SODIUM DIETHYLDITHIOCARBAMATE

Sodium diethyldithiocarbamate is the chemical compound with the formula NaS2CN(C2H5)2.
Sodium diethyldithiocarbamate is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide.
Sodium diethyldithiocarbamate is used as chelating agents for transition metal ions and as building blocks in the organic synthesis of herbicides and vulcanization reagents.

CAS Number: 148-18-5
Chemical formula: C5H10NS2Na
Molar mass: 171.259 g/mol (anhydrous)

General description of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate may be used:
To synthesize cis-dichlorobis(N,N-diethyldithiocarbamato) tin(IV) by reacting with tin(II) chloride.
As an alternative to xanthates to generate carbamoyl radical precursors.
To synthesize a soluble precursor polymer for poly(thienylene vinylene).
To synthesize dichlorotetrakis(dimethyl sulfoxide)ruthenium (II), which can be a precursor to prepare other ruthenium complexes.

Applications of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is used in conjunction with Fe2+ to detect NO in brain, kidney, liver, and other tissues.
Simultaneous direct measurement of NO* and pO2 has been reported.
A copper chelator, Sodium diethyldithiocarbamate has been used to quantitate copper in biological materials by ESR and is an inhibitor of superoxide dismutase, ascorbate oxidase, and other enzymes.

Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN(C2H5)2.
Sodium diethyldithiocarbamate is a pale yellow, water soluble salt.
Many dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide.

Chemical Properties of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is a white or colorless crystalline powder, easily soluble in water and alkaline, soluble in alcohol, rapidly decomposed in acidic aqueous solution to separate out carbon disulfide and make the solution cloudy.
In ammonia medium, Sodium diethyldithiocarbamate generates precipitate or brown colloidal solution with copper ion.
Copper reagent is applied in the color development reaction of copper, used as precipitant and solvent extractant of soft metal ions, also used as photometric reagent for the determination of bismuth, copper, nickel and other metals.

Uses of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is an organic molecular entity.
Sodium diethyldithiocarbamate is an inhibitor of superoxide dismutase, having both antioxidant and oxidant effects.

Uses of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate reacts with even more metal ions than does dithizone.
However, Sodium diethyldithiocarbamates analytical application is seriously limited by its considerably lower stability in acidic aqueous media.

According to the examinations of Bode,the reagent undergoes considerable decomposition within 5 minutes at pH 5.
The analytical application of the reagent is therefore restricted to a very narrow pH range.
There is no chance with this reagent to enhance the analytical selectivity of extractions by making use of the difference between the stabilities of its complexes with various metal ions and to choose the pH of the reaction mixture accordingly.

Preparation of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide:
CS2+ HN(C2H5)2+ NaOH → NaS2CN(C2H5)2+ H2O

General Description of Sodium diethyldithiocarbamate:
Odorless white or slightly brown or slightly pink crystals.

Air & Water Reactions of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is water soluble.
Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines.
Such decompositions are accelerated by acids.

Reactivity Profile of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is not compatible with strong oxidizing agents.
Aqueous solutions slowly decompose to form carbon disulfide and an amine.

Such decompositions are accelerated by acids.
Addition of acid to the aqueous solution produces a white turbidity.

Fire Hazard of Sodium diethyldithiocarbamate:
Flash point data for Sodium diethyldithiocarbamate are not available; however, Sodium diethyldithiocarbamate is probably combustible.

Flammability and Explosibility:
Nonflammable

Safety Profile of Sodium diethyldithiocarbamate:
Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes.
Experimental reproductive effects.
Questionable carcinogen with experimental neoplastigenic and teratogenic data.

Human mutation data reported.
When heated to decomposition it emits very toxic fumes of NOx, SOx, and Na2O.
Sodium diethyldithiocarbamate is used as a pesticide.

Other dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide.
Sodium diethyldithiocarbamate is used as chelating agents for transition metal ions and as precursors to herbicides and vulcanization reagents.

