2-Mercaptobenzothiazole

An aromatic thiol, C7H5NS2, 167.258 g/mol. Boiling point Decomposes, melting point 180.2-181.7 °C, as published.

verified recordOrganic — aromatic thiol7 measured properties

Identifiers

Molecular formula: C₇H₅NS₂
Molecular weight: 167.258 g/mol
Exact mass: 166.986341 g/mol
IUPAC name: 1,3-benzothiazole-2-thiol
SMILES: Sc1nc2ccccc2s1
InChI: InChI=1S/C7H5NS2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChIKey: YXIWHUQXZSMYRE-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: Decomposes (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; Not determinable experimentally by EU Method A.2 (Boiling Temperature) due to overlapping endothermic and exothermic reactions.measured · ECHA; Search for Chemicals. Benzothiazole-2-thiol (CAS 149-30-4) Registered Substances Dossier. European Chemical Agency. Available from, as of Feb 3, 2015: https://echa.europa.eu/
Melting Point: 351 to 358 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 180.2-181.7 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1089; MP: 170-173 °C /Technical mercaptobenzothiazole/measured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1089; 177 - 179 °Cmeasured · reference compound database; 180-182 °Cmeasured · reference compound database; 181 °Cmeasured · reference compound database
Flash Point: 392 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 392 °Fmeasured · reference compound database; 243 °Cmeasured · reference compound database
Solubility: less than 1 mg/mL at 66 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; In water at 25 °C, 51 mg/L (pH 5), 118 mg/L (pH 7), 900 mg/L (pH 9)measured · ECHA; Search for Chemicals. Benzothiazole-2-thiol (CAS 149-30-4) Registered Substances Dossier. European Chemical Agency. Available from, as of Feb 3, 2015: https://echa.europa.eu/; In pure water, 120 mg/L at 24 °C; in buffered creek water at 24 °C, 190 mg/L (pH 6.5), 230 mg/l (pH 7.5), 260 mg/L (pH 8.5)measured · Brownlee BG et al; Environ Toxicol Chem 11: 1153-68 (1992); Solubility at 25 °C (g/100 mL) in alcohol: 2.0; ether 1.0; acetone 10.0; benzene 1.0; carbon tetrachloride <0.2; naphtha <0.5. Moderately soluble in glacial acetic acid. Soluble in alkalies and alkali carbonate solutionsmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1089; Soluble in dilute caustic soda, alcohol, acetone, benzene, chloroform; insoluble in water and gasoline.measured · Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 798; For more Solubility (Complete) data for 2-MERCAPTOBENZOTHIAZOLE (6 total), please visit the HSDB record page.measured · reference compound database; 0.12 mg/mL at 24 °Cmeasured · reference compound database; Solubility in water, g/100ml at 20 °C: 0.01 (very poor)measured · reference compound database
Density: 1.42 at 68 °F (NTP, 1992) - Denser than water; will sinkmeasured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 1.42 g/cu cm at 20 °Cmeasured · Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-42; 1.42 g/cm³measured · reference compound database; 1.42 @ 20°Cmeasured · reference compound database
Vapor Pressure: 0.000464 [mmHg]measured · reference compound database; 2.25X10-8 mm Hg at 20 °C; <1.9X10-6 mm Hg at 25 °Cmeasured · ECHA; Search for Chemicals. Benzothiazole-2-thiol (CAS 149-30-4) Registered Substances Dossier. European Chemical Agency. Available from, as of Feb 3, 2015: https://echa.europa.eu/
LogP: log Kow = 2.41measured · Brownlee BG et al; Environ Toxicol Chem 11: 1153-68 (1992); 2.42measured · reference compound database; 2.41measured · reference compound database; 2.41measured · reference compound database

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 167.3 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 166.98634151 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 2.7calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 42.1 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 129calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 3calculated · reference compound database
logP: 2.585calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 12.89 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 1calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 3calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 46.872 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.595calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon7 atoms · 50.3% by mass
S Sulfur2 atoms · 38.3% by mass
N Nitrogen1 atom · 8.4% by mass
H Hydrogen5 atoms · 3.0% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 10
Total atoms, hydrogen included: 15
Rings: 2
Aromatic rings: 2
Stereocentres: 0
Formal charge: 0

Functional groups

Thiol
An –SH group, the sulfur analogue of an alcohol.
Aromatic ring
A flat six-membered ring with delocalised electrons.
Aromatic ring (five-membered)
A flat five-membered ring with delocalised electrons, such as furan, thiophene or pyrrole.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves 2-Mercaptobenzothiazole yet.

Other names for it

The systematic name on this record is 1,3-benzothiazole-2-thiol.

The sources also call it 2-Benzothiazolethiol, Captax, 1,3-Benzothiazole-2-thiol, Benzothiazolethiol, MERCAPTOBENZOTHIAZOLE, 2(3H)-Benzothiazolethione, Dermacid, Kaptax, Mertax, Thiotax, Rotax, Accelerator M.

Structurally related

Molecules sharing this formula, or whose fingerprint is at least 40% similar to this one. Similarity is Tanimoto on Morgan fingerprints over this library only — it is a measure of structural overlap, not of how alike they behave.

1,3-Benzothiazole-2-carbaldehyde

C8H5NOS

Where these values came from

reference compound database8997
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.