphabetical;Amino Acids;Analytical Reagents;Analytical/Chromatography;Application Specific Reagents;Biochemicals and Reagents;Building Blocks;C8;Chemical Synthesis;Derivatization Reagents;Derivatization Reagents HPLC;Detection;Electrochemical;Fluorescence;Fluorescent Indicators and Probes;Fluorescent Probes;Labels;Particles and Stains;Peptide Analysis and Characterization;Carbohydrates;Core Bioreagents;Functional Group Reactive Labels for Flow Cytometry;Organic Building Blocks;Peptides;Research Essentials;Analytical Reagents for Gene
• Mol File: 643-79-8.mol
• Article Data: 106

Chemical Properties

• Melting Point: 55-58 °C(lit.)
• Boiling Point: 83-84 °C (0.7501 mmHg)
• Flash Point: >230 °F
• Appearance: yellow/powder
• Density: 1.13
• Vapor Pressure: 0.0088mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 53g/l
• Water Solubility: soluble
• Sensitive: Air Sensitive
• Stability: Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.
• Merck: 14,7368
• BRN: 878317
• CAS DataBase Reference: o-Phthalaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: o-Phthalaldehyde(643-79-8)
• EPA Substance Registry System: o-Phthalaldehyde(643-79-8)

Safety Data

• Hazard Codes: Xi,T,N,C
• Statements: 36/37/38-43-34-25-50-52/53
• Safety Statements: 26-28-36-45-36/37/39-61-37/39
• RIDADR: UN2923 8/PG 2
• WGK Germany: 3
• RTECS: TH6950000
• F: 1-8-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: Ⅱ
• Hazardous Substances Data: 643-79-8(Hazardous Substances Data)

Usage

Chemical Description

o-Phthalaldehyde is a chemical compound used in organic synthesis and as a fluorescent probe for amino acids.

InChI:InChI=1/C8H6O2/c9-5-7-3-1-2-4-8(7)6-10/h1-6H

Synthetic route

phthalyl alcohol (612-14-6) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With bis(pyridine)silver(I) permanganate In benzene for 1h;	95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In neat (no solvent) at 20℃; for 2h; Milling;	86%
With tetrakis(pyridine)silver dichromate In benzene for 2h; Heating;	85%

1,3-dihydroisobenzofuran-1-ol (59868-79-0) + N-hydroxyphthalimide (524-38-9) + nitrogen(II) oxide (10102-43-9) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
In acetonitrile	95%

1,3-dihydroisobenzofuran (496-14-0) + N-hydroxyphthalimide (524-38-9) + nitrogen(II) oxide (10102-43-9) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
In acetonitrile	94%

C11H13NOS2 (1313208-32-0) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With copper(II) choride dihydrate; water In acetonitrile at 75℃; for 1h;	92%

1,2-bis(dibromomethyl)benzene (13209-15-9) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
Stage #1: 1,2-bis(dibromomethyl)benzene With sulfuric acid Stage #2: With water; sodium hydrogencarbonate Product distribution / selectivity;	91%
With sulfuric acid Product distribution / selectivity;	79%
With sulfuric acid

phthalyl alcohol (612-14-6) → 2-(hydroxymethyl)benzaldehyde (55479-94-2) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Product distribution; Heating; effect of various chromium(VI) based oxidants;	A 10% B 90%
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Heating;	A 10% B 90%
With cucurbit[8]uril; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water for 0.0833333h; Catalytic behavior; Reagent/catalyst; Temperature; Reflux;	A 76% B 7%

1,2-bis-diacetoxymethyl-benzene (6500-54-5) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With ethanol at 50 - 60℃; for 0.0833333h;	90%
With poly(4-vinylpyridinium) hydrogen sulfate solid acid In methanol at 20℃; for 0.25h; Irradiation;	86%
With N-sulfonic acid poly(4-vinylpyridinium) chloride In methanol at 20℃; for 0.583333h;	82%

Phthaloyl dichloride (88-95-9) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With 1 Product distribution; further reagent;	89%
With pentacoordinated hydrogenosilane 3 further reagent;	89%
With Cp2M(CO)H (M= Nb or Ta) In diethyl ether Yield given;
With thexyl-s-butoxyborane In tetrahydrofuran at 25℃; for 120h; Yield given;

