Basic information
- Standard SMILES
CN(C)c1ccc(N=Nc2ccccc2C(=O)O)cc1- InChIKey
CEQFOVLGLXCDCX-UHFFFAOYSA-N- Molecular formula
- C15H15N3O2
- Average molar mass
- 269.3 g/mol
- Monoisotopic mass
- 269.11642672
Overview
Methyl red is an azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group. It has a role as a dye. It is a member of azobenzenes, a monocarboxylic acid and a tertiary amino compound. It is a conjugate acid of a methyl red(1-).
Names & identifiers
- Preferred name
- 2-((4-(Dimethylamino)phenyl)diazenyl)benzoic acid
- IUPAC
- 2-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid
- English name
- Methyl Red
- Molecular formula
- C15H15N3O2
- Molecular weight
- 269.3
Names & synonyms
Show more names
Database identifiers
- CAS
493-52-7- PubChem CID
- 10303
- DTXSID
DTXSID90859408- ChEMBL
CHEMBL375971- ChEBI
CHEBI:49770- UNII
- 69083AX1ZX
- Nikkaji
- J1.557A
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 65.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 349
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 179 · 179-182 °C (lit.)
- Boiling point
- 412.44 °C · 412.44°C (rough estimate)
- Density
- 0.839 g/mL · 0.839 g/mL at 25 °C
- bulk density
- 300 · 300-500kg/m3
- vapor density
- 9.3 · 9.3 (vs air)
- refractive index
- 1.593 · 1.5930 (estimate)
- Flash point
- 11 °C · 11 °C
- storage temp.
- 5 °C · Store at +5°C to +30°C.
- solubility
- 1 mg/mL · ethanol: soluble1mg/mL
- form
- Solid
- pka
- 4.95 · 4.95(at 25℃)
- Colour Index
- 13020 · 13020
- color
- Reddish-violet
- PH Range
- 4.4 · 4.4(red)-6.3(yellow)
- Odor
- Odorless
- Water Solubility
- Practically insoluble in water. Soluble in alcohol, acetic acidSoluble in ethanol. Insoluble in water.
- λmax
- 410 nm, · 410nm, 530nm, 427nm, 519nm
- ε(extinction coefficient)
- 10000 at · ≥10000 at 282-288nm in methanol≥20000 at 509-519nm in methanol≥7000 at 329-335nm in methanol
- Merck
- 14 · 14,6119
- BRN
- 750102 · 750102
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- Waveguides, LED sensors, photoresists, liquid crystals, sol-gel matrix, optical sensors, paints, toys, detection of thiols, food freshness sensors, dental product, saliva sampling method, detecting lactic acid, carbohydrates
- InChI
- 1S/C15H15N3O2/c1-18(2)12-9-7-11(8-10-12)16-17-14-6-4-3-5-13(14)15(19)20/h3-10H,1-2H3,(H,19,20)
- InChIKey
- CEQFOVLGLXCDCX-MSUUIHNZSA-N
- SMILES
- N(C)(C)c1ccc(cc1)N=Nc2c(cccc2)C(=O)O
- CAS DataBase Reference
- 493 · 493-52-7
- FDA UNII
- 69083 AX1ZX · 69083AX1ZX
- IARC
- 3 · 3 (Vol. 8, Sup 7) 1987
- NIST Chemistry Reference
- 2 · Benzoic acid, 2-[[4-(dimethylamino)phenyl]azo]-(493-52-7)
- EPA Substance Registry System
- Methyl red (493-52-7)
- UNSPSC Code
- 41171621 · 41171621
- NACRES
- 85 · NA.85
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319-H371
- Precautionary statements
- 210 · P210-P260-P280-P308+P311-P337+P313-P403+P235
- Hazard Codes
- Xn,T,F,Xi,C,N
- Risk Statements
- 10 · 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 · 36/37-24/25-22-45-33-24-16-7-36-26-36/37/39-61
- RIDADR
- 1170 · UN 1170 3/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 8960000 · DG8960000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29270000 · 29270000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 493 · 493-52-7(Hazardous Substances Data)
Safety & regulation
Safety data
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- DG8960000
- ridadr
- UN 1170 3/PG 2
- hs_code
- 29270000
- risk_code
- 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
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07,GHS08
- hazard_code
- Xn,T,F,Xi,C,N
- safety_code
- 36/37-24/25-22-45-33-24-16-7-36-26-36/37/39-61
- hazard_class
- 3
- Storage Class
- 11 - Combustible Solids
- packing_group
- II
- Hazard statements
- H225-H319-H371
- Precautionary statements
- P210-P260-P280-P308+P311-P337+P313-P403+P235
- Hazardous Substances Data
- 493-52-7(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionMethyl 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.
UsesUsed as pH indicator.
UsespH 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.
UsesAs 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.
General DescriptionMethyl red solution is an azo dye which turns to red when pH is below 4.4 (yellow pH < 6.2, orange pH 4.4-6.2). Some bacteria utilize glucose to form large amounts of acid with the result that the pH value of the medium falls distinct. Other species produce no or less free acid. This difference can be visualized by using methyl red. This test is used to differentiate enteric bacteria.
Preparation methods
Preparation2-Aminobenzoic aciddiazo, and N,N-dimethylaniline coupling.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: An azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group.
DefinitionAn acid–base indicator that is red in solutions below a pH of 4.2 and yellow above a pH of 6.3. It is often used for the same types of titration as methyl orange but the transition range of methyl red is nearer neutral (pH7) than that of methyl orange. The two molecules are structurally similar.
Definitionmethyl red: An organic dye similarin structure and use to methyl orange.It changes from red below pH4.4 to yellow above pH 6.0 (at 25°C).
Related reactions
Linked notes
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