128-04-1 Usage
Description
Dithiocarbamates (DCs) are a well-known group of pesticides
which have been used to control a number of species belonging
to taxonomically different groups, e.g., bacteria, fungi, nematodes,
and molluscs for over 60 years. The first integrated
product containing sodium dimethyldithiocarbamate (SDMC)
was registered in 1949.
Chemical Properties
Sodium dimethyldithiocarbamate is a clear yellow liquid or yellow crystalline solid. The pure product is a scaly white crystal, which is easily soluble in water. The crystal obtained by the crystallization method contains 2.5 molecules of crystal water, which loses 2 molecules of crystal water when heated to 115 °C, and completely loses crystal water at 130 °C. The industrial intermediate is a 15% aqueous solution, a yellowish or grass-green transparent liquid, a relative density of 1.06, and a pH of 9 to 11. Used as soil disinfectant.
Uses
Sodium dimethyldithiocarbamate(SDMC) is used as a disinfectant, corrosion inhibitor, coagulant, vulcanizing agent, chelating agent, and fungicide. SDMC is used in water treatment, the rubber industry, and is a registered biocide for cutting oils and aqueous systems in industries such as leather tanning and paper manufacturing. It is also used as an antimicrobial agent in paints. generally SDMC are able to function as metal chelators and have been used in metal finishing operations and wastewater treatments to enhance the precipitation of metals. As a free radical inhibitor, it has been used in the rubber industry to rapidly stop the polymerization of synthesis. It is also used as a biocide for cutting oils and aqueous systems such as leather tanning and paper manufacturing.
Preparation
Sodium dimethyldithiocarbamate is prepared by combining dimethylamine with carbon disulfide in a solution of sodium hydroxide, forming the water-soluble dithiocarbamate salt.
Application
The methyl ester of dimethyldithiocarbamic acid is produced by the reaction of sodium dimethyldithiocarbamate with dimethyl sulfate in aqueous medium in the presence of a small amount of emulsifier at 40° to 50° C.Dimethyldithiocarbamic Acid Sodium Salt was used in studies to develop removal of heavy metals from water by sulfide precipitation.Sodium N,N-dimethylthithiocarbamate is use as a disinfectant, corrosion inhibitor, coagulant, vulcanizing agent, chelating agent, and fungicide may result in its release to the environment through various waste streams(SRC). It is also used as an antimicrobial agent in paints.
General Description
Crystals or liquid. Becomes anhydrous at 266°F.
Air & Water Reactions
Slowly decomposes in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.
Reactivity Profile
Flammable gases are generated by the combination with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition it emits very toxic fumes.
Fire Hazard
Flash point data for Sodium dimethyldithiocarbamate are not available. Sodium dimethyldithiocarbamate is probably not flammable.
Safety Profile
Moderately toxic by ingestion and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, SOx, and Na2O. See also CARBAMATES.
Potential Exposure
The slow release of poisonous gases from hydrolysis of many thio and dithiocarbamates requires the use of respirators during handling. Used as an antimicrobial/fungicidal agent in paints, water treatment; a registered biocide for cutting oils and aqueous systems in industries such as leather tanning and paper manufacturing. Used in the rubber industry as a vulcanization accelerator for making synthetic and natural rubbers (i.e., butadiene rubber, latex). Used as a fungicide on melons (tolerance set as 25 ppm). Also used as an indirect food additive for use only as a component of adhesives.
Environmental Fate
Routes and Pathways and Relevant Physicochemical
Properties
The estimated pKa of SDMC is 5.4, indicating that this
compound will primarily exist in the dissociated form at environmentally
relevant pHs. If released to air, SDMC will exist
solely in the particulate phase in the ambient atmosphere, since
it is a salt and will be nonvolatile. Due to the short chemical
lifetime of SDMC in air, it is not expected to accumulate in air or
transported in the gaseous phase over long distances. Furthermore,
based on the estimated Henry’s law constant at
25°C ＝ 6.972 1015 atmm3 mol-1at 20 °C for it and Log Pow
equal to 2.41, air will not be an environmental compartment
of concern and sodium N,N-dimethyldithiocarbamate can be
classified as a nonadsorbed substance.
