SODIUM N,N-DIMETHYLDITHIOCARBAMATE

Sodium N,N-dimethyldithiocarbamate 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 N,N-dimethyldithiocarbamate was registered in 1949.
Sodium N,N-dimethyldithiocarbamate becomes anhydrous at 266°F.

CAS:    128-04-1
MF:    C3H6NNaS2
MW:    143.21
EINECS:    204-876-7

Sodium N,N-dimethyldithiocarbamate is particularly useful in the treatment of wastewater from plating operations. 
Sodium N,N-dimethyldithiocarbamate is effective over a wide pH range and, when used as recommended, provides nearly complete precipitation of metals even in the presence of other chelating or sequestering agents.

Sodium N,N-dimethyldithiocarbamate is composed of a 40% aqueous solution of sodium dimethyldithiocarbamate. 
The sludge cake produced from Sodium N,N-dimethyldithiocarbamate's use as a heavy metal precipitant is compact, highly insoluble and easily dewatered. 
Sodium N,N-dimethyldithiocarbamate's low solubility means that it is less susceptible to leaching.

Sodium N,N-dimethyldithiocarbamate belongs to the class of organic compounds known as organic alkali metal salts. 
These are organic salts of an alkali metal. 
The alkali metal atom is usually in its ionic form. 
Based on a literature review very few articles have been published on Sodium N,N-dimethyldithiocarbamate.

Sodium N,N-dimethyldithiocarbamate is a pale yellow coloured aqueous solution having a formula of C3H6NNaS2. 
Sodium N,N-dimethyldithiocarbamate finds application as a disinfectant, fungicide, biocide, corrosion inhibitor. 
Main uses are as antifoulants in industrial cooling and air washer water systems, as well as pulp and paper mills and gas/oil drilling muds.

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 Sodium N,N-dimethyldithiocarbamate compounds, including carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. 
Sodium N,N-dimethyldithiocarbamate 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. 
Sodium N,N-dimethyldithiocarbamate are incompatible with carboxylic acid acids, peroxides, and acid halides.
Dispose of contents and container to an approved waste disposal plant. 
All federal, state, and local environmental regulations must be observed.

The slow release of poisonous gases from hydrolysis of many thio and Sodium N,N-dimethyldithiocarbamate 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.

Sodium N,N-dimethyldithiocarbamate Chemical Properties
Melting point: 120-122 °C (dec.)(lit.)
Density: 1.17
Vapor pressure: 0Pa at 25℃
Storage temp.: 0-6°C
Solubility: Soluble in water
Form: powder to crystal
Color: White to Almost white
Specific Gravity: 1.18
Water Solubility: 374g/L at 20℃
Hydrolytic Sensitivity: 0: forms stable aqueous solutions
BRN: 3569024
InChIKey: NQVBYQPOGVWUPK-UHFFFAOYSA-M
LogP: -1 at 20℃
CAS DataBase Reference: 128-04-1(CAS DataBase Reference)
EPA Substance Registry System: Sodium N,N-dimethyldithiocarbamate (128-04-1)

Sodium N,N-dimethyldithiocarbamate is a clear yellow liquid or yellow crystalline solid. 
Sodium N,N-dimethyldithiocarbamate 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. 
Sodium N,N-dimethyldithiocarbamate used as soil disinfectant.

The pure fosfomedium is scaly white crystal, which is easily soluble in water, the crystals obtained by the crystallization method contained 2.5 molecules of water of crystallization, and lost 2 molecules of water of crystallization when heated to 115 ° C.
And completely lost water of crystallization at 130 ° C.
The industrial intermediate is 15% aqueous solution, which is a yellowish or grass green transparent liquid with a relative density of 1.06 and pH = 9~11. 
Fumarate can also be used as a soil disinfectant.

Uses    
Sodium N,N-dimethyldithiocarbamate is used as a disinfectant, corrosion inhibitor, coagulant, vulcanizing agent, chelating agent, and fungicide. 
Sodium N,N-dimethyldithiocarbamate 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. 
Sodium N,N-dimethyldithiocarbamate is also used as an antimicrobial agent in paints. 
generally Sodium N,N-dimethyldithiocarbamate 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, Sodium N,N-dimethyldithiocarbamate has been used in the rubber industry to rapidly stop the polymerization of synthesis. 
Sodium N,N-dimethyldithiocarbamate is also used as a biocide for cutting oils and aqueous systems such as leather tanning and paper manufacturing.

