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375462

Sigma-Aldrich

3H-1,2-Benzodithiol-3-one

97%

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About This Item

Empirical Formula (Hill Notation):
C7H4OS2
CAS Number:
1677-27-6
Molecular Weight:
168.24
Beilstein:
119513
EC Number:
216-829-8
MDL number:
MFCD00134412
UNSPSC Code:
12352100
PubChem Substance ID:
24863388
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

74-77 °C (lit.)

solubility

toluene: soluble 2.5%, clear, yellow

functional group

disulfide

SMILES string

O=C1SSc2ccccc12

InChI

1S/C7H4OS2/c8-7-5-3-1-2-4-6(5)9-10-7/h1-4H

InChI key

GZTYTTPPCAXUHB-UHFFFAOYSA-N

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General description

3H-1,2-Benzodithiol-3-one is a heterocyclic building block.
3H-1,2-Benzodithiol-3-one is reported to react with triphenylphosphine to afford dithiosalicylide.

Application

3H-1,2-Benzodithiol-3-one (1,2-benzodithiol-3-one) may be used as sulfur-transferring agent for the transformation of H-phosphonothioate and H-phosphonate diesters into the corresponding phosphorodi- and phosphoromonothioates.
3H-1,2-Benzodithiol-3-one may be employed as sulfurizing reagent in the preparation of phosphorothioate-containing oligodeoxyribonucleotides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

375462-VAR:
375462-5G:
375462-BULK:
375462-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK4296
MKCD7674
MKCC7334
MKCB2475V
MKBZ0025V

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Q Xu et al.
Nucleic acids research, 24(9), 1602-1607 (1996-05-01)
Previous methods for the preparation of phosphorothioate-containing oligodeoxyribonucleotides rely on the reaction of phosphite triesters with sulfurizing reagents such as tetraethylthiuram disulfide (TETD) and 3H-1,2-benzodithiol-3-one 1,1-dioxide (Beaucage reagent). However, these and other sulfurizing reagents suffer from several disadvantages, and there
Nucleoside H-phosphonates. 13. Studies on 3H-1, 2-benzodithiol-3-one derivatives as sulfurizing reagents for H-phosphonate and H-phosphonothioate diesters.
Stawinski J and Thelin M.
The Journal of Organic Chemistry, 56(17), 5169-5175 (1991)
Novel syntheses of dithiosalicylide.
Mitra K and Gates KS.
Tetrahedron Letters, 36(9), 1391-1394 (1995)
Santhosh Sivaramakrishnan et al.
Bioorganic & medicinal chemistry letters, 18(10), 3076-3080 (2007-12-11)
Though less potent than the parent natural product leinamycin, S-deoxyleinamycin displays activity against human cancer cell lines that is comparable to many clinically used agents. The results reported here suggest that the 1,2-dithiolan-3-one heterocycle found in S-deoxyleinamycin reacts with thiols

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