Partition Behavior in Water, Sediment, and Soil
The Koc of SDMC is estimated as 2.2, suggesting that SDMC is
expected to have very high mobility in soil and is not adsorbed
to suspended solids or sediment.
Environmental Persistency
Particulate-phase SDMC will be removed from the atmosphere
by wet and dry depositions. Photolysis in aqueous solution and
soil was found to be an important degradation process for
SDMC. Depending on the geographical latitude (30–50 N)
and the climatic season, the calculated environmental half-lives
of SDMC range from 0.3 to 2.26 days. Hydrolysis of SDMC
occurs at neutral and acidic pHs. The hydrolysis half-life of
18 min, 25.9, and 433.3 h was reported for SDMC at pH 5, 7,
and 9, respectively. The products of degradation are less toxic
than the product itself. 14C-SDMC is rapidly photodegraded in
buffered solution at pH 9 with a calculated experimental halflife
of 0.79 days, corresponding to 19 h. Direct photolysis in
surface water and soil is an important degradation process for
SDMC.
Purification Methods
Crystallise it from a small volume of H2O, or dissolve it in the minimum volume of H2O and add cold Me2CO, collect it and dry it in air. The solubility in Me2CO is 50g/400mL. The dihydrate loses H2O on heating at 115o to give the hemi-hydrate which decomposes on further heating [Kulka Can J Chem 34 1096 1956]. [Beilstein 4 IV 233.]
Toxicity evaluation
sodium dimethyldithiocarbamate is toxic to aquatic life and can combine to form, or break down to, a number of other toxic chemicals, including thiram (an EPA registered fungicide) and other thiurams, other dithiocarbamates, carbon disulfide, and dimethylamine. The distal peripheral and peripheral neuropathies induced by DCs are postulated to arise via a common mechanism of toxicity, that is, the formation of carbon disulfide. Chronic exposure increases brain neurotransmitters and stimulates sex hormone cycle, especially in women.
Incompatibilities
Slowly decomposes in water, forming carbon disulfide, oxides of sulfur and nitrogen, hydrogen sulfide, ammonia, and amines, including methylamine; this decomposition is accelerated in the presence of acids. Flammable gases are generated by the combination with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides. Thiocarbamate esters are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Poisonous gases are generated by the thermal decomposition of thiocarbamate compounds, including carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of thiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates are incompatible with carboxylic acid acids, peroxides, and acid halides.
Waste Disposal
Dispose of contents and container to an approved waste disposal plant. All federal, state, and local environmental regulations must be observed.
Check Digit Verification of cas no
The CAS Registry Mumber 128-04-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 8 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 128-04:
(5*1)+(4*2)+(3*8)+(2*0)+(1*4)=41
41 % 10 = 1
So 128-04-1 is a valid CAS Registry Number.
InChI:InChI=1/C3H7NS2.Na/c1-4(2)3(5)6;/h1-2H3,(H,5,6);/q;+1/p-1/rC3H6NNaS2/c1-4(2)3(6)7-5/h1-2H3
128-04-1Relevant articles and documents
Syntheses, crystal structures and non-linear optical responses of two new heteroselenometallic cluster compounds containing dithiocarbamate ligands
Zhang, Qian-Fcng
, p. 605 - 610 (2000)
Two novel dialkyldithiocarbamate-containing heteroselenometallic clusters, [NEt4]2[(WSe4)(Et2NCS 2Cu)3] 1 and [NEt4]2[(WSe4)(Me2NCS 2Cu)4] 2, have'been synthesized through reactions of [NEt4]2[WSe4] with CuCl and R2NCS2Na (R = Et or Me) in DMF. The [(WSe4)(Et2NCS2Cu)3]2- anion in 1 comprises three El2NCS2Cu fragments ligated by a slightly distorted tetrahedral VSe4 moiety. The [(WSe4)(Me2NCS2Cu)4]2- anion structure in 2 possesses a nearly planar WCu4 core and consists of four Me2NCS2Cu fragments co-ordinated across four edges of the tetrahedral [WSe4]2- moiety. The optical limiting effects of the two clusters were examined at a 0.5 Hz repetition rate. The thresholds of two samples were 6.0 and 1.1 J cm-1 for 1 and 2, respectively. The non-linear responses for the two clusters in DMF have also been studied in picosecond time-resolved pump-probe experiments. The Royal Society of Chemistry 2000.
