Product Name

  • Name

    o-Phthalaldehyde

  • EINECS 211-402-2
  • CAS No. 643-79-8
  • Article Data144
  • CAS DataBase
  • Density 1.189 g/cm3
  • Solubility Soluble in water
  • Melting Point 55-58 °C(lit.)
  • Formula C8H6O2
  • Boiling Point 266.1 °C at 760 mmHg
  • Molecular Weight 134.134
  • Flash Point 98.5 °C
  • Transport Information UN2923 8/PG 2
  • Appearance Light yellow powder
  • Safety 26-28-36-45-36/37/39-61-37/39
  • Risk Codes 36/37/38-43-34-25-50
  • Molecular Structure Molecular Structure of 643-79-8 (o-Phthalaldehyde)
  • Hazard Symbols ToxicT, IrritantXi, DangerousN
  • Synonyms 1,2-Benzenedicarboxaldehyde;Phthalic dialdehyde;Phtalaldehydes [French];Phthalic aldehyde;o-Phthaldialdehyde;Phthalyldicarboxaldehyde;Benzene-1,2-dicarboxaldehyde;2-Phthalaldehyde;o-Phthaladlehyde;Phthalic dicarboxaldehyde;
  • PSA 34.14000
  • LogP 1.31160

Synthetic route

phthalyl alcohol
612-14-6

phthalyl alcohol

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

1,3-dihydroisobenzofuran-1-ol

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
In acetonitrile95%
1,3-dihydroisobenzofuran
496-14-0

1,3-dihydroisobenzofuran

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
In acetonitrile94%
C11H13NOS2
1313208-32-0

C11H13NOS2

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With copper(II) choride dihydrate; water In acetonitrile at 75℃; for 1h;92%
1,2-bis(dibromomethyl)benzene
13209-15-9

1,2-bis(dibromomethyl)benzene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

phthalyl alcohol

A

2-(hydroxymethyl)benzaldehyde
55479-94-2

2-(hydroxymethyl)benzaldehyde

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

1,2-bis-diacetoxymethyl-benzene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

Phthaloyl dichloride

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

α,α'-dibromo-o-xylene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

1,3-dihydro-1,3-dimethoxybenzo[c]furan

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

ethyl 2-formylbenzoate

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;81%
cis-1,3-dihydro-1,3-dimethoxyisobenzofuran
22882-30-0

cis-1,3-dihydro-1,3-dimethoxyisobenzofuran

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With hydrogenchloride; water In tetrachloromethane81%
1,3-diethoxyphthalan
24388-71-4

1,3-diethoxyphthalan

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

phthalyl alcohol

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

naphthalene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

2-(azidomethyl)benzaldehyde

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With iron(III) chloride; dihydrogen peroxide In dichloromethane; water for 16h; Reflux; Air;75%
1,3-dihydroisobenzofuran
496-14-0

1,3-dihydroisobenzofuran

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

phthalic anhydride
85-44-9

phthalic anhydride

C

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

D

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

N'-(2-hydroxybenzylidene)formohydrazide

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With lead(IV) acetate In tetrahydrofuran for 2h; Ambient temperature;67%
1,3-dihydroisobenzofuran
496-14-0

1,3-dihydroisobenzofuran

phthalyl alcohol
612-14-6

phthalyl alcohol

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With nitric acid; acetic acid In water at 70℃; for 1h; Product distribution / selectivity;A 11%
B 67%
phthalonitrile
91-15-6

phthalonitrile

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

5-hydroxy-4,5-dihydroisobenzofuran

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

5-methoxy-4,5-dihydroisobenzofuran

A

4-methoxybenzene-1,2-dicarbaldehyde
6500-51-2

4-methoxybenzene-1,2-dicarbaldehyde

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

1,2-Bis-phenyltellanylmethyl-benzene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With oxygen In acetonitrile for 24h; Irradiation;56%
o-xylene
95-47-6

o-xylene

A

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

naphthalene

A

(E)-2-(3-oxoprop-1-enyl)benzaldehyde
61650-52-0

(E)-2-(3-oxoprop-1-enyl)benzaldehyde

B

2-Formyl-cis-cinnamaldehyde
93273-84-8

2-Formyl-cis-cinnamaldehyde

C

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

D

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
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