α,α'-dibromo-o-xylene (91-13-4) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With bis-{4-methoxy-phenyl}-selenoxyde; sodium hydrogencarbonate In acetonitrile at 75℃; for 5h;	84%
With air; sodium phenyltelluride 1.) THF, ethanol, reflux, 2 h, 2.) THF, ethanol, 25 deg C; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: eosin y; oxygen / dimethyl sulfoxide / 12 h / 25 °C / Irradiation 2: eosin y / dimethyl sulfoxide / 24 h / 80 °C / Irradiation View Scheme

1,3-dihydro-1,3-dimethoxybenzo[c]furan (24388-70-3) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With hydrogenchloride In tetrachloromethane; water Reflux;	81%
With sulfuric acid; water under 112.511 Torr; for 4h; pH=2.0; Purification / work up;	61.5%
With water; benzene-1,2-dicarboxylic acid at 20℃; for 48h;	95 % Chromat.

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%

cis-1,3-dihydro-1,3-dimethoxyisobenzofuran (22882-30-0) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With hydrogenchloride; water In tetrachloromethane	81%

1,3-diethoxyphthalan (24388-71-4) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With sodium hydroxide; water for 0 - 1200h; pH=8.9; Product distribution / selectivity;	78.2%
With sodium hydroxide; water for 48 - 960h; pH=10.8; Product distribution / selectivity;	1%
With water; benzene-1,2-dicarboxylic acid at 20℃; for 24h;	95 % Chromat.

phthalyl alcohol (612-14-6) → 2-benzofuran-1(3H)-one (87-41-2) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 2h;	A 77% B 15%
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In chloroform at 20℃; for 36h; Green chemistry;	A 67% B 30%
With ferric nitrate at 60℃; for 0.25h;	A 35% B 65%

naphthalene (91-20-3) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With potassium metaperiodate; potassium aquapentachlororuthenate(III) In dichloromethane; water; acetonitrile at 20℃; for 2h; Sonication;	75%
With potassium bromate In dichloromethane; water; acetonitrile at 20℃; for 1h; Reagent/catalyst; Temperature; Sonication;	68%
With sodium periodate In dichloromethane; water; acetonitrile at 20℃; for 1h; Irradiation;	60%

2-(azidomethyl)benzaldehyde (887143-97-7) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With iron(III) chloride; dihydrogen peroxide In dichloromethane; water for 16h; Reflux; Air;	75%

1,3-dihydroisobenzofuran (496-14-0) → 2-benzofuran-1(3H)-one (87-41-2) + phthalic anhydride (85-44-9) + o-carboxybenzaldehyde (119-67-5) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With dihydrogen peroxide; trifluoroacetic acid; zinc dibromide In 1,4-dioxane; water at 100℃; for 16h;	A 68% B n/a C n/a D n/a

N'-(2-hydroxybenzylidene)formohydrazide (3155-65-5) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With lead(IV) acetate In tetrahydrofuran for 2h; Ambient temperature;	67%

1,3-dihydroisobenzofuran (496-14-0) + phthalyl alcohol (612-14-6) → 2-benzofuran-1(3H)-one (87-41-2) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With nitric acid; acetic acid In water at 70℃; for 1h; Product distribution / selectivity;	A 11% B 67%

phthalonitrile (91-15-6) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;	64%
With sodium tris(dibutylamino)aluminum hydride In tetrahydrofuran at 25℃; for 3h; Yield given;
Stage #1: phthalonitrile With lithium tris(dihexylamino)aluminum hydride In tetrahydrofuran at 0℃; for 1h; Reduction; Stage #2: With hydrogenchloride In tetrahydrofuran Hydrolysis;

5-hydroxy-4,5-dihydroisobenzofuran (99758-16-4) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With selenium(IV) oxide In water for 0.166667h; Heating;	64%
Multi-step reaction with 3 steps 1.1: sodium hydride / 1,4-dioxane / 0.25 h 1.2: 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 48 h / 20 °C 3.1: toluene-4-sulfonic acid; lithium chloride / N,N-dimethyl-formamide View Scheme

5-methoxy-4,5-dihydroisobenzofuran → 4-methoxybenzene-1,2-dicarbaldehyde (6500-51-2) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 20℃; for 48h;	A 63% B n/a

