509-34-2

Basic information

• Product Name: Solvent Red 49
• Synonyms: SOLVENT RED 49;RHODAMINE B STEARATE;RHODAMINE B BASE;RHODAMINE B BASE, ALCOHOL SOLUBLE;9’-(9H)xanthen]-3-one,3’,6’-bis(diethylamino)-Spiro[isobenzofuran-1(3H);9’-[9h]xanthen]-3-one,3’,6’-bis(diethylamino)-spiro[isobenzofuran-1(3h;abcolrhodaminebbase;CI 45170.1
• CAS NO: 509-34-2
• Molecular Formula: C₂₈H₃₀N₂O₃
• Molecular Weight: 442.55
• EINECS: 208-096-8
• Product Categories: Organics;Solvent Dyestuff
• Mol File: 509-34-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 553.14°C (rough estimate)
• Flash Point: 339.1 °C
• Appearance: Lilac/Fine Crystalline Powder
• Density: 1.1536 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5800 (estimate)
• PKA: 5.80±0.20(Predicted)
• Water Solubility: 4.83g/L at 30℃
• CAS DataBase Reference: Solvent Red 49(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Red 49(509-34-2)
• EPA Substance Registry System: Solvent Red 49(509-34-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 509-34-2(Hazardous Substances Data)

Usage

Chemical Properties

LILAC FINE CRYSTALLINE POWDER

Uses

Rhodamine B base is a fluorescent biological staining dye. Rhodamine B base is also used as a laser dye, tunable around 610 nm with the fluorescence yield being temperature dependent. Dyes and metabolites, Environmental Testing

Purification Methods

Major impurities are partially dealkylated compounds not removed by recrystallisation. Purify the dye by chromatography, using ethyl acetate/isopropanol/ammonia (conc)(9:7:4, RF 0.75 on Kieselgel G). It has also been crystallised from a concentrated solution in MeOH by slow addition of dry diethyl ether; or from EtOH containing a drop of conc HCl by slow addition of ten volumes of dry diethyl ether. The solid is washed with ether and air dried. The dried material has also been extracted with *benzene to remove oil-soluble material prior to recrystallisation. Store it in the dark. [Beilstein 18 II 486, 18 III/IV 8246, 19/8 V 669.]

Properties and Applications

TEST ITEMS SPECIFICATION APPEARANCE PINK POWDER SHADE BLUISH HEAT RESISTANCE 180 °C min LIGHT FASTNESS 4-5 ACID RESISTANCE 4 ALKALI RESISTANCE 5 WATER RESISTANCE 5 DENSITY 1.30 g/cm 3 RESIDUE ON 80 MESH 5.0% max WATER SOLUBLE 1.0% max VOLATITE 105 °C 1.0% max TINTING STRENGTH 100-105 %

TEST ITEMS

SPECIFICATION

APPEARANCE

PINK POWDER

SHADE

BLUISH

HEAT RESISTANCE

180 °C min

ACID RESISTANCE

4

ALKALI RESISTANCE

5

WATER RESISTANCE

5

RESIDUE ON 80 MESH

5.0% max

WATER SOLUBLE

1.0% max

VOLATITE 105 °C

1.0% max

TINTING STRENGTH

100-105 %

Synthetic route

rhodamine B (81-88-9) → rhodamine B (509-34-2)

Conditions	Yield
With sodium hydroxide In water for 2h; Inert atmosphere;	94%
With sodium hydroxide In water	90%
With sodium hydroxide	90.2%
With sodium hydroxide In ethyl acetate

rhodamine B → rhodamine B (509-34-2)

Conditions	Yield
With sodium hydroxide In ethyl acetate	93%

phthalonic acid (528-46-1) + 3-diethylaminophenol (91-68-9) → rhodamine B (509-34-2)

Conditions	Yield
With sulfuric acid at 180 - 190℃;
at 180℃;

2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) + 3-diethylaminophenol (91-68-9) → rhodamine B (509-34-2)

Conditions	Yield
With sulfuric acid
With sulfuric acid

rhodamine B (3375-25-5) → rhodamine B (509-34-2)

Conditions	Yield
erythromycin In dimethyl sulfoxide Rate constant; various solvents;
In chloroform at 25 - 50℃; Equilibrium constant; Rate constant; effect of erythromycin A;
In ethanol at 25℃; Equilibrium constant; Thermodynamic data; other temperatures; other solvents;
In methanol at 24.9℃; under 735.8 Torr; Equilibrium constant; var. solvents and pressure;
In ethanol Equilibrium constant;

diethylamine (109-89-7) + 6-chloro-3-diethylamino-fluorane → rhodamine B (509-34-2)

3.6-dichloro-fluorane + hydrochloride of diethylamine → rhodamine B (509-34-2)

Conditions	Yield
With ethanol; sodium acetate at 200 - 220℃; im Autoklaven;

rhodamine B (1118784-85-2) → rhodamine B (509-34-2)

