Product Name

  • Name

    Metham sodium

  • EINECS 205-293-0
  • CAS No. 137-42-8
  • Article Data4
  • CAS DataBase
  • Density 1.2[at 20℃]
  • Solubility 72.2 g/100 mL at 20 °C in water
  • Melting Point
  • Formula C2H4NNaS2
  • Boiling Point 120.3 °C at 760 mmHg
  • Molecular Weight 129.182
  • Flash Point 26.6 °C
  • Transport Information UN 2811
  • Appearance yellow to light yellow-green aqueous solution
  • Safety 26-36/37/39-45-60-61
  • Risk Codes 22-31-34-50/53-43
  • Molecular Structure Molecular Structure of 137-42-8 (Metham sodium)
  • Hazard Symbols CorrosiveC, DangerousN
  • Synonyms Carbamicacid, methyldithio-, monosodium salt (8CI);BAY 5590;Carbam;Geort;Karbation;Maposol;Metam-sodium;Monam;Nematin;Sepivam;Sistan;Sodium metam;Sodium methyldithiocarbamate;Sodium monomethyldithiocarbamate;Trimaton;VPM;Vapam HL;Woodfume;Metham sodium;
  • PSA 69.42000
  • LogP 1.07910

Synthetic route

carbon disulfide
75-15-0

carbon disulfide

methylamine
74-89-5

methylamine

sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

Conditions
ConditionsYield
With sodium hydroxide In water100%
With sodium hydroxide In methanol; diethyl ether at 20℃; for 24h;98%
With sodium hydroxide In ethanol; water at 20℃; pH=9.5 - 10; Addition;
With sodium hydroxide In water at 20℃; for 3h; Sealed tube;
N-methyldithiocarbamic acid
144-54-7

N-methyldithiocarbamic acid

sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 2.5h; Sealed tube;
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

cinnamoyl chloride
102-92-1

cinnamoyl chloride

6-phenyl-3-methylpropiorhodanine
120189-50-6

6-phenyl-3-methylpropiorhodanine

Conditions
ConditionsYield
In water; acetone at 45℃; for 2h;95%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

N-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

A

methyl thioisocyanate
556-61-6

methyl thioisocyanate

B

N-Phenylbenzothioamide
636-04-4

N-Phenylbenzothioamide

Conditions
ConditionsYield
In diethyl ether 0 deg C to r.t.;A 51%
B 95%
...Expand
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

acryloyl chloride
814-68-6

acryloyl chloride

3-Methyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin
7629-41-6

3-Methyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin

Conditions
ConditionsYield
In water; acetone for 1h; Ambient temperature;94%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

p-nitrocinnamoyl chloride
61921-33-3, 22440-58-0

p-nitrocinnamoyl chloride

3-Methyl-6-(4-nitro-phenyl)-2-thioxo-[1,3]thiazinan-4-one
121216-02-2

3-Methyl-6-(4-nitro-phenyl)-2-thioxo-[1,3]thiazinan-4-one

Conditions
ConditionsYield
In water; acetone for 1h; Ambient temperature;94%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

ethyl 2-chloro-3-oxo-butyrate
609-15-4

ethyl 2-chloro-3-oxo-butyrate

ethyl α-(N-methyl)dithiocarbamoylacetoacetate
313513-95-0

ethyl α-(N-methyl)dithiocarbamoylacetoacetate

Conditions
ConditionsYield
In water at 15 - 20℃; for 3h; Substitution;94%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

1-methyl-5-mercaptotetrazole
13183-79-4

1-methyl-5-mercaptotetrazole

Conditions
ConditionsYield
With sodium azide; sodium hydroxide In water at 95℃; for 14h; Temperature;93.6%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

crotonyl chloride
10487-71-5

crotonyl chloride

3,6-dimethyl-2-thioxo-[1,3]thiazinan-4-one
25201-16-5

3,6-dimethyl-2-thioxo-[1,3]thiazinan-4-one

Conditions
ConditionsYield
In water; acetone for 1h; Ambient temperature;90%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

p-methoxycinnamoyl chloride
42996-84-9, 34446-64-5

p-methoxycinnamoyl chloride

6-(4-Methoxy-phenyl)-3-methyl-2-thioxo-[1,3]thiazinan-4-one
121215-96-1

6-(4-Methoxy-phenyl)-3-methyl-2-thioxo-[1,3]thiazinan-4-one

Conditions
ConditionsYield
In water; acetone at 45℃; for 2h;88%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