1,2-Bis-phenyltellanylmethyl-benzene (109179-40-0) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With oxygen In acetonitrile for 24h; Irradiation;	56%

o-xylene (95-47-6) → 2-methylphenyl aldehyde (529-20-4) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With oxygen In water at 150℃; under 30002.4 Torr; for 2h;	A 20% B 42%
With oxygen; 10-methyl-9-phenylacridin-10-ium perchlorate In chloroform at 24.85℃; for 10h; photoirradiation; Title compound not separated from byproducts;
With oxygen; 10-methyl-9-phenylacridin-10-ium perchlorate In chloroform at 24.84℃; for 10h; Oxidation; Pyrolysis; visible light; Title compound not separated from byproducts.;
With oxygen at 300℃; Gas phase; Flow reactor;

naphthalene (91-20-3) → (E)-2-(3-oxoprop-1-enyl)benzaldehyde (61650-52-0) + 2-Formyl-cis-cinnamaldehyde (93273-84-8) + o-phthalic dicarboxaldehyde (643-79-8) + [1,4]naphthoquinone (130-15-4)

Conditions	Yield
With florisil; helium dimer; oxygen at -78℃; for 2h;	A 30% B 40% C 20% D n/a
With florisil; helium dimer; oxygen at -78℃; for 2h; Mechanism;	A 30% B 40% C 20% D n/a
With florisil; ozone Product distribution; var. reaction time;

1,3-dihydroisobenzofuran (496-14-0) → 2-benzofuran-1(3H)-one (87-41-2) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With nitric acid; acetic acid In water at 60 - 80℃; for 0.5 - 4h; Product distribution / selectivity;	A 9% B 35%
With nitric acid In dichloromethane at 20℃; for 1h;	A 39 % Spectr. B 61 % Spectr.

1,3-dihydroisobenzofuran (496-14-0) → 2-benzofuran-1(3H)-one (87-41-2) + 1,3-dihydroisobenzofuran-1-ol (59868-79-0) + phthalic anhydride (85-44-9) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
Stage #1: 1,3-dihydroisobenzofuran With N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile); oxygen In acetonitrile at 75℃; under 760.051 Torr; for 20h; Stage #2: With triphenylphosphine In acetonitrile at 25℃; Further stages.;	A 14% B 29% C 1% D 34%

C30H22O2 → 1,4-diphenylnaphthalene (796-30-5) + o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 80℃; for 1.5h;	A 33% B 33%

formic acid (64-18-6) + 1,2-Diiodobenzene (615-42-9) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 6h; Sealed tube; Inert atmosphere;	12%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 4h; Sealed tube;	11%

o-phthalic dicarboxaldehyde (643-79-8) → 2-benzofuran-1(3H)-one (87-41-2)

Conditions	Yield
With calcium oxide In benzene at 39.84℃; for 0.25h; Tishchenko reaction;	100%
[La2(tBu2pz)6] In benzene-d6 at 21℃; Tishchenko reaction;	100%
With [(ImDippN)Th{N(SiMe3)2}3] In benzene-d6 at 20℃; for 6h;	100%

bis-1,3-dithiomethyl acetone (39199-23-0) + o-phthalic dicarboxaldehyde (643-79-8) → 6,8-Bis(methylthio)-7H-benzocyclohepten-7-on

Conditions	Yield
With triethylamine In methanol Ambient temperature;	100%

phenylacetylene (536-74-3) + o-phthalic dicarboxaldehyde (643-79-8) → 1-[2-(1-hydroxy-3-phenylprop-2-ynyl)phenyl]-3-phenylprop-2-yn-1-ol (36229-69-3)

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere;	100%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 0.5h;	99%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	87%

methanol (67-56-1) + o-phthalic dicarboxaldehyde (643-79-8) + 1-nitrocyclohexane (1122-60-7) → 1-Methoxy-3-(1-nitrocyclohexyl)-1,3-dihydroisobenzofuran (189019-65-6)

Conditions	Yield
With sodium methylate Ambient temperature;	100%

4-n-chlorophenylacetylene (873-73-4) + o-phthalic dicarboxaldehyde (643-79-8) → C24H16O2Cl2 (942229-68-7)

Conditions	Yield
Stage #1: 4-n-chlorophenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere; Schlenk technique;	100%
Stage #1: 4-n-chlorophenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 0.5h;	92%
Stage #1: 4-n-chlorophenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	55%
Stage #1: 4-n-chlorophenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran at 20℃; for 1.5h;
Stage #1: 4-n-chlorophenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Sealed tube;

