Conditions | Yield |
---|---|
With poly(vinylbenzyltriphenylphosphonium chloride) In benzene for 2h; Heating; | 88% |
dimethyl phosphoroisothiocyanatidite
dimethylglyoxal
A
methyl thiocyanate
B
2-methoxy-4,5-dimethyl-[1,3,2]dioxaphosphole 2-oxide
Conditions | Yield |
---|---|
In dichloromethane at 0℃; | A n/a B 80% |
3-methylsulfanyl-5,6-diphenyl-[1,4,2]dithiazine
A
methyl thiocyanate
B
2,3,5,6-tetraphenyl-1,4-dithia-2,5-cyclohexadiene
C
diphenyl acetylene
Conditions | Yield |
---|---|
In dichloromethane for 4h; Irradiation; | A n/a B 72% C n/a |
In dichloromethane for 8h; Quantum yield; Mechanism; Irradiation; |
6-methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
methyl iodide
methyl thiocyanate
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 1h; Ambient temperature; | 64% |
1-azido-2,2-dimethylcyclopropyl methylsulfide
A
methyl thiocyanate
C
2-(methylthio)-3,3-dimethyl-1-azetine
D
isobutene
Conditions | Yield |
---|---|
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; |
C19H18NS(1+)*CNS(1-)
methyl thiocyanate
Conditions | Yield |
---|---|
at 240℃; | 52% |
Conditions | Yield |
---|---|
In hexane at 20℃; for 72h; | 50% |
potassium thioacyanate
A
thiophene
B
methyl thiocyanate
C
erucin
D
4-(methylthio)butyl thiocyanate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 70℃; for 7h; Yields of byproduct given; | A n/a B n/a C n/a D 45% |
potassium thioacyanate
A
methyl thiocyanate
B
methyl 4-(methylsulfanyl)butyl sulfide
C
3-(methylthio)propyl thiocyanate
D
1-(4-Methylsulfanyl-butylsulfanyl)-4-thiocyanato-butane
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; for 1.5h; | A 20% B 7% C 25% D 18% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 5h; Yields of byproduct given; | A n/a B n/a C 4% |
Conditions | Yield |
---|---|
With diethyl ether at -5℃; |
methanol
thiocyanic acid
p-nitrophenyldimethylsulphonium methylsulphate
A
methyl thiocyanate
B
1-methylthio-4-nitro-benzene
Conditions | Yield |
---|---|
at 25 - 45℃; Rate constant; |
Conditions | Yield |
---|---|
at 100℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
at 60 - 70℃; |
bromocyane
[(methylthio)methyl]-benzene
A
methyl thiocyanate
B
benzyl bromide
Conditions | Yield |
---|---|
at 60 - 70℃; im Rohr; |
methoxycarbonylisothiocyanate
methyl thiocyanate
Conditions | Yield |
---|---|
beim Erhitzen; |
methyl thiocyanate
Conditions | Yield |
---|---|
at 110℃; |
A
methyl thiocyanate
B
S,S'-dimethyl-dithiodiisobiurea
C
Dimethyldisulphide
D
ethanedinitrile
Conditions | Yield |
---|---|
at 110℃; Zersetzen; Produkt 5: 5-Methylmercapto-3-imino-1.2.4-triazolidin; |
potassium thioacyanate
tertamethylammonium iodide
A
methyl thiocyanate
B
methyl thioisocyanate
C
trimethylamine
Conditions | Yield |
---|---|
at 210℃; |
Conditions | Yield |
---|---|
at 304 - 305℃; |
Conditions | Yield |
---|---|
With water |
3-methylsulfanyl-5,6,7,8-tetrahydro-benzo[1,4,2]dithiazine
A
methyl thiocyanate
B
diphenyl acetylene
Conditions | Yield |
---|---|
In dichloromethane for 8h; Quantum yield; Irradiation; |
Conditions | Yield |
---|---|
With potassium thioacyanate In dimethyl sulfoxide Product distribution; Mechanism; |
dimethyl-p-tolylsulfonium tetrafluoroborate
A
methyl thiocyanate
B
4-methylphenyl methylsulfide
Conditions | Yield |
---|---|
With cyclophane (1); HPLC buffer; potassium thioacyanate at 45.9℃