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Quality Control of Methyl Red Purity: acid-base indicator grade,4.5(red)-6.2(yellow) SDS Specification

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Product Details of Methyl Red

CAS No. :	493-52-7
Formula :	C₁₅H₁₅N₃O₂
M.W :	269.30
SMILES Code :	O=C(O)C1=CC=CC=C1N=NC2=CC=C(N(C)C)C=C2
English Name :	2-((4-(Dimethylamino)phenyl)diazenyl)benzoic acid
MDL No. :	MFCD00002425
InChI Key :	CEQFOVLGLXCDCX-UHFFFAOYSA-N
Pubchem ID :	10303

Safety of Methyl Red

GHS Pictogram:
Signal Word:
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Application In Synthesis of Methyl Red

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 493-52-7 ]

[ 493-52-7 ] Synthesis Path-Downstream 1~14

1
[ 51-85-4 ]
[ 493-52-7 ]
[ 139895-90-2 ]

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

References: [1]Mullen, Ken I.; Wang, DaoXin; Crane, L. Gayle; Carron, Keith T. [Analytical Chemistry, 1992, vol. 64, # 8, p. 930 - 936].

2
[ 493-52-7 ]
[ 623548-90-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tin; hydrazine hydrate In methanol at 20℃; for 0.416667h;
60%	With ammonium chloride; magnesium In methanol at 20℃; for 0.0833333h;
	With titanium oxide Irradiation; anaerobe, buffered soln., effect of the pH, TiO₂ concn.;

References: [1]Dinesh; Abiraj; Srinivasa; Gowda, D. Channe [Journal of Chemical Research, 2006, # 7, p. 422 - 423].
[2]Sridhara; Srinivasa; Gowda, D. Channe [Journal of Chemical Research, 2004, # 1, p. 74 - 75].
[3]Brown, Graham T.; Darwent, James R. [Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1984, vol. 80, p. 1631 - 1644].

3
[ 493-52-7 ]
[ 118-92-3 ]
[ 99-98-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 92% 2: 85%	With hydrazine hydrate; aluminium In ethanol Heating;
1: 88% 2: 91%	With formic acid; zinc In methanol at 20℃; for 0.25h;
91%	With ammonium acetate; zinc In methanol at 20℃; for 0.0833333h;

80%	With zinc; hydrazinium monoformate In methanol for 0.25h; Heating;
80%	With ammonium chloride; zinc In methanol at 20℃; for 0.333333h;
	With potassium phosphate buffer; Clostridium diaphorase; NAD at 25℃; for 0.0833333h; inhibitor constant; var. inhibitors;
	With ammonium formate; magnesium In methanol at 20℃; for 0.333333h;
	With ammonium bromide; aluminium In methanol for 0.166667h; sonication;
	With hydrogen In ethanol at 20℃; for 0.0333333h; aq. buffer;
	With metallothionein α-domain tetranuclear iron(II) complex at 25℃; for 6h; Inert atmosphere; aq. phosphate buffer;
	With sodium tetrahydroborate; water; fullerene C₆₀; sodium hydroxide at 20℃; for 5h; UV-irradiation;
	With 1,4-dihydronicotinamide adenine dinucleotide; recombinant Escherichia coli CpXFMN flavin mononucleotide-containing azobenzene reductase In aq. buffer at 30℃; Enzymatic reaction;
	With FMN-dependent NADH-azoreductase from Burkholderia thailandensis; NADH
	With sodium tetrahydroborate; sodium hydroxide In water at 20℃; for 0.75h; UV-irradiation;
	With sodium tetrahydroborate In water at 20℃;	2.5 General method for the reduction of RhB and MR General procedure: 3mL of RhB or MR aqueous solution (0.05mM), 0.5mL of NaBH4 aqueous solution (0.05mM) and catalyst (1mg) were added to a quartz cuvette and desired mixture stirred at room temperature. The progress of the reaction was recorded by UV-visible spectroscopy.
	With ethanol; caesium carbonate at 130℃; Inert atmosphere; Sealed tube; Overall yield = 83 percentSpectr.;
	With sodium tetrahydroborate; water; 4'-((4-((2-(thiazol-4-yl)-1H-benzo[d]imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile-CoCl₂.6H₂O for 0.15h;

