1497-49-0

Usage

Uses

Used in Chemical Synthesis:
Glutacondianil hydrochloride is used as a reagent in the synthesis of novel vinylsulfone cyanine dyes. These dyes are specifically designed for labeling biomolecules and metabolites, which is crucial in various research and diagnostic applications.
Used in Biotechnology and Research:
In the biotechnology and research fields, Glutacondianil hydrochloride plays a significant role in the development of new dyes that can effectively label and track biomolecules. This helps researchers gain a better understanding of the molecular interactions and mechanisms within biological systems.
Used in Pharmaceutical Industry:
The pharmaceutical industry may also benefit from the use of Glutacondianil hydrochloride in the synthesis of dyes for various diagnostic and therapeutic applications. These dyes can be used to label and track drug molecules, enabling the development of more effective and targeted treatments.

InChI:InChI=1/C17H16N2.ClH/c1-4-10-16(11-5-1)18-14-8-3-9-15-19-17-12-6-2-7-13-17;/h1-15,18H;1H/b9-3+,14-8+,19-15+;

Synthetic route

pyridine (110-86-1) + perchloro-2-cyclopentene-1-one (2514-52-5) + aniline (62-53-3) → 2,4,4,5,5-Pentachloro-3-(phenylamino)-2-cyclopenten-1-one (61108-14-3) + 2,4,4,5,5-Pentachloro-3-amino-2-cyclopenten-1-one (60592-72-5) + glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
In 1,4-dioxane for 4h;	A 31% B 12.9% C 37.5%

pyridine (110-86-1) + N-phenyl-benzimidoyl chloride (4903-36-0) + aniline (62-53-3) → glutacondianil hydrochloride (1497-49-0)

pyridine (110-86-1) + aniline (62-53-3) + p-toluenesulfonyl chloride (98-59-9) → glutacondianil hydrochloride (1497-49-0)

pyridine (110-86-1) + aniline (62-53-3) → glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
With phosphorus pentachloride

5-(2,4-dinitro-anilino)-penta-2,4-dienal (53405-99-5) → glutacondianil hydrochloride (1497-49-0) + 2,4-Dinitroanilin (97-02-9)

Conditions	Yield
With hydrogenchloride; water; acetic acid Abfiltrieren vom 2.4-Dinitro-anilin, Zufuegen Anilin zum Filtrat;

1-(2,4-dinitrophenyl)-pyridinium chloride (4185-69-7) + aniline (62-53-3) → glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
With ethanol

pentenedial; sodium enolate (1593-50-6) + aniline (62-53-3) → glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
With hydrogenchloride

malondialdehyde bis(diethyl acetal) (122-31-6) + trimethylsiloxyethene (6213-94-1) + aniline hydrochloride (142-04-1) → 1,1,3,5,7,7-hexaethoxy-heptane (60584-64-7) + glutacondianil hydrochloride (1497-49-0) + 3,5,7,7-tetraethoxy-1-heptanal (102525-97-3)

Conditions	Yield
With zinc(II) chloride 1.) ethyl acetate, 40 deg C, 0.25 hr., 2.) ethanol, 20 deg C, 4 hrs.; Yield given. Multistep reaction. Yields of byproduct given;

aniline (62-53-3) + 3'-Cyano-5'-nitro-[1,2']bipyridinyl-1-ylium; chloride → glutacondianil hydrochloride (1497-49-0) + 2-amino-3-cyano-5-nitropyridine (31309-11-2)

Conditions	Yield
With hydrogenchloride 1.) H2O, reflux, 5 min, 2.) H2O, pH=1; Yield given. Multistep reaction. Yields of byproduct given;

pyridine (110-86-1) + (+-)-2-<1-chloro-ethyl>-4-propyl-anisole → glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / acetonitrile / 3.5 h / 15 °C 2: 2.) HCl / 1.) H2O, reflux, 5 min, 2.) H2O, pH=1 View Scheme

5-(2,4-dinitro-anilino)-penta-2,4-dienal (53405-99-5) → glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; hydrogen chloride / 100 °C / im Rohr 2: alcohol View Scheme

1-(2,4-dinitrophenyl)-pyridinium chloride (4185-69-7) → glutacondianil hydrochloride (1497-49-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: alkali; water 2: glacial acetic acid; concentrated hydrochloric acid; water / Abfiltrieren vom 2.4-Dinitro-anilin, Zufuegen Anilin zum Filtrat View Scheme

