3520-42-1

Basic information

• Product Name: SULFORHODAMINE B
• Synonyms: SULFORHODAMINE B MONOSODIUM SALT;SULFORHODAMINE B;PHLOXINE RHODAMINE;XYLENE RED;XYLENE RED B;(6-(diethylamino)-9-(2,4-disulfophenyl)-3h-xanthen-3-ylidene)diethyl-ammoniu;acidleatherredkb;AcidroseredB
• CAS NO: 3520-42-1
• Molecular Formula: C₂₇H₂₉N₂O₇S₂*Na
• Molecular Weight: 580.65
• EINECS: 222-529-8
• Product Categories: Organics;Analytical Chemistry;Food Colors by Food Sanitation Law in Japan;Stains, Dyes and Indicators;Cell Viability and Proliferation;Reagents and Supplements;S;Stains and Dyes;Stains&Dyes, A to;acid dyes
• Mol File: 3520-42-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /powder
• Density: 1.472[at 20℃]
• Storage Temp.: room temp
• Solubility: methanol: 1 mg/mL
• Water Solubility: 95.3g/L at 20℃
• BRN: 3886008
• CAS DataBase Reference: SULFORHODAMINE B(CAS DataBase Reference)
• NIST Chemistry Reference: SULFORHODAMINE B(3520-42-1)
• EPA Substance Registry System: SULFORHODAMINE B(3520-42-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-26-36/37/39
• WGK Germany: 2
• RTECS: BP6750000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 3520-42-1(Hazardous Substances Data)

Usage

Description

Sulforhodamine B (SRB) is a bright-pink aminoxanthene dye that is extensively used for in vitro cytotoxicity screening. It binds to the protein constituents of cells in a stoichiometric manner, making the amount of dye extracted from stained cells directly proportional to the cell mass. SRB is also used for cell density determination and has various applications in different industries.

Uses

Used in Nonpermanent Tattoos:
SULFORHODAMINE B is used as a dye for creating nonpermanent tattoos.
Used in Acute Respiratory Distress Syndrome Treatment:
SULFORHODAMINE B is used as a potential new therapeutic agent for the treatment of acute respiratory distress syndrome.
Used in Environmental Testing:
SULFORHODAMINE B is used for relative total cell mass quantification, investigating the viscosity of coacervates, and as a molecular rotor for microviscosity determination in aerosol droplets.
Used in Cytotoxicity and Proliferation Assays:
SULFORHODAMINE B is used as a staining agent in the SRB assay for the determination of in vitro cytotoxicity, observation of live cells, proliferation, and drug screening.
Used in Blood-Brain Barrier Integrity Assessment:
SULFORHODAMINE B is used as a microscopic tracer for the assessment of blood-brain barrier integrity by post-mortem inspection of frozen sections.
Used in Dental Applications:
SULFORHODAMINE B is used as a caries detector dye with subsequent inspection of histological material.
Used in Textile Industry:
SULFORHODAMINE B is used as a dye for wool, silk, and polyamide fiber dyeing. It can also be used for wool and various fabric dyeing, as well as for direct printing on wool and silk fabrics, and for leather dyeing.
Standard:
The light fastness, soaping, perspiration fastness, oxygen bleaching, and fastness to seawater of SULFORHODAMINE B are rated according to ISO and AATCC standards, with ratings ranging from 1 to 4, indicating varying levels of resistance and performance.

Preparation

4-Formylbenzene-1,3-disulfonic acid and 3-(Diethylamino)phenol condensation, the products with sulfuric acid dehydration, and ferric chloride oxidation, and finally into sodium salt.

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Sulforhodamine B sodium salt is useful to measure cell biomass and also for cytotoxicity screening.

Standard

Light Fastness

Fading

Stain

ISO

3

AATCC

2-3

InChI:InChI=1/C27H30N2O7S2.Na/c1-5-28(6-2)18-9-12-21-24(15-18)36-25-16-19(29(7-3)8-4)10-13-22(25)27(21)23-14-11-20(37(30,31)32)17-26(23)38(33,34)35;/h9-17H,5-8H2,1-4H3,(H-,30,31,32,33,34,35);/q;+1/p-1

Synthetic route

sulforhodamine B (3520-42-1) → rhodamine B sulfonyl chloride (62796-29-6)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 16h;	88%
With oxalyl dichloride
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 3.5h;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 22h; Inert atmosphere;

1-amino-2-azidoethane (87156-40-9) + sulforhodamine B (3520-42-1) → C29H34N6O6S2

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; Darkness;	76%

sulforhodamine B (3520-42-1) + rhodamine 6G (1232233-19-0) → C28H30N2O3*C27H30N2O7S2

Conditions	Yield
In methanol for 2h;	50%

trihexyl(tetradecyl)phosphonium chloride (258864-54-9) + sulforhodamine B (3520-42-1) → N-[6-(diethylamino)-9-(2,4-disulfophenyl)-3H-xanthen-3-ylidene]-N-ethyl-ethanaminium hydroxide inner salt trihexyltetradecylphosphonium salt

Conditions	Yield
In methanol; dichloromethane for 24h;

sulforhodamine B (3520-42-1) → C47H65N5O14S2

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride 2: triethylamine 3: hydrogenchloride / water View Scheme

sulforhodamine B (3520-42-1) → Reaxys ID: 32620162

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 3.5 h / 0 - 20 °C View Scheme

benzyltriphenylphosphonium chloride (1100-88-5) + sulforhodamine B (3520-42-1) → C27H29N2O7S2(1-)*C25H22P(1+)

Conditions	Yield
In water at 20 - 85℃; for 1h;	5.93 g

sulforhodamine B (3520-42-1) + cetyltributylphosphonium bromide (14937-45-2) → C27H29N2O7S2(1-)*C28H60P(1+)

Conditions	Yield
In water at 20 - 85℃; for 1h;	6.1 g

dibenzo-18-crown-6 (14187-32-7) + sulforhodamine B (3520-42-1) → [(dibenzo-18-crown-6)(Na)(sulforhodamine B)]

Conditions	Yield
In dichloromethane

sulforhodamine B (3520-42-1) → 2C27H29N2O7S2(1-)*Ca(2+)

Conditions	Yield
With calcium chloride In water at 20 - 30℃; for 1h;
With calcium chloride In water at 20 - 30℃; for 1h;

sulforhodamine B (3520-42-1) → 2C27H29N2O7S2(1-)*Ba(2+)

Conditions	Yield
With barium(II) chloride In water at 20 - 30℃; for 1h;

sulforhodamine B (3520-42-1) → C27H29N2O7S2(1-)*H(1+)

Conditions	Yield
With hydrogenchloride In water at 20 - 30℃; for 1h;

sulforhodamine B (3520-42-1) + 18-amino-8,11,13-abietatriene → C27H29N2O7S2(1-)*C20H31N*H(1+)

Conditions	Yield
With acetic acid In water at 20 - 25℃; for 1.5h;

sulforhodamine B (3520-42-1) → 5-(N-(3-azidopropyl)sulfamoyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl)benzenesulfonate (1092380-66-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 22 h / 20 °C / Inert atmosphere 2: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 22 h / 20 °C View Scheme

Downstream Products

• 62796-29-6 rhodamine B sulfonyl chloride 

Relevant articles and documents

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