16420-13-6

Basic information

• Product Name: Dimethylthiocarbamoyl chloride
• Synonyms: N,N-Dimethylaminothioformyl;N,N-Dimethylcarbamothioic chloride, tech;DiMethylthiocarbaMoyl Chloride (DMTCC);DiMethylthiocarbaMoyl chloride, 99% 100GR;DiMethylthiocarbaMoy;CarbaMothioic chloride,N,N-diMethyl-;DiMethylthiocarbaMoyl chloride 97%;DiMethyl aMinothioxoMethyl chloride
• CAS NO: 16420-13-6
• Molecular Formula: C₃H₆ClNS
• Molecular Weight: 123.6
• EINECS: 240-468-5
• Product Categories: Thiocarbonyl Compounds;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 16420-13-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 39-43 °C(lit.)
• Boiling Point: 90-95 °C0.5 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: Slightly yellow to yellow/Low Melting Crystalline Solid or Crystals
• Density: 1.204 (estimate)
• Vapor Pressure: 0.00249mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in chloroform and tetrahydrofuran.
• PKA: 0.30±0.50(Predicted)
• Water Solubility: reacts
• Sensitive: Moisture Sensitive
• BRN: 635823
• CAS DataBase Reference: Dimethylthiocarbamoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylthiocarbamoyl chloride(16420-13-6)
• EPA Substance Registry System: Dimethylthiocarbamoyl chloride(16420-13-6)

Safety Data

• Hazard Codes: C
• Statements: 22-34-29-14
• Safety Statements: 26-36/37/39-45-8-30-22-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 2
• F: 10-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 16420-13-6(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow to yellow low melting crystalline

Uses

Different sources of media describe the Uses of 16420-13-6 differently. You can refer to the following data:
1. Dimethylthiocarbamoyl chloride is used as an intermediate in the synthesis of pharmaceuticals. It finds application in chemoselective deoxygenation of pyridine-N-oxides. It is also used as a starting reagent in the synthesis of dimethylthiocarbamates.
2. 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.

Purification Methods

Crystallise it twice from pentane and/or distil it at low pressure. [Beilstein 4 III 147.]

InChI:InChI=1/C3H6ClNS/c1-5(2)3(4)6/h1-2H3

Synthetic route

Thiram (137-26-8) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

Conditions	Yield
With sulfuryl dichloride In dichloromethane for 0.25h; Ambient temperature;	97%
With sulfuryl dichloride In tetrachloromethane 1) room temp., 10 min; 2) reflux, 20 min;	94%
With thionyl chloride In tetrachloromethane at 20℃; for 0.5h;	92%

Thiram (137-26-8) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + N,N-Dimethylcarbamoyl chloride (79-44-7)

Conditions	Yield
With sulfuryl dichloride In benzene at 50℃; for 6h;	A 83.2% B 3.1%
With sulfuryl dichloride In benzene at 60℃; for 4h;	A 83.2% B 4.8%

3,5-dibromo-4-hydroxyphenylacetic acid ethyl ester (24744-59-0) → ethyl 3,5-dibromo-4-(N,N-dimethylthiocarbamoyloxy)phenylacetate + N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

Conditions	Yield
	A 62% B n/a

μ-tetrasulfido-1,2-dithio-dicarbonic acid bis-dimethylamide (97-91-6) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

Conditions	Yield
With tetrachloromethane; chlorine
With tetrachloromethane; chlorine

bis(dimethylthiocarbamoyl)sulfide (97-74-5) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

Conditions	Yield
With tetrachloromethane; chlorine
With tetrachloromethane; chlorine

thiophosgene (463-71-8) + dimethyl amine (124-40-3) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

N,N-dimethylthioformamide (758-16-7) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

Conditions	Yield
With pyridine; disulfur dichloride In dichloromethane
With chlorine In tetrachloromethane

dichloromethylenedimethyliminium chloride (33842-02-3, 529510-96-1) → N,N-Dimethylthiocarbamoyl chloride (16420-13-6)

Conditions	Yield
With LiAlHSH at 0℃; for 1.5h;