1,5-dioxaspiro[5.5]undecane-2,4-dione (1658-27-1) + glutacondianil hydrochloride (1497-49-0) → C23H26O8 (455329-62-1)

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 8h;	97%
With triethylamine In isopropyl alcohol at 20 - 30℃; for 3h;

2,4,5,7-tetranitro-9H-fluorene (29210-71-7) + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → N-phenyl-N-[(1E,3E)-5-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)penta-1,3-dienyl]acetamide (1440539-16-1)

Conditions	Yield
Reflux;	96%

acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) + 1,1,2-trimethyl-3-(6-carboxylatohexyl)benzindolium (181933-98-2) → C34H36N2O3

Conditions	Yield
at 100℃; for 1h; Inert atmosphere;	95%

1-ethyl-2,3,3-trimethyl-3H-indol-1-ium bromide + glutacondianil hydrochloride (1497-49-0) → C31H37N2(1+)*Br(1-)

Conditions	Yield
With sodium acetate; acetic anhydride at 60℃; for 2h;	95%

3,4-dihydro-1-ethyl-2,1-benzothiazin-4-one-7-carboxylic acid 2,2-dioxide (577971-77-8) + glutacondianil hydrochloride (1497-49-0) → C27H24N2O10S2

Conditions	Yield
Stage #1: 3,4-dihydro-1-ethyl-2,1-benzothiazin-4-one-7-carboxylic acid 2,2-dioxide; glutacondianil hydrochloride With triethylamine In ethanol at 20℃; Stage #2: With acetic acid at 0℃;	92%

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → 1,3,3-trimethyl-2-(6-(N-phenylacetamido)hexa-1,3,5-trienyl)-3H-indolium iodide (24136-79-6)

Conditions	Yield
With pyridine at 25℃; for 0.666667h; Inert atmosphere;	90%

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate (63149-24-6) + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → 4-(1,1-dimethyl-2-(6-(N-phenylacetamido)hexa-1,3,5-trien-1-yl)-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate (1351043-94-1, 63450-66-8)

Conditions	Yield
at 100℃; for 1h; Inert atmosphere;	88%
for 0.5h; Reflux; Inert atmosphere;	86.1%
With acetic acid at 120℃; for 3h;	42%
In acetic acid Heating;
With triethylamine Heating;

glutacondianil hydrochloride (1497-49-0) + 1-(2-hydroxycarbonylethyl)-2,3,3-trimethylbenzo[e]indoleninium bromide → cypate

Conditions	Yield
Stage #1: glutacondianil hydrochloride With acetic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 5℃; for 3h; Stage #2: 1-(2-hydroxycarbonylethyl)-2,3,3-trimethylbenzo[e]indoleninium bromide With sodium acetate In dichloromethane; water; acetonitrile for 18h; Reflux; Darkness;	88%

C18H23NO2 + glutacondianil hydrochloride (1497-49-0) → C41H49N2O4(1+)*I(1-)

Conditions	Yield
Stage #1: C18H23NO2; glutacondianil hydrochloride With acetic anhydride; triethylamine In dichloromethane at 20 - 40℃; for 15h; Stage #2: With sodium iodide In dichloromethane for 2h;	86%

glutacondianil hydrochloride (1497-49-0) + 5-carboxy-1-(δ-sulfobutyl)-2,3,3-trimethyl-3H-indolium betaine → bis-1,1‘-(4-sulfobutyl)indotricarbocyanine-5,5‘-dicarboxylic acid sodium salt

Conditions	Yield
With sodium acetate; acetic anhydride; acetic acid at 120℃; for 0.75h; Inert atmosphere; Schlenk technique;	85%

tetramethyl ammoniumhydroxide (75-59-2) + glutacondianil hydrochloride (1497-49-0) + malononitrile (109-77-3) → tetramethylammonium 1,1,7,7-tetracyano-1,3,5-heptatrienide (98826-84-7)

Conditions	Yield
In N,N-dimethyl acetamide for 1h;	84%

(1r,3r,5r,7r)-spiro-[adamantane-2,2′-[1,3]dioxane]-4′,6′-dione (455329-56-3) + glutacondianil hydrochloride (1497-49-0) → C31H34O8 (455329-65-4)