1,3-dihydroisobenzofuran

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

1,3-dihydroisobenzofuran

A

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

B

1,3-dihydroisobenzofuran-1-ol
59868-79-0

1,3-dihydroisobenzofuran-1-ol

C

phthalic anhydride
85-44-9

phthalic anhydride

D

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

C30H22O2

A

1,4-diphenylnaphthalene
796-30-5

1,4-diphenylnaphthalene

B

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 80℃; for 1.5h;A 33%
B 33%
formic acid
64-18-6

formic acid

1,2-Diiodobenzene
615-42-9

1,2-Diiodobenzene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

Conditions
ConditionsYield
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

o-phthalic dicarboxaldehyde

2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

Conditions
ConditionsYield
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

bis-1,3-dithiomethyl acetone

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

6,8-Bis(methylthio)-7H-benzocyclohepten-7-on

6,8-Bis(methylthio)-7H-benzocyclohepten-7-on

Conditions
ConditionsYield
With triethylamine In methanol Ambient temperature;100%
phenylacetylene
536-74-3

phenylacetylene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1-[2-(1-hydroxy-3-phenylprop-2-ynyl)phenyl]-3-phenylprop-2-yn-1-ol
36229-69-3

1-[2-(1-hydroxy-3-phenylprop-2-ynyl)phenyl]-3-phenylprop-2-yn-1-ol

Conditions
ConditionsYield
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

methanol

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1-nitrocyclohexane
1122-60-7

1-nitrocyclohexane

1-Methoxy-3-(1-nitrocyclohexyl)-1,3-dihydroisobenzofuran
189019-65-6

1-Methoxy-3-(1-nitrocyclohexyl)-1,3-dihydroisobenzofuran

Conditions
ConditionsYield
With sodium methylate Ambient temperature;100%
4-n-chlorophenylacetylene
873-73-4

4-n-chlorophenylacetylene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

C24H16O2Cl2
942229-68-7

C24H16O2Cl2

Conditions
ConditionsYield
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

4-methoxyphenylacetylen

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,1'-(1,2-phenylene)bis(3-(4-methoxyphenyl)prop-2-yn-1-ol)

1,1'-(1,2-phenylene)bis(3-(4-methoxyphenyl)prop-2-yn-1-ol)

Conditions
ConditionsYield
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

4-trifluoromethylphenylacetylene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,1'-(1,2-phenylene)bis(3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol)
1415646-42-2

1,1'-(1,2-phenylene)bis(3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol)

Conditions
ConditionsYield
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

potassium cyanide

2-amino-phenol
95-55-6

2-amino-phenol

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

2-(2-hydroxyphenyl)-2H-isoindole-1-carbonitrile

2-(2-hydroxyphenyl)-2H-isoindole-1-carbonitrile

Conditions
ConditionsYield
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

2-ethynylnaphthalene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

C32H22O2

C32H22O2

Conditions
ConditionsYield
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

1-ethynylnaphthalene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1-[2-(1-hydroxy-3-naphthalen-1-ylprop-2-ynyl)phenyl]-3-naphthalen-1-ylprop-2-yn-1-ol

1-[2-(1-hydroxy-3-naphthalen-1-ylprop-2-ynyl)phenyl]-3-naphthalen-1-ylprop-2-yn-1-ol

Conditions
ConditionsYield
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

3-methoxy-2-oxopropylidenetriphenylphosphorane

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,2-bis(4-methoxy-3-oxo-1-trans-butenyl)benzene
75522-06-4

1,2-bis(4-methoxy-3-oxo-1-trans-butenyl)benzene

Conditions
ConditionsYield
In dichloromethane 1.) 15-16 deg C 15 min; 2.) refluxed for 20 h;99.5%
4-bromophenylhydrazine hydrochloride
622-88-8

4-bromophenylhydrazine hydrochloride

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

2-(4-Bromo-phenyl)-1,2-dihydro-phthalazin-1-ol
113386-48-4

2-(4-Bromo-phenyl)-1,2-dihydro-phthalazin-1-ol

Conditions
ConditionsYield
With sodium hydroxide In water for 2h;99%
o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

