148-18-5

Basic information

• Product Name: Sodium diethyldithiocarbamate
• Synonyms: dithiocarbamate;ditiocarbsodium;imuthiol;kupral;n,n-diethyldithiocarbamicacid,sodiumsalt;na-ddtc;ncico2835;sodiumdedt
• CAS NO: 148-18-5
• Molecular Formula: C₅H₁₀NNaS₂
• Molecular Weight: 171.26
• EINECS: 205-710-6
• Product Categories: Pharmaceutical Intermediates;Aliphatics;Amines;Sulfur & Selenium Compounds
• Mol File: 148-18-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 95°C
• Boiling Point: 176.4 °C at 760 mmHg
• Flash Point: 60.5 °C
• Appearance: Clear, colorless/Liquid
• Density: 1.1000
• Vapor Pressure: 0Pa at 20℃
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: about 35 % in water, less soluble in organic solvents. However, the free acid, diethyldithiocarbamic acid, is readily soluble in organic solvents and less soluble in water. Thus, on acidification of an aqueous solution of a diethyldithiocarbamate, the free acid can be extracted with chloroform or carbon tetrachloride. The distribution ratio is 2,360 for chloroform and 343 for carbon tetrachloride.
• Water Solubility: >=10 g/100 mL at 14 ºC
• CAS DataBase Reference: Sodium diethyldithiocarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium diethyldithiocarbamate(148-18-5)
• EPA Substance Registry System: Sodium diethyldithiocarbamate(148-18-5)

Safety Data

• RIDADR: 3077
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 148-18-5(Hazardous Substances Data)

Usage

Chemical Properties

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, it 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

Different sources of media describe the Uses of 148-18-5 differently. You can refer to the following data:
1. Sodium diethyldithiocarbamate reacts with even more metal ions than does dithizone. However, its 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.
2. Sodium diethyldithiocarbamate is an organic molecular entity. It is an inhibitor of superoxide dismutase, having both antioxidant and oxidant effects.

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

General Description

Odorless white or slightly brown or slightly pink crystals.

Air & Water Reactions

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

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

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

Flammability and Explosibility

Nonflammable

Safety Profile

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. Used as a pesticide. See also CARBAMATES

InChI:InChI=1/C4H10.CH3NS2.Na/c1-3-4-2;2-1(3)4;/h3-4H2,1-2H3;(H3,2,3,4);/q;;+1/p-1

Synthetic route

carbon disulfide (75-15-0) + diethylamine (109-89-7) → sodium N,N-diethyldithiocarbamate (148-18-5)

Conditions	Yield
With sodium hydroxide In ethanol; water cooling;	90%
With sodium hydroxide In ethanol at 20 - 40℃;	73%
With sodium hydroxide In water at 20℃; for 1h; Cooling with ice;	69%

disulfiram (97-77-8) + sodium O-ethyl dithiocarbonate (140-90-9) → sodium N,N-diethyldithiocarbamate (148-18-5) + C8H15NOS4 (327989-09-3)

Conditions	Yield
With sodium nitrate; C8MoN8(3-)*3Na(1+) In water; acetone at 25℃; Rate constant; Equilibrium constant; μ 0.2 mol/l;

disulfiram (97-77-8) + sodium N,N'-diisopropyldithiocarbamate (4092-82-4) → sodium N,N-diethyldithiocarbamate (148-18-5) + C12H24N2S4

Conditions	Yield
With sodium nitrate; potassium hexacyanoferrate(III) In water; acetone at 25℃; Equilibrium constant; μ 0.2 mol/l;

sodium O-ethyl dithiocarbonate (140-90-9) + C8H15NOS4 (327989-09-3) → bis-ethoxythiocarbonyldisulfane (502-55-6) + sodium N,N-diethyldithiocarbamate (148-18-5)

Conditions	Yield
With sodium nitrate; C8MoN8(3-)*3Na(1+) In water; acetone at 25℃; Rate constant; Equilibrium constant; μ 0.2 mol/l;

sodium N,N'-diisopropyldithiocarbamate (4092-82-4) + C12H24N2S4 → tetraisopropylothiuram disulphide (4136-91-8) + sodium N,N-diethyldithiocarbamate (148-18-5)

Conditions	Yield
With sodium nitrate; potassium hexacyanoferrate(III) In water; acetone at 25℃; Equilibrium constant; μ 0.2 mol/l;

Tributyltin diethyldithiocarbamate (138523-63-4) → sodium N,N-diethyldithiocarbamate (148-18-5)

Conditions	Yield
With sodium hydrogensulfide In methanol at 4℃;