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 5h;	84%

1-(4-sulfophenyl)-pyrazol-5-on-3-carboxylic acid (51307-71-2) + glutacondianil hydrochloride (1497-49-0) → 4-(3-carboxy-4-{5-[3-carboxy-5-hydroxy-1-(4-sulfonatophenyl)-1H-pyrazol-4-yl]penta-2,4-dien-1-ylidene}-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzene-1-sulfonate dipotassium salt

Conditions	Yield
Stage #1: 1-(4-sulfophenyl)-pyrazol-5-on-3-carboxylic acid; glutacondianil hydrochloride In N,N-dimethyl-formamide for 1h; Reflux; Stage #2: With triethylamine In N,N-dimethyl-formamide at 45 - 60℃; for 3h; Stage #3: With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; for 1.5h; Concentration; Reagent/catalyst; Solvent;	84%

2,3,3-trimethyl-1-(ethyl)-3H-benzindolinium-5,7-disulfonate (791576-54-0) + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → C30H30N2O7S2 (751480-26-9, 761394-10-9)

Conditions	Yield
at 100℃; for 1h;	83%

1-methyl-2-phenylindolizine (1019-12-1) + glutacondianil hydrochloride (1497-49-0) → (Z)-1-methyl-3-((2E,4E)-5-(1-methyl-2-phenylindolizin-3-yl)-penta-2,4-dien-1-ylidene)-2-phenyl-3H-indolizin-4-ium perchlorate

Conditions	Yield
Stage #1: 1-methyl-2-phenylindolizine With perchloric acid; acetic anhydride at 20℃; for 0.0833333h; Stage #2: glutacondianil hydrochloride With triethylamine at 20℃; for 24h;	82%

m-dPEG3-1,1,2-trimethylbenzoindolium bromide + glutacondianil hydrochloride (1497-49-0) → m-dPEG3-1,1-dimethyl-N-phenylacetamidohexa-1,3,5-trienylbenzoindolium bromide

Conditions	Yield
With acetic anhydride at 10℃; for 0.5h; Inert atmosphere;	81%

1,3-dimethylbarbituric acid (769-42-6) + glutacondianil hydrochloride (1497-49-0) → 5-<5-(hexahydro-1,3-dimethyl-2,4,6-trioxo-5-pyrimidinyl)-2,4-pentadienylidene>-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione (78902-42-8)

Conditions	Yield
With C6H15N*C25H31N3O5S2 In DMF (N,N-dimethyl-formamide) at 20℃; for 2h;	80%

glutacondianil hydrochloride (1497-49-0) + 1-ethyl-2-methylbenz[cd]indolium perchlorate → 2-<7-Ethylbenzoindol-2(1H)-ylidene)-2,4,6-heptatrienyl>-1-ethylbenzoindolium perchlorate

Conditions	Yield
With pyridine In acetic anhydride for 0.5h; Heating;	77%

4-(1-methylindolizin-2-yl)benzonitrile + glutacondianil hydrochloride (1497-49-0) → (Z)-2-(4-cyanophenyl)-3-((2E,4E)-5-(2-(4-cyanophenyl)-1-methylindolizin-3-yl)penta-2,4-dien-1-ylidene)-1-methyl-3H-indolizin-4-ium perchlorate

Conditions	Yield
Stage #1: 4-(1-methylindolizin-2-yl)benzonitrile With perchloric acid; acetic anhydride at 20℃; for 0.0833333h; Stage #2: glutacondianil hydrochloride With triethylamine at 20℃; for 24h;	77%

C8H9BF2N2O4 (1035092-82-0) + glutacondianil hydrochloride (1497-49-0) + triethylamine (121-44-8) → C6H15N*C21H19B2F4N4O8(1-)*H(1+)

Conditions	Yield
With acetic anhydride at 75℃; for 0.5h;	76%

glutacondianil hydrochloride (1497-49-0) + acetic acid (64-19-7) + 1-Ethyl-2,3,3-Trimethylindolenineninium 5-Sulfone (146368-07-2) → C26H28N2O4S (1251915-09-9)

