92-31-9

Basic information

• Product Name: Basic Blue 17
• Synonyms: DIMETHYLTOLUTHIONINE CHLORIDE;CI NO 52040;CI BASIC BLUE 17;CI 52040;CARBOL TOLUIDINE BLUE;BASIC BLUE;BASIC BLUE 17;BLUTENE CHLORIDE
• CAS NO: 92-31-9
• Molecular Formula: C₁₅H₁₆N₃S*Cl
• Molecular Weight: 305.83
• EINECS: 202-146-2
• Product Categories: Dyes and Pigments;pharmacetical;TOLAZUL;Phenothiazine
• Mol File: 92-31-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: >200℃
• Appearance: Dark green to black/Solid
• Storage Temp.: Store at RT.
• Solubility: H2O: soluble1mg/mL
• PKA: 2.4, 11.6(at 25℃)
• Water Solubility: 3.82 g/100 mL
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9520
• CAS DataBase Reference: Basic Blue 17(CAS DataBase Reference)
• NIST Chemistry Reference: Basic Blue 17(92-31-9)
• EPA Substance Registry System: Basic Blue 17(92-31-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: SP5670000
• TSCA: Yes
• Hazardous Substances Data: 92-31-9(Hazardous Substances Data)

Usage

Originator

Blutene,Abbott,US,1953

Uses

Different sources of media describe the Uses of 92-31-9 differently. You can refer to the following data:
1. hemostatic
2. A metachromatic dye suitable for a wide variety of histological staining procedures.
3. Direct dyeing, printing of wool, silk. Biological stain.

Definition

ChEBI: An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both i metachromatic and orthochromatic techniques.

Preparation

by heavy chromate salt in the presence of sodium content and deal with N1,N1-dimethylbenzene-1,4-diamine, transforming it into the content and sulfonic acid, this product then through heavy chromate salt and O-Methylaniline processing, into a unique of sulfur acid amine generation, then use heavy chromate salt and copper sulfate closed loop and oxidation, Finally,?the?zinc chloride?salt?precipitation

Manufacturing Process

As taken from US Patent 416,055 (probably the oldest patent on the manufacture of a currently-used drug): In carrying out this process about 6 pbw of dimethyl-p-phenylenediamine was dissolved in about 18 pbw of hydrochloric acid of about 1.16 specific gravity and then a solution of about 3.8 pbw of nitrite of soda in about 6 pbw of water was gradually added. The hydrochlorate of nitroso-dimethylaniline thus produced in the well-known manner is then submitted to the reducing action of zinc-dust by adding, first about 30 pbw of hydrochloric acid of about 1.16 specific gravity and then (in small portions at a time) about 10 pbw of zinc-dust as is well understood by chemists. The solution of hydrochlorate of paramido-dimethylaniline thus obtained is afterwards diluted with about 250 pbw of water and then the uncombined hydrochloric acid contained in the solution is, if any, neutralized by the addition of an alkali. There are then added about 16 pbw of sulfate of alumina and about 13 pbw of thiosulfate of sodium, (hyposulfite of soda) and immediately afterwards a solution of about 5 pbw of bichromate of potash in about 60 pbw of water is quickly run in. In this stage of the process the formation of an acid sulfureted compound of paramidodimethylaniline takes place, possessing the formula C8H11N2SSO3H(paramido-dimethylaniline-thiosulfonic acid). Without previous separation of this intermediate compound a solution of about 5.3 pbw of orthotoluidine, in the requisite amount of dilute hydrochloric acid (about 6 pbw of hydrochloric acid, SG about 1.16, diluted with about 6 pbw water) and shortly afterwards a solution of about 14 pbw of bichromate of potash in about 160 parts by weight of water is then added under constant agitation, when a precipitate will be formed chiefly consisting of a green indamine possessing in its dry condition the formula C15H17N3S2O3. In order to transform the same into toluidine-blue, about 50 pbw of a solution of chloride of zinc of about 1.5 specific gravity are added and the mixture thus obtained is boiled during about half an hour, when, after cooling, the toluidine-blue thus formed will separate out and may then be filtered and purified, if necessary, by repeated solution in water and precipitation by means of chloride of sodium and chloride of zinc. In the above described process the sulfate of alumina may be dispensed with and replaced by as much hydrochloric, sulfuric, or acetic acid as will be required to liberate the thiosulfuric acid from the thiosulfate of sodium employed. Toluidine-blue prepared as above described presents the following characteristic properties: It consists principally of the hydrochlorate of dimethyltoluthionine, the composition of which corresponds to the formula C15H15N3SHCl.

Properties and Applications

Soluble in water for blue purple, soluble in ethanol to blue. The strong sulfuric acid for yellow green, diluted to blue. The dye solution to join sodium hydroxide have dark purple precipitation. Standard( Cotton ) Light Fastness Persperation Fastness Ironing Fastness Soaping Fading Stain Fading Stain Fading Stain C 2-3 1-2

Standard( Cotton )

Light Fastness

Fading

Stain

C

2-3

InChI:InChI=1/C15H16N3S.ClH/c1-9-6-13-15(8-11(9)16)19-14-7-10(18(2)3)4-5-12(14)17-13;/h4-8H,16H2,1-3H3;1H/q+1;/p-1

Upstream product

• 636-21-5 o-toluidine hydrochloride 
• 536-46-9 4-dimethylaminophenylamine dihydrochloride 

Downstream Products

• 136582-31-5 3-[(3,5-Bis-hydroxymethyl-2,4,6-trioxo-[1,3,5]triazinan-1-ylmethoxymethyl)-amino]-7-dimethylamino-2-methyl-phenothiazin-5-ylium; chloride 

Relevant articles and documents

TOLUIDINE BLUE O DRUG SUBSTANCE AND USE THEREOF FOR IN VIVO STAINING AND CHEMOTHERAPEUTIC TREATMENT OF DYSPLASTIC TISSUES

The invention comprises an improved process for preparing TBO drug products includes the steps: (1) synthesising an indamine; (2) converting said indamine into an S-indaminyl thiosulfate; and (3) adding an oxidizing catalyst agent, complexing agent, and an acid to said S-indaminyl thiosulfate to formulate TBO and C-4-methyl regioisomer, and derivatives thereof. The invention further comprises new compositions of matter that are useful for detecting dysplastic tissue, as well as, treating dysplastic tissue, namely, TBO products predominantly comprised of peaks eight, peak six, or a combination thereof. N,N-dimenthyl-p-phenylenediamine as a starting material results in a TBO product composition comprised of peaks eight, seven, six, and five in the approximate ratios 33:5:5:1, respectively. Whereas N-dimethyl-p-phenylenediamine as a starting material results in a TBO demetylated product composition comprised of peaks six, five, tree and two in the approximate ratio 33:5:5:1, respectively. The invention further comprises an improved PLC method for analyzing the improved TBO drug product, the improvement comprising the addition of an ion-pairing reagent in a first mobile phase and forming a second mobile phase composition comprising 5o% alcohol by volume.