Toluidine Blue O , CAS No.92-31-9

CAS: 92-31-9 Cat. No.: T492282 Molecular Weight: 305.83 Beilstein Registry Number: 27402 EC Number: 202-146-2 PubChem CID: 7083

Synonyms

CCRIS 4933 | NSC36758 | NSC-36758 | NSC760421 | NSC-760421 | Basic Blue 17 | Menodin | n-(7-amino-8-methyl-3h-phenothiazin-3-ylidene)-n-methylmethanaminium chloride | Toloni chloridum | Tolonii chloridum [INN-Latin] | CHEBI:87647 | F Klot | Phenothiazin-5

Storage

Room temperature

Shipped In

Normal

Overview

Toluidine Blue O (TBO) is a thiazine dye of the quinone-imine family and is cationic in nature. It has been employed in polychromatic staining of paraffin embedded plant cell walls. It is a metachromatic dye suitable for a wide variety of histological staining procedures.
A metachromatic dye suitable for a wide variety of histological staining procedures.

Specifications

Synonyms

CCRIS 4933 | NSC36758 | NSC-36758 | NSC760421 | NSC-760421 | Basic Blue 17 | Menodin | n-(7-amino-8-methyl-3h-phenothiazin-3-ylidene)-n-methylmethanaminium chloride | Toloni chloridum | Tolonii chloridum [INN-Latin] | CHEBI:87647 | F Klot | Phenothiazin-5

Storage

Room temperature

Shipped In

Normal

Names and Identifiers

• Pubchem Sid: 488180277
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180277
• Canonical Smiles: CC1=CC2=C(C=C1N)SC3=CC(=[N+](C)C)C=CC3=N2.[Cl-]
• IUPAC Name: (7-amino-8-methylphenothiazin-3-ylidene)-dimethylazanium;chloride
• InChIKey: GEDVVYWLPUPJJZ-UHFFFAOYSA-N
• INCHI: 1S/C15H15N3S.ClH/c1-9-6-13-15(8-11(9)16)19-14-7-10(18(2)3)4-5-12(14)17-13;/h4-8,16H,1-3H3;1H
• Isomeric SMILES: CC1=CC2=C(C=C1N)SC3=CC(=[N+](C)C)C=CC3=N2.[Cl-]
• WGK Germany: 3
• RTECS: SP5670000
• PubChem CID: 7083
• Molecular Weight: 305.83
• Beilstein: 27402

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Benzothiazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Benzothiazines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzothiazines
• Alternative Parents: Benzenoids Secondary ketimines Heteroaromatic compounds Azacyclic compounds Primary amines Organopnictogen compounds Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Benzothiazine - Benzenoid - Heteroaromatic compound - Secondary ketimine - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organic chloride salt - Organic salt - Primary amine - Organonitrogen compound - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 305.800 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 305.075 Da
• Monoisotopic Mass: 305.075 Da
• Topological Polar Surface Area: 66.700 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 511.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

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63. Na Chen, Yu-Die Xiong, Chi Zou, Yu-Wei Zhong, Hui Du, Yu-Jie Chi, Chan Zhao, Shu-Sheng Liu, Xiao-Wei Wang.  (2025)  A GDSL lipase confers resistance to piercing-sucking insects in tobacco by strengthening leaf cuticle.  PLANT JOURNAL,  123  (4): (e70440).  [PMID:40853759] [10.1111/tpj.70440]

64. Shenghua Xu, Weihong Guo.  (2025)  Stepwise Surface Engineering of Sr10-HA-g-PBLG Porous Microspheres: Precise Functionalization for In Situ Scaffold Formation via Dynamic Crosslinking.  POLYMERS FOR ADVANCED TECHNOLOGIES,  36  (8): (e70303).  [PMID:] [10.1002/pat.70303]

65. Yu Cheng, Yu Chen, Tao Song, Luojia Jiang, Yuhan He, Yupei Li, Weifeng Zhao, Baihai Su.  (2025)  Simultaneous Removal of Endotoxin and Circulating Histones by Heparin-Grafted Chitosan-Cellulose Composite Microspheres for Multitargeted Hemoperfusion in Septic Blood.  BIOMACROMOLECULES,      [PMID:40997831] [10.1021/acs.biomac.5c01085]

