626-19-7

Basic information

• Product Name: m-Phthalaldehyde
• Synonyms: M-PHTHALICDICARBOXALDEHYDE;M-PHTHALALDEHYDE;BENZENE-1,3-DICARBOXALDEHYDE;ISOPHTHALIC DICARBOXALDEHYDE;ISOPHTHALDIALDEHYDE;ISOPHTHALALDEHYDE;3-PHTHALALDEHYDE;1,3-BENZENEDICARBALDEHYDE
• CAS NO: 626-19-7
• Molecular Formula: C₈H₆O₂
• Molecular Weight: 134.13
• EINECS: 210-935-8
• Mol File: 626-19-7.mol
• Article Data: 60

Chemical Properties

• Melting Point: 87-88 °C(lit.)
• Boiling Point: 136 °C (12.7517 mmHg)
• Flash Point: 136°C/17mm
• Appearance: White to slightly yellow/Needle-Like Crystalline Powder
• Density: 1.1603 (rough estimate)
• Vapor Pressure: 0.0164mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1561038
• CAS DataBase Reference: m-Phthalaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: m-Phthalaldehyde(626-19-7)
• EPA Substance Registry System: m-Phthalaldehyde(626-19-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: NT1981000
• Hazardous Substances Data: 626-19-7(Hazardous Substances Data)

Usage

Chemical Properties

colourless or light yellow crystals

Uses

Different sources of media describe the Uses of 626-19-7 differently. You can refer to the following data:
1. Isophthalaldehyde is used in the synthesis of binuclear ruthenium complex. It participates in base-catalyzed Knoevenagel condensation reaction.
2. Isophthalaldehyde is used in the synthesis of binuclear ruthenium complex.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 455, 1995 DOI: 10.1016/0040-4039(94)02284-I

General Description

Isophthalaldehyde participates in base-catalyzed Knoevenagel condensation reaction.

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

Synthetic route

1,3-dimethanol benzene (626-18-6) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With manganese(IV) oxide; molecular sieve In hexane for 3h; Heating;	98%
With manganese(II) nitrate; C70H128N16O4; oxygen; copper(II) nitrate In acetic acid at 20℃; for 4h; Mechanism;	90%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl In ethyl acetate; toluene at 0℃;	83%

1,3-bis-diacetoxymethyl-benzene (167862-23-9) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With ethanol at 50 - 60℃; for 0.0833333h;	95%
With rice husk supported FeCl3 nanoparticles In ethanol at 70℃; for 0.583333h;	90%
With N-sulfonic acid poly(4-vinylpyridinium) chloride In methanol at 20℃; for 0.583333h;	87%

m-xylene (108-38-3) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With dihydrogen peroxide In acetonitrile at 85℃; for 4h; Reagent/catalyst; Temperature;	94%
With C15H11ClN4SZn; p-benzoquinone In tert-butyl alcohol for 8h; Reagent/catalyst;	72%
With tert.-butylhydroperoxide; C29H25Cl2N4Ru(1+)*F6P(1-) In acetonitrile at 60℃; for 3h; Schlenk technique; Inert atmosphere;	62%

1,3-dimethanol benzene (626-18-6) → Isophthalaldehyde (626-19-7) + 3-(hydroxymethyl)benzaldehyde (52010-98-7)

Conditions	Yield
With oxygen; potassium carbonate; palladium diacetate In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h;	A 93% B 3%
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 41% B 43%
With manganese(IV) oxide In tetrahydrofuran at 45℃; Rate constant; k2/k1;

1,3-bis-(bromomethyl)benzene (626-15-3) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With bis-{4-methoxy-phenyl}-selenoxyde; sodium hydrogencarbonate In acetonitrile at 75℃; for 5h;	90%
Stage #1: 1,3-bis-(bromomethyl)benzene With 2-nitropropane; sodium methylate In methanol; ethyl acetate at 30℃; for 6h; Stage #2: With water In methanol; ethyl acetate	25.8%
With hydrogenchloride; hexamethylenetetramine; acetic acid
Multi-step reaction with 2 steps 2: aqueous NaOH View Scheme

