989-38-8

Basic information

• Product Name: Basic Red 1
• Synonyms: Conbasic Red A;Dycosbasic Rhodamine 6GDN;Rhodamine 6GDN 346;Simbase Rhodamine 6G.;Benzoic acid, o-[6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]-, ethyl ester, monohydrochloride;Xanthylium, 9-[2-(ethoxycarbonyl)phenyl]-3,6-bis(ethylamino)-2,7-dimethyl-, chloride (1:1);Rhodamine 6g, 99%, pure;Rhodamine 6g, 99%, laser grade, pure
• CAS NO: 989-38-8
• Molecular Formula: C₂₈H₃₁N₂O₃*Cl
• Molecular Weight: 479.01
• EINECS: 213-584-9
• Product Categories: Pyridines;Analytical Chemistry;Ion Association;Xanthene
• Mol File: 989-38-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 290 °C
• Boiling Point: <200ºC
• Flash Point: 318.6ºC
• Appearance: Red-brown to brown/Powder
• Density: 1.15g/cm3
• Vapor Pressure: 1.68E-14mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Store at +15°C to +30°C.
• Solubility: H2O: soluble1mg/mL, dark red
• Water Solubility: SOLUBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 3900071
• CAS DataBase Reference: Basic Red 1(CAS DataBase Reference)
• NIST Chemistry Reference: Basic Red 1(989-38-8)
• EPA Substance Registry System: Basic Red 1(989-38-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36/37/39-26-36-24/25
• WGK Germany: 3
• RTECS: DH0175000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 989-38-8(Hazardous Substances Data)

Usage

Description

Basic Red 1, also known as Rhodamine 6G, is an organic laser dye that is highly fluorescent and can be used with various alternate light sources. It is one of the most effective laser dyes in recovering latent prints on various non-porous surfaces and can also be used on porous or semi-porous surfaces under certain conditions.

Uses

Used in Forensic Science:
Basic Red 1 is used as a fluorescent dye for recovering latent prints on non-porous surfaces, as it is highly efficient and can be used with various alternate light sources.
Used in Biotechnology Applications:
Basic Red 1 is used as a fluorescence tracker in various biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy, and ELISA. It helps in defining the spectroscopic characteristics for achieving a high conversion efficiency and precision of measurements.
Used in Cell Biology Research:
Basic Red 1 is used as a leukocyte marker to study the interaction between leukocytes and the vascular endothelium. It is also used to label platelets, enabling researchers to track and visualize these cells in various experiments.
Used in Fluorescence Spectroscopy:
Basic Red 1 is used as a probe in fluorescence spectroscopy due to its high quantum yield for fluorescence. The absorption of Basic Red 1 in different solvents can range between 400-700 nm, making it a versatile tool for studying various chemical and physical properties.

Preparation

3-(Ethylamino)-4-methylphenol and Phthalic anhydride to afford the product was obtained ethanol and an inorganic acid esterification; O-Methylaniline with ethylene oxide Alkylation , sulfonated, alkali fusion, and Phthalic anhydride condensation, and then use ethylene oxide esterification.

Air & Water Reactions

Insoluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Basic Red 1 emits very toxic fumes.

Fire Hazard

Flash point data for Basic Red 1 are not available. Basic Red 1 is probably combustible.

Flammability and Explosibility

Notclassified

Biological Activity

Rhodamine 6G is a rhodamine analog useful in P-glycoprotein (Pgp) efflux assays. It has been used to characterize kinetics of multidrug resistance protein 1 (MRP1)-mediated efflux.A rhodamine analog useful in Pgp efflux assays. Has been used to characterize kinetics of MRP1- mediated efflux.

Biochem/physiol Actions

Rhodamine 6G is a rhodamine analog useful in P-glycoprotein (Pgp) efflux assays. It has been used to characterize kinetics of multidrug resistance protein 1 (MRP1)-mediated efflux.

Safety Profile

Poison by ingestion and intraperitoneal routes. An experimental teratogen. Mutation data reported. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of Cland NOx.

