Methyl red supplier | CasNO.493-52-7

Name
Methyl Red
EINECS 207-776-1
CAS No. 493-52-7
Density 1.17 g/cm³
Solubility Practically insoluble in water. Soluble in alcohol, acetic acidSoluble in ethanol. Insoluble in water.
Melting Point 178-182 °C
Formula C₁₅H₁₅N₃O₂
Boiling Point 479.5 °C at 760 mmHg
Molecular Weight 269.303
Flash Point 243.8 °C
Transport Information UN 1170 3/PG 2
Appearance dark red crystalline powder
Safety 36/37-24/25-22-45-33-24-16-7-36-26-36/37/39
Risk Codes 10-20/21/22-68/20/21/22-68-36/38-23/25-11-36/37/38-34
Molecular Structure
Hazard Symbols T, F,Xi, C, Xn
Synonyms Benzoicacid, 2-[[4-(dimethylamino)phenyl]azo]- (9CI);C.I. Acid Red 2 (8CI);2-Carboxy-4'-(dimethylamino)azobenzene;2-[(p-Dimethylamino)phenyl]azobenzoicacid;2-[[4-(Dimethylamino)phenyl]azo]benzoic acid;4-(2-Carboxyphenylazo)-N,N-dimethylaniline;4'-(Dimethylamino)azobenzene-2-carboxylic acid;Acid Red 2;C.I. 13020;Methyl red C.I. 13020;NSC 215212;NSC 34729;NSC 9597;o-Methyl red;o-[[p-(Dimethylamino)phenyl]azo]benzoic acid;p-(Dimethylamino)azobenzene-o-carboxylic acid;Methyl Red;
PSA 65.26000
LogP 3.86620

Synthetic route

: 118-92-3
anthranilic acid

: 493-52-7
methyl red

Conditions

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

: 17333-86-7
o-Carboxybenzenediazonium

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

: 493-52-7
methyl red

: 7647-01-0
hydrogenchloride

: 2-carboxy-benzenediazonium; chloride

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

: 493-52-7
methyl red

...Expand

: [PtL2]

: 7681-11-0
potassium iodide

A: 493-52-7
methyl red

B: platinum(II) iodide

Conditions

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

...Expand

: 493-52-7
methyl red

: 2450-71-7
Propargylamine

: C18H18N4O

Conditions

Conditions	Yield
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%

: 62-38-4
phenylmercuric acetate

: 493-52-7
methyl red

: C6H5HgC15H14N3O2

Conditions

Conditions	Yield
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%

: 1592-20-7
4-Vinylbenzyl chloride

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 24h;	94%
With triethylamine In N,N-dimethyl-formamide for 24h;	94%

: 493-52-7
methyl red

A: 118-92-3
anthranilic acid

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

Conditions

Conditions	Yield
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%

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol Heating;	92%

: 493-52-7
methyl red

: 118-92-3
anthranilic acid

Conditions

Conditions	Yield
With ammonium formate; nickel In methanol at 20℃; for 0.25h;	88%

: 13822-56-5
3-(trimethoxysilyl)propan-1-amine

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
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%

: 56-35-9
bis(tri-n-butyltin)oxide

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
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%

: 493-52-7
methyl red

: N,N'-dihydromethylred

Conditions

Conditions	Yield
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.;

: 64-17-5
ethanol

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;	76%

: 1262-21-1
bis(triphenyltin) oxide

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
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%

: 15529-49-4, 41756-81-4
tris(triphenylphosphine)ruthenium(II) chloride

: 493-52-7
methyl red

: C51H43ClN3O2P2Ru

Conditions

Conditions	Yield
With triethylamine In methanol at 85℃; for 4h;	60%

: 493-52-7
methyl red

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

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

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 3h;	57%

: 2273-51-0
diphenyltin(IV) oxide

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
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%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;	50%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;

: 4782-25-6
divinyltin oxide

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
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%

: 153086-78-3
tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide at 20℃;	44%

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform at 0℃; for 3h;	33.1%

: 1067-29-4
bis(tri-n-propylstannyl)oxide

: 493-52-7
methyl red

: (C3H7)3SnOOCC6H4N2C6H4N(CH3)2

Conditions

Conditions	Yield
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%

: 2627-86-3
(S)-1-phenyl-ethylamine

: 493-52-7
methyl red

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

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform at 0℃; for 3h;	21.3%

: 106-40-1
4-bromo-aniline

: 493-52-7
methyl red

: C21H19BrN4O

Conditions

Conditions	Yield
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%

: 51-85-4
2,2'-dithio-bis[ethylamine]

: 493-52-7
methyl red

: 139895-90-2
C34H38N8O2S2

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 24h; Ambient temperature;

: 98-88-4
benzoyl chloride

: 493-52-7
methyl red

: C22H19N3O3

Conditions

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

Methyl red Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 8 , 1975,p. 161.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Methyl red Specification

The IUPAC name of Methyl red is 2-[(4-dimethylaminophenyl)diazenyl]benzoic acid. With the CAS registry number 493-52-7, it is also named as Benzoic acid, o-((p-(dimethylamino)phenyl)azo)-. The product's categories are organics; analytical chemistry; indicator (pH); biochemical reagents for identification; microbiology; indicator solutions; indicators; stains and dyes; titration. It is dark red crystalline powder which is soluble in ethanol, acetic acid, and almost insoluble in water. In addition, Methyl red is stable and incompatible with strong oxidizing agents.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.91; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.15; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 54.64; (6)ACD/BCF (pH 7.4): 2.93; (7)ACD/KOC (pH 5.5): 192.16; (8)ACD/KOC (pH 7.4): 10.3; (9)#H bond acceptors: 5; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.592; (12)Molar Refractivity: 77.97 cm³; (13)Molar Volume: 230.1 cm³; (14)Polarizability: 30.91×10^-24 cm³; (15)Surface Tension: 44.3 dyne/cm; (16)Enthalpy of Vaporization: 78.36 kJ/mol; (17)Vapour Pressure: 5.27E-10 mmHg at 25°C; (18)Rotatable Bond Count: 4; (19)Exact Mass: 269.116427; (20)MonoIsotopic Mass: 269.116427; (21)Topological Polar Surface Area: 65.3; (22)Heavy Atom Count: 20.

Preparation of Methyl red: It is obtained by diazotization of anthranilic acid, followed by reaction with dimethylaniline:

Uses of Methyl red: is one of acid-base indicator used for identification, such as: indicator solutions. It is red in pH under 4.4, yellow in pH over 6.2, and orange in between, with a pKa of 5.1. And it is also used for staining protozoa in vivo.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so it should be kept away from sources of ignition. And it is harmful by inhalation, in contact with skin and if swallowed. In addition, Methyl red is irritating to eyes, respiratory system and skin, so people must not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse aimmediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Take precautionary measures against static discharges.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(O)c2ccccc2/N=N/c1ccc(N(C)C)cc1;
2. InChI: InChI=1/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)/b17-16+.

Product Name

Methyl Red

Synthetic route

Methyl red Consensus Reports

Methyl red Specification

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