Sodium diethyldithiocarbamate is a spin trapping reagent used in conjunction with ferrous ion to detect nitric oxide in brain, kidney, liver and other tissues.
Sodium diethyldithiocarbamate is used as sensitive reagent for the determination of copper, rubber vulcanization accelerator and finds application in the determination of other metals such as zinc, cobalt, platinum and palladium.
Furthermore, Sodium diethyldithiocarbamate is an inhibitor of superoxide dismutase, ascorbate oxidase and other enzymes as well as inhibits the induction of macrophage nitric oxide synthase.

About Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
Sodium diethyldithiocarbamate is used at industrial sites and in manufacturing.

Consumer Uses of Sodium diethyldithiocarbamate:
ECHA has no public registered data indicating whether or in which chemical products Sodium diethyldithiocarbamate might be used.
ECHA has no public registered data on the routes by which Sodium diethyldithiocarbamate is most likely to be released to the environment.

Article service life of Sodium diethyldithiocarbamate:
ECHA has no public registered data on the routes by which Sodium diethyldithiocarbamate is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles Sodium diethyldithiocarbamate might have been processed.

Widespread uses by professional workers of Sodium diethyldithiocarbamate:
ECHA has no public registered data indicating whether or in which chemical products Sodium diethyldithiocarbamate might be used.
ECHA has no public registered data on the types of manufacture using Sodium diethyldithiocarbamate.
ECHA has no public registered data on the routes by which Sodium diethyldithiocarbamate is most likely to be released to the environment.

Formulation or re-packing of Sodium diethyldithiocarbamate:
ECHA has no public registered data indicating whether or in which chemical products Sodium diethyldithiocarbamate might be used.
ECHA has no public registered data on the routes by which Sodium diethyldithiocarbamate is most likely to be released to the environment.

Uses at industrial sites of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate is used in the following products: metal working fluids and extraction agents.
Sodium diethyldithiocarbamate is used in the following areas: mining.
Release to the environment of Sodium diethyldithiocarbamate can occur from industrial use: in processing aids at industrial sites and as processing aid.

Manufacture of Sodium diethyldithiocarbamate:
Release to the environment of Sodium diethyldithiocarbamate can occur from industrial use: manufacturing of the substance.

Reactions of Sodium diethyldithiocarbamate:
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

Sodium 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.

Laboratory and practical uses of Sodium diethyldithiocarbamate:
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 Sodium diethyldithiocarbamate inhibits metalloproteinases, which in turn prevents the degradation of extracellular matrix, an initial step in cancer metastasis and angiogenesis.
Sodium diethyldithiocarbamate inhibits superoxide dismutase, which can both have antioxidant and oxidant effects on cells, depending on the time of administration.

Preferred IUPAC name:
Sodium diethylcarbamodithioate

Applications of Sodium diethyldithiocarbamate:
Spin trap used in conjunction with Fe2+ to detect NO in brain, kidney, liver, and other tissues.
Simultaneous direct measurement of NO* and pO2 has been reported.
A copper chelator, Sodium diethyldithiocarbamate has been used to quantitate copper in biological materials by ESR and is an inhibitor of superoxide dismutase, ascorbate oxidase, and other enzymes.

Biochem/physiol Actions of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate inhibits induction of macrophage nitric oxide synthase.

General description of Sodium diethyldithiocarbamate:
Sodium diethyldithiocarbamate may be used:To synthesize cis-dichlorobis(N,N-diethyldithiocarbamato) tin(IV) by reacting with tin(II) chloride.
As an alternative to xanthates to generate carbamoyl radical precursors.
To synthesize a soluble precursor polymer for poly(thienylene vinylene).
To synthesize dichlorotetrakis(dimethyl sulfoxide)ruthenium (II), which can be a precursor to prepare other ruthenium complexes.

Sodium diethyldithiocarbamate is used as chelating agents for transition metal ions and as building blocks in the organic synthesis of herbicides and vulcanization reagents.

