2-(Thiocyanatomethylthio)benzothiazole

Base Information

• Chemical Name: 2-(Thiocyanatomethylthio)benzothiazole
• CAS No.: 21564-17-0
• Deprecated CAS: 56532-60-6,56996-45-3,6441-45-8,64441-45-8
• Molecular Formula: C9H6N2S3
• Molecular Weight: 238.358
• Hs Code.: 29342000
• European Community (EC) Number: 244-445-0
• ICSC Number: 1161
• UNII: 5GE166YVQV
• DSSTox Substance ID: DTXSID6032647
• Nikkaji Number: J10.910J
• Wikipedia: TCMTB
• Wikidata: Q158532
• ChEMBL ID: CHEMBL1903976
• Mol file: 21564-17-0.mol

Synonyms:2-(Thiocyanatomethylthio)benzo[d]thiazole;Thiocyanic acid,(2-benzothiazolylthio)methyl ester;2-[(Thiocyanatomethyl)thio]benzothiazole;(2-Benzothiazolylthio)methyl thiocyanate;2-Tiocianometiltiobenzotiazolo;AI3-29396-X;BRN 1213014;Benthiazole;(Benzothiazol-2-ylthio)methyl thiocyanate;TCMTB;1,3-Benzothiazol-2-ylsulfanylmethyl thiocyanate;

Chemical Property of 2-(Thiocyanatomethylthio)benzothiazole

Chemical Property:

• Appearance/Colour: Brown-red liquid
• Vapor Pressure: 8.65E-07mmHg at 25°C
• Melting Point: <-10 °C
• Refractive Index: 1.743
• Boiling Point: 405.6 °C at 760 mmHg
• PKA: -0.09±0.10(Predicted)
• Flash Point: 199.1 °C
• PSA: 115.52000
• Density: 1.47 g/cm³
• LogP: 3.56018
• Storage Temp.: 0-6°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 237.96931172
• Heavy Atom Count: 14
• Complexity: 238

Purity/Quality:

99.9% ^*data from raw suppliers

Tolcide2230(90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, N, Xn
• Hazard Codes: T+,N,Xn
• Statements: 22-26-36/38-43-50/53-36/37/38
• Safety Statements: 28-36/37-38-45-60-61-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1=CC=C2C(=C1)N=C(S2)SCSC#N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes. The substance is irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: (Benzothiazol-2-ylthio)methyl thiocyanate?(TCMTB) is a?chemical compound?classified as a?benzothiazole. 2-(thiocyanomethylthio)benzothiazole is a a soil and seed treatment used to control various fungal and bacterial infections. It is moderately soluble in water, has a low volatility and is not expected to be persistent in soil systems. It is not eexpected to leach to groundwater. It has a pungent odour, is highly toxic to most aquatic species and moderately toxic to birds. 2-(thiocyanomethylthio)benzothiazole is highly toxic to humans via the oral route and is a recognised irritant.
• Physical properties: It is a viscous reddish liquid and is insoluble in vater， but soluble in organic solvents such as acetone,dimethylformamide,cyclohexanone， benzene and xylene. It has a specific gravityof 1.38,a boiling point greater than 120℃ and a vapour pressure of about 0.05 torr. The supplier normally dissolves TCMTB in a mixture of organic solvents to form a concentrate. Emulsifiers or surfactants may be added to the concentrate to improve the stability of emulsions formed when the concentrate is diluted withwater. TCMTB is sold commercially as 80% technical material under thetrade name "TCMTB" by Buckman Laboratories，Which is the soleanufacturer of the material.The patented preparationinvolves a reaction of 2-mercaptobenzothiazole and chloromethylthiocyanate,but confidential data obtained from Buckman Laboratories indicates another preparative method may now be used.
• Uses: 2-(Thiocyanatomethylthio)benzothiazole is an antimicrobial agent used as a substitute for chlorophenols in industrial applications. Wood preservative, marine biocide, fungicide.

Technology Process of 2-(Thiocyanatomethylthio)benzothiazole

There total 8 articles about 2-(Thiocyanatomethylthio)benzothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(2-chloromethylthio)benzothiazole (28908-00-1) + sodium thiocyanide (540-72-7) → 2-(thiocyanomethylthio)benzothiazole (21564-17-0)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; at 90 ℃; for 10h;

Reference yield: 78.0%

(2-chloromethylthio)benzothiazole (28908-00-1) + ammonium thiocyanate (1147550-11-5) → 2-(thiocyanomethylthio)benzothiazole (21564-17-0)

Guidance literature:

With aluminum oxide; In acetone; for 4h; Heating;

DOI:10.1080/00397919908086063

Reference yield:

2-Mercaptobenzothiazole (149-30-4,118090-09-8) → 2-(thiocyanomethylthio)benzothiazole (21564-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / aq.NaOH / acetone / 1 h / 0 °C

2: 80 percent / aq. benzyltriethylammonium chloride / 10 h / 90 °C

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In acetone;

upstream raw materials:

chloromethyl thiocyanate

2-Mercaptobenzothiazole

(2-chloromethylthio)benzothiazole

sodium thiocyanide

Refernces

• 1、 -. "Protective agents for wood". . . Retrieved 2008/06/13.
• 2、 Ramadas,Janarthanan. "Convenient synthesis of chloromethyl thioaromatics". . p. 1003 - 1007. Retrieved 2007/10/03.