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493-52-7

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493-52-7 Usage

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.

Chemical Properties

dark red crystalline powder

Uses

Different sources of media describe the Uses of 493-52-7 differently. You can refer to the following data:
1. Used as pH indicator.
2. 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.
3. 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.

Definition

Different sources of media describe the Definition of 493-52-7 differently. You can refer to the following data:
1. ChEBI: An azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group.
2. An 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.
3. methyl 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).

Preparation

2-Aminobenzoic acid?diazo, and N,N-dimethylaniline coupling.

General Description

Methyl 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.

Hazard

Questionable carcinogen.

Biochem/physiol Actions

Methyl Red is a maroon red crystal azo dye. Methyl Red is a pH indicator and changes color at a pH of 5.5. Methyl Red is widely used in saliva sampling method. In addition, it is also employed in carbohydrate and lactic acid detection. Methyl Red has been effectively used for intrageneric differentiation of Enterobacteriaceae.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Properties and Applications

moderate soluble in ethanol, insoluble in water. Alcohol solution to join hydrochloric acid for purple; Add sodium hydroxide to dim yellow.

Purification Methods

The acid is extracted with boiling toluene using a Soxhlet apparatus. The crystals which separate on slow cooling to room temperature are filtered off, washed with a little toluene and recrystallised from glacial acetic acid, *benzene or toluene followed by pyridine/water. Alternatively, dissolve it in aqueous 5% NaHCO3 solution, and precipitate it from a hot solution by dropwise addition of aqueous HCl. Repeat this until the extinction coefficients do not increase. [Beilstein 16 IV 504.]

Check Digit Verification of cas no

The CAS Registry Mumber 493-52-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 3 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 493-52:
(5*4)+(4*9)+(3*3)+(2*5)+(1*2)=77
77 % 10 = 7
So 493-52-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H15N3O2/c1-18(2)12-8-9-14(13(10-12)15(19)20)17-16-11-6-4-3-5-7-11/h3-10H,1-2H3,(H,19,20)/b17-16+

493-52-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A16690)  Methyl Red   

  • 493-52-7

  • 25g

  • 123.0CNY

  • Detail
  • Alfa Aesar

  • (A16690)  Methyl Red   

  • 493-52-7

  • 100g

  • 415.0CNY

  • Detail
  • Alfa Aesar

  • (A16690)  Methyl Red   

  • 493-52-7

  • 500g

  • 1430.0CNY

  • Detail
  • Alfa Aesar

  • (36682)  Methyl Red, ACS   

  • 493-52-7

  • 25g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (36682)  Methyl Red, ACS   

  • 493-52-7

  • 100g

  • 636.0CNY

  • Detail
  • Sigma-Aldrich

  • (08714)  MethylRedsolution  for microbiology

  • 493-52-7

  • 08714-100ML-F

  • 320.58CNY

  • Detail
  • Fluka

  • (32941)  MethylRedsolution  acid-base indicator

  • 493-52-7

  • 32941-100ML

  • 249.21CNY

  • Detail
  • Fluka

  • (32654)  MethylRed  acid-base indicator, Reag. Ph. Eur.

  • 493-52-7

  • 32654-25G

  • 402.48CNY

  • Detail
  • Fluka

  • (32654)  MethylRed  acid-base indicator, Reag. Ph. Eur.

  • 493-52-7

  • 32654-100G

  • 982.80CNY

  • Detail
  • Sigma-Aldrich

  • (250198)  MethylRed  ACS reagent, crystalline

  • 493-52-7

  • 250198-25G

  • 294.84CNY

  • Detail
  • Sigma-Aldrich

  • (250198)  MethylRed  ACS reagent, crystalline

  • 493-52-7

  • 250198-100G

  • 895.05CNY

  • Detail

493-52-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl red

1.2 Other means of identification

Product number -
Other names 2-[4-(dimethylamino)phenylazo]benzoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:493-52-7 SDS

493-52-7Synthetic route

anthranilic acid
118-92-3

anthranilic acid

methyl red
493-52-7

methyl red

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite durch Diazotierung und Kupplung der Diazoverbindung mit Dimethylanilin, geloest in salzsaurehaltigem Alkohol;
o-Carboxybenzenediazonium
17333-86-7

o-Carboxybenzenediazonium

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

methyl red
493-52-7

methyl red

hydrogenchloride
7647-01-0

hydrogenchloride

2-carboxy-benzenediazonium; chloride

2-carboxy-benzenediazonium; chloride

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

methyl red
493-52-7

methyl red

[PtL2]