{C5H5Ni(P(C4H9-n)3)2}Cl

{C5H5Ni(P(C4H9-n)3)2}Cl

C5H5Ni(P(C4H9-n)3)SC(S)NHCH3
52201-66-8

C5H5Ni(P(C4H9-n)3)SC(S)NHCH3

Conditions
ConditionsYield
In water room temp.; with excess of NaSC(S)NHCH3; extn. of the brown ppt. with ether or benzene; drying, evapn. in vac.; recrystn. from benzene or benzene/hexane;87%
In water
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

2-chloro-N-phenyl-3-oxobutanamide
31844-92-5

2-chloro-N-phenyl-3-oxobutanamide

α-(N-methyl)dithiocarbamoylacetoacetanilide

α-(N-methyl)dithiocarbamoylacetoacetanilide

Conditions
ConditionsYield
In water at 20℃; for 24h; Substitution;86%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

Mo(allyl)(carbonyl)2(acetonitrile)2(bromide)

Mo(allyl)(carbonyl)2(acetonitrile)2(bromide)

K[Mo(N-methyl dithiocarbamate)(π-allyl)(CO)2]

K[Mo(N-methyl dithiocarbamate)(π-allyl)(CO)2]

Conditions
ConditionsYield
In acetone 1:2 molar ratio (complex:dithio compd.), stirring at room temp. for 20-45 min; filtration, evapn. of filtrate under vac., product was pptd. by addn. of hexane to diethyl ether soln. of filtrate with stirring, product was filtered off, washed with diethyl ether or ether/hexane and dried in vac., elem. anal.;84.4%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

methyl iodide
74-88-4

methyl iodide

S-methyl N-methyl dithiocarbamate
13037-11-1

S-methyl N-methyl dithiocarbamate

Conditions
ConditionsYield
In methanol; ethanol; water at 0 - 20℃; for 2h; Methylation;83%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

Diphenylmethyl (6R,7R)-7-[2-(2-Chloroacetamidothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-cyclopropylceph-3-em-4-carboxylate

Diphenylmethyl (6R,7R)-7-[2-(2-Chloroacetamidothiazol-4-yl)-2(Z)-methoxyiminoacetamido]-3-cyclopropylceph-3-em-4-carboxylate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

Sodium (6R,7R)-7-[2-(2-Aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-cyclopropylceph-3-em-4-carboxylate
128226-75-5

Sodium (6R,7R)-7-[2-(2-Aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-cyclopropylceph-3-em-4-carboxylate

Conditions
ConditionsYield
In dichloromethane; water; methoxybenzene82%
...Expand
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

MoBr(η-allyl)(CO)2(bipyridyl)
12245-55-5, 382596-61-4

MoBr(η-allyl)(CO)2(bipyridyl)

Mo(methyldithiocarbamate)(η-allyl)(CO)2(bipyridyl)
80501-82-2

Mo(methyldithiocarbamate)(η-allyl)(CO)2(bipyridyl)

Conditions
ConditionsYield
In acetone alkaline xantate added in mole ratio 1:1 to MoBr-complex in acetone soln. under N2, stirred for 30-40 min; filtered, washed with water, dried over P2O5 under vac., elem. anal.;81.3%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

ammonium dithiocarbamate
513-74-6

ammonium dithiocarbamate

3-Methyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin
7629-41-6

3-Methyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin

Conditions
ConditionsYield
With triethylamine In water; acetone for 0.25h; Ambient temperature;77%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

3-Methyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin
7629-41-6

3-Methyl-4-oxo-2-thioxo-tetrahydro-1,3-thiazin

Conditions
ConditionsYield
With triethylamine In water; acetone for 0.25h; Product distribution; Ambient temperature; other sodium N-alkyl(aryl)dithiocarbamates investigated;77%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

(2-bromo-1-(4-(methoxycarbonyl)phenyl)ethyl)dimethylsulfonium bromide

(2-bromo-1-(4-(methoxycarbonyl)phenyl)ethyl)dimethylsulfonium bromide

methyl 4-(2-(methylimino)-1,3-dithiolan-4-yl)benzoate

methyl 4-(2-(methylimino)-1,3-dithiolan-4-yl)benzoate

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 20.3h;76%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

triphenyltelluronium chloride
1224-13-1

triphenyltelluronium chloride

C20H19NS2Te

C20H19NS2Te

Conditions
ConditionsYield
In water at 60 - 70℃; for 0.5h;75%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

Mo(Br)(π-allyl)(CO)2(pyridine)2

Mo(Br)(π-allyl)(CO)2(pyridine)2

Mo(N-methyl dithiocarbamate)(π-allyl)(CO)2(pyridine)

Mo(N-methyl dithiocarbamate)(π-allyl)(CO)2(pyridine)

