Methyl red

Base Information

• Chemical Name: Methyl red
• CAS No.: 493-52-7
• Molecular Formula: C15H15N3O2
• Molecular Weight: 269.303
• Hs Code.: 29270000
• European Community (EC) Number: 207-776-1
• NSC Number: 215212,34729,9597
• UNII: 69083AX1ZX
• DSSTox Substance ID: DTXSID1042154,DTXSID90859408
• Nikkaji Number: J1.557A
• Wikipedia: Methyl_red
• Wikidata: Q412276
• ChEMBL ID: CHEMBL375971,CHEMBL1090439
• Mol file: 493-52-7.mol

Synonyms:C.I. Acid Red 2;methyl red;methyl red, sodium salt

Chemical Property of Methyl red

Chemical Property:

• Appearance/Colour: dark red crystalline powder
• Vapor Pressure: 2.89E-10mmHg at 25°C
• Melting Point: 178-182 °C
• Refractive Index: 1.592
• Boiling Point: 479.5 °C at 760 mmHg
• PKA: 4.95(at 25℃)
• Flash Point: 243.8 °C
• PSA: 65.26000
• Density: 1.17 g/cm³
• LogP: 3.86620
• Storage Temp.: −20°C
• Solubility.: ethanol: soluble1mg/mL
• Water Solubility.: Practically insoluble in water. Soluble in alcohol, acetic acidSoluble in ethanol. Insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 269.116426730
• Heavy Atom Count: 20
• Complexity: 349

Purity/Quality:

Assay99%,Assay80%, ^*data from raw suppliers

Methyl Red free acid ACS ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, F,Xi, C, Xn
• Hazard Codes: Xn,T,F,Xi,C,N
• Statements: 10-20/21/22-68/20/21/22-68-36/38-23/25-11-36/37/38-34-51/53-39/23/24/25-23/24/25
• Safety Statements: 36/37-24/25-22-45-33-24-16-7-36-26-36/37/39-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Azo Dyes
• Canonical SMILES: CN(C)C1=CC=C(C=C1)N=NC2=CC=CC=C2C(=O)O
• Description: Methyl red is a commonly used indicator for acid-base titrations. This chemical is usually yellow but turns red below pH 4.0. Bacteria exhibiting mixed acids fermentation will accumulate acids in the medium, resulting in a color change. Approximately five drops of methyl red reagent are added to an overnight culture grown in MRVP broth to determine the test result. Different bacteria convert dextrose and glucose to pyruvate using different metabolic pathways. Some of these pathways produce unstable acidic products which quickly convert to neutral compounds. Some organisms use the butylene glycol pathway, which produces neutral end products, including acetoin and 2,3-butanediol. Other organisms use the mixed acid pathway, which produces acidic end products such as lactic, acetic, and formic acid. These acidic end products are stable and will remain acidic. The Methyl Red test involves adding the pH indicator methyl red to an inoculated tube of MR-VP broth. If the organism uses the mixed acid fermentation pathway and produces stable acidic end-products, the acids will overcome the buffers in the medium and produce an acidic environment in the medium. When methyl red is added, if acidic end products are present, the methyl red will stay red.
• Uses: Used as pH indicator. As indicator in 0.1% alcoholic solution; pH: 4.4 red, 6.2 yellow. Used for titrating NH3, weak organic bases, e.g., alkaloids; not suitable for organic acids, except oxalic and picric acid. Methyl red is easily reduced, thereby losing its color, and readings should be made promptly. It is gradually being replaced by sulfonphthalein indicators, such as bromcresol green, which are more stable and exhibit a sharper change in color. pH indicator in pH range 4.2 - 6.3Methyl red is used as a pH indicator. It is red in pH less than 4.4 and yellow in pH over 6.2. It is used to study its degradation using Fenton's reagent. In microbiology, it is used to identify bacteria producing stable acids by mechanisms of mixed acid fermentation of glucose.

Technology Process of Methyl red

There total 5 articles about Methyl red which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → methyl red (493-52-7)

Guidance literature:

With hydrogenchloride; sodium nitrite; durch Diazotierung und Kupplung der Diazoverbindung mit Dimethylanilin, geloest in salzsaurehaltigem Alkohol;

Reference yield:

o-Carboxybenzenediazonium (17333-86-7) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → methyl red (493-52-7)

Guidance literature:

DOI:10.1021/ie50163a037

Reference yield:

[PtL2] + potassium iodide (7681-11-0) → methyl red (493-52-7) + platinum(II) iodide (7790-39-8)

Guidance literature:

In water; water bath (4 h); ppt. filtration off, washing (water), drying (70°C); elem. anal.;

upstream raw materials:

anthranilic acid

o-Carboxybenzenediazonium

N,N-dimethyl-aniline

hydrogenchloride

Downstream raw materials:

2-{[4-(dimethylamino)phenyl]azo}-benzoic acid ethyl ester

C₁₅H₁₄IN₃O₂

succinimidyl 2-[4-(dimethylamino)phenylazo]benzoate

(CH₂CH)3Sn(OOC-2-C₆H₄N=NC₆H₄N(CH₃)2-4)

Refernces