[PtL2]

potassium iodide
7681-11-0

potassium iodide

A

methyl red
493-52-7

methyl red

B

platinum(II) iodide

platinum(II) iodide

Conditions
ConditionsYield
In water water bath (4 h); ppt. filtration off, washing (water), drying (70°C); elem. anal.;
methyl red
493-52-7

methyl red

Propargylamine
2450-71-7

Propargylamine

C18H18N4O

C18H18N4O

Conditions
ConditionsYield
Stage #1: methyl red With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Cooling with ice;
Stage #2: Propargylamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
98%
phenylmercuric acetate
62-38-4

phenylmercuric acetate

methyl red
493-52-7

methyl red

C6H5HgC15H14N3O2

C6H5HgC15H14N3O2

Conditions
ConditionsYield
With sodium hydroxide In ethanol byproducts: NaO2CCH3; a mixt. of the ligand in ethanolic NaOH and Hg(II) salt in EtOH was refluxed for 6 h, EtOH was removed, the product was extg. with benzene; puirified by recrystallisation from benzene and petroleum ether; identified by elem. anal., IR, NMR and UV spectra;95%
4-Vinylbenzyl chloride
1592-20-7

4-Vinylbenzyl chloride

methyl red
493-52-7

methyl red

2-(4-dimethylamino-phenylazo)-benzoic acid 4-vinyl-benzyl ester
681430-02-4

2-(4-dimethylamino-phenylazo)-benzoic acid 4-vinyl-benzyl ester

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 24h;94%
With triethylamine In N,N-dimethyl-formamide for 24h;94%
methyl red
493-52-7

methyl red

A

anthranilic acid
118-92-3

anthranilic acid

B

4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

Conditions
ConditionsYield
With hydrazine hydrate; aluminium In ethanol Heating;A 85%
B 92%
With formic acid; zinc In methanol at 20℃; for 0.25h;A 88%
B 91%
With ammonium acetate; zinc In methanol at 20℃; for 0.0833333h;A n/a
B 91%
methyl red
493-52-7

methyl red

4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

Conditions
ConditionsYield
With hydrazine hydrate In ethanol Heating;92%
methyl red
493-52-7

methyl red

anthranilic acid
118-92-3

anthranilic acid

Conditions
ConditionsYield
With ammonium formate; nickel In methanol at 20℃; for 0.25h;88%
3-(trimethoxysilyl)propan-1-amine
13822-56-5

3-(trimethoxysilyl)propan-1-amine

methyl red
493-52-7

methyl red

2-((4-(dimethylamino)phenyl)diazenyl)-N-(3-(trimethoxysilyl)propyl)benzamide

2-((4-(dimethylamino)phenyl)diazenyl)-N-(3-(trimethoxysilyl)propyl)benzamide

Conditions
ConditionsYield
Stage #1: methyl red With 1,1'-carbonyldiimidazole In tetrahydrofuran at 35℃; for 1.5h; Inert atmosphere; Reflux; Schlenk technique;
Stage #2: 3-(trimethoxysilyl)propan-1-amine In tetrahydrofuran for 24h; Inert atmosphere; Reflux; Schlenk technique;
86%
bis(tri-n-butyltin)oxide
56-35-9

bis(tri-n-butyltin)oxide

methyl red
493-52-7

methyl red

(C4H9)3SnOOCC6H4NNC6H4N(CH3)2-4
82184-40-5

(C4H9)3SnOOCC6H4NNC6H4N(CH3)2-4

Conditions
ConditionsYield
In ethanol mixt. of Sn compd. and ligand in EtOH refluxed with stirring for 1 h; concd. in vac.; filtered; solid washed with cold EtOH; dried in vac.; elem. anal.;82.2%
methyl red
493-52-7

methyl red

N,N'-dihydromethylred

N,N'-dihydromethylred

Conditions
ConditionsYield
With tin; hydrazine hydrate In methanol at 20℃; for 0.416667h;80%
With ammonium chloride; magnesium In methanol at 20℃; for 0.0833333h;60%
With titanium(IV) oxide Rate constant; Irradiation; anaerobe, buffered soln., effect of the pH, TiO2 concn.;
ethanol
64-17-5

ethanol

methyl red
493-52-7

methyl red

2-{[4-(dimethylamino)phenyl]azo}-benzoic acid ethyl ester
1167421-09-1

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

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;76%
bis(triphenyltin) oxide
1262-21-1

bis(triphenyltin) oxide

methyl red
493-52-7

methyl red

triphenyltin-o-(4-N,N-dimethylaminophenylazo)benzoate
82184-39-2

triphenyltin-o-(4-N,N-dimethylaminophenylazo)benzoate

Conditions
ConditionsYield
In ethanol under N2, 2 equiv. of acid was used, reflux for 0.3 h; soln. was filtered, concd., solid was washed with cold hexane, dried in vac., elem. anal.;68%
tris(triphenylphosphine)ruthenium(II) chloride
15529-49-4, 41756-81-4

