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D188700

Sigma-Aldrich

N,N′-Dimethylthiourea

99%

Synonym(s):

1,3-Dimethyl-2-thiourea, 1,3-Dimethylisothiourea, Dimethylthiocarbamide

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About This Item

Linear Formula:
CH3NHCSNHCH3
CAS Number:
534-13-4
Molecular Weight:
104.17
Beilstein:
605454
EC Number:
208-588-2
MDL number:
MFCD00004923
UNSPSC Code:
12352100
PubChem Substance ID:
24893565
NACRES:
NA.22
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Assay

99%

form

crystals

SMILES string

CNC(=S)NC

InChI

1S/C3H8N2S/c1-4-3(6)5-2/h1-2H3,(H2,4,5,6)

InChI key

VLCDUOXHFNUCKK-UHFFFAOYSA-N

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General description

N,N′-Dimethylthiourea, also known as 1,3-Dimethylisothiourea, is commonly used in organic reactions to synthesize N-containing compounds such as N-acyl-substituted 1,1-diaminoethylenes, amidines, ureas, and thioureas. [1] [2]It also acts as a nucleophilic catalyst in the bromination of alcohols using N-bromosuccinimide (NBS), during the conversion to the corresponding bromides. [3]

Application

  • Pharmaceutical Analysis: Mao et al. developed an itaconic acid-based organic-polymer monolithic column for hydrophilic capillary electrochromatography, which was used in pharmaceutical analysis. N,N′-Dimethylthiourea could be utilized to improve the column′s performance by acting as a potential organic modifier to enhance the separation processes (Mao et al., 2024).
  • Agricultural Research: Li et al. examined the effect of the reactive oxygen scavenger N,N′-Dimethylthiourea on seed germination and radicle elongation of maize. This research could help in understanding how this chemical can be used to influence plant growth under stress conditions, potentially improving agricultural productivity (Li et al., 2023).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280

Hazard Classifications

Skin Sens. 1

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK5673
STBJ5395
STBH6965
STBG4386V
STBG2499V

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Synthesis, Characterization, and Reactivity of N-Acyl Chloroformamidines: Useful Building Blocks for the Construction of N-Acyl-Substituted 1, 1-Diaminoethylenes, Amidines, Ureas, and Thioureas
Yang W, et al.
Synthesis, 45, 347-354 (2013)
Thiourea-mediated halogenation of alcohols
Amar M R, et al.
The Journal of Organic Chemistry, 85, 12901-12911 (2020)
Crystal structure of the 1: 2 adduct of bis (piperidinium) sulfate and 1, 3-dimethylthiourea
Cindy D, et al.
Acta Crystallographica Section E: Crystallographic Communications, 73, 651-653 (2017)
Watcharaporn Hoisang et al.
Nanomaterials (Basel, Switzerland), 9(12) (2019-12-15)
Highly luminescent silver indium sulfide (AgInS2) nanoparticles were synthesized by dropwise injection of a sulfur precursor solution into a cationic metal precursor solution. The two-step reaction including the formation of silver sulfide (Ag2S) nanoparticles as an intermediate and their conversion
Emily E Chea et al.
Biophysical journal, 118(1), 128-137 (2019-12-08)
Cytochrome c (cyt c) is known for its role in the electron transport chain but transitions to a peroxidase-active state upon exposure to oxidative species. The peroxidase activity ultimately results in the release of cyt c into the cytosol for
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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