Conditions	Yield
at 100℃; for 1h;	76%

glutacondianil hydrochloride (1497-49-0) + 5-acetamido-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide → 2-[5-(1-ethyl-1,3-dihydro-5-acetylamino-3,3-dimethyl-2H-indol-2-ylidene)-1,3,5-heptatrien-1-yl]-1-ethyl-5-acetylamino-3,3-dimethyl-3H-indolium iodide (1618132-21-0)

Conditions	Yield
Stage #1: glutacondianil hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane; acetic anhydride at 20℃; for 3h; Stage #2: 5-acetamido-1-ethyl-2,3,3-trimethyl-3H-indol-1-ium iodide With sodium acetate In methanol; acetic anhydride for 8h; Reflux;	76%

2,3,3-trimethyl-1-(pent-4-yn-1-yl)-3H-indol-1-ium iodide (1354932-44-7) + glutacondianil hydrochloride (1497-49-0) → C37H41N2(1+)*ClO4(1-)

Conditions	Yield
Stage #1: 2,3,3-trimethyl-1-(pent-4-yn-1-yl)-3H-indol-1-ium iodide; glutacondianil hydrochloride With sodium acetate; acetic acid at 50℃; for 3h; Stage #2: With perchloric acid In water	75%

1,2,3,3-tetramethyl-5-iodo-3H-indolium iodide + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → C25H26IN2O(1+)*I(1-) (1259949-14-8)

Conditions	Yield
With pyridine at 25℃; for 1h; Inert atmosphere;	74%

bis(2,2,3,3,4,4,5,5-octafluoropentyl) 4,5-dinitro-9H-fluorene-2,7-disulfonate + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → bis(2,2,3,3,4,4,5,5-octafluoropentyl) 4,5-dinitro-9-[(2E,4E)-5-(N-phenylacetamido)penta-2,4-dien-1-ylidene]-9H-fluorene-2,7-disulfonate

Conditions	Yield
Heating;	71%

glutacondianil hydrochloride (1497-49-0) + 2,7-diphenylcyclopenteno[1,2-c]pyrylium perchlorate + orthoformic acid triethyl ester (122-51-0) → 1,3-Diphenyl-5-<-5-<(1,3-diphenylcyclopenteno<3,2:c>pyran-5-yl)-2,4-pentadienylidene>>-cyclopentapyrylium Perchlorate

Conditions	Yield
With sodium acetate In acetic acid at 120℃; for 0.5h;	70%

C10H14O6 (871313-86-9) + 1,5-dioxaspiro[5.5]undecane-2,4-dione (1658-27-1) + glutacondianil hydrochloride (1497-49-0) → C24H28O10

Conditions	Yield
Stage #1: 1,5-dioxaspiro[5.5]undecane-2,4-dione; glutacondianil hydrochloride With triethylamine In isopropyl alcohol at 30℃; for 48h; Stage #2: C10H14O6 In isopropyl alcohol at 35℃; for 3h;	66%

C17H27N2(1+)*I(1-) (1355342-74-3) + acetic anhydride (108-24-7) + glutacondianil hydrochloride (1497-49-0) → C30H38N3O(1+)*Cl(1-) (1355342-75-4)

Conditions	Yield
With acetic acid for 1h; Reflux; Inert atmosphere;	65%

bis(2,2,3,3,4,4,5,5-octafluoropentyl) 4,5-dinitro-9H-fluorene-2,7-disulfonate + glutacondianil hydrochloride (1497-49-0) → triethylammonium 9-{(1E,3E)-5-[4,5-dinitro-2,7-bis(2,2,3,3,4,4,5,5-octafluoropentyloxysulfonyl)-9H-fluoren-9-ylidene]penta-1,3-dien-1-yl}-4,5-dinitro-2,7-bis(2,2,3,3,4,4,5,5-octafluoropentyloxysulfonyl)-9H-fluoren-9-ide

Conditions	Yield
With triethylamine In acetic anhydride for 0.05h; Reflux;	65%

cycl-isopropylidene malonate (2033-24-1) + glutacondianil hydrochloride (1497-49-0) → 5-[5-(6-hydroxy-2,2-dimethyl-4-oxo-1,3-dioxin-5-yl)-2,4-pentadienylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (251984-72-2)