Conditions	Yield
With sodium hydroxide

rhodamine B (509-34-2) → N-(9-(2-(chlorocarbonyl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium chloride

Conditions	Yield
With trichlorophosphate In dichloromethane for 3h; Reflux; Inert atmosphere;	100%
With trichlorophosphate In dichloromethane for 4h; Heating;
With trichlorophosphate In dichloromethane for 4h; Reflux;

rhodamine B (509-34-2) + 4-Hydroxybenzophenone (1137-42-4) → C28H30O3N2*C13H10O2

Conditions	Yield
In acetonitrile at 20℃; for 24h;	98%

piperazine (110-85-0) + rhodamine B (509-34-2) → N‐(6‐(diethylamino)‐9‐(2‐(piperazine‐1‐carbonyl)phenyl)‐3H-xanthen‐3‐ylidene)‐N‐ethylethanaminium chloride

Conditions	Yield
Stage #1: piperazine With trimethylaluminum In dichloromethane; toluene at 20℃; for 1h; Stage #2: rhodamine B In dichloromethane; toluene for 1h; Inert atmosphere; Microwave irradiation;	98%
Stage #1: piperazine With trimethylaluminum In dichloromethane; toluene for 1h; Inert atmosphere; Stage #2: rhodamine B In dichloromethane; toluene for 24h; Inert atmosphere; Reflux;	56.8%
Stage #1: piperazine With trimethylaluminum In dichloromethane; toluene at 20℃; for 1h; Inert atmosphere; Stage #2: rhodamine B In dichloromethane; toluene for 72h; Inert atmosphere; Reflux;	20%

ethyl bromoacetate (105-36-2) + rhodamine B (509-34-2) → ethylcarboxymethyl rhodamine B bromide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 90℃; for 1h;	98%

rhodamine B (509-34-2) + ethylenediamine (107-15-3) → rhodamine B ethylenediamine (950846-89-6)

Conditions	Yield
for 24h; Reflux;	95%
In ethanol for 12h; Heating;	77%
In ethanol for 12h; Reflux;	76%

Ethyl protocatechuate (3943-89-3) + rhodamine B (509-34-2) → C28H30O3N2*C9H10O4

Conditions	Yield
In acetonitrile at 20℃; for 2.5h;	93%

rhodamine B (509-34-2) + methylhydrazine (60-34-4) → C29H34N4O2 (1151831-71-8)

Conditions	Yield
In ethanol for 8h; Reflux;	91%

rhodamine B (509-34-2) → rhodamine hydroxamic acid

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 10h; Reflux;	91%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 25℃; for 2h;	75%
Stage #1: rhodamine B With trichlorophosphate In dichloromethane for 6h; Reflux; Stage #2: With hydroxylamine hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;	72%

rhodamine B (509-34-2) + Trimethylenediamine (109-76-2) → 2-(3-aminopropyl)-3',6'-bis(diethylamino)spiro[isoindoline-1,9'-xanthen]-3-one (1217892-39-1)

Conditions	Yield
In ethanol for 12h; Reflux;	90%

rhodamine B (509-34-2) + N,N-dimethylethylenediamine (108-00-9) → C32H40N4O2

Conditions	Yield
In ethanol for 12h; Reflux;	88%

rhodamine B (509-34-2) → rhodamine B hydrazide (74317-53-6)

Conditions	Yield
With hydrazine hydrate In ethanol at 120℃; for 8h;	85%
With hydrazine hydrate In ethanol at 20℃; for 0.5h; Reflux;	85%
With hydrazine hydrate In ethanol at 20℃; for 12.5h; Reflux;	85%

2,2',2''-triaminotriethylamine (4097-89-6) + rhodamine B (509-34-2) → rhodamine trisamine (956336-75-7)

Conditions	Yield
In ethanol for 73h; Inert atmosphere; Reflux;	83.1%
In ethanol for 36h; Inert atmosphere; Reflux;	83.1%
In ethanol for 36h; Inert atmosphere; Reflux;	77.6%

bis(nonafluorobutanesulfonyl)imide (39847-39-7) + rhodamine B (509-34-2) → C28H31N2O3(1+)*C8F18NO4S2(1-)

Conditions	Yield
In dichloromethane; acetone at 20℃; for 4h;	82%

N-methoxylamine hydrochloride (593-56-6) + rhodamine B (509-34-2) → C29H33N3O3

Conditions	Yield
Stage #1: rhodamine B With trichlorophosphate In 1,2-dichloro-ethane for 4h; Heating; Stage #2: N-methoxylamine hydrochloride With triethylamine In dichloromethane at 20℃; for 0.5h; Further stages.;	81%

rhodamine B (509-34-2) + N-Methyl-1,3-propanediamine (6291-84-5) → sMRh

Conditions	Yield
In ethanol at 85℃; for 48h;	80.3%

bis(3-aminopropyl)amine (56-18-8) + rhodamine B (509-34-2) → sDRh

Conditions	Yield
In ethanol at 85℃; for 72h;	76.7%

ethanolamine (141-43-5) + rhodamine B (509-34-2) → N-(rhodamine-B)lactam-ethanolamine (1119217-92-3)