Facile synthesis of thiophene derivatives using a cyclopropenyl cation
Kojima, Hideo,Nakamura, Keiichi,Yamamoto, Kazuhiko,Inoue, Hiroo
, p. 1193 - 1195 (1996)
A novel convenient method for the synthesis of thiophene derivatives was developed using a tris(isopropylthio)cyclopropenyl cation, carbon disulfide, and the anions of secondary amines, 2-propanethiol, and ethanol.
Solid-state spin crossover of Ni(II) in a bioinspired N3S 2 ligand field
Ma, Huaibo,Petersen, Jeffrey L.,Young, Victor G.,Yee, Gordon T.,Jensen, Michael P.
, p. 5644 - 5647 (2011)
The complex TpPh,MeNiS2CNMe2 [Tp Ph,Me = hydrotris(3-phenyl-5-methyl-1-pyrazolyl)borate] features a bioinspired N3S2 ligand set supporting a five-coordinate, trigonally distorted square-pyramidal geometry in the solid state. Spin crossover of Ni(II) was demonstrated by temperature-dependent X-ray crystallography and magnetic susceptibility measurements. The crystal lattice contains two independent molecules (i.e., Ni1 and Ni2). At 293 K, the observed bond lengths and susceptibility are consistent with high-spin (S = 1) Ni(II), and both molecules exhibit relatively short axial Ni-N bonds and long Ni-N and Ni-S equatorial bonds. At 123 K, the Ni1 complex remains high-spin, but the Ni2 molecule substantially crosses to a structurally distinct diamagnetic (S = 0) state with significant elongation of the axial Ni-N bond and offsetting contraction of the equatorial bonds. The temperature-dependent susceptibility data were fit to a spin equilibrium at Ni2 [ΔH° = 1.13(2) kcal/mol and ΔS° = +7.3(1) cal mol-1 K-1] consistent with weak coupling to lattice effects. Cooling below 100 K results in crossover of the Ni1 complex.
Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Krishna, Shagun,Srivastava, Nidhi,Shukla, Mahendra,Singh, Pratiksha,Chauhan, Bhavana S.,Goyani, Ravi,Maikhuri, Jagdamba P.,Sashidhara, Koneni V.,Kumar, Brijesh,Tripathi, Renu,Shukla, Praveen K.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
, p. 632 - 645 (2017/12/08)
Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77–294.1 μM and 32.46–735.20 μM against MTZ-susceptible and -resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50–240.38 μM. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance.
Energy-saving environment-friendly sodium dimethyldithiocarbamate production device and production method
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Paragraph 0064-0072, (2017/08/27)
The invention provides an energy-saving environment-friendly sodium dimethyldithiocarbamate production device and production method, and belongs to the field of preparation of chemical products. The production device comprises a reaction kettle and a first pipeline reactor for performing pre-reaction of dimethylamine and CS2, wherein an outlet of the first pipeline reactor communicates with the reaction kettle, and the reaction kettle is provided with a first feed port for introducing a NaOH solution. The production method comprises the following steps: introducing the dimethylamine and CS2 into the first pipeline reactor; performing pre-reaction to form a first material; then introducing the first material in the first pipeline reactor into the reaction kettle, simultaneously introducing the NaOH solution in the reaction kettle, and mixing for reaction. According to the production device and production method provided by the invention, by changing the addition sequence of the three raw materials, the one-step reaction for sodium dimethyldithiocarbamate generation can be very conveniently divided into two steps, so that the side reaction between the CS2 and the NaOH solution is effectively avoided, thereby improving the sodium dimethyldithiocarbamate purity and product quality.