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → dichloromethylenedimethyliminium chloride (33842-02-3, 529510-96-1)

Conditions	Yield
With chlorine under 750.06 Torr; for 10h; Ambient temperature;	100%
With phosphorus pentachloride In tetrachloromethane for 1h; Heating;	90%

3-(trimethylsilyl)phenol (17881-95-7) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(3-trimethylsilylphenyl)-N,N-dimethylaminothiocarbamate (497180-94-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 85℃;	100%

4-(trimethylsilyl)phenol (13132-25-7) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(4-trimethylsilylphenyl)-N,N-dimethylaminothiocarbamate (497180-93-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 85℃;	100%
With sodium hydride In N,N-dimethyl-formamide at 85℃; for 6h;	100%

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + methyl (4-hydroxy-2-methylphenoxy)acetate (317319-10-1) → (4-dimethylthiocarbamoyloxy-2-methyl-phenoxy)-acetic acid methyl ester (583883-84-5)

Conditions	Yield
With dmap; triethylamine In 1,4-dioxane for 16h; Heating;	100%

p-hexylphenol (2446-69-7) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-p-hexylphenyl N,N-dimethylthiocarbamate (153310-07-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 85℃; for 15h;	100%

p-heptylphenol (1987-50-4) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-p-heptylphenyl N,N-dimethylthiocarbamate (869650-49-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 85℃;	100%

rac-6-bromo-3-nitro-2'-phenyl-[1,1'-binaphthalen]-2-ol (881171-40-0) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → rac-O-(6-bromo-3-nitro-2'-phenyl-[1,1'-binaphthalen]-2-yl) dimethylthiocarbamate (881171-49-9)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 23℃; for 24h;	100%

4-bromo-2-hydroxyphenylcyclopentyl ketone (81865-35-2) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → dimethylthiocarbamic acid O-(5-bromo-2-cyclopentanecarbonylphenyl) ester (494799-53-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 3h;	100%

methyl 5-methoxy-2-hydroxybenzoate (2905-82-0) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → methyl 2-((dimethylcarbamothioyl)oxy)-5-methoxybenzoate (104795-61-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20 - 60℃; for 4h; Inert atmosphere;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 55℃; for 3h;	78%
With sodium hydride In N,N-dimethyl-formamide; mineral oil for 3h; Inert atmosphere;	65%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 50℃; for 19h; Inert atmosphere;	57%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃;

2-(5-hydroxyindane-2-yl)isoindole-1,3-dione (685832-34-2) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → dimethylthiocarbamic acid O-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)indan-5-yl] ester (685832-35-3)

Conditions	Yield
Stage #1: 2-(5-hydroxyindane-2-yl)isoindole-1,3-dione; N,N-Dimethylthiocarbamoyl chloride With 1,4-diaza-bicyclo[2.2.2]octane In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; Stage #2: With water at 0 - 20℃; for 18h;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 16h;	70%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2-(5-hydroxyindane-2-yl)isoindole-1,3-dione (685832-34-2) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → dimethylthiocarbamic acid O-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)indan-5-yl] ester (685832-35-3)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 18h;	100%

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + ethyl 2-ethoxy-3-(4-hydroxy-phenyl)-propionate (197299-16-4) → 3-(4-dimethylthiocarbamoyloxy-phenyl)-2-ethoxy-propionic acid ethyl ester (719293-66-0)

Conditions	Yield
With triethylamine; dmap In 1,4-dioxane at 100℃; for 10h; Heating / reflux;	100%
With dmap; triethylamine In 1,4-dioxane; dichloromethane	140.1 g (~100%)

6-bromo-naphthalen-2-ol (15231-91-1) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(6-bromonaphthalene-2-yl) dimethylcarbamothioate (247174-55-6)

Conditions	Yield
Stage #1: 6-bromo-naphthalen-2-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide; mineral oil at 20 - 80℃; for 17h;	100%
With sodium hydride In N,N-dimethyl-formamide at 80℃;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;	82%

