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Methyl thiocyanate

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Name

Methyl thiocyanate

EINECS 209-134-6
CAS No. 556-64-9 Density 1.06
PSA 49.09000 LogP 0.83048
Solubility Practically insoluble in water Melting Point -5 ºC
Formula C2H3 N S Boiling Point 131 ºC
Molecular Weight 73.1185 Flash Point 38 ºC
Transport Information N/A Appearance CLEAR COLOURLESS TO LIGHT YELLOW LIQUID
Safety Poison by ingestion, intravenous, and subcutaneous routes. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also THIOCYANATES. Risk Codes R10;R23/24/25   
Molecular Structure Molecular Structure of 556-64-9 (Methyl thiocyanate) Hazard Symbols
Synonyms

Methylsulfocyanate; Methyl thiocyanate; NSC 9368

Article Data 51

Methyl thiocyanate Synthetic route

333-20-0

potassium thioacyanate

74-88-4

methyl iodide

556-64-9

methyl thiocyanate

Conditions
ConditionsYield
With poly(vinylbenzyltriphenylphosphonium chloride) In benzene for 2h; Heating;88%
75532-40-0

dimethyl phosphoroisothiocyanatidite

431-03-8

dimethylglyoxal

A

556-64-9

methyl thiocyanate

B

933-43-7

2-methoxy-4,5-dimethyl-[1,3,2]dioxaphosphole 2-oxide

Conditions
ConditionsYield
In dichloromethane at 0℃;A n/a
B 80%
59103-08-1

3-methylsulfanyl-5,6-diphenyl-[1,4,2]dithiazine

A

556-64-9

methyl thiocyanate

B

23181-79-5

2,3,5,6-tetraphenyl-1,4-dithia-2,5-cyclohexadiene

C

501-65-5

diphenyl acetylene

Conditions
ConditionsYield
In dichloromethane for 4h; Irradiation;A n/a
B 72%
C n/a
In dichloromethane for 8h; Quantum yield; Mechanism; Irradiation;
2911-22-0

6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine

74-88-4

methyl iodide

556-64-9

methyl thiocyanate

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Ambient temperature;64%
79306-34-6

1-azido-2,2-dimethylcyclopropyl methylsulfide

A

556-64-9

methyl thiocyanate

B

2-(methylthio)-4,4-dimethyl-1-azetine

C

79780-50-0

2-(methylthio)-3,3-dimethyl-1-azetine

D

115-11-7

isobutene

Conditions
ConditionsYield
In tetrachloromethane for 3h; Heating;A 30%
B 6%
C 63%
D n/a
In tetrachloromethane for 3h; Rate constant; Heating;A 30%
B 6%
C 63%
D n/a
In tetrachloromethane for 3h; Heating;
83319-07-7

C19H18NS(1+)*CNS(1-)

556-64-9

methyl thiocyanate

Conditions
ConditionsYield
at 240℃;52%
poly(N-methyl-4-vinyl-pyridinium)thiocyanate

poly(N-methyl-4-vinyl-pyridinium)thiocyanate

74-88-4

methyl iodide

556-64-9

methyl thiocyanate

Conditions
ConditionsYield
In hexane at 20℃; for 72h;50%
333-20-0

potassium thioacyanate

S-methylthiolanium fluorosulphate

A

110-01-0

thiophene

B

556-64-9

methyl thiocyanate

C

4430-36-8

erucin

D

41756-12-1

4-(methylthio)butyl thiocyanate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 70℃; for 7h; Yields of byproduct given;A n/a
B n/a
C n/a
D 45%
333-20-0

potassium thioacyanate

S-methylthietanium fluorosulphate

A

556-64-9

methyl thiocyanate

B

15394-33-9

methyl 4-(methylsulfanyl)butyl sulfide

C

86702-84-3

3-(methylthio)propyl thiocyanate

D

103707-78-4

1-(4-Methylsulfanyl-butylsulfanyl)-4-thiocyanato-butane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 1.5h;A 20%
B 7%
C 25%
D 18%
333-20-0

potassium thioacyanate

S-methylthianium fluorosulphate

A

1613-51-0

sulfure de pentamethylene

B

556-64-9

methyl thiocyanate

C

1-Methylsulfanyl-5-thiocyanato-pentane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 5h; Yields of byproduct given;A n/a
B n/a
C 4%

Methyl thiocyanate Chemical Properties

Molecule structure of Methyl thiocyanate (CAS NO.556-64-9) :

