2-((4-(Dimethylamino)phenyl)diazenyl)benzoic acid

HCID 10303CAS 493-52-7

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

2-((4-(dimethylamino)phenyl)diazenyl)benzoic acid2-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid2-{[4-(dimethylamino)phenyl]diazenyl}benzoic acidDTXSID90859408RefChem:1060520DTXCID70809724Methyl red493-52-7O-METHYL REDC.I. Acid Red 2Acid Red 22-Carboxy-4'-(dimethylamino)azobenzene
Show more names
ACID REDMETHYL RED INDICATORMETHYL RED ETHANOLMETHYL RED, NEUTRALMETHYL RED MIXED SOLUTIONMETHYL RED, WATER SOLUBLEMETHYL RED, SPIRIT SOLUBLEMETHYL RED MIXED SOLUTION RMETHYL RED SOLUTION R
4-Dimethylamino-2'-carboxylazobenzenep-(Dimethylamino)azobenzene-o-carboxylic acidCerven methylova2-(4-Dimethylaminophenylazo)benzoic acidCerven kysela 2o-((p-(Dimethylamino)phenyl)azo)benzoic acidBenzoic acid, 2-[[4-(dimethylamino)phenyl]azo]-2-((4-Dimethylamino)phenylazo)benzoic acid

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

Experimental & physicochemical properties

Collision Cross Section175.2 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1042154]

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)

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

Chemistry & industry

Applications · 5 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Additional notes · 3 items

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

1 records

Linked notes

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