References: [1]Pasha; Nanjundaswamy [Journal of Chemical Research, 2004, # 11, p. 750 - 752].
[2]Gowda, Shankare; Abiraj; Gowda, D.Channe [Tetrahedron Letters, 2002, vol. 43, # 7, p. 1329 - 1331].
[3]Srinivasa; Abiraj; Gowda, D. Channe [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 192 - 195].
[4]Gowda, Shankare; Abiraj; Gowda, D. Channe [Journal of Chemical Research - Part S, 2002, # 8, p. 384 - 385].
[5]Sridhara; Srinivasa; Gowda, D. Channe [Synthetic Communications, 2004, vol. 34, # 8, p. 1441 - 1446].
[6]Yatome, Chizuko; Fujimi, Kazuhiko; Ogawa, Toshihiko [Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 9, p. 2349 - 2351].
[7]Abiraj; Gowda, Shankare; Gowda, D. Channe [Journal of Chemical Research - Part S, 2003, # 5, p. 299 - 300].
[8]Pasha; Jayashankara [Journal of Chemical Research, 2004, # 4, p. 282 - 283].
[9]Dai, Yunqian; Lim, Byungkwon; Yang, Yong; Cobley, Claire M.; Li, Weiyang; Cho, Eun Chul; Grayson, Benjamin; Fanson, Paul T.; Campbell, Charles T.; Sun, Yueming; Xia, Younan [Angewandte Chemie - International Edition, 2010, vol. 49, # 44, p. 8165 - 8168].
[10]Location in patent: experimental part Sano, Yohei; Onoda, Akira; Sakurai, Rie; Kitagishi, Hiroaki; Hayashi, Takashi [Journal of Inorganic Biochemistry, 2011, vol. 105, # 5, p. 702 - 708].
[11]Guo, Yong; Li, Wengang; Yan, Jingjing; Moosa, Basem; Amad, Ma'An; Werth, Charles J.; Khashab, Niveen M. [Chemistry - An Asian Journal, 2012, vol. 7, # 12, p. 2842 - 2847].
[12]Langer, Simone; Nakanishi, Shinobu; Mathes, Tilo; Knaus, Tanja; Binter, Alexandra; Macheroux, Peter; Mase, Tomoko; Miyakawa, Takuya; Tanokura, Masaru; Mack, Matthias [Biochemistry, 2013, vol. 52, # 25, p. 4288 - 4295].
[13]Kolb, Roman; Bach, Nina C.; Sieber, Stephan A. [Chemical Communications, 2014, vol. 50, # 4, p. 427 - 429].
[14]Mazzier, Daniela; Carraro, Francesco; Crisma, Marco; Rancan, Marzio; Toniolo, Claudio; Moretto, Alessandro [Soft Matter, 2015, vol. 12, # 1, p. 238 - 245].
[15]Khosravi, Faezeh; Gholinejad, Mohammad; Sansano, José M.; Luque, Rafael [Molecular catalysis, 2022, vol. 522].
[16]Panja, Dibyajyoti; Dey, Sadhan; Saha, Rohini; Sahu, Rajib; Das, Gourab Kanti; Bhobe, Preeti; Kundu, Sabuj [Green Chemistry, 2023, vol. 25, # 22, p. 9374 - 9387].
[17]Singh, Gurjaspreet; Diskit, Tsering; Singh, Akshpreet; Dege, Necmi; Ozturk, Seyhan; Rana, Shweta; Singh, Jaiveer; Dalal, Anurag; Devi, Swati [Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2025, vol. 330].

4
[ 2627-86-3 ]
[ 493-52-7 ]
[ 193343-26-9 ]

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

References: [1]Yamamoto; Maeda; Kitano [Journal of Physical Chemistry B, 1997, vol. 101, # 35, p. 6855 - 6860].

5
[ 3886-69-9 ]
[ 493-52-7 ]
[ 193343-25-8 ]

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

References: [1]Yamamoto; Maeda; Kitano [Journal of Physical Chemistry B, 1997, vol. 101, # 35, p. 6855 - 6860].

6
[ 541-41-3 ]
[ 493-52-7 ]
[ 303054-03-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at -10℃;

References: [1]Kaloyanov, Nikolay; Stoyanova, Rossitza [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 7, p. 652 - 655].