Conditions	Yield
With triethylamine In methanol at 20℃; for 3h;	63.6%

Upstream product

• 110-86-1 pyridine 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 62-53-3 aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 53405-99-5 5-(2,4-dinitro-anilino)-penta-2,4-dienal 
• 4185-69-7 1-(2,4-dinitrophenyl)-pyridinium chloride 
• 1593-50-6 pentenedial; sodium enolate 
• 2514-52-5 perchloro-2-cyclopentene-1-one 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 6213-94-1 trimethylsiloxyethene 
• 142-04-1 aniline hydrochloride 
• 63383-46-0 1-(trimethylsiloxy)-1,3-butadiene 

Downstream Products

• 98826-84-7 tetramethylammonium 1,1,7,7-tetracyanohepta-1,3,5-trienide 
• 147-82-0 2,4,6-tribromoaniline 
• 62-53-3 aniline 
• 913198-94-4 6-[(2E)-4,5,6,7-tetrafluoro-3-methyl-2-[(2E,4E,6E)-6-(phenylimino)hexa-2,4-dienylidene]-3-(4-sulfobutyl)-2,3-dihydro-1H-indol-1-yl]hexanoic acid 
• 1144107-84-5 C₂₉H₂₉N₂O⁽¹⁺⁾*I^(1-) 
• 1202554-84-4 C₂₈H₂₅N₂O⁽¹⁺⁾*I^(1-) 
• 1164241-01-3 2-(6-anilinohexatrienyl)-1-5-(5-carboxypentyl)-3,3-dimethyl-5-sulfoindolinium inner salt 
• 751480-26-9 C₃₀H₃₀N₂O₇S₂ 
• 1383274-62-1 1-(5-carboxypentyl)-3-methyl-2-((1E,3E,5E)-6-phenylamino-hexa-1,3,5-trienyl)-5-sulfo-3-(3-sulfopropyl)-3H-indolium 
• 24136-79-6 1,3,3-trimethyl-2-(6-(N-phenylacetamido)hexa-1,3,5-trienyl)-3H-indolium iodide 
• 1251915-09-9 C₂₆H₂₈N₂O₄S 

Relevant academic research and scientific papers

ω-substituted-2-(polyenamino)- or annelated nitropyridines from 1-(3- cyano-5-nitropyridyl-2)-pyridinium salts

The interaction of 1-(3-cyano-5-nitropyridyl-2)pyridinium salts with different nucleophilic reagents yields 2-substituted 3-cyano-5-nitropyridine including 2-polyenamino derivatives. 3-Nitro-5(H)-5-iminodipyridol[1,2- a:3,2-c]pyrimidine hydrochloride is synthesized by the react of 2-chloro-3- cyano-5-nitropyridine with 2-aminopyridine.

CHEMISTRY OF ENOL ETHERS. AMINOFORMYLATION OF SILYLENOL AND SILYLDIENOL ETHERS

The reaction of 1-trimethylsilyloxy-1-alkenes and 1-trimethylsilyloxy-1,3-butadienes with an aminoformylating complex and subsequent treatment by aniline hydrochloride gave tri- and pentamethine salts, namely, the hydrochloride salts of the dianils of malonic and glutaconic aldehydes.

CHEMISTRY OF ENOL ETHERS. LXXI. CONDENSATION OF THE TETRAETHYL ACETAL OF MALONIC ALDEHYDE WITH ENOL SILYL ETHERS

The action of trimethylsilyl ethers on the tetraethyl acetal of malonic aldehyde gave derivatives of 1,5- and 1,7-diketones and dialdehydes.The dialdehyde derivatives readily react with the hydrochloride salt of aniline in ethanol to form alkyl-substituted penta- and heptamethine salts.

REACTIONS OF PERCHLORO-2-CYCLOPENTEN-1-ONE AND PERCHLORO-4-CYCLPENTENE-1,3-DIONE WITH PYRIDINE AND QUINOLINE DERIVATIVES

By the reaction of perchloro-2-cyclopenten-1-one with pyridine and quinoline derivatives the corresponding onium salts of 2,4,4,5,5-pentachloro-3-hydroxy-2-cyclopentenone were obtained.The analogous reactions of perchloro-4-cyclopentene-1,3-dione lead either to onium salts of 2,2,5-trichloro-4-hydroxy-4-cyclopentene-1,3-dione or to betaines.The effect of the nature of the solvent and the structure of the amine on the reaction path was examined.