4-methoxyphenylacetylen (768-60-5) + o-phthalic dicarboxaldehyde (643-79-8) → 1,1'-(1,2-phenylene)bis(3-(4-methoxyphenyl)prop-2-yn-1-ol)

Conditions	Yield
Stage #1: 4-methoxyphenylacetylen With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique;	100%
Stage #1: 4-methoxyphenylacetylen With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 0.5h;	98%
Stage #1: 4-methoxyphenylacetylen With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran at 20℃; for 1.5h;
Stage #1: 4-methoxyphenylacetylen With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Sealed tube;

4-trifluoromethylphenylacetylene (705-31-7) + o-phthalic dicarboxaldehyde (643-79-8) → 1,1'-(1,2-phenylene)bis(3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol) (1415646-42-2)

Conditions	Yield
Stage #1: 4-trifluoromethylphenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique;	100%
Stage #1: 4-trifluoromethylphenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran at 20℃; for 1.5h;

potassium cyanide + 2-amino-phenol (95-55-6) + o-phthalic dicarboxaldehyde (643-79-8) → 2-(2-hydroxyphenyl)-2H-isoindole-1-carbonitrile

Conditions	Yield
Stage #1: 2-amino-phenol; o-phthalic dicarboxaldehyde With sodium hydrogensulfite In water at 40℃; for 0.5h; Stage #2: potassium cyanide In water at 40℃; for 1.5h;	100%

2-ethynylnaphthalene (2949-26-0) + o-phthalic dicarboxaldehyde (643-79-8) → C32H22O2

Conditions	Yield
Stage #1: 2-ethynylnaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 0.5h;	100%

1-ethynylnaphthalene (15727-65-8) + o-phthalic dicarboxaldehyde (643-79-8) → 1-[2-(1-hydroxy-3-naphthalen-1-ylprop-2-ynyl)phenyl]-3-naphthalen-1-ylprop-2-yn-1-ol

Conditions	Yield
Stage #1: 1-ethynylnaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 0.5h;	100%

3-methoxy-2-oxopropylidenetriphenylphosphorane (33513-55-2) + o-phthalic dicarboxaldehyde (643-79-8) → 1,2-bis(4-methoxy-3-oxo-1-trans-butenyl)benzene (75522-06-4)

Conditions	Yield
In dichloromethane 1.) 15-16 deg C 15 min; 2.) refluxed for 20 h;	99.5%

4-bromophenylhydrazine hydrochloride (622-88-8) + o-phthalic dicarboxaldehyde (643-79-8) → 2-(4-Bromo-phenyl)-1,2-dihydro-phthalazin-1-ol (113386-48-4)

Conditions	Yield
With sodium hydroxide In water for 2h;	99%

o-phthalic dicarboxaldehyde (643-79-8) → PHTHALAZINE (253-52-1)

Conditions	Yield
With hydrazine hydrate In ethanol 1.) 0 deg C, 1 h, 2.) r.t., 2 h,;	99%
With hydrogenchloride; neodymium(II) diiodide; nitrogen In water; toluene at 70℃; under 1500.15 Torr; for 12h; Inert atmosphere;	48%

o-phthalic dicarboxaldehyde (643-79-8) + 4-n-methylphenylacetylene (766-97-2) → o-Bis-(1-hydroxy-3-p-tolylprop-2-inyl)-benzol (36229-70-6)

Conditions	Yield
Stage #1: 4-n-methylphenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 0.5h;	99%
(i) EtMgBr, THF, (ii) /BRN= 878317/; Multistep reaction;
Stage #1: 4-n-methylphenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane for 1.5h; Inert atmosphere;
Stage #1: 4-n-methylphenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: o-phthalic dicarboxaldehyde In tetrahydrofuran; hexane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; Sealed tube;

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane (68737-65-5) + o-phthalic dicarboxaldehyde (643-79-8) → (+)-(3aR,7aR)-octahydro-2-(2-((3aR,7aR)-octahydro-1,3-dimethyl-1H-benzo[d]imidazol-2-yl)phenyl)-1,3-dimethyl-1H-benzo[d]imidazole (891271-46-8)