4-[(4-hydroxyphenyl)sulfonyl]benzonitrile + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-[4-((4-cyanophenyl)sulfonyl)phenyl] dimethylthiocarbamate

Conditions	Yield
With hydrogenchloride; potassium hydroxide In water; acetone	100%

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + 4-bromo-2,3-dichlorophenol (1940-44-9) → dimethyl-thiocarbamic acid O-(4-bromo-2,3-dichloro-phenyl) ester (845907-29-1)

Conditions	Yield
Stage #1: 4-bromo-2,3-dichlorophenol With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h; Stage #2: N,N-Dimethylthiocarbamoyl chloride In DMF (N,N-dimethyl-formamide) at 20℃;	100%

2-bromo-6-nitro-phenol (13073-25-1) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → C9H9BrN2O3S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide	100%

p-[4-(trifluoromethyl)phenoxy]phenol (39634-42-9) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → Dimethyl-thiocarbamic acid O-[4-(4-trifluoromethyl-phenoxy)-phenyl] ester

Conditions	Yield
Stage #1: p-[4-(trifluoromethyl)phenoxy]phenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	100%

methyl 7-hydroxy-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → methyl 7-dimethylthiocarbamoyloxy-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

Conditions	Yield
With dmap; triethylamine In 1,4-dioxane at 80℃; for 15h;	100%

4-nitro-phenol (100-02-7) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(4-nitrophenyl) N,N-dimethylcarbamothioate (10345-40-1)

Conditions	Yield
Stage #1: 4-nitro-phenol With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 50℃; Stage #2: N,N-Dimethylthiocarbamoyl chloride In 1-methyl-pyrrolidin-2-one at 50℃; for 2.5h;	99%
Stage #1: 4-nitro-phenol With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 50℃; Stage #2: N,N-Dimethylthiocarbamoyl chloride In 1-methyl-pyrrolidin-2-one at 50℃; for 2h;	92%
With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 50℃; for 2.5h;	91%

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + 7-(tert-butyldimethylsilyloxy)heptan-1-ol (126696-08-0) → 1-(tert-butyldimethylsilanyloxy)-7-(dimethylthiocarbamoyloxy)heptane (627871-61-8)

Conditions	Yield
With sodium hydride; sodium iodide In tetrahydrofuran at 20℃; for 10h;	99%

GW694301X + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → 6α,9α-difluoro-17α-[(2-furylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrost-1,4-dien-17β-thiocarboxylic acid S-N,N-dimethylcarbamoyl ester (948565-92-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; triethylamine In tetrahydrofuran at 10 - 20℃; for 4h;	99%
With tetra-(n-butyl)ammonium iodide; triethylamine In tetrahydrofuran at 10 - 20℃; for 4h;	99%
Stage #1: GW694301X With triethylamine In butanone at 10 - 20℃; for 0.166667h; Stage #2: N,N-Dimethylthiocarbamoyl chloride In butanone for 0.166667h; Stage #3: With sodium iodide In water; butanone at 15 - 20℃; for 5h;	87%
With triethylamine; sodium iodide In butanone at 70 - 75℃; for 2h;

methyl 2-hydroxy-5-nitrobenzoate (17302-46-4) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → 2-dimethylthiocarbamoyloxy-5-nitrobenzoic acid methyl ester (1403384-95-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 48h;	99%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide for 3h; Inert atmosphere;	68%

5-bromo-2-hydroxy-3-nitrobenzoic acid ethyl ester (773136-20-2) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → 5-bromo-2-dimethylthiocarbamoyloxy-3-nitrobenzoic acid ethyl ester (1090903-99-3)

Conditions	Yield
Stage #1: 5-bromo-2-hydroxy-3-nitrobenzoic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	99%

2,6-dibromo-4-(trifluoromethyl)phenol (35852-57-4) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(2,6-dibromo-4-(trifluoromethyl)phenyl)-N,N-dimethylthiocarbamate

Conditions	Yield
Stage #1: 2,6-dibromo-4-(trifluoromethyl)phenol With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: N,N-Dimethylthiocarbamoyl chloride In tetrahydrofuran at 0 - 60℃; for 20h;	99%