PHTHALAZINE
253-52-1

PHTHALAZINE

Conditions
ConditionsYield
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

o-phthalic dicarboxaldehyde

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

o-Bis-(1-hydroxy-3-p-tolylprop-2-inyl)-benzol
36229-70-6

o-Bis-(1-hydroxy-3-p-tolylprop-2-inyl)-benzol

Conditions
ConditionsYield
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

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

(+)-(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

(+)-(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

Conditions
ConditionsYield
at 120℃; for 16h;99%
[(ImDippN)Th{N(SiMe3)2}3]

[(ImDippN)Th{N(SiMe3)2}3]

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

3-(bis-(trimethylsilyl)amino)isobenzofuran-1(3H)-one

3-(bis-(trimethylsilyl)amino)isobenzofuran-1(3H)-one

Conditions
ConditionsYield
In benzene-d6 for 3h;99%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

buta-2,3-dienoic acid benzyl ester
187661-86-5

buta-2,3-dienoic acid benzyl ester

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

benzyl 3-((4-methylphenylsulfonamido)methyl)-2-naphthoate

benzyl 3-((4-methylphenylsulfonamido)methyl)-2-naphthoate

Conditions
ConditionsYield
With triphenylphosphine In acetonitrile at 0℃; Inert atmosphere;99%
ethyl 2,3-butadienoate
14369-81-4

ethyl 2,3-butadienoate

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

phenol
108-95-2

phenol

ethyl 3-(phenoxymethyl)-2-naphthoate

ethyl 3-(phenoxymethyl)-2-naphthoate

Conditions
ConditionsYield
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

4,13-diamino<2.2>paracyclophane + 4,15-diamino<2.2>paracyclophane

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

C24H20N2

C24H20N2

Conditions
ConditionsYield
In ethanol for 18h; Reflux;99%
triethylsilane
617-86-7

triethylsilane

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,2-bis(((triethylsilyl)oxy)methyl)benzene
18724-46-4

1,2-bis(((triethylsilyl)oxy)methyl)benzene

Conditions
ConditionsYield
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

ethyl iodide

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,2-bis-(1-hydroxy-propyl)-benzene
196871-46-2

1,2-bis-(1-hydroxy-propyl)-benzene

Conditions
ConditionsYield
With magnesium In diethyl ether for 1h; Heating;98%
2-amino-5-chlorobenzenesulfonamide
5790-69-2

2-amino-5-chlorobenzenesulfonamide

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

3-Chloro-11H-isoindolo<1,2-c><1,2,4>benzothiadiazine 5,5-dioxide

3-Chloro-11H-isoindolo<1,2-c><1,2,4>benzothiadiazine 5,5-dioxide

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 24h;98%
methanol
67-56-1

methanol

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

nitrocyclopentane
2562-38-1

nitrocyclopentane

1-Methoxy-3-(1-nitrocyclopentyl)-1,3-dihydroisobenzofuran
189019-67-8

1-Methoxy-3-(1-nitrocyclopentyl)-1,3-dihydroisobenzofuran

Conditions
ConditionsYield
With sodium methylate Ambient temperature;98%
o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

phthalyl alcohol
612-14-6

phthalyl alcohol

Conditions
ConditionsYield
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

7-isopropyl-1,4-dimethyl-azulene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

1,2-phenylenebis(3-guaiazulenylmethylium) bis(hexafluorophosphate)

Conditions
ConditionsYield
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

5-piperidin-1-yl-pentylamine

sodium cyanide
143-33-9

sodium cyanide

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

2-(5-piperidin-1-yl-pentyl)-2H-isoindole-1-carbonitrile

2-(5-piperidin-1-yl-pentyl)-2H-isoindole-1-carbonitrile

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 18h;98%
(Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene
911286-46-9

(Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

cis-2-(6-pentyl-5,6-dihydro-2H-pyran-2-yl)benzaldehyde

cis-2-(6-pentyl-5,6-dihydro-2H-pyran-2-yl)benzaldehyde

Conditions
ConditionsYield
bismuth(III) bromide In dichloromethane at 20℃; for 12h;98%
4-Isopropylaniline
99-88-7