66. Mengdi Liang, Dulin Zuo, Feng Wang, Bei Zhang, Jingjing Tian, Xianchen Huang, Yuan Sun, Guanqiang Li, Xicheng Zhang, Gang Li.  (2025)  Drug-eluting vascular stents with surface modification of anticoagulation and pro-endothelialization.  BIOMACROMOLECULES,      [PMID:40990391] [10.1021/acs.biomac.5c01382]

67. Jiamin Zhang, Lifeng Chen, Yongqing Bai, Minghao Xue, Weiwei Sheng, Baofeng Hou, Huiyong Zeng, Xiaoxia Shang.  (2025)  A Novel Multi-Block High-Cationic Density Side-Chain Quaternary Ammonium Polymer: Preparation and Performance Evaluation of Clay Stabilizer for Efficient Water Injection.  JOURNAL OF APPLIED POLYMER SCIENCE,      [PMID:] [10.1002/app.58021]

68. Zhiyou Zeng, Xiaoyu Yang, Yongguo Cao, Sanshan Pu, Xinyu Zhou, Rongli Gu, Yiqian Zhang, Caijun Wu, Xiaojun Luo, Yi He.  (2023)  High-efficiency SERS platform based on 3D porous PPDA@Au NPs as a substrate for the detection of pesticides on vegetables.  Analytical Methods,  15  (37): (4842-4850).  [PMID:37702073] [10.1039/D3AY00808H]

69. Siyuan Sui, Hongmei Sun, Guohua Ni, Yafeng Liu, Huan Zheng, Tao Sun, Ling Kong, Zhongyang Ma, Fangli Yuan.  (2023)  Ar-H2O-NH3 plasma grafting and polymerization of dopamine onto polytetrafluoroethylene to promote heparin immobilization.  Plasma Processes and Polymers,  20  (5): (2200228).  [PMID:] [10.1002/ppap.202200228]

70. Bo Zhou, Yuling Tang, Liming Zhao, Lijun Guo, Jianfei Zhou.  (2021)  Novel Fe3O4–poly(methacryloxyethyltrimethyl ammonium chloride) adsorbent for the ultrafast and efficient removal of anionic dyes.  RSC Advances,  11  (2): (1172-1181).  [PMID:35423698] [10.1039/D0RA09296G]

71. Yuxuan Chen, Xiaoming Xu, Zhiwei Wang, Guoyan Hua, Yanhong Zhang, Fuqiang Liu.  (2024)  Dehydration-modulated pomelo peel cellulose nanofiber interlayer customized polyamide membrane with highly uniform pores for efficient nanofiltration.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.154128]

72. Liang Guo, Shijin Zhou, Yanju Liu, Huaixia Yang, Mingsan Miao, Wei Gao.  (2024)  Facile and controllable hybrid-nanoengineering of MWCNTs/Au@ZIF-8 and AuPt@CeO2 based sandwich electrochemical aptasensor for AFB1 determination in foods and herbs.  Journal of Saudi Chemical Society,      [PMID:] [10.1016/j.jscs.2024.101946]

73. Ziru Sun, Enxiang Jiao, Chengchen Deng, Meihong Xu, Jinglan He, Peizhao Shi, Xiaoguang Lin, Sai Chen, Yuanbiao Liu, Kai Guo, Xiaowei Li, Kun Li, Lebing Chang, Huimin Wang, Xuehai Zhang, Yuechuan Li, Duanqiang Xiao, Xiaoshan Cui, Guiying Li, Jiao Li, Haijun Zhang.  (2025)  Functionally Segmented Small-Diameter Vascular Grafts with Excellent Mechanical Matchability Prepared by Emulsion Spinning Method.  Materials Today Communications,      [PMID:] [10.1016/j.mtcomm.2025.113798]

74. Tianwen Liu, Wei Yuan, Mengyao Si, Xiaoning Wang, Xiangping Liu, Xiaoying Wang.  (2025)  A sensitive electrochemical sensor for detection of c-Myc protein leveraging dual-function of gold–palladium alloy nanoparticles.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.114051]

75. Yu-yao Qin, Zi-yi Qin, Tao Liang, Dong-er Qin, Sheng-yi Hua, Ming-hui Tan, Shun Guo, Fan Yang, Le Shi, Yun Yu, Guang-ji Zhang.  (2025)  Phellodendrine chloride alleviates gouty arthritis through IL-6/STAT3 signaling pathway.  IMMUNOBIOLOGY,      [PMID:40472707] [10.1016/j.imbio.2025.152918]

76. Linyan Yang, Man Xu, Jaewoo Lee, Wenchao Xue, Xuesong Li.  (2025)  From pore-confined to surface-controlled interfacial Polymerization: Strategic interfacial repositioning for high-performance fully aromatic polyamide membranes.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2025.124378]