BPA (80-05-7) + concentrated NaOH + N-(hydroxyethyl)-ethylenediamine + Diethylene glycol monobutyl ether (112-34-5) + chlorophene (120-32-1) → sodium N,N-diethyldithiocarbamate (148-18-5)

sodium N,N-diethyldithiocarbamate (148-18-5) + 5'-I-d(TTT)-CPG resin → C35H49N7O18P2S2

Conditions	Yield
Stage #1: sodium N,N-diethyldithiocarbamate; 5'-I-d(TTT)-CPG resin In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: With ammonium hydroxide at 60℃; for 17h;	100%

[Re(S3CPh)2(S2CPh)] + sodium N,N-diethyldithiocarbamate (148-18-5) → bis(trithioperoxybenzoato)-(diethyldithiocarbamato)rhenium (III)

Conditions	Yield
In methanol; dichloromethane at 20℃; for 1h;	100%

sodium N,N-diethyldithiocarbamate (148-18-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate

Conditions	Yield
In acetone for 1h; Reflux;	99%
In acetonitrile at 25℃; for 1h;	63%

bis(tetraethylammonium) tri-μ2-disulfido-μ3-thio-hexabromo-triangular-trimolybdenum(IV) + sodium N,N-diethyldithiocarbamate (148-18-5) → tris(diethyldithiocarbamato-S,S')tris(μ2-η(2)-disulfido)(μ3-sulfido)trimolybdenum(IV)(3 Mo-Mo) diethyldithiocarbamate

Conditions	Yield
In solid byproducts: Et4NBr, NaBr; mixt. was evacuated at 80 °C for 2 h, mech. activation for 1.5 h in a vac. vibration mill with steel ball (23 Hz); H2O was added, ppt. was washed with hot H2O and EtOH, dried in vac. at 75 °C, residue was treated with hot MeCN, washed with H2O and EtOH, dried in vac. at 75 °C, recrystn. from DMSO, elem. anal.;	99%

[AuCl(2-thia-1,3,5-triaza-7-phosphaadamantane-2,2-dioxide)] (1243627-92-0) + sodium N,N-diethyldithiocarbamate (148-18-5) → [Au(diethyldithiocarbamate)(2-thia-1,3,5-triaza-7-phosphaadamantane-2,2-dioxide)] (1243628-11-6)

Conditions	Yield
In methanol Na salt was added to suspn. of Au complex in MeOH; stirred for 18 h; filtered; washed (H2O, MeOH, Et2O); dried in air; elem. anal.;	99%

sodium N,N-diethyldithiocarbamate (148-18-5) + (1R,6S)-1-Methyl-7-(toluene-4-sulfonyl)-7-aza-bicyclo[4.1.0]heptane → C19H30N2O2S3

Conditions	Yield
In acetonitrile at 80℃; for 12h; stereoselective reaction;	99%

sodium N,N-diethyldithiocarbamate (148-18-5) + 7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[4.1.0]hept-3-ene (112297-29-7) → C18H26N2O2S3

Conditions	Yield
In acetonitrile at 80℃; for 0.5h; stereoselective reaction;	99%

sodium N,N-diethyldithiocarbamate (148-18-5) + 2-(N-acetylanilino)-4-iodomethyl-1,3-selenazole (121995-12-8) → [2-(N-acetylanilino)-1,3-selenazol-4-ylmethyl]-N,N-diethyldithiocarbamate

Conditions	Yield
In acetone for 0.5h; Heating;	98%

sodium N,N-diethyldithiocarbamate (148-18-5) + copper dichloride → bis(N,N-diethyldithiocarbamato)copper(II) (13681-87-3)

Conditions	Yield
In neat (no solvent, solid phase) byproducts: NaCl; placing of CuCl2 and NaS2CNEt2 in 1:2 ratio to the reactor; sealing, vibrating for 60 min; sublimating in vac. at 180-190°C; crystn.; elem. anal.;	98%

sodium N,N-diethyldithiocarbamate (148-18-5) + tetraphenylchloroantimony(V) (16894-68-1) → tetraphenylantimony N,N-diethyldithiocarbamate (109423-89-4)

Conditions	Yield
In water byproducts: NaCl; soln. of ligand in water was added to soln. of Sb-complex in water; filtered off, dried, crystd. from toluene-heptane;	98%

2-(bromomethyl)-1,3-thiaselenole (1112152-67-6) + sodium N,N-diethyldithiocarbamate (148-18-5) → (Z)-2-([(diethylamino)carbothioyl]sulfanylselanyl)ethenyl vinyl sulfide

