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135895

Sigma-Aldrich

Dimethylthiocarbamoyl chloride

97%

Synonym(s):

1-Chloro-N,N-dimethylthioformamide

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About This Item

Linear Formula:
(CH3)2NCSCl
CAS Number:
16420-13-6
Molecular Weight:
123.60
Beilstein:
635823
EC Number:
240-468-5
MDL number:
MFCD00004919
UNSPSC Code:
12352100
PubChem Substance ID:
24848243
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

bp

90-95 °C/0.5 mmHg (lit.)

mp

39-43 °C (lit.)

solubility

chloroform: soluble 100 mg/mL, clear to very slightly hazy, very faintly yellow

storage temp.

2-8°C

SMILES string

CN(C)C(Cl)=S

InChI

1S/C3H6ClNS/c1-5(2)3(4)6/h1-2H3

InChI key

PHWISQNXPLXQRU-UHFFFAOYSA-N

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Application

Dimethylthiocarbamoyl chloride was used in chemoselective deoxygenation of pyridine-N-oxides. It was used in the synthesis of (±)-thia-calanolide A. It was used as starting reagent in the synthesis of dimethylthiocarbamates.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

208.4 °F - closed cup

Flash Point(C)

98 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of Heterocyclic Chemistry, 44, 487-487 (2007)
D K Barma et al.
Organic letters, 5(25), 4755-4757 (2003-12-05)
Dimethylthiocarbamates (DMTCs), prepared from the corresponding alcohols using commercial dimethylthiocarbamoyl chloride, are spectrally simple, achiral, and nonpolar. DMTCs are moderately to highly stable to a wide range of reagents and conditions including metal hydrides, hydroboration, ylides, NaOH, HCl, organolithiums, Grignards
A synthesis of (?)-thia-calanolide A, its resolution and in vitro biological evaluation.
Chopade AU, et al. et al.
Arabian Journal of Chemistry (2012)
Harley D Betts et al.
Molecules (Basel, Switzerland), 25(19) (2020-10-07)
Silver(I)-based coordination polymers or metal-organic frameworks (MOFs) display useful antibacterial properties, whereby distinct materials with different bonding can afford control over the release of silver(I) ions. Such silver(I) materials are comprised of discrete secondary building units (SBUs), and typically formed

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