Fading

Stain

ISO

2

Purification Methods

Crystallise the dye from MeOH or EtOH, and dry it in a vacuum oven. [Beilstein 18 III/IV 8244, 18/12 V 283.]

InChI:InChI=1/C28H30N2O3/c1-6-29-23-15-25-21(13-17(23)4)27(19-11-9-10-12-20(19)28(31)32-8-3)22-14-18(5)24(30-7-2)16-26(22)33-25/h9-16,29H,6-8H2,1-5H3/b30-24+

Synthetic route

N,N'-diethyl-2,7-dimethyl-rhodamine hydrochloride → rhodamine 6G (989-38-8)

Conditions	Yield
With ethanol; sulfuric acid

C20H12O5*C16H11N + rhodamine 6G (989-38-8) → C20H12O5*C16H11N*C28H30N2O3

Conditions	Yield
In dichloromethane for 48h; pH=7.4;	89%

rhodamine 6G (989-38-8) + ethylenediamine (107-15-3) → N-(rhodamine-6G)lactam-ethylenediamine (440666-99-9)

Conditions	Yield
With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;	88%
In methanol for 3h; Reflux;	78.4%
In ethanol at 70℃; for 12h;	75%

rhodamine 6G (989-38-8) → rhodamine 19 (41382-37-0)

Conditions	Yield
at 265 - 275℃; for 5h; vacuum;	86%

rhodamine 6G (989-38-8) + 1,5-diamino-3-azapentane (111-40-0) → C30H37N5O2

Conditions	Yield
In ethanol at 90℃; Inert atmosphere;	83%
In ethanol Reflux;

rhodamine 6G (989-38-8) → rhodamine hydrazide (932013-08-6)

Conditions	Yield
With hydrazine hydrate In ethanol Reflux;	79%
Stage #1: rhodamine 6G With hydrazine hydrate In ethanol for 12h; Reflux; Stage #2: With sodium hydroxide In dichloromethane; water	74%
With hydrazine hydrate In ethanol Reflux; Sonication;	73%

rhodamine 6G (989-38-8) → 3',6'-bis(ethylamino)-2',7'-dimethyl-2,3-dihydrospiro[isoindole-1,9'-xanthene]-3-one

Conditions	Yield
With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;	79%

rhodamine 6G (989-38-8) → C26H30N4O2

Conditions	Yield
With hydrazine hydrate In ethanol for 2h; Reflux;	78%

2,2',2''-triaminotriethylamine (4097-89-6) + rhodamine 6G (989-38-8) → C32H42N6O2

Conditions	Yield
With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;	76%

rhodamine 6G (989-38-8) + benzylamine (100-46-9) → C33H33N3O2

Conditions	Yield
In ethanol for 10h; Reflux;	75%

potassium trifluoromethansulfonate (2926-27-4) + rhodamine 6G (989-38-8) → C28H31N2O3(1+)*CF3O3S(1-)

Conditions	Yield
In chloroform; water at 20℃; for 7h;	72%

propylamine (107-10-8) + rhodamine 6G (989-38-8) → rhodamine 6G ethylamine (1422430-50-9)

Conditions	Yield
In ethanol for 12h; Reflux;	70%

C55H51NO12 + rhodamine 6G (989-38-8) → C66H65N3O12

Conditions	Yield
With piperidine In N,N-dimethyl-formamide at 90℃; for 0.5h; Microwave irradiation; Inert atmosphere;	68%

rhodamine 6G (989-38-8) + 1-aminooctadecane (124-30-1) → C44H63N3O2 (1422430-49-6)

Conditions	Yield
In ethanol for 24h; Reflux;	67%

rhodamine 6G (989-38-8) → 2-(4-(ethylamino)-2-hydroxy-5-methylbenzoyl)benzoic acid