The methyl ester of dimethyldithiocarbamic acid is produced by the reaction of Sodium N,N-dimethyldithiocarbamate with dimethyl sulfate in aqueous medium in the presence of a small amount of emulsifier at 40° to 50° C.
Sodium N,N-dimethyldithiocarbamate was used in studies to develop removal of heavy metals from water by sulfide precipitation.
Sodium N,N-dimethyldithiocarbamate 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). 
Sodium N,N-dimethyldithiocarbamate is also used as an antimicrobial agent in paints.

Sodium N,N-dimethyldithiocarbamate is used as a Terminator for Emulsion Styrene-butadiene rubber, styrene-butadiene latex, industrial bactericide, metal precipitant, vulcanization accelerator for rubber products and agricultural pesticides, etc. 
Sodium N,N-dimethyldithiocarbamate is an intermediate of bactericide fumed bis, fumed iron, fumed ammonium, fumed zinc and fumed nickel.

sodium forme is Sodium N,N-dimethyldithiocarbamate, which is an intermediate of fungicides forme, forme iron, forme ammonium, forme zinc and forme nickel.
Sodium N,N-dimethyldithiocarbamate is a disinfectant and can be used as 1% medicinal soap. 
Sodium N,N-dimethyldithiocarbamate is also used as a styrene-butadiene rubber polymerization terminator. 
Intermediates of the rubber accelerator TMTD and the pesticide Formedo.
Sodium N,N-dimethyldithiocarbamate is used as a terminator for emulsion polymerized styrene-butadiene rubber, styrene-butadiene latex, industrial fungicide, metal precipitant, vulcanization accelerator for rubber products, and agricultural insecticides. 
Sodium N,N-dimethyldithiocarbamate is an intermediate of fungicides, fumedouble, fumeirite, fumeammonium, fumezine, and fumenickel.

Preparation    
Sodium N,N-dimethyldithiocarbamate is prepared by combining dimethylamine with carbon disulfide in a solution of sodium hydroxide, forming the water-soluble dithiocarbamate salt.

Fire Hazard    
Flash point data for Sodium N,N-dimethyldithiocarbamate are not available. 
Sodium N,N-dimethyldithiocarbamate is probably not flammable.
Flammable gases are generated by the combination with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides.
Slowly decomposes in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.
When heated to decomposition Sodium N,N-dimethyldithiocarbamate emits very toxic fumes.

Toxicity evaluation    
Sodium N,N-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.

Production method    
Sodium N,N-dimethyldithiocarbamate is obtained by adding dimethylamine and carbon disulfide, and then salt with sodium hydroxide solution.
the preparation method is to add water in the reaction kettle, add lye and 40% dimethylamine solution under stirring, cool to about 10 ℃ and add carbon disulfide dropwise, control the dropwise reaction temperature not to exceed 30 ℃, continue the reaction for 1~2 hours after the dropwise addition of carbon disulfide, then stand still, separate insoluble residue, and obtain thiram sodium solution. 
If you want to obtain solid thiram sodium, you need to perform reduced pressure concentration and crystallization.

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, Sodium N,N-dimethyldithiocarbamate 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 Sodium N,N-dimethyldithiocarbamate 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 10 15 atmm3 mol-1at 20 °C for Sodium N,N-dimethyldithiocarbamate 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.
The Koc of Sodium N,N-dimethyldithiocarbamate 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 Sodium N,N-dimethyldithiocarbamate 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 Sodium N,N-dimethyldithiocarbamate. 
Depending on the geographical latitude (30–50 N) and the climatic season, the calculated environmental half-lives of Sodium N,N-dimethyldithiocarbamate range from 0.3 to 2.26 days. 
Hydrolysis of Sodium N,N-dimethyldithiocarbamate occurs at neutral and acidic pHs. 
The hydrolysis half-life of 18 min, 25.9, and 433.3 h was reported for Sodium N,N-dimethyldithiocarbamate at pH 5, 7, and 9, respectively. 
The products of degradation are less toxic than the product itself. 
14C-Sodium N,N-dimethyldithiocarbamate 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 Sodium N,N-dimethyldithiocarbamate.