4-Isopropylaniline

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

1-p-isopropylphenylimino-2-p-isopropylphenylisoindoline
1093076-04-0

1-p-isopropylphenylimino-2-p-isopropylphenylisoindoline

Conditions
ConditionsYield
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

4-furan-2-yl-4-oxo-but-2-enoic acid ethyl ester

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

ethyl 2-(2-(furan-2-yl)-2-oxoethyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-indene-2-carboxylate

ethyl 2-(2-(furan-2-yl)-2-oxoethyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-indene-2-carboxylate

Conditions
ConditionsYield
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

penta-3,4-dien-2-one

o-phthalic dicarboxaldehyde
643-79-8

o-phthalic dicarboxaldehyde

phenol
108-95-2

phenol

1-(3-(phenoxymethyl)naphthalen-2-yl)ethanone

1-(3-(phenoxymethyl)naphthalen-2-yl)ethanone

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

o-Phthalaldehyde Chemical Properties

Molecular Structure:

Molecular Formula: C8H6O2
Molecular Weight: 134.132
IUPAC Name: Phthalaldehyde
Synonyms of Phthalaldehyde (CAS NO.643-79-8): 4-07-00-02138 (Beilstein Handbook Reference) ; BRN 0878317 ; EINECS 211-402-2 ; NSC 13394 ; Phtalaldehydes ; Phtalaldehydes [French] ; Phthalic aldehyde ; Phthalic dialdehyde ; Phthalyldicarboxaldehyde ; UNII-4P8QP9768A ; o-Phthalaldehyde ; o-Phthaldialdehyde ; 1,2-Benzenedicarboxaldehyde
CAS NO: 643-79-8
Classification Code: Anti-Infective Agents ; Disinfectants ; Enzyme inhibitors ; Indicators and reagents
Melting point: 55-58 °C 
Polar Surface Area: 34.14 Å2
Index of Refraction: 1.622
Molar Refractivity: 39.75 cm3
Molar Volume: 112.7 cm3
Surface Tension: 48.3 dyne/cm
Density: 1.189 g/cm3
Flash Point: 98.5 °C
Enthalpy of Vaporization: 50.41 kJ/mol
Boiling Point: 266.1 °C at 760 mmHg
Vapour Pressure: 0.0088 mmHg at 25°C 
Form: powder
Color: yellow
Water: Solubility soluble
Sensitive: Air Sensitive
Merck: 7368
BRN: 878317
Stability: Stable. Air sensitive. Incompatible with strong oxidizing agents, strong bases.

o-Phthalaldehyde Uses

 Phthalaldehyde (CAS NO.643-79-8) is pharmaceutical intermediate, and it is used in pharmaceutical inspection. It is mainly used in medicine, dyestuff, etc. It is commonly used as a high-level disinfectant for medical instruments.

o-Phthalaldehyde Production

There are two synthesis method of Phthalaldehyde (CAS NO.643-79-8): the first described in 1887 when it was prepared from α,α,α',α’-tetrachloro-ortho-xylene. And the second that hydrolysis of the related tetrabromoxylene using potassium oxalate, followed by purification by steam distillation.

o-Phthalaldehyde Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo unreported 7mg/kg (7mg/kg)   Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 246, Pg. 851, 1958.

o-Phthalaldehyde Consensus Reports

Reported in EPA TSCA Inventory.

o-Phthalaldehyde Safety Profile

Poison by an unspecified route. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Hazard Codes of Phthalaldehyde (CAS NO.643-79-8): Xi,T,N
Risk Statements: 36/37/38-43-34-25-50
36/37/38:  Irritating to eyes, respiratory system and skin 
43:  May cause sensitization by skin contact 
34:  Causes burns 
25:  Toxic if swallowed 
50:  Very Toxic to aquatic organisms  
Safety Statements: 26-28-36-45-36/37/39-61-37/39
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
61:  Avoid release to the environment. Refer to special instructions safety data sheet 
37/39:  Wear suitable gloves and eye/face protection 
RIDADR: UN2923 8/PG 2
WGK Germany: 3
RTECS: TH6950000
F: 1-8-10: Sensitive to air and humidity. Photosensitive. Keep under argon.
Hazard Note: Irritant/Air Sensitive
HS Code: 29122900

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