Conditions	Yield
With sodium hydroxide at 165℃; for 57h;	65%

piperazine (110-85-0) + rhodamine 6G (989-38-8) → C30H37N5O2

Conditions	Yield
With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;	60%

rhodamine 6G (989-38-8) → rhodamine 19 hydrochloride salt

Conditions	Yield
With lithium hydroxide In tetrahydrofuran for 4h; Heating;

rhodamine 6G (989-38-8) → N-acetyl-rhodamine

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 21 percent / Et3N; DMAP / CH2Cl2 / Heating View Scheme

rhodamine 6G (989-38-8) → N-acetyl-N'-benzyloxycarbonyl-rhodamine

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 21 percent / Et3N; DMAP / CH2Cl2 / Heating 3: 85 percent / NaH / tetrahydrofuran / 3 h / Heating View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 hydroxycarbonylmethyl ester bromide

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 77 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3: 79 percent / H2 / Pd/C / ethanol / 24 h / 20 °C View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 ethoxycarbonylmethyl ester bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: LiOH*H2O / tetrahydrofuran / 4 h / Heating 2: 221 mg / NaI; i-Pr2NEt / acetonitrile / 20 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 80 percent / NaI; i-Pr2NEt / acetonitrile / 24 h / Heating View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 benzyl ester bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 66 percent / NaI; i-Pr2NEt / acetonitrile / 4 h / Heating View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 4-chloromethyl-1-phenylmethyl ester chloride

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 88 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 benzyloxycarbonylmethyl ester bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 5 h / 265 - 275 °C / vacuum 2: 77 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 4-(2'-methyl-propionyl)-oxymethyl-1-phenylmethyl ester iodide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 86 percent / 5 h / 265 - 275 °C / vacuum 2.1: 88 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3.1: Cs2CO3 / dimethylformamide / 1 h / 20 °C 3.2: 79 percent / NaI / dimethylformamide / 24 h / 20 °C View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 (L-methyl-phenylalaninyl)-carbonylmethyl ester bromide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 86 percent / 5 h / 265 - 275 °C / vacuum 2.1: 77 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3.1: 79 percent / H2 / Pd/C / ethanol / 24 h / 20 °C 4.1: N-hydroxysuccinimide; 1,3-dicyclohexylcarbodiimide / dimethylformamide / 0.5 h / 20 °C 4.2: 69 percent / dimethylformamide / 20 °C View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 4-(N-t-butoxycarbonyl-glycinyl-oxymethyl)-1-phenylmethyl ester iodide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 86 percent / 5 h / 265 - 275 °C / vacuum 2.1: 88 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3.1: Cs2CO3 / dimethylformamide / 1 h / 20 °C 3.2: 88 percent / NaI / dimethylformamide / 24 h / 20 °C View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 4-(N-t-butoxycarbonyl-L-valinyl-oxymethyl)-1-phenylmethyl ester iodide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 86 percent / 5 h / 265 - 275 °C / vacuum 2.1: 88 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3.1: Cs2CO3 / dimethylformamide / 1 h / 20 °C 3.2: 84 percent / NaI / dimethylformamide / 24 h / 20 °C View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 4-(N-benzyloxycarbonyl-L-phenylalaninyl-oxymethyl)-1-phenylmethyl ester iodide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 86 percent / 5 h / 265 - 275 °C / vacuum 2.1: 88 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3.1: Cs2CO3 / dimethylformamide / 1 h / 20 °C 3.2: 84 percent / NaI / dimethylformamide / 24 h / 20 °C View Scheme

rhodamine 6G (989-38-8) → rhodamine 19 4-(N-t-butoxycarbonyl-L-isoleucinyl-glycinyl-oxymethyl)-1-phenylmethyl ester iodide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 86 percent / 5 h / 265 - 275 °C / vacuum 2.1: 88 percent / NaI; i-Pr2NEt / acetonitrile / 2.5 h / Heating 3.1: Cs2CO3 / dimethylformamide / 1 h / 20 °C 3.2: 76 percent / NaI / dimethylformamide / 24 h / 20 °C View Scheme

Downstream Products

• 41382-37-0 rhodamine 19