KEYWORDS:
148-18-5, Sodium N N-diethyldithiocarbamate, Dithiocarb, Ditiocarb sodium, DDTC, Carbamodithioic acid diethyl- sodium salt, Sodium DEDT, CHEBI:82587, Diethyldithiocarbamic acid sodium salt, Diethyl sodium dithiocarbamate

Identifiers of Sodium diethyldithiocarbamate:
CAS Number: 148-18-5
ChEMBL: ChEMBL107217
ChemSpider: 8642
ECHA InfoCard: 100.005.192
PubChem CID: 533728
UNII: A5304YEB5E
CompTox Dashboard (EPA): DTXSID3022956

Properties of Sodium diethyldithiocarbamate:
Chemical formula: C5H10NS2Na
Molar mass: 171.259 g/mol (anhydrous)
Appearance: White, slightly brown, or slightly pink crystalline solid
Density: 1.1 g/cm3
Melting point: 95 °C (203 °F; 368 K)
Solubility in water: Soluble

Solubility:
soluble in alcohol, acetone
insoluble in ether, benzene

Sodium diethyldithiocarbamate has been tested by oral administration and by single subcutaneous injection in two strains of mice.
Although Sodium diethyldithiocarbamate produced an increase in the incidence of liver-cell tumours in males of one strain and a slight increase of lung tumours in males of the other strain following its oral administration, the available data are insufficient to make an evaluation of the carcinogenicity of this compound.

Sodium diethyldithiocarbamate is a chelating agent of value in the treatment of acute nickel carbonyl poisoning; it greatly increases the excretion of nickel in the urine.
Sodium diethyldithiocarbamate can be given orally in moderately severe poisoning, initially at a rate of 50 mg/kg in divided doses.

At the low pH of gastric juice, Sodium diethyldithiocarbamate is degraded to ethylamine and carbon disulfide.
This reaction can be minimized by the concomitant administration of 2 g sodium bicarbonate by mouth.

Sodium diethyldithiocarbamate forms lipophilic chelates with divalent nickel, which reduces the nickel burden in the lungs.
On the other hand, this complex has a high affinity for lipid-rich brain tissue, leading to increased nickel concentrations in the brain.

There is currently insufficient evidence to recommend chelating agents such as diethyldithiocarbamate, and if dithiocarb is to be employed, it should be given parenterally soon after exposure, as increasing delay may increase nickel carbonyl toxicity.
Sodium diethyldithiocarbamate may have a place in the treatment of nickel dermatitis.

Similarly, disulfiram (DS, Antabuse) is a nonconventional pharmacological agent that can be used for treatment of nickel contact dermatitis.
After absorption in the gut, disulfiram is metabolized into Sodium diethyldithiocarbamate in the liver.

Sodium diethyldithiocarbamate chelates with nickel, giving an increased concentration in the blood, with the major excretion through urine, bile, and perspiration.
Sodium diethyldithiocarbamate has decreased the frequency and intensity of flare-ups in nickel-sensitized subjects with chronic relapsing contact dermatitis.
There are insufficient data to recommend disulfiram as an alternative to DDC for nickel carbonyl intoxication even when DDC is not available.

Synonym(s): Cupral, Diethyldithiocarbamic acid sodium salt
Linear Formula: (C2H5)2NCSSNa · 3H2O
Molecular Weight: 225.31
Beilstein: 3920507
EC Number: 205-710-6
MDL number: MFCD00150617
PubChem Substance ID: 24853702
NACRES: NA.21

Product Information of Sodium diethyldithiocarbamate:
EC number: 205-710-6
Grade: ACS
Hill Formula: C₅H₁₀NNaS₂ * 3 H₂O
Molar Mass: 225.31 g/mol
HS Code: 2930 20 00

PROPERTIES of Sodium diethyldithiocarbamate:
grade:
ACS reagent

Quality Level:
200

vapor density:
5.9 (vs air)

composition:
Na (as Na2SO4), 30.5-32.5%

mp:
95-98.5 °C (lit.)

