1497-49-0

Basic information

• Product Name: Glutacondianil hydrochloride
• Synonyms: Pentadienal diethylene aniline hydrochloride;N-((2E,4E)-5-(Phenylamino)penta-2,4-dien-1-ylidene)aniline hydrochloride;n-[5-(phenylamino)-2,4-pentadienylidene]-benzenaminmonohydrochloride;N-[5-(Phenylamino)-2,4-pentadienylidene]aniline hydrochloride;N-[5-(PHENYLAMINO)-2,4-PENTADIENYLIDENE]ANILINE MONOHYDROCHLORIDE;N-(5-ANILINO-2,4-PENTADIENYLIDENE)ANILINE HCL SALT;N-(5-ANILINO-2,4-PENTADIENYLIDENE)ANILINE HYDROCHLORIDE;1,5-PENTAMETHINEDIANILIDE-HYDROCHLORIDE
• CAS NO: 1497-49-0
• Molecular Formula: C₁₇H₁₆N₂*ClH
• Molecular Weight: 284.78
• EINECS: 216-094-3
• Product Categories: P;Stains and Dyes;Stains&Dyes, A to
• Mol File: 1497-49-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 152 °C
• Boiling Point: 402.3 °C at 760 mmHg
• Flash Point: 197.1 °C
• Appearance: Bordeaux to purple/Powder
• Density: 0.95 g/cm³
• Vapor Pressure: 8.36E-08mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• Water Solubility: Soluble in methanol. Insoluble in water..
• Sensitive: Hygroscopic
• BRN: 3916924
• CAS DataBase Reference: Glutacondianil hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Glutacondianil hydrochloride(1497-49-0)
• EPA Substance Registry System: Glutacondianil hydrochloride(1497-49-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-37/39-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1497-49-0(Hazardous Substances Data)

Usage

Chemical Properties

bordeaux to purple powder

Uses

Glutacondianil Hydrochloride is used as a reagent in the synthesis of novel vinylsulfone cyanine dyes used for labelling biomolecules. Dyes and metabolites.

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 
• 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 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 6213-94-1 trimethylsiloxyethene 
• 142-04-1 aniline hydrochloride 
• 63383-46-0 1-(trimethylsiloxy)-1,3-butadiene 
• 2514-52-5 perchloro-2-cyclopentene-1-one 
• 4903-36-0 N-phenyl-benzimidoyl chloride 

Downstream Products

• 147-82-0 2,4,6-tribromoaniline 
• 62-53-3 aniline 
• 712273-65-9 2-{3-cyano-4-[6-(N-formylanilino)-trans,trans-1,3,5-hexatrienyl]-5,5-dimethyl-2,5-dihydrofuran-2-ylidene}propanedinitrile 
• 1144107-84-5 C₂₉H₂₉N₂O⁽¹⁺⁾*I^(1-) 
• 1202554-84-4 C₂₈H₂₅N₂O⁽¹⁺⁾*I^(1-) 
• 1353546-77-6 1-(5-carboxypentyl)-3,3-dimethyl-2-((1E,3E,5E)-6-(N-phenylacetamido)hexa-1,3,5-trienyl)-5-sulfo-3H-indolium 
• 751480-26-9 C₃₀H₃₀N₂O₇S₂ 
• 1440539-19-4 1,3-diphenyl-2-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]-2,3-dihydro-1H-benzimidazole 
• 1440539-22-9 (2E)-1-benzyl-2-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]-1,2-di-hydrobenzo[cd]indole 
• 1440539-25-2 2,6-diphenyl-4-[(2E,4E)-6-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)hexa-2,4-dienylidene]-4H-pyran 
• 1440539-16-1 N-phenyl-N-[(1E,3E)-5-(2,4,5,7-tetranitro-9H-fluoren-9-ylidene)penta-1,3-dienyl]acetamide 

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