Conditions
ConditionsYield
In acetone; benzene 1:1 molar ratio (complex:dithio compd.), stirring 45 min; filtration, concn. of filtrate at reduced pressure, product was pptd. by addn. of diethyl ether, n-hexane with stirring and cooling to 0°C, pppt. was filtered off, washed with hexane at 0°C, drying under vac., elem. anal.;75%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

(2-bromo-1-(4-fluorophenyl)ethyl)dimethylsulfonium bromide

(2-bromo-1-(4-fluorophenyl)ethyl)dimethylsulfonium bromide

4-(4-fluorophenyl)-N-methyl-1,3-dithiolan-2-imine

4-(4-fluorophenyl)-N-methyl-1,3-dithiolan-2-imine

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 20.3h;72%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

6-chloro-N-methyl-5-nitropyrimidin-4-amine
23126-82-1

6-chloro-N-methyl-5-nitropyrimidin-4-amine

N,N'-dimethyl-5-nitro-pyrimidine-4,6-diamine
6964-30-3

N,N'-dimethyl-5-nitro-pyrimidine-4,6-diamine

Conditions
ConditionsYield
In ethanol at 20℃;70%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

[2-bromo-1-(4-methylphenyl)ethyl]dimethylsulfonium bromide
1032818-10-2

[2-bromo-1-(4-methylphenyl)ethyl]dimethylsulfonium bromide

N-methyl-4-(p–tolyl)-1,3-dithiolan-2-imine

N-methyl-4-(p–tolyl)-1,3-dithiolan-2-imine

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 20.3h;68%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

(3R,5aS,6R,8aS,9R,10R,12S,12aR)-octahydro-3-chloromethylene-6,9-dimethyl-3,12-oxo-12H-pyrano[4,3-j]-1,2-benzodithiophen-10(3H)alcohol

(3R,5aS,6R,8aS,9R,10R,12S,12aR)-octahydro-3-chloromethylene-6,9-dimethyl-3,12-oxo-12H-pyrano[4,3-j]-1,2-benzodithiophen-10(3H)alcohol

(3R,5aS,6R,8aS,9R,10R,12S,12aR)-octahydro-3-(N-methylaminodithioformate)methylene-6,9-dimethyl-3,12-oxo-12H-pyrano[4,3-j]-1,2-benzodithiophen-10(3H)alcohol

(3R,5aS,6R,8aS,9R,10R,12S,12aR)-octahydro-3-(N-methylaminodithioformate)methylene-6,9-dimethyl-3,12-oxo-12H-pyrano[4,3-j]-1,2-benzodithiophen-10(3H)alcohol

Conditions
ConditionsYield
With potassium iodide In isopropyl alcohol for 12h;67%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

(2-bromo-1-(4-chlorophenyl)ethyl)dimethylsulfonium bromide
1032818-12-4

(2-bromo-1-(4-chlorophenyl)ethyl)dimethylsulfonium bromide

4-(4-chlorophenyl)-N-methyl-1,3-dithiolan-2-imine

4-(4-chlorophenyl)-N-methyl-1,3-dithiolan-2-imine

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 20.3h;63%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

4-Amino-2-dimethylamino-6,7-dihydro-oxazolo[3,2-a][1,3,5]triazin-5-ylium; chloride

4-Amino-2-dimethylamino-6,7-dihydro-oxazolo[3,2-a][1,3,5]triazin-5-ylium; chloride

2-amino-N(3)-(2-methyldithiocarbamoylethyl)-6-dimethylamino-sym-triazin-4-one

2-amino-N(3)-(2-methyldithiocarbamoylethyl)-6-dimethylamino-sym-triazin-4-one

Conditions
ConditionsYield
In water at 20℃; for 6h;61%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

4-chloro-6-methoxy-5-nitropyrimidine
52854-14-5

4-chloro-6-methoxy-5-nitropyrimidine

(6-methoxy-5-nitro-pyrimidin-4-yl)-methyl-amine
100114-07-6

(6-methoxy-5-nitro-pyrimidin-4-yl)-methyl-amine

Conditions
ConditionsYield
In ethanol at 20℃;57%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

(2-bromo-1-phenylethyl)dimethylsulphonium bromide
75326-15-7

(2-bromo-1-phenylethyl)dimethylsulphonium bromide

N-methyl-4-phenyl-1,3-dithiolan-2-imine

N-methyl-4-phenyl-1,3-dithiolan-2-imine

Conditions
ConditionsYield
In dichloromethane; water at 25℃; for 20.3h;54%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

Sodium 3-[(2-chloroacetamido-1,3,4-thiadiazol-5-yl)thiomethyl]-7β-[D,2-(3,4-dihydroxyphenyl)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]acetamido]-7α-formamidoceph-3-em-4-carboxylate