1-{3-[1-Hydroxy-2-methylsulfanyl-2-(toluene-4-sulfonyl)-ethyl]-phenyl}-2-methylsulfanyl-2-(toluene-4-sulfonyl)-ethanol → Isophthalaldehyde (626-19-7)

Conditions	Yield
With potassium carbonate In isopropyl alcohol for 1.5h; Ambient temperature;	90%

benzene-1,3-dicarbonyl dichloride (99-63-8) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With pentacoordinated hydrogenosilane 1	89%
With sodium tris(tert-butoxo)aluminium hydride In tetrahydrofuran; diethylene glycol dimethyl ether at -78℃; for 3h;	88%
With lithium tri-t-butoxyaluminum hydride
Multi-step reaction with 2 steps 1: triethylsilane; triethylamine / tetrahydrofuran / 1 h / 20 °C 2: triethylsilane / tetrahydrofuran / 1 h View Scheme

C32H54O2S2 → Isophthalaldehyde (626-19-7)

Conditions	Yield
With triethylsilane In tetrahydrofuran for 1h; Reagent/catalyst; Fukuyama Reduction;	89%

1,3-dibromobenzene (108-36-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Isophthalaldehyde (626-19-7)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With tert.-butyl lithium In pentane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide In pentane at -78 - 20℃; Inert atmosphere; Schlenk technique;	88%

C15H16O9 → Isophthalaldehyde (626-19-7)

Conditions	Yield
With sulfonated rice husk ash In acetonitrile at 60℃; for 0.166667h;	87%

ammonium vanadate + m-chloromethylbenzylidene chloride (30220-25-8) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With nitric acid In m-xylene	84.9%

m-iodobenzaldehyde (696-41-3) + carbon monoxide (201230-82-2) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 48h;	84%

1,3-di(aminomethyl)benzene (1477-55-0) → Isophthalaldehyde (626-19-7)

Conditions	Yield
Stage #1: 1,3-di(aminomethyl)benzene With hexamethylenetetramine In water at 20℃; for 3h; pH=3.6 - 4.5; Stage #2: With hydrogenchloride for 3h; pH=3.5 - 4.5; Reflux;	83.7%
With hydrogenchloride; hexamethylenetetramine; acetic acid

danishefsky's diene (54125-02-9) + 3-[(phenylimino)methyl]benzaldehyde (488081-87-4) → Isophthalaldehyde (626-19-7) + 3-(4-oxo-1-phenyl-1,2,3,4-tetrahydro-pyridin-2-yl)-benzaldehyde + 2-[3-(4-oxo-3,4-dihydro-2H-pyran-2-yl)-phenyl]-1-phenyl-2,3-dihydro-1H-pyridin-4-one + C28H24N2O2

Conditions	Yield
Stage #1: danishefsky's diene; 3-[(phenylimino)methyl]benzaldehyde; scandium tris(trifluoromethanesulfonate) In acetonitrile at 0℃; for 0.05h; Diels-Alder reaction; Stage #2: With water In acetonitrile Further stages.;	A 4% B 83% C 3% D 5%

1,1'-<(N,N-dimethylisophthalimido) bis-(3-methyl-3H-imidazol-1-ium)> diiodide → Isophthalaldehyde (626-19-7) + 3-methyl-1-methylamino-3H-imidazol-1-ium iodide

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane for 0.5h; Ambient temperature;	A 82% B n/a

1,1'-<(N,N-dimethylisophthalimido) bis-(3-methyl-3H-imidazol-1-ium)> diiodide → Isophthalaldehyde (626-19-7)

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -10 - 20℃; for 0.5h;	82%

α,α,α',α'-tetrabromo-m-xylene (36323-28-1) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With dimethyl amine at 60℃; for 2h;	80%
With sulfuric acid at 70 - 110℃;

C17H14O3 → Isophthalaldehyde (626-19-7)

Conditions	Yield
With iron(II) fluoride; 1,3-bis(3,3,3-trifluoropropyl)-1,1,3,3-tetramethyldisiloxane In ethanol at 80℃; for 24h;	80%