Laboratory and practical use
By the technique of spin trapping, complexes of dithiocarbamates with iron provide one of the very few methods to study the formation of nitric oxide (NO) radicals in biological materials. 
Although the lifetime of NO in tissues is too short to allow detection of this radical itself, NO readily binds to iron-dithiocarbamate complexes. 
The resulting mono-nitrosyl-iron complex (MNIC) is stable, and may be detected with Electron Paramagnetic Resonance (EPR) spectroscopy.

The zinc chelation of diethyldithiocarbamate inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, an initial step in cancer metastasis and angiogenesis.
Sodium N,N-dimethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.

Reactions
Oxidation of sodium diethyldithiocarbamate gives the disulfide, also called a thiuram disulfide (Et = ethyl):
2 NaS2CNEt2 + I2 → (S2CNEt2)2 + 2 NaI
Dithiocarbamates are nucleophiles and thus can be alkylated. Even dichloromethane suffices:
2 NaS2CNEt2 + CH2Cl2 → CH2(S2CNEt2)2 + 2 NaCl
Diethyldithiocarbamate reacts with many metal salts to give transition metal dithiocarbamate complexes. The ligands coordinate via the two sulfur atoms.
Other more complicated bonding modes are known including binding as unidentate ligand and a bridging ligand using one or both sulfur atoms.

Preparation
This salt is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide:
CS2 + HN(C2H5)2 + NaOH → NaS2CN(C2H5)2 + H2O
Other dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide. 
They are used as chelating agents for transition metal ions and as precursors to herbicides and vulcanization reagents.

Synonyms
Sodium dimethyldithiocarbamate
128-04-1
Sodium dimethyl dithiocarbamate
Sanceler S
Sodium dimethylcarbamodithioate
Wing Stop B
Dimethyldithiocarbamic acid sodium salt
Diaprosim AB 13
Aceto SDD 40
Carbamodithioic acid, dimethyl-, sodium salt
Dibam
Methyl namate
Thiostop N
Vulnopol NM
Alcobam NM
Dibam A
Sodium N,N-dimethyldithiocarbamate
Sharstop 204
Brogdex 555
DMDK
SDDC
Sta-fresh 615
Steriseal liquid #40
769GO8W6QQ
Carbamodithioic acid, N,N-dimethyl-, sodium salt (1:1)
Sodium dimethylaminecarbodithioate
Sodium dimethylaminocarbodithioate
Carbamic acid, dimethyldithio- sodium salt
N,N-Dimethyldithiocarbamate sodium salt
DIMETHYLDITHIOCARBAMIC ACID, SODIUM SALT
Vinditat
Vinstop
Diram
Sdmdtc
Sodam
Nocceler S
Carbam S
Carbam-S
CHEMBL569460
MSL (carbamate)
CAS-128-04-1
Amersep MP 3R
MetalPlex 143
Nalmet A 1
NSC-85566
Caswell No. 762
MSL
UNII-769GO8W6QQ
CCRIS 5535
CCRIS 9109
Carbamic acid, dimethyldithio-, sodium salt
HSDB 6811
sodium;N,N-dimethylcarbamodithioate
EINECS 204-876-7
NSC 85566
EPA Pesticide Chemical Code 034804
Dimethyldithiocarbamate sodium dihydrate
AI3-14673
N,N-Dimethyldithiocarbamic acid, sodium salt
EC 204-876-7
SCHEMBL23192
Carbamodithioic acid, dimethyl-, sodium salt, dihydrate
DTXSID6027050
Sodium Dimethyl Dithio Carbamate
CARBAMIC ACID, DIMETHYLDITHIO-, SODIUM SALT, DIHYDRATE
Dimethyldithiocarbamate, sodium salt
Tox21_201971
Tox21_300391
MFCD00044839
(DIMETHYLDITHIOCARBAMATO)SODIUM
AKOS000120803
NCGC00254258-01
NCGC00259520-01
SODIUM DIMETHYLAMINODITHIOCARBAMATE
AS-16148
D0716
FT-0631748
SODIUM DIMETHYLDITHIOCARBAMATE [HSDB]
128D041
J-005564
J-013553
Q27266473
SODIUM 2-(DIMETHYLAMINO)-2-THIOXOETHANETHIOLATE