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| Name |
Methyl red |
EINECS | 207-776-1 |
| CAS No. | 493-52-7 | Density | 1.17 g/cm3 |
| PSA | 65.26000 | LogP | 3.86620 |
| 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; |
Methyl red Synthetic route
| Conditions | Yield |
|---|---|
| With hydrogenchloride; sodium nitrite durch Diazotierung und Kupplung der Diazoverbindung mit Dimethylanilin, geloest in salzsaurehaltigem Alkohol; |
| Conditions | Yield |
|---|---|
| In water water bath (4 h); ppt. filtration off, washing (water), drying (70°C); elem. anal.; |
| 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% |
| 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 | Yield |
|---|---|
| With triethylamine In N,N-dimethyl-formamide for 24h; | 94% |
| With triethylamine In N,N-dimethyl-formamide for 24h; | 94% |
| 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% |
| Conditions | Yield |
|---|---|
| With hydrazine hydrate In ethanol Heating; | 92% |
| Conditions | Yield |
|---|---|
| With ammonium formate; nickel In methanol at 20℃; for 0.25h; | 88% |
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:
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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+.
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