1,3-Bis-phenyltellanylmethyl-benzene → Isophthalaldehyde (626-19-7)

Conditions	Yield
With oxygen In acetonitrile for 24h; Irradiation;	78%

m-formylphenyl benzoic acid (619-21-6) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With 2,6-dimethylpyridine; 4,4'-dimethoxyphenyl disulfide; iridium(lll) bis[2-(2,4-difluorophenyl)-5-methylpyridine-N,C20]-4,40-di-tert-butyl-2,20-bipyridine hexafluorophosphate; triphenylphosphine In toluene for 24h; Irradiation;	78%

1,3-divinylbenzene (108-57-6) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With cadmium sulphide In neat (no solvent) at 20℃; for 12h; Irradiation;	77%
With air; Ag/AgBr/TiO2 nanotubes In acetonitrile at 20℃; for 48h; Irradiation;	69%

carbon monoxide (201230-82-2) + 1,3-Diiodobenzene (626-00-6) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 48h;	76%

formic acid (64-18-6) + 1,3-Diiodobenzene (626-00-6) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 4h; Sealed tube;	76%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 6h; Sealed tube; Inert atmosphere;	75%

1,3-di-tert-butoxymethyl benzene → Isophthalaldehyde (626-19-7) + 3-tert-butoxymethylbenzaldehyde

Conditions	Yield
With N-hydroxyphthalimide; nitrogen(II) oxide In acetonitrile at 60℃; for 10h;	A 75% B 10%

m-tolyl aldehyde (620-23-5) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With dirhodium tetraacetate; Selectfluor In trifluoroacetic acid; trifluoroacetic anhydride at 80℃; for 7h; Sealed tube; Inert atmosphere; chemoselective reaction;	71%

dimethyl Isophthalate (1459-93-4) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With 1-methyl-piperazine; sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 5℃; for 1h;	65.6%

3-(hydroxymethyl)benzaldehyde (52010-98-7) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With dimethyl sulfoxide UV-irradiation;	62%
With manganese(IV) oxide In tetrahydrofuran at 45℃; Rate constant;

1,3,5-benzene tris(carbonyl chloride) (4422-95-1) → Isophthalaldehyde (626-19-7) + benzene-1,3,5-trialdehyde (3163-76-6)

Conditions	Yield
With hydrogen; thiourea; Pd-BaSO4 In xylene for 10h; Heating;	A 19% B 59%

isophthalic acid (121-91-5) → Isophthalaldehyde (626-19-7)

Conditions	Yield
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere;	42%
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 24h;	94 % Spectr.
With hydrogen; 2,2-dimethylpropanoic anhydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; under 22501.8 Torr; for 24h;	94 % Spectr.
Multi-step reaction with 2 steps 1: 63 percent / 5-methyl-2-chloro-3-phenyl-2,3-dihydro-1,3,4,2-oxadiazaphosphole, pyridine / Ambient temperature 2: 82 percent / DIBALH / CH2Cl2 / 0.5 h / -10 - 20 °C View Scheme

3-[(phenylimino)methyl]benzaldehyde (488081-87-4) → Isophthalaldehyde (626-19-7) + N,N'-(1,3-phenylenebis(methan-1-yl-1-ylidene))dianiline (16742-78-2)

Conditions	Yield
scandium tris(trifluoromethanesulfonate) In [D3]acetonitrile at 0℃; for 1h;	A 23% B 27%

(1S,2R)-2-Amino-1,2-diphenylethanol (23364-44-5) + Isophthalaldehyde (626-19-7) → (1S,2R)-2-{[1-(3-{[(E)-(1R,2S)-2-Hydroxy-1,2-diphenyl-ethylimino]-methyl}-phenyl)-meth-(E)-ylidene]-amino}-1,2-diphenyl-ethanol (155906-82-4)

Conditions	Yield
With molecular sieve In dichloromethane Ambient temperature;	100%

Isophthalaldehyde (626-19-7) + (1S,2R)-(+)-ephedrine (321-98-2) → C28H32N2O2

Conditions	Yield
With molecular sieve In dichloromethane Ambient temperature;	100%