Conditions	Yield
at 120℃; for 16h;	99%

[(ImDippN)Th{N(SiMe3)2}3] + o-phthalic dicarboxaldehyde (643-79-8) → 3-(bis-(trimethylsilyl)amino)isobenzofuran-1(3H)-one

Conditions	Yield
In benzene-d6 for 3h;	99%

toluene-4-sulfonamide (70-55-3) + buta-2,3-dienoic acid benzyl ester (187661-86-5) + o-phthalic dicarboxaldehyde (643-79-8) → benzyl 3-((4-methylphenylsulfonamido)methyl)-2-naphthoate

Conditions	Yield
With triphenylphosphine In acetonitrile at 0℃; Inert atmosphere;	99%

ethyl 2,3-butadienoate (14369-81-4) + o-phthalic dicarboxaldehyde (643-79-8) + phenol (108-95-2) → ethyl 3-(phenoxymethyl)-2-naphthoate

Conditions	Yield
With triphenylphosphine In acetonitrile at 0℃; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;	99%

4,13-diamino<2.2>paracyclophane + 4,15-diamino<2.2>paracyclophane (56439-05-5, 78655-01-3, 942982-34-5) + o-phthalic dicarboxaldehyde (643-79-8) → C24H20N2

Conditions	Yield
In ethanol for 18h; Reflux;	99%

triethylsilane (617-86-7) + o-phthalic dicarboxaldehyde (643-79-8) → 1,2-bis(((triethylsilyl)oxy)methyl)benzene (18724-46-4)

Conditions	Yield
Stage #1: o-phthalic dicarboxaldehyde With C8H10BiCl2N; C4H6AgN2(1+)*C24H12BCl8(1-) In dichloromethane-d2 at 25℃; Stage #2: triethylsilane In dichloromethane at 25℃;	99%

ethyl iodide (75-03-6) + o-phthalic dicarboxaldehyde (643-79-8) → 1,2-bis-(1-hydroxy-propyl)-benzene (196871-46-2)

Conditions	Yield
With magnesium In diethyl ether for 1h; Heating;	98%

2-amino-5-chlorobenzenesulfonamide (5790-69-2) + o-phthalic dicarboxaldehyde (643-79-8) → 3-Chloro-11H-isoindolo<1,2-c><1,2,4>benzothiadiazine 5,5-dioxide

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 24h;	98%

methanol (67-56-1) + o-phthalic dicarboxaldehyde (643-79-8) + nitrocyclopentane (2562-38-1) → 1-Methoxy-3-(1-nitrocyclopentyl)-1,3-dihydroisobenzofuran (189019-67-8)

Conditions	Yield
With sodium methylate Ambient temperature;	98%

o-phthalic dicarboxaldehyde (643-79-8) → phthalyl alcohol (612-14-6)

Conditions	Yield
With sodium tetrahydroborate; sodium hydrogen sulfate In acetonitrile at 20℃; for 0.0333333h;	98%
With sodium tetrahydroborate; water; titanium(IV) oxide In acetonitrile at 20℃; for 0.0833333h; regioselective reaction;	97%
With sodium tetrahydroborate; TiO(acac)2 In acetonitrile at 20℃; for 0.0333333h;	96%

7-isopropyl-1,4-dimethyl-azulene (489-84-9) + o-phthalic dicarboxaldehyde (643-79-8) → 1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

Conditions	Yield
In diethyl ether; acetonitrile at 25℃;	98%
With hexafluorophosphoric acid In water; acetic acid at 25℃; for 2h;	88%

5-piperidin-1-yl-pentylamine (70403-69-9) + sodium cyanide (143-33-9) + o-phthalic dicarboxaldehyde (643-79-8) → 2-(5-piperidin-1-yl-pentyl)-2H-isoindole-1-carbonitrile

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 18h;	98%

(Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene (911286-46-9) + o-phthalic dicarboxaldehyde (643-79-8) → cis-2-(6-pentyl-5,6-dihydro-2H-pyran-2-yl)benzaldehyde

Conditions	Yield
bismuth(III) bromide In dichloromethane at 20℃; for 12h;	98%

4-Isopropylaniline (99-88-7) + o-phthalic dicarboxaldehyde (643-79-8) → 1-p-isopropylphenylimino-2-p-isopropylphenylisoindoline (1093076-04-0)

Conditions	Yield
With formic acid In diethyl ether at 20℃; for 12h; Inert atmosphere;	98%