IUPAC Name: methyl thiocyanate 
Molecular Weight: 73.11692 g/mol
Molecular Formula: C2H3NS
Density: 1.061 g/cm3
Melting Point: -5 °C
Boiling Point: 123.1 °C at 760 mmHg   
Flash Point: 38.3 °C
Index of Refraction: 1.47
Molar Refractivity: 19.22 cm3
Molar Volume: 68.9 cm3
Polarizability: 7.62×10-24 cm3
Surface Tension: 37.6 dyne/cm 
Enthalpy of Vaporization: 36.1 kJ/mol 
log P (octanol-water): 0.730 
Water Solubility: 4.27E+04 mg/L 
Vapor Pressure: 12.1 mm Hg 
Henry's Law Constant: 4.38E-05 atm-m3/mole 
Atmospheric OH Rate Constant: 1.06E-12 cm3/molecule-sec
XLogP3-AA: 0.9
H-Bond Acceptor: 1
Exact Mass: 72.99862
MonoIsotopic Mass: 72.99862
Topological Polar Surface Area: 23.8
Heavy Atom Count: 4
Complexity: 41.2
Canonical SMILES: CSC#N
InChI: InChI=1S/C2H3NS/c1-4-2-3/h1H3
InChIKey: VYHVQEYOFIYNJP-UHFFFAOYSA-N
Storage Temp.: poison room
Merck: 6127 
EINECS: 209-134-6

Methyl thiocyanate Uses

 Methyl thiocyanate (CAS NO.556-64-9) is used as an agricultural insecticide, a fumigant and as a research chemical. No evidence of commercial production in the U.S. It is also used for the synthesis of pesticides, medicine and other fine chemicals.

Methyl thiocyanate Production

By the reaction of dimethyl sulfate and potassium cyanide sulfur derived. Be KSCN dissolved in water, dropwise dimethyl sulfate to control the temperature below 60 °C, about 3h dropping finish. And then continue stirring 2h. Place overnight. Taken by the water reservoir while the system was finished washing.

Methyl thiocyanate Toxicity Data With Reference

1.    

orl-rat LD50:60 mg/kg

    85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1036.
2.    

ipr-mus LD50:23 mg/kg

    PCBPBS    Pesticide Biochemistry and Physiology. 2 (1972),95.
3.    

ivn-mus LD50:18 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02864 .
4.    

orl-cat LDLo:8500 µg/kg

    MEIEDD    Merck Index. 11 (1989),963.
5.    

scu-rbt LDLo:20 mg/kg

    AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 150 (1930),257.

Methyl thiocyanate Consensus Reports

Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.

Methyl thiocyanate Safety Profile

Poison by ingestion, intravenous, and subcutaneous routes. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also THIOCYANATES.
Hazard Codes: ToxicT
Risk Statements: 23/24/25-10-36/37
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R10:Flammable. 
R36/37:Irritating to eyes and respiratory system.
Safety Statements: 28A-27-26-16-45-36/37/39 
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S27:Take off immediately all contaminated clothing. 
S16:Keep away from sources of ignition. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN1992
RTECS: XL1575000
HazardClass: 3
PackingGroup: III
Hazardous Substances Data: 556-64-9(Hazardous Substances Data)

Methyl thiocyanate Specification

 Methyl thiocyanate (CAS NO.556-64-9) is also called 4-03-00-00327 (Beilstein Handbook Reference) ; AI3-16178 ; BRN 1098357 ; HSDB 5691 ; Methane, thiocyanato- ; Methyl rhodanate ; Methyl sulfocyanate ; Methylrhodanid
 ; Methylthiokyanat ; NSC 9368 ; Thiocyanic acid, methyl ester . Methyl thiocyanate (CAS NO.556-64-9) is colorless liquid with an odor of onions and is very slightly soluble in water.  Methyl thiocyanate is a moderately toxic liquid, flammable. Violent, possibly explosive oxidation reaction when mixed with chlorates, nitrates, nitric acid, organic or inorganic peroxides, perchlorates. On contact with mineral acids or acid fumes deadly toxic hydrogen cyanide gas is produced. When heated to decomposition or on contact with mineral acids, Methyl thiocyanate emits highly toxic fumes of nitriles, oxides of sulfur and nitrogen. Methyl thiocyanate is highly toxic if ingested. It is a rapidly acting poison. Methyl thiocyanate (CAS NO.556-64-9) is Incompatible with nitric acid. Violent reactions have occurred when mixed with chlorates, nitrates, nitric acid, organic peroxides, peroxides, potassium chlorate, and sodium chlorate. Methyl thiocyanate is volatile. So the storage environment should be ventilate, low-temperature and dry. Keep  Methyl thiocyanate (CAS NO.556-64-9) separate from oxidants, acids, and food additives.

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