Isophthalaldehyde (626-19-7) + (1S,2R)-2-benzylamino-1-phenylpropan-1-ol (93303-74-3) → C40H40N2O2

Conditions	Yield
With molecular sieve In dichloromethane Ambient temperature;	100%

Isophthalaldehyde (626-19-7) + NH-benzyl-(1R,2S)-norephedrine (61347-76-0) → C40H40N2O2

Conditions	Yield
With molecular sieve In dichloromethane Ambient temperature;	100%

Isophthalaldehyde (626-19-7) + (1S,2R)-2-(ethylamino)-1-phenylpropan-1-ol (37577-32-5) → C30H36N2O2

Conditions	Yield
With molecular sieve In dichloromethane Ambient temperature;	100%

Isophthalaldehyde (626-19-7) + (-)-(S)-2-amino-4-methyl-1,1-diphenylpentanol (161832-74-2) → (S)-2-{[1-(3-{[(E)-(S)-1-(Hydroxy-diphenyl-methyl)-3-methyl-butylimino]-methyl}-phenyl)-meth-(E)-ylidene]-amino}-4-methyl-1,1-diphenyl-pentan-1-ol (155906-83-5)

Conditions	Yield
With molecular sieve In dichloromethane Ambient temperature;	100%

Isophthalaldehyde (626-19-7) + thioxobis(1-methylhydrazino)phosphoranyl azide (156457-68-0) → (2E,7E,14E,19E)-5,17-Diazido-4,6,16,18-tetramethyl-3,4,6,7,15,16,18,19-octaaza-5,17-diphospha-tricyclo[19.3.1.19,13]hexacosa-1(24),2,7,9,11,13(26),14,19,21(25),22-decaene 5,17-disulfide

Conditions	Yield
	100%

1,2-Dihydro-N-methylcyclohepta[b]pyrrol-2-one (3336-87-6) + Isophthalaldehyde (626-19-7) → 1,3-bis[bis(1,2-dihydro-2-oxo-N-methylcyclohepta[b]pyrrol-3-yl)methyl]benzene

Conditions	Yield
In dichloromethane; trifluoroacetic acid at 20℃; for 48h;	100%

Isophthalaldehyde (626-19-7) + 3,5-dimethylaminoaniline (108-69-0) → C24H26N2

Conditions	Yield
at 20℃;	100%

3-methylpyridin-2-ylamine (1603-40-3) + Isophthalaldehyde (626-19-7) → C20H18N4 (1445377-27-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; for 17h; Dean-Stark;	100%

4-methyl-morpholine (109-02-4) + Isophthalaldehyde (626-19-7) + ethyl 2-cyanoacetate (105-56-6) → tetraethyl3,3′-(1,3-phenylene)bis(1,2-dicyanocyclopropane-1,2-dicarboxylate) + C5H11NO*C5H6BrNO2

Conditions	Yield
With bromocyane In ethanol at 0 - 20℃; for 0.00138889h; Michael Addition; Sealed tube; stereoselective reaction;	A 100% B n/a

Isophthalaldehyde (626-19-7) + ethyl acetoacetate (141-97-9) + dimedone (126-81-8) → C22H25NO4

Conditions	Yield
With 4,4′-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo[2.2.2]octane-1,4-diium) tetrachloride; ammonium acetate In neat (no solvent) at 100℃; for 0.25h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	100%

Isophthalaldehyde (626-19-7) + (1R,2R)-1,2-diaminocyclohexane (20439-47-8) → C42H48N6

Conditions	Yield
In dichloromethane at 20℃; for 24h;	100%

Isophthalaldehyde (626-19-7) + malonic acid (141-82-2) → 1,3-phenylene-3,3'-bis(2-propenoic) acid (23713-86-2)

Conditions	Yield
With piperidine; pyridine at 100℃;	99%
With piperidine; pyridine for 24h; Doebner reaction; Heating;	91%
With pyridine at 50℃;
With sodium acetate; acetic anhydride at 140 - 150℃;
With piperidine; pyridine for 24h; Reflux;