7
[ 1592-20-7 ]
[ 493-52-7 ]
[ 681430-02-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine In N,N-dimethyl-formamide for 24h;
94%	With triethylamine In N,N-dimethyl-formamide for 24h;	1 Dye-substituted styrene monomer was prepared by dissolving 1.4 mL of 4-vinylbenzylchloride and 1.346 g of METHYL RED in 5 mL of distilled dimethylformamide (DMF) in the presence of 1.05 mL of triethylamine. The solution was stirred for 24 h and then poured into 50 mL of water. The resulting solid precipitate was isolated by filtration and purified by column chromatography using 4:1 (vol:vol) hexane:ethyl acetate as the eluent. The product was isolated in 94% yield. 1H NMR (CDCl3): δ 8.2 (d, 8.8 Hz, 2H), 7.9 (dd, J=8.8, 9.3 Hz, 4H), 7.4 (s, 4H), 6.8 (d, 9.3 Hz, 2H), 6.7 (dd, J=11.0, 17.6 Hz, 1H), 5.8 (d, 17.6 Hz, 1H), 5.4 (s, 2H), 5.3 (d, 11.0 Hz, 1H), 3.1 (s, 6H). 13C NMR: δ 166.4, 156.3, 153.1, 143.9, 137.8, 136.6, 135.7, 130.9, 130.2, 128.7, 126.6, 125.7, 122.2, 114.6, 111.7, 66.8, 40.5. MS (ESI): 386 (M+Ht, calcd 386.454. found 386.185.

References: [1]Bergbreiter, David E.; Li, Chunmei [Organic Letters, 2003, vol. 5, # 14, p. 2445 - 2447].
[2]Current Patent Assignee: TEXAS A M UNIVERSITY SYSTEM - US7211705, 2007, B2 Location in patent: Page/Page column 8.

8
[ 493-52-7 ]
[ 118-92-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With ammonium formate; nickel In methanol at 20℃; for 0.25h;
80%	With ammonia borane; copper(II) oxide In methanol at 40℃; for 0.5h; Sealed tube;

References: [1]Gowda, D. Channe; Gowda, Shankare; Abiraj [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 7, p. 1774 - 1776].
[2]Thakur, Seema D.; Gupta, Shivangi; Dey, Sadhan; Kundu, Sabuj [Chemistry - A European Journal, 2025, vol. 31, # 23].

9
[ 493-52-7 ]
[ 99-98-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrazine hydrate In ethanol Heating;
80%	With ammonia borane; copper(II) oxide In methanol at 40℃; for 0.5h; Sealed tube;
	With azoreductase from Escherichia coli; NADH; sodium chloride In dimethyl sulfoxide at 25℃; for 3h; Enzymatic reaction;

References: [1]Pasha; Nanjundaswamy [Synthetic Communications, 2005, vol. 35, # 7, p. 897 - 900].
[2]Thakur, Seema D.; Gupta, Shivangi; Dey, Sadhan; Kundu, Sabuj [Chemistry - A European Journal, 2025, vol. 31, # 23].
[3]Peng, Yu-Ju; Xu, Bing; Rokita, Steven E. [ACS Chemical Biology, 2025, vol. 20, # 1, p. 229 - 237].

10
[ 493-52-7 ]
[ 784128-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Et₃N / CH₂Cl₂ / -10 °C 2: Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C 3: H₂O

References: [1]Kaloyanov, Nikolay; Stoyanova, Rossitza [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 7, p. 652 - 655].

11
[ 493-52-7 ]
[ 732975-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Et₃N / CH₂Cl₂ / -10 °C 2: Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C 3: H₂O

References: [1]Kaloyanov, Nikolay; Stoyanova, Rossitza [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 7, p. 652 - 655].

12
[ 493-52-7 ]
[ 763072-40-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Et₃N / CH₂Cl₂ / -10 °C 2: Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C 3: H₂O

References: [1]Kaloyanov, Nikolay; Stoyanova, Rossitza [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 7, p. 652 - 655].

13
[ 493-52-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / CH₂Cl₂ / -10 °C 2: Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C

References: [1]Kaloyanov, Nikolay; Stoyanova, Rossitza [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 7, p. 652 - 655].

14
[ 493-52-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Et₃N / CH₂Cl₂ / -10 °C 2: Et₃N / CH₂Cl₂ / 2 h / -10 - 20 °C

References: [1]Kaloyanov, Nikolay; Stoyanova, Rossitza [Arzneimittel-Forschung/Drug Research, 2000, vol. 50, # 7, p. 652 - 655].

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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 493-52-7

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CAS No.: 493-52-7

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[ 493-52-7 ] Synthesis Path-Downstream 1~14

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