tris(triphenylphosphine)ruthenium(II) chloride

methyl red
493-52-7

methyl red

C51H43ClN3O2P2Ru

C51H43ClN3O2P2Ru

Conditions
ConditionsYield
With triethylamine In methanol at 85℃; for 4h;60%
methyl red
493-52-7

methyl red

1-(3-iodopropyl)-pyrrole
167867-84-7

1-(3-iodopropyl)-pyrrole

3-(N-pyrrolyl)propyl 2-(4-dimethylaminophenylazo)benzoate

3-(N-pyrrolyl)propyl 2-(4-dimethylaminophenylazo)benzoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 80℃; for 3h;57%
diphenyltin(IV) oxide
2273-51-0

diphenyltin(IV) oxide

methyl red
493-52-7

methyl red

triphenyltin-o-(4-N,N-dimethylaminophenylazo)benzoate
82184-39-2

triphenyltin-o-(4-N,N-dimethylaminophenylazo)benzoate

Conditions
ConditionsYield
In ethanol under N2, 1 equiv. of acid was used, reflux for 4 h; soln. was filtered, concd., solid was washed with cold hexane, dried in vac., elem. anal.;50%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

methyl red
493-52-7

methyl red

succinimidyl 2-[4-(dimethylamino)phenylazo]benzoate
344303-47-5

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

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;50%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;
divinyltin oxide
4782-25-6

divinyltin oxide

methyl red
493-52-7

methyl red

(CH2CH)3Sn(OOC-2-C6H4N=NC6H4N(CH3)2-4)
1022919-97-6

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

Conditions
ConditionsYield
In ethanol under N2, 1 equiv. of acid was used, reflux for 4 h; soln. was filtered, concd., solid was crystd. from hot toluene/dioxane mixt. (1:4, v/v), crystals were washed with Et2O and dried in vac., elem.anal.;47%
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate
153086-78-3

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

methyl red
493-52-7

methyl red

(N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2-((4-(dimethylamino)phenyl)diazenyl)benzamide)

(N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)-2-((4-(dimethylamino)phenyl)diazenyl)benzamide)

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide at 20℃;44%
(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

methyl red
493-52-7

methyl red

2-(4-Dimethylamino-phenylazo)-N-((R)-1-phenyl-ethyl)-benzamide

2-(4-Dimethylamino-phenylazo)-N-((R)-1-phenyl-ethyl)-benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform at 0℃; for 3h;33.1%
bis(tri-n-propylstannyl)oxide
1067-29-4

bis(tri-n-propylstannyl)oxide

methyl red
493-52-7

methyl red

(C3H7)3SnOOCC6H4N2C6H4N(CH3)2

(C3H7)3SnOOCC6H4N2C6H4N(CH3)2

Conditions
ConditionsYield
In benzene byproducts: H2O; molar ratio (C3H7)3SnOSn(C3H7)3 : acid = 1:2, gentle reflux for 12 h; removal of water formed, recrystn. from petroleum ether;25%
In benzene byproducts: H2O; molar ratio (C3H7)3SnOSn(C3H7)3 : acid = 1:2, gentle reflux for 12 h; removal of water formed, recrystn. from petroleum ether;25%
(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

methyl red
493-52-7

methyl red

2-(4-Dimethylamino-phenylazo)-N-((S)-1-phenyl-ethyl)-benzamide

2-(4-Dimethylamino-phenylazo)-N-((S)-1-phenyl-ethyl)-benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform at 0℃; for 3h;21.3%
4-bromo-aniline
106-40-1

4-bromo-aniline

methyl red
493-52-7

methyl red

C21H19BrN4O

C21H19BrN4O

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 24h;17%
2,2'-dithio-bis[ethylamine]
51-85-4

2,2'-dithio-bis[ethylamine]

methyl red
493-52-7

methyl red

C34H38N8O2S2
139895-90-2

C34H38N8O2S2

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 24h; Ambient temperature;
benzoyl chloride
98-88-4

benzoyl chloride

methyl red
493-52-7

methyl red

C22H19N3O3

C22H19N3O3

Conditions
ConditionsYield
With pyridine N-oxide; triethylamine In 1,4-dioxane at 25℃; Rate constant;

493-52-7Relevant articles and documents

Interaction of Platinum(II) Complexes with Methyl Red

Gel'fman,Kirsanova

, p. 1090 - 1093 (2008/10/08)

The interaction of K2[PtCl4], K2[PtI4], [PtThio4]Cl2, cis- and trans-[Pt(NH3)2Cl2], and [Pt(NH3)4]Cl2 with Methyl Red (HL) was studied. It was found that HL forms stable complexes, where it may be a mono- or bidentate ligand. The thermodinamical stability of trans-[Pt(NH3)2(LH)Cl]NO3 was studied potentiometrically. The results obtained show that the azo group possesses π acceptor abilities.

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