SMILES string:
[H]O[H].[H]O[H].[H]O[H].CCN(CC)C(=S)S[Na]

InChI:
1S/C5H11NS2.Na.3H2O/c1-3-6(4-2)5(7)8;;;;/h3-4H2,1-2H3,(H,7,8);;3*1H2/q;+1;;;/p-1

InChI key:
WWGXHTXOZKVJDN-UHFFFAOYSA-M

Molecular Weight: 171.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 171.01523595
Monoisotopic Mass: 171.01523595
Topological Polar Surface Area: 36.3 Å²
Heavy Atom Count: 9
Formal Charge: 0
Complexity: 83
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 2
Compound Is Canonicalized: Yes

Synonyms:
Carbamic acid, diethyldithio-, sodium salt
Carbamodithioic acid, diethyl-, sodium salt
Cupral
DDTC
DEDC
DTC
DeDTC
Diethyl dithiocarbamate sodium salt
Diethyl sodium dithiocarbamate
Diethylcarbamodithioic acid, sodium salt
Diethyldithiocarbamate sodium
Diethyldithiocarbamic acid, sodium
Diethyldithiocarbamic acid, sodium salt
Dithiocarb; Ditiocarbe sodique [French]
Ditiocarbo sodico [Spanish]
Ditiocarbum natricum [Latin]
Imuthiol
Kupral
N,N-Diethyldithiocarbamic acid, sodium salt
Na-ddtc
Nocceler SDC
Sodium DEDT
Sodium N,N-diethyldithiocarbamate
Sodium diethylaminocarbodithioate
Sodium diethylcarbamodithioate
Sodium diethyldithiocarbamate
Sodium salt of N,N-diethyldithiocarbamic acid
Soxinol ESL
Thiocarb
USAF EK-2596