Sodium 3-[(2-chloroacetamido-1,3,4-thiadiazol-5-yl)thiomethyl]-7β-[D,2-(3,4-dihydroxyphenyl)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]acetamido]-7α-formamidoceph-3-em-4-carboxylate

Sodium 3-[(2-amino-1,3,4-thiadiazol-5-yl)thiomethyl]-7β-[D,2-(3,4-dihydroxyphenyl)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]acetamido]-7α-formamidoceph-3-em-4-carboxylate

Sodium 3-[(2-amino-1,3,4-thiadiazol-5-yl)thiomethyl]-7β-[D,2-(3,4-dihydroxyphenyl)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]acetamido]-7α-formamidoceph-3-em-4-carboxylate

Conditions
ConditionsYield
In water46%
sodium N-methyldithiocarbamate
137-42-8

sodium N-methyldithiocarbamate

2-propynyl chloride
624-65-7

2-propynyl chloride

3-N-methylthiocarbamoylthio-1-propyne

3-N-methylthiocarbamoylthio-1-propyne

Conditions
ConditionsYield
In diethyl ether; water at 5 - 7℃; for 3.5h;30%

Metham sodium Specification

The Metham sodium, with the CAS registry number 137-42-8,is also known as Methylcarbamodithioic acid sodium salt; Sodium monomethyldithiocarbamate. It belongs to the product categories of META - METH;Pesticides&Metabolites. This chemical's molecular formula is C2H4NNaS2 and molecular weight is 129.17.Its EINECS number is 205-293-0. What's more,Its systematic name is Metham sodium. It is a yellow to light yellow-green aqueous solution which is generally used as a broad-spectrum soil fumigant for fungi, bacteria, nematodes and insects.It decomposes, when diluted with water, to methyl isothiocyanate (MITC, a lachrymator) and/or to hydrogen sulfide. It can also decompose to carbon disulfide and monomethylamine if contacted with a strong acid. The decomposition products are flammable and toxic. It is compatible with additional water and strong aqueous acids. In addition, it is corrosive to copper, brass and zinc, and may soften and/or discolor iron. Store it in a cool, dry, locked place out of  reach of children. Do not store it below 32 ℉. It crystallizes at lower temperatures.

Physical properties about  Metham sodium are:
(1)ACD/LogP:  0.782; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  -1.77; (4)ACD/LogD (pH 7.4):  -2.89; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  1.00; (8)ACD/KOC (pH 7.4):  1.00; (9)#H bond acceptors:  1; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  0; (12)Flash Point:  26.6 °C; (13)Enthalpy of Vaporization:  35.84 kJ/mol; (14)Boiling Point:  120.3 °C at 760 mmHg; (15)Vapour Pressure:  15.3 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:[Na+].[S-]C(=S)NC;
(2)Std. InChI:InChI=1S/C2H5NS2.Na/c1-3-2(4)5;/h1H3,(H2,3,4,5);/q;+1/p-1;
(3)Std. InChIKey:AFCCDDWKHLHPDF-UHFFFAOYSA-M.

Safety Information of Metham sodium:
The Metham sodium Contact with acids liberates toxic gas and Causes burns. It may cause sensitization by skin contact.And it is very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.So it should be avoid release to the environment. Refer to special instructions safety data sheet.And this material and/or its container must be disposed of as hazardous waste.When you use it,you should  wear suitable protective clothing, gloves and eye/face protection.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

The toxicity data of  Metham sodium are as follows:

cat LDLo oral 100mg/kg (100mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(5), Pg. 33, 1969.
guinea pig LD50 oral 815mg/kg (815mg/kg)   Hygiene and Sanitation Vol. 32(2), Pg. 169, 1967.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   Farmakologiya i Toksikologiya Vol. 32, Pg. 356, 1969.
mouse LD50 oral 50mg/kg (50mg/kg)   Residue Reviews. Vol. 10, Pg. 97, 1965.
mouse LD50 unreported 285mg/kg (285mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 213, 1971.
quail LD50 unreported 500mg/kg (500mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C196, 1991.
rabbit LD50 oral 320mg/kg (320mg/kg)   Hygiene and Sanitation Vol. 32(2), Pg. 169, 1967.
rabbit LD50 skin 800mg/kg (800mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat LD50 oral 450mg/kg (450mg/kg)   Farmakologiya i Toksikologiya Vol. 32, Pg. 356, 1969.
rat LD50 skin 636mg/kg (636mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 106, 1982.
rat LD50 unreported 550mg/kg (550mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(6), Pg. 21, 1982.

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