Conditions	Yield
Stage #1: rhodamine B With p-toluenesulfonyl chloride In acetonitrile for 0.25h; Stage #2: With dmap In acetonitrile for 0.25h; Stage #3: ethanolamine In acetonitrile	71.5%
In ethanol Reflux; Inert atmosphere;	68%

piperazine (110-85-0) + rhodamine B (509-34-2) + trifluoroacetic acid (76-05-1) → N-(6-(diethylamino)-9-(2-(piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium 2,2,2-trifluoroacetate (1100365-01-2)

Conditions	Yield
Stage #1: piperazine; rhodamine B With trimethylaluminum In dichloromethane for 20h; Reflux; Stage #2: trifluoroacetic acid	71%

piperazine (110-85-0) + rhodamine B (509-34-2) → N-(6-(diethylamino)-9-(2-(piperazine-1-carbonyl)phenyl)-3H-xanthen-3-ylidene)-N-ethylethanaminium (608136-11-4)

Conditions	Yield
Stage #1: piperazine With trimethylaluminum In dichloromethane; toluene at 20℃; for 1h; Stage #2: rhodamine B In dichloromethane; toluene for 24h; Heating;	70%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide
With trimethylaluminum
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide Inert atmosphere;

2-(2-fluoroethoxy)ethyl 4-methylbenzenesulfonate (1118567-11-5) + rhodamine B (509-34-2) → 5-fluoro-3-oxapentyl ester of rhodamine B

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 2h; Reflux;	70%

rhodamine B (509-34-2) → rhodamine B thiospirolactone (111883-10-4)

Conditions	Yield
With Lawessons reagent In benzene for 4h; Heating;	65%

1H-benzimidazol-2-amine (934-32-7) + rhodamine B (509-34-2) → C35H35N5O2 (1363481-93-9)

Conditions	Yield
With trichlorophosphate In acetonitrile for 4h; Reflux;	62%

rhodamine B (509-34-2) + 4′-(4-amino-phenyl)-2,2′:6′,2′′-terpyridine (178265-65-1) → rhodamine B base

Conditions	Yield
With triethylamine; trichlorophosphate In 1,2-dichloro-ethane for 24h; Reflux;	61%

2-aminopyridine (504-29-0) + rhodamine B (509-34-2) → C33H34N4O2

Conditions	Yield
With trichlorophosphate at 70℃; for 0.5h;	60%

rhodamine B (509-34-2) → 3',6'-diamino-spiro[phthalan-1,9'-xanthen]-3-one (509-72-8)

Conditions	Yield
With trifluoroacetic acid In ethanol for 2.55h; Photolysis;	59%

rhodamine B (509-34-2) + 1,2-diamino-benzene (95-54-5) → C34H36N4O2 (1034863-51-8)

Conditions	Yield
Stage #1: rhodamine B With trichlorophosphate for 4h; Reflux; Stage #2: 1,2-diamino-benzene With triethylamine In acetonitrile at 20℃;	56%

dansyl hydrazine (33008-06-9) + rhodamine B (509-34-2) → C40H43N5O4S

Conditions	Yield
Stage #1: rhodamine B With trichlorophosphate Reflux; Stage #2: dansyl hydrazine With triethylamine In dichloromethane at 20℃; for 12h;	54%
Stage #1: rhodamine B With trichlorophosphate for 6h; Reflux; Stage #2: dansyl hydrazine With triethylamine In dichloromethane at 20℃; for 12h;	46%

piperazine (110-85-0) + rhodamine B (509-34-2) → C32H39N4O2(1+)*ClH*Cl(1-) (1177261-93-6)

Conditions	Yield
Stage #1: piperazine; rhodamine B With trimethylaluminum In hexane; dichloromethane for 24h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In hexane; dichloromethane; water Inert atmosphere;	52%

Upstream product

• 528-46-1 phthalonic acid 
• 91-68-9 3-diethylaminophenol 
• 5809-23-4 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon 
• 81-88-9 rhodamine B 
• 1118784-85-2 rhodamine B 
• 109-89-7 diethylamine 
• 3375-25-5 rhodamine B 

Downstream Products

• 38660-35-4 3',6'-bis(diethylamino)-2-phenylspiro<1H-isoindole-1,9'(9H)xanthene>-3(2H)-one 
• 950846-89-6 rhodamine B ethylenediamine 
• 1115867-62-3 rhodamine hydroxamic acid 
• 1177261-93-6 C₃₂H₃₉N₄O₂⁽¹⁺⁾*ClH*Cl^(1-) 
• 1118784-85-2 rhodamine B 
• 1034863-51-8 C₃₄H₃₆N₄O₂ 
• 509-72-8 3',6'-diamino-spiro[phthalan-1,9'-xanthen]-3-one 

Relevant articles and documents

ERYTHROMYCIN AS A SUPRAMOLECULAR RECEPTOR

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