Isophthalaldehyde (626-19-7) + (2-aminoethyl)bis(2-pyridylmethyl)amine (189440-33-3) → C36H38N8 (1227512-79-9)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	99%
In methanol for 24h; Molecular sieve; Inert atmosphere; Reflux;
In tetrahydrofuran at 0 - 20℃; for 15h;

Isophthalaldehyde (626-19-7) + 1,3,5-tris(aminomethyl)-2,4,6-trimethylbenzene (149525-64-4) → C48H48N6 (1260940-97-3)

Conditions	Yield
In methanol; dichloromethane at 20℃; Inert atmosphere;	99%

1.3-propanedithiol (109-80-8) + Isophthalaldehyde (626-19-7) → 1,3-Bis(1,3-dithian-2-yl)benzol (41047-90-9)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h;	99%

Isophthalaldehyde (626-19-7) + (4R,5R)-1,3-dioxolane-4,5-dicarbohydrazide (1380440-07-2) → C26H24N8O8

Conditions	Yield
With acetic acid In methanol for 7h; Reflux;	99%

Isophthalaldehyde (626-19-7) + (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazide (1380440-08-3) → C26H24N8O8

Conditions	Yield
With acetic acid In methanol for 7h; Reflux;	99%

triethylsilane (617-86-7) + Isophthalaldehyde (626-19-7) → 1,3-bis(((triethylsilyl)oxy)methyl)benzene (1376253-63-2)

Conditions	Yield
With C42H43BN3P2(1+)*C18HBF15(1-) In chloroform at 40℃; for 1h; Reagent/catalyst; Temperature; Schlenk technique; Glovebox;	99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In toluene at 50℃; for 15h; Inert atmosphere;	77%
With rhenium(I) pentacarbonyl chloride for 4h; Photolysis; Vacuum;

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) + Isophthalaldehyde (626-19-7) → (2E,2′E)-3,3′-(1,3-phenylene)bis(1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one)

Conditions	Yield
With potassium hydroxide In ethanol at 0 - 20℃; Inert atmosphere;	99%

Isophthalaldehyde (626-19-7) + 1H-indole-5-carbohydrazide → C26H20N6O2

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide for 0.116667h; Solvent; Microwave irradiation; Reflux;	99%

Isophthalaldehyde (626-19-7) + N,N-diethylethylenediamine (100-36-7) → bis[diethylaminoethyl]-N,N‘-m-xylylendiimine

Conditions	Yield
In ethanol	99%

Isophthalaldehyde (626-19-7) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → bis[diisopropylaminoethyl]-N,N‘-m-xylylenediimine

Conditions	Yield
In ethanol	99%

Isophthalaldehyde (626-19-7) + N,N-dibenzylhydrazine (5802-60-8) → 1,3-bis[(E)-(2,2-dibenzylhydrazineylidene)methyl]benzene

Conditions	Yield
With magnesium sulfate In dichloromethane at 40℃; for 20h; Inert atmosphere;	99%

Isophthalaldehyde (626-19-7) + (+/-)-3-exo-indol-3-yl-bicyclo-<2.2.1>-heptane-2-endo-amine → N,N'-bis(3-endo-indol-3-yl-bicyclo<2.2.1>hept-2-exo-yl)-benzene-1,3-dimethanimine (157379-36-7)

Conditions	Yield
With 4 A molecular sieve In chloroform for 48h; Ambient temperature;	98%

Isophthalaldehyde (626-19-7) → 3-((hydroxyimino)methyl)benzaldoxime (46133-07-7)

Conditions	Yield
With hydroxylamine hydrochloride	98%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol at 0℃; for 1h;	96%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 0 - 60℃; for 8h;	85%

Isophthalaldehyde (626-19-7) + (R)-2-methylpropane-2-sulfinamide (196929-78-9) → 2-Methyl-propane-2-sulfinic acid 1-(3-{[(E)-(R)-2-methyl-propane-2-sulfinylimino]-methyl}-phenyl)-meth-(E)-ylideneamide