Synonyms:
148-18-5
SODIUM DIETHYLDITHIOCARBAMATE
Ditiocarb sodium
Sodium N,N-diethyldithiocarbamate
Dithiocarb
Thiocarb
Imuthiol
DeDTC
Sodium diethylcarbamodithioate
DEDC
Ditiocarb sodium [INN]
DDTC
Carbamodithioic acid, diethyl-, sodium salt
Diethyldithiocarbamate sodium
Cupral
Diethyldithiocarbamic acid, sodium salt
Sodium DEDT
N,N-Diethyldithiocarbamic acid, sodium salt
A5304YEB5E
Usaf ek-2596
CHEBI:82587
Diethyldithiocarbamic acid sodium salt
Diethyl sodium dithiocarbamate
NSC-38583
NCI CO2835
Carbamodithioic acid, N,N-diethyl-, sodium salt (1:1)
Sodium diethylaminocarbodithioate
Diethyldithiocarbamic acid, sodium
GS 694A
Diethyl dithiocarbamate sodium salt
Diethylcarbamodithioic acid, sodium salt
N,N-diethyl(sodiosulfanyl)carbothioamide
Sodium salt of N,N-diethyldithiocarbamic acid
Kupral
DTC
Ditiocarbo sodico
Na-ddtc
Nocceler SDC
CHEMBL107217
Soxinol ESL
Ditiocarbe sodique
NSC4857
CAS-148-18-5
Ditiocarbum natricum
NCGC00166328-01
Ditiocarbe sodique [French]
Ditiocarbo sodico [Spanish]
UNII-A5304YEB5E
Ditiocarbum natricum [Latin]
CCRIS 235
HSDB 4091
EINECS 205-710-6
NSC 38583
sodium (diethylcarbamothioyl)sulfanide
AI3-14688
Carbamic acid, diethyldithio-, sodium salt
EC 205-710-6
Sodiumdiethylcarbamodithioate
DITIOCARB SODIUM [MI]
SCHEMBL168133
DITIOCARB SODIUM [HSDB]
DTXSID3022956
DITIOCARB SODIUM [MART.]
DITIOCARB SODIUM [WHO-DD]
sodium;N,N-diethylcarbamodithioate
HY-B1637
Tox21_112412
Tox21_200403
MFCD00066667
AKOS015897389
AKOS016358586
AKOS025310122
NCGC00257957-01
AS-12092
SODIUM DIETHYLDITHIOCARBAMATE [IARC]
CS-0013580
FT-0631848
EN300-30081
C19599
D78053
Q413008
J-008449
F8880-1809
Z1522566622
148-18-5 [RN]
205-710-6 [EINECS]
A5304YEB5E
Carbamodithioic acid, diethyl-, sodium salt
Carbamodithioic acid, N,N-diethyl-, sodium salt (1:1) [ACD/Index Name]
Ddtc
DEDTC
Diéthylcarbamodithioate de sodium [French] [ACD/IUPAC Name]
Diéthyldithiocarbamate de sodium [French]
diethyldithiocarbamate sodium
Diethyldithiocarbamate, sodium
Diethyldithiocarbamic acid, sodium salt
ditiocarb sodium [INN]
Ditiocarbe sodique [French] [INN]
ditiocarbo de sodio [Spanish] [INN]
Ditiocarbo sodico [Spanish]
ditiocarbum natricum [Latin] [INN]
DTC
Imuthiol [Trade name]
Natriumdiethylcarbamodithioat [German] [ACD/IUPAC Name]
Natriumdiethyldithiocarbamat [German]
Sodium diethylcarbamodithioate [ACD/IUPAC Name]
Sodium diethyldithiocarbamate [INN] [Wiki]
Sodium N,N-diethyldithiocarbamate
дитиокарб натрия [Russian] [INN]
ديتيوكارب صوديوم [Arabic] [INN]
二硫卡钠 [Chinese] [INN]
[148-18-5] [RN]
1261395-23-6 [RN]
1329834-65-2 [RN]
1704069-62-4 [RN]
392-74-5 [RN]
4-08-00-01747 [Beilstein]
BB_SC-0418
Carbamic acid, diethyldithio-, sodium salt
cupral
DEDC
Diethylcarbamodithioic Acid Sodium Salt
DIETHYLCARBAMODITHIOIC ACID, SODIUM SALT
diethylcarbamodithioic acid; sodium
Diethyldithiocarbamic acid sodium salt
Diethyldithiocarbamic acid, sodium
dithiocarb
ditiocarb
ditiocarbe sodique
ditiocarbo de sodio
ditiocarbum natricum
EINECS 205-710-6
GS 694A
Kupral
MFCD00041028 [MDL number]
MFCD00066667
MFCD00150617 [MDL number]
N,N-diethyl(sodiosulfanyl)carbothioamide
N,N-diethyldithiocarbamate sodium
N,N-Diethyldithiocarbamic acid, sodium salt
Na-ddtc
Nocceler SDC
sodium (diethylcarbamothioyl)sulfanide
sodium and N,N-diethylcarbamodithioate
sodium dedt
Sodium diethylaminocarbodithioate
sodium diethylaminomethanedithioate
sodium diethyl-dithiocarbamate
Sodium Diethyldithiocarbamate-d10
sodiumdiethyldithiocarbamate
Soxinol ESL
Thiocarb
UNII:A5304YEB5E
UNII-A5304YEB5E
дитиокарб натрия
ديتيوكارب صوديوم
二硫卡钠

Regulatory process names:
Sodium diethyldithiocarbamate
sodium diethyldithiocarbamate

CAS names:
Carbamodithioic acid, N,N-diethyl-, sodium salt (1:1)

IUPAC names:
Natriumdiethyldithiocarbaminat
SDEC
Sodio Dietilditiocarbamato 3-hidrato
sodium (diethylcarbamothioyl)sulfanide
Sodium Diethyldithiocarbamate
Sodium diethyldithiocarbamate
sodium diethyldithiocarbamate
Sodium diethyldithiocarbamate trihydrate

Trade names:
Perkacit SDEC liq-w26%

Other identifiers:
1086257-94-4
1240386-50-8
143189-63-3
148-18-5
149099-81-0
19622-06-1
20624-25-3