77. Riji Qiu, Junjian Zheng, Xingran Zhang, Fang Li.  (2025)  Mechanistic Insights into Mitigation of Combined Scaling–Biofouling for a Novel Thin-Film Composite Membrane Based on Incorporated Defensive–Offensive Strategy.  ENVIRONMENTAL SCIENCE & TECHNOLOGY,      [PMID:40538162] [10.1021/acs.est.5c05189]

78. Guoying Dong, Yuxiao Liu, Huijun Liu, Chen Qiao, Xia Chen, Linxiao Wang.  (2025)  Effect of Hyperbaric Oxygen Treatment on Lipid Metabolism and Neurovascular Microenvironment in an Apolipoprotein E Knockout Mouse Model.  Journal of Integrative Neuroscience,  24  (7): (39656).  [PMID:40767018] [10.31083/JIN39656]

79. Yanan Yan, Youhong Tang, Dan Chang, Shengmei Song, Ayesha Aziz, Muhammad Asif, Shaomin Shuang, Chuan Dong.  (2025)  Engineering solvent-controlled multi-color emission carbon dots in single carbon source and their application in multi-channel Ag+ detection.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.115876]

80. Yujie Wang, Jingxin Li, Honghua Wang, Shixin Zhang, Jie Zhang, Hailin Yang, Xiaomin Tang, Huaili Zheng.  (2025)  The improvement of flocculation performance of organic polymer flocculants via regulation of their branched structure and block structure in removal of soluble dyes from wastewater.  Journal of Environmental Chemical Engineering,      [PMID:] [10.1016/j.jece.2025.119960]

81. Zihang Shi, Yangyang Hu, Changyu Zhou, Qiang Xia, Yangying Sun, Hongbing Yan, Kaiyong Yao, Chen Chen, Weitao Zhao, Daodong Pan.  (2025)  Preparation and characterisation of novel quaternized chitosan-based hollow salt and its sodium-reducing effect in air-dried ducks.  FOOD CHEMISTRY,      [PMID:41166818] [10.1016/j.foodchem.2025.146799]

82. Minqiao Feng, Chengyan Yin, Hailiang Qin, Wei Liu, Yunqi Wang, Ruth Antwi-Baah, Yao Rao, Shuxia Xu.  (2025)  An electrochemical biosensor based on DNAzyme and TB-loading mesoporous silica nanoparticles for detection of TdT in serum.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.116073]

83. Ruixue Meng, Yuan Li, Jiawei Peng, Huanhuan Guo, Yanhui Li, Long Chen.  (2025)  Conjugated cationic dye modulates the ion-confined partitioning of anions/cations in graphene membrane to enhance seawater desalination.  DESALINATION,      [PMID:] [10.1016/j.desal.2025.119825]

84. Cai Minghui, Zhang Wenwen, Yao Haixu, Su Huiyu, Cao Yang, Li Jiaxin, Min Xinyu, Cui Feiyun, Zhu Hui.  (2026)  A one-for-four redox probe strategy for multiplex electrochemical POCT of thrombotic biomarkers.  MICROCHIMICA ACTA,  193  (2): (94).  [PMID:41543777] [10.1007/s00604-025-07822-6]

85. Yuxuan Chen, Xiaoming Xu, Zhiwei Wang, Sunxinyi Wang, Guoyan Hua, Fuqiang Liu.  (2026)  Eco-friendly and cost-effective modification strategy for high-performance polyamide membranes: Synergistic regulation of interfacial tension reduction and diffusion inhibition.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2026.125184]

86. Luojia Jiang, Ying Li, Fang Wan, Yi Su, Meixian Lei, Yupei Li, Haibo Xu.  (2026)  The Effect of Heparin-Grafted Chitosan-Cellulose Composite Microspheres on the Removal of Endotoxins and Circulating Histones in a Septic Rabbit Model: An In Vivo Study.  Biomedicines,  14  (3): (661).  [PMID:] [10.3390/biomedicines14030661]

87. Tiantian Ding, Chunxia Ren, Liyuan Meng, Xu Zhang, Hengchong Shi, Bai Yang, Yunfeng Li.  (2026)  Nanocolloidal Hydrogel Coatings With Multiple Functions for Antithrombogenic Biointerfaces.  Advanced Healthcare Materials,      [PMID:] [10.1002/adhm.202504424]