Conditions	Yield
In acetonitrile at 20℃; for 0.0333333h; regioselective reaction;	98%

{Mo(CPh)Br(CO)2(4-picoline)2} + tetraethylammonium chloride (56-34-8) + sodium N,N-diethyldithiocarbamate (148-18-5) → {N(C2H5)4}(1+)*{Mo(S2CN(C2H5)2)2(CO)(C6H5CCO)}(1-)={N(C2H5)4}{Mo(S2CN(C2H5)2)2(CO)(C6H5CCO)}

Conditions

Yield

In tetrahydrofuran byproducts: NaBr; under inert atm.; addn. of soln. of Na-compd. to soln. of complex at -78°C, removed from cold bath and stirred at ambient temp. for 1.45 h; evapd. (vac.), dissolved in CH2Cl2, addn. of NEt4Cl, stirred for 45 min, filtered (cellulose), dried (vac., 2.5 h), treated with THF, cooled to -8°C for 30 min, supernatant decanted, , washed (THF), recrystd. (CH2Cl2/Et2O);

97.5%

sodium N,N-diethyldithiocarbamate (148-18-5) + zinc(II) chloride (7646-85-7) → bis(N,N-diethyldithiocarbamato)zinc(II) (14324-55-1)

Conditions	Yield
In neat (no solvent, solid phase) byproducts: NaCl; placing of ZnCl2 and NaS2CNEt2 in 1:2 ratio to the reactor; sealing, vibrating for 10 min; sublimating at 150-165°C in vac.; crystn.; elem. anal.;	97%

dichloro(2,2'-bipyridine)platinum(II) (13965-31-6) + sodium N,N-diethyldithiocarbamate (148-18-5) → bis(N,N-diethyldithiocarbamate)platinum(II) (15730-38-8)

Conditions	Yield
In not given stoich. amts., stirring for 1 h (pptn.); collection (filtration), washing (water), drying (vac.);	97%

sodium N,N-diethyldithiocarbamate (148-18-5) + dichlorophenylstibine (5035-52-9) → phenylantimony chloride diethyldithiocarbamate

Conditions	Yield
In chloroform equimolar amts. at 25°C;	97%

sodium N,N-diethyldithiocarbamate (148-18-5) + dichlorophenylstibine (5035-52-9) → phenylantimony diethyldithiocarbamate (18615-16-2)

Conditions	Yield
In chloroform equimolar amts. of educts at 25°C;	97%

RuCl2(CO)(P(CH3)(CH(CH3)2)2)2 + sodium N,N-diethyldithiocarbamate (148-18-5) → RuCl(CO)(S2CN(C2H5)2)(P(CH3)(CH(CH3)2)2)2

Conditions	Yield
In dichloromethane (inert atmosphere); stirring (12 h); filtration (Celite), solvent removal (vac.), washing (light petroleum); elem. anal.;	97%

(±)-trans-N-tosyl-2-isopropyl-3-methylaziridine + sodium N,N-diethyldithiocarbamate (148-18-5) → C18H30N2O2S3

Conditions	Yield
In acetonitrile at 80℃; for 12h; stereoselective reaction;	97%

cyclohexyl-N-tosyl aziridine (68820-12-2) + sodium N,N-diethyldithiocarbamate (148-18-5) → C18H28N2O2S3

Conditions	Yield
In acetonitrile at 80℃; for 0.166667h; stereoselective reaction;	97%

sodium N,N-diethyldithiocarbamate (148-18-5) + N-tosyl-6-azabicyclo[3.1.0]hexane (81097-48-5) → C17H26N2O2S3

Conditions	Yield
In acetonitrile at 80℃; for 1h; stereoselective reaction;	97%

4-Vinylbenzyl chloride (1592-20-7) + sodium N,N-diethyldithiocarbamate (148-18-5) → N,N-(diethylamino)dithiocarbamoylmethylstyrene

Conditions	Yield
In acetone at 40℃; for 1h;	97%

bis(4-methyl-2-chloroacetamidothiazole)sulfide + sodium N,N-diethyldithiocarbamate (148-18-5) → C22H32N6O2S7

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 6h;	97%

sodium N,N-diethyldithiocarbamate (148-18-5) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → C13H22NO7S3(1-)*Na(1+)

Conditions	Yield
In methanol at 20℃;	97%

4-fluoro-2-iodoaniline (61272-76-2) + sodium N,N-diethyldithiocarbamate (148-18-5) → 6-fluoro-N,N-diethylbenzo[d]thiazol-2-amine

Conditions	Yield
With copper diacetate; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 6h; Sealed tube;	97%

sodium N,N-diethyldithiocarbamate (148-18-5) + cadmium(II) chloride (10108-64-2) → cadmium(II) diethyldithiocarbamate (14239-68-0)

Conditions	Yield
In neat (no solvent, solid phase) byproducts: NaCl; placing of CdCl2 and NaS2CNEt2 in 1:2 ratio to the reactor; sealing, vibrating for 60 min; sublimating in vac. at 180-230°C; crystn.; elem. anal.;	96.6%
In water byproducts: NaCl; pptn. of complex from soln. at room temp., filtration while hot, drying (80°C, vac.); recrystn. (benzene); (1)H- and (13)C-NMR;
In water byproducts: NaCl; ZnCl2, the thiocarbamate in water, immediately pptn.; filtered hot to remove NaCl and any excess of unreacted thiocarbamate, dried (vac. at 80°C), recrystn. (boiling benzene);
In water solution of CdCl2 added to stirred solution of the ligand; filtered, dried, recrystd. from chloroform;

sodium N,N-diethyldithiocarbamate (148-18-5) → disulfiram (97-77-8)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 2h;	96%
With iodine In methanol at 0℃;	95%
With oxygen; sodium hydroxide In water at 25℃; for 1.08333h; pH=10; Kinetics; pH-value; Reagent/catalyst;	94%

dimethyl 2-bromosuccinate (760-90-7) + sodium N,N-diethyldithiocarbamate (148-18-5) → dimethyl (diethylthiocarbamoylthio)succinate (94725-95-8)

Conditions	Yield
In water for 8h;	96%

ethyl 2-bromoisobutyrate (600-00-0) + sodium N,N-diethyldithiocarbamate (148-18-5) → S-(1-methyl-1-ethoxycarbonylethyl) N,N-diethyl-dithiocarbamate (120924-70-1)

Conditions	Yield
In acetone at 40℃;	96%

2-chloro-1-acetoxyethane (542-58-5) + sodium N,N-diethyldithiocarbamate (148-18-5) → N,N-diethyldithiocarbamic acid 2-(acetoxy)ethyl ester

Conditions	Yield
In acetone at 40℃;	96%
With water In N,N-dimethyl-formamide at 75 - 80℃;	88%

3-benzyltetrahydro-1,3-oxazine-2-thione (700840-90-0) + sodium N,N-diethyldithiocarbamate (148-18-5) → polymer, product of cationic ring-opening polymerization, Mn 20400 Da by SEC in THF, Mn 12200 by light scattering, PDI 1.04; monomer(s): 3-benzyltetrahydro-1,3-oxazine-2-thione; sodium N,N-diethyldithiocarbamate

Conditions	Yield
Stage #1: 3-benzyltetrahydro-1,3-oxazine-2-thione With boron trifluoride diethyl etherate In nitrobenzene at 50℃; for 24h; Stage #2: sodium N,N-diethyldithiocarbamate In nitrobenzene; acetonitrile	96%

Upstream product

• 148184-12-7 2-ethoxy-2-oxoethyl ethyl methylidenepropanedioate 
• 148183-93-1 2-(4-methoxyphenoxy)-1-(morpholin-4-yl)ethanone 
• 148183-92-0 2-(2-methoxyphenoxy)-1-(morpholin-4-yl)ethanone 
• 148183-91-9 2-(2,5-dimethylphenoxy)-1-(morpholin-4-yl)ethanone 
• 148183-90-8 2-(2,4-dimethylphenoxy)-1-(morpholin-4-yl)ethanone 
• 148183-89-5 2-(2,4-dimethylphenoxy)-1-(pyrrolidin-1-yl)ethanone 
• 148183-87-3 Pyrrolidine, 1-acetyl-2-(2,2,2-trifluoro-1-hydroxyethylidene)-, (E)- (9CI) 
• 148183-85-1 Pyrrolidine, 1-acetyl-2-(2,2,2-trifluoro-1-hydroxyethylidene)-, (Z)- (9CI) 
• 148183-65-7 3H-Pyrrol-5-ol,2-ethoxy-4-phenyl-(9CI) 
• 14818-35-0 2,6-DIMETHYL-4-NITROSOPHENOL 
• 1481-83-0 2-phenyl-3,4-dihydro-2H-chromen-3-ol 
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• 148179-99-1 9-(4-(1,2-dihydroxyethyl)cyclopent-2-en-1-yl)-9H-adenine 
• 148179-94-6 spongistatin 1 

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• 70667-26-4 ORNOPROSTIL 

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