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + (aR)-2,2'-dihydroxy-6,6'-dimethoxy-1,1'-binaphthyl (145372-06-1, 174510-94-2, 184377-54-6) → C28H28N2O4S2

Conditions	Yield
Stage #1: (aR)-2,2'-dihydroxy-6,6'-dimethoxy-1,1'-binaphthyl With sodium hydride In N,N-dimethyl-formamide at 15℃; for 2h; Inert atmosphere; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide at 80℃; for 2h;	99%

N,N-Dimethylthiocarbamoyl chloride (16420-13-6) + para-Chlorobenzyl alcohol (873-76-7) → O-(4-chlorobenzyl) N,N-dimethylthiocarbamate

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 1h; Inert atmosphere;	99%

C66H66N2O5 + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → C72H76N4O5S2

Conditions	Yield
Stage #1: C66H66N2O5 With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Cooling with ice; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Cooling with ice;	99%

7-hydroxy-2,2-dimethyl-chroman-4-one (17771-33-4) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → 2,2-Dimethyl-7-((N,N-dimethylthiocarbamoyl)oxy)-4-chromanone (143260-13-3)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide for 2h; Ambient temperature;	98%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide for 2h; Ambient temperature;	98%

methyl 4-hydroxylbenzoate (99-76-3) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(4-carbomethoxyphenyl) N,N-dimethylthiocarbamate (13492-59-6)

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile for 16h; Ambient temperature;	98%
With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 50℃; for 78h;	92%
With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 50℃; for 3h;	92%

3,5-dihydroxyphenol (108-73-6) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → Dimethyl-thiocarbamic acid O-(3,5-bis-dimethylthiocarbamoyloxy-phenyl) ester (113954-68-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 0℃; for 3h;	98%

Upstream product

• 137-26-8 Thiram 
• 33842-02-3 dichloromethylenedimethyliminium chloride 
• 24744-59-0 3,5-dibromo-4-hydroxyphenylacetic acid ethyl ester 
• 758-16-7 N,N-dimethylthioformamide 
• 463-71-8 thiophosgene 
• 124-40-3 dimethyl amine 
• 97-74-5 bis(dimethylthiocarbamoyl)sulfide 
• 97-91-6 μ-tetrasulfido-1,2-dithio-dicarbonic acid bis-dimethylamide 

Downstream Products

• 142751-48-2 Dimethyl-thiocarbamic acid O-(5-hydroxy-2-methyl-4-oxo-3-phenyl-4H-chromen-7-yl) ester 
• 83707-38-4 O-<2-(2-Pyridyl)-4-nitrophenyl>dimethylthiocarbamate 
• 52417-38-6 N_.N-Dimethyl-2-hydroxy-2-phenylthioacetamid 
• 10345-52-5 4-chlorophenyl-O-(N,N-dimethylthiocarbamate) 
• 10345-49-0 O-(4-methoxyphenyl) N,N-dimethylcarbamothioate 
• 121347-10-2 2-ethyl 0-phenyldimethylthiocarbamate 
• 16906-71-1 dimethyl-dithiocarbamic acid 2-chloro-phenyl ester 
• 84910-78-1 3-methyl-4-(methylthio)phenyl N,N-dimethylthiocarbamate 
• 74875-14-2 O-(2,6-dichloro-4-nitrophenyl) dimethylcarbamothioate 
• 142751-36-8 Dimethyl-thiocarbamic acid O-(3-hydroxy-4-phenylacetyl-phenyl) ester 
• 107514-46-5 O-2-acetyl-5-methoxyphenyl N,N-dimethylcarbamothioate 
• 19387-18-9 O-pentachlorophenyl dimethylthiocarbamate 
• 142751-38-0 Dimethyl-thiocarbamic acid O-{3-hydroxy-4-[2-(4-methoxy-phenyl)-acetyl]-phenyl} ester 
• 16241-02-4 O-(4-methylphenyl) N,N-dimethylthiocarbamate 

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