Conditions	Yield
With copper(II) sulfate In dichloromethane at 22℃; for 18h;	98%

1,3-dimethylbarbituric acid (769-42-6) + Isophthalaldehyde (626-19-7) → 5,5'-(1,3-phenylenebis(methanylylidene))bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione)

Conditions	Yield
With sulfuric acid-modified polyethyleneglycol-6000 In neat (no solvent) at 70℃; for 0.0333333h; Knoevenagel Condensation; Green chemistry;	98%
With sulfuric acid In acetic acid Heating;	94%

Upstream product

• 54125-02-9 danishefsky's diene 
• 488081-87-4 3-[(phenylimino)methyl]benzaldehyde 
• 108-38-3 m-xylene 
• 66753-58-0 1,1'-bis(pyridinium)-1,3-phenyldimethylene dibromide 
• 64-17-5 ethanol 
• 36323-28-1 α,α,α',α'-tetrabromo-m-xylene 
• 583-52-8 potassium oxalate 
• 1477-55-0 1,3-di(aminomethyl)benzene 
• 82292-40-8 N₁,N₃-di-tert-butylisophthalamide 
• 108-57-6 1,3-divinylbenzene 
• 1374992-73-0 C₉H₈O₂ 
• 19955-99-8 3-ethenylbenzaldehyde 
• 619-21-6 m-formylphenyl benzoic acid 
• 64-18-6 formic acid 

Downstream Products

• 16832-59-0 1,3-bis(oxiran-2-yl)benzene 
• 21915-02-6 1,3-bis((E)-2-(pyridin-4-yl)vinyl)benzene 
• 2695-65-0 1,3-bis-(4-nitro-trans-styryl)-benzene 
• 120613-22-1 1,3-bis-[bis-(4-ethoxycarbonyl-3,5-dimethyl-pyrrol-2-yl)-methyl]-benzene 
• 3316-22-1 1,3-bis-(2-nitropropenyl)benzene 
• 3316-22-1 1.3-Bis-(2-nitro-propenyl)-benzol 
• 1752-07-4 opt.-inakt. 1,3-Bis-(1-hydroxy-isopentyl)-benzol 
• 71189-76-9 2-(3-{cyano[(trimethylsilyl)oxy]methyl}phenyl)-2-[(trimethylsilyl)oxy]acetonitrile 
• 37710-81-9 1,3-phenylene-3,3′-bis(2-propenoic) acid 
• 74815-17-1 3-Formyl cinnamic acid 
• 2695-64-9 4'-Nitro-trans-stilben-3-carbaldehyd 
• 2695-72-9 2',4'-Dinitro-trans-stilben-3-carbaldehyd 
• 2695-76-3 1,3-Bis-(2-Cyan-4-nitro-trans-styryl)-benzol 
• 2695-75-2 3'-Formyl-4-nitro-trans-stilben-2-carbonitril 

Relevant articles and documents

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.

Selective TEMPO-Oxidation of Alcohols to Aldehydes in Alternative Organic Solvents

The TEMPO-catalyzed oxidation of alcohols to aldehydes has emerged to one of the most widely applied methodologies for such transformations. Advantages are the utilization of sodium hypochlorite, a component of household bleach, as an oxidation agent and the use of water as a co-solvent. However, a major drawback of this method is the often occurring strict limitation to use dichloromethane as an organic solvent in a biphasic reaction medium with water. Previous studies show that dichloromethane cannot easily be substituted because a decrease of selectivity or inhibition of the reaction is observed by using alternative organic solvents. Thus, up to now, only a few examples are known in which after a tedious optimization of the reaction dichloromethane could be replaced. In order to overcome the current limitations, we were interested in finding a TEMPO-oxidation method in alternative organic solvents, which is applicable for various alcohol oxidations. As a result, we found a method for N-oxyl radical-catalyzed oxidation using sodium hypochlorite as an oxidation agent in nitriles as an organic solvent component instead of dichloromethane. Besides the oxidation of aromatic primary alcohols also aliphatic primary alcohols, secondary alcohols as well as dialcohols were successfully converted when using this method, showing high selectivity towards the carbonyl compound and low amounts of the acid side-product.