4-furan-2-yl-4-oxo-but-2-enoic acid ethyl ester (861251-81-2) + o-phthalic dicarboxaldehyde (643-79-8) → ethyl 2-(2-(furan-2-yl)-2-oxoethyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-indene-2-carboxylate

Conditions	Yield
With C12H14NO2S(1+)*Cl(1-); caesium carbonate In tetrahydrofuran at 20℃; Inert atmosphere; diastereoselective reaction;	98%

penta-3,4-dien-2-one (2200-53-5) + o-phthalic dicarboxaldehyde (643-79-8) + phenol (108-95-2) → 1-(3-(phenoxymethyl)naphthalen-2-yl)ethanone

Conditions	Yield
With triphenylphosphine In acetonitrile at 0℃; Inert atmosphere;	98%

Upstream product

• 64-17-5 ethanol 
• 13209-15-9 1,2-bis(dibromomethyl)benzene 
• 583-52-8 potassium oxalate 
• 66546-58-5 1,5-dihydro-benzo[e][1,3,2]dioxaselenepin-3-oxide 
• 6329-16-4 N,N,N',N'-tetramethyl-phthalamide 
• 7556-55-0 1-formyl-4-methylpiperidine 
• 85-44-9 phthalic anhydride 
• 270-75-7 isobenzofuran 
• 91-20-3 naphthalene 
• 612-14-6 phthalyl alcohol 
• 88-95-9 Phthaloyl dichloride 
• 253-52-1 PHTHALAZINE 
• 120-12-7 anthracene 
• 10028-15-6 ozone 

Downstream Products

• 28873-89-4 2-Formylcinnamic acid 
• 6500-54-5 1,2-bis-diacetoxymethyl-benzene 
• 861326-54-7 2-[3-(4-dimethylamino-phenyl)-1-oxo-inden-2-yl]-benzaldehyde 
• 25401-41-6 2,7-Nonamethylen-4,5-benzotropon 
• 483-55-6 phthiocol 
• 3144-47-6 6-hydroxybenzocyclohepten-7-one 
• 103890-70-6 2-(diethoxymethyl)benzaldehyde 
• 5388-42-1 N-phenylphthalimidine 
• 97166-94-4 1-phenylimino-2-phenylisoindoline 
• 5323-75-1 2-benzoyl-2,3-dihydro-1H-inden-1-one 
• 5350-68-5 2-acetylindan-1-one 
• 2484-16-4 6,8-dimethyl-benzocyclohepten-7-one 
• 91-14-5 1,2-divinylbenzene 
• 121977-02-4 2,2'-diphenyl-4H,4'H-4,4'-o-phenylenebismethylene-bis-oxazol-5-one 

Relevant articles and documents

Smart solution chemistry: Prolonging the lifetime of ortho-phthalaldehyde disinfection solutions

The oxidation of ortho-phthalaldehyde to phthalic acid in aqueous solutions can be remedied by the addition of various cyclic acetals, which, when reacted with phthalic acid, yields ortho-phthalaldehyde, thus prolonging the lifetime of the ortho-phthalaldehyde disinfection solution.

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes

A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.

Oxidaition of cyclic benzylic ethers by an electronically tuned nitroxyl radical

The reactivity of an electronically tuned nitroxyl radical catalyst for the oxidation of cyclic benzylic ethers has been investigated. The oxidation of phthalan resulted in oxidative cleavage of the saturated ring to give an aromatic dialdehyde. Additionally, oxidation of isochromans afforded isochromanones, which are often seen in natural products, in a rapid manner.

Synthesis of Phthalic Aldehyde and Its Diacetals

Acyclic phthalaldehyde diacetal without cyclic 1,3-dihydro-1,3-dimethoxybenzo[c]furan impurity has been obtained via the reaction of 1,2-bis(dibromomethyl)benzene with trimethyl orthoformate (1:6) at 90°C in the presence of 10 mol% of ZnCl2. Hydrolysis of phthalaldehyde diacetal has led to the formation of phthalaldehyde without HBr evolution. The reaction of phthalaldehyde with trimethyl orthoformate in the presence of trifluoroacetic acid has proceeded abnormally, with the formation of the cyclic diacetal. The acyclic diacetal has been phosphorylated by chlorophosphines and the action of PCl3 and a P(III) acid ester in sequence.