1,3-benzothiazole

• ChemBase ID: 108744
• Molecular Formular: C7H5NS
• Molecular Mass: 135.1863
• Monoisotopic Mass: 135.01427017
• SMILES: s1cnc2ccccc12
• Canonical SMILES: c1ccc2c(c1)scn2
• InChI: InChI=1S/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
• InChIKey: IOJUPLGTWVMSFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-benzothiazole
• IUPAC Traditional name: benzothiazole
• Synonyms: BENZOTHIAZOLE; Benzothiazole; 1-Thia-3-azaindene; Benzo[d]thiazole; Benzosulfonazole; NSC 8040; Vangard BT; Benzo[d]thiazole; 苯并噻唑

Database IDs

• CAS Number: 95-16-9
• EC Number: 202-396-2
• MDL Number: MFCD00005775
• Beilstein Number: 109468
• Merck Index: 141107
• PubChem SID: 24901589; 162094420; 24846538; 24847809
• PubChem CID: 7222
• CHEBI ID: 45993
• CHEMBL: 510309
• Chemspider ID: 6952
• FEMA ID: 3256
• Unique Ingredient Identifier: G5BW2593EP
• Wikipedia Title: Benzothiazole
• Council of Europe Number: 11594
• Flavis Number: 15.016

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.1133084
• LogD (pH = 7.4): 2.1134696
• Log P: 2.1134717
• Molar Refractivity: 37.1287 cm^3
• Polarizability: 15.639701 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Slightly soluble in water. Soluble in alcohol, carbon disulfide
• Apperance: Clear Colourless Oil
• Melting Point: 2 °C(lit.); 2°C; 2°C
• Boiling Point: 227 - 228°C; 230°C; 231 °C(lit.)
• Flash Point: 107°C(224°F); 113 °C; 235.4 °F
• Density: 1.238 g/mL; 1.238 g/mL at 25 °C(lit.); 1.241; 1.246 g/ml
• Refractive Index: 1.6420; n20/D 1.642(lit.); n20/D 1.643
• Vapor Pressure: 34 mmHg ( 131 °C)
• Vapor Density: 4.66 (vs air)

Safety Information

• Storage Condition: Refrigerator
• RTECS: DL0875000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: UN2810
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 20/21/22-36; 22; R:22-27
• Safety Statements: 23-26-36; 26-36/37; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H311-H332-H319; H302
• GHS Precautionary statements: P280H-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥90% (GC); ≥96%; 95+%; 96%; 97%
• Grade: NI; technical
• Impurities: ≤0.1% aniline
• Empirical Formula (Hill Notation): C7H5NS

DETAILS

MP Biomedicals - 05208576

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 101338

Packaging
5, 100, 500 g in glass bottle
Application
Interesting carbonyl equivalent. Reacts with aldehydes or ketones to generate α-hydroxy carbonyl compounds.1

Sigma Aldrich - W325600

Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in comp drum

Toronto Research Chemicals - B206640

Various benzothiazole-benzamides synthesized were evaluated for their analgesic and antidepressant activities.

REFERENCES

• Porsolt, R., et al.: Nature, 266, 730 (1977)
• Foster, J., et al.: Bioorg. Med. Chem., 7, 2415 (1977)
• Caliendo, G., et al.: Eur. J. Med. Chem., 36, 517 (1977)
• Rana, A., et al.: Eur. J. Med. Chem., 43, 1114 (1977)
• n-BuLi gives the 2-lithio-derivative, stable below -50^o, which behaves as a formyl anion equivalent, reacting with aldehydes and ketones. The derived alcohols have been transformed into various useful products, e.g. ɑ-hydroxy ketones: Tetrahedron Lett., 5, 9, 13, (1978); Bull. Chem. Soc. Jpn., 61, 3637 (1988):
  
• The lithio-derivative can also be acylated with esters, lactones, amides or nitriles. In these applications, benzothiazole is claimed to be superior to the better known 1,3-dithiane as a formyl anion synthon.
• See also 2-(Trimethylsilyl)benzothiazole, L11625, and 2-(Trimethylsilyl)thiazole, B21903.
• Reaction of the lithio-derivative at low temperatures with PCl₃ gives, as the major product, 2,2'-bibenzothiazole instead of the expected tertiary phosphine: Heterocycles, 30, 347 (1990). POCl₃ or SOCl₂ also promote the symmetrical coupling reaction: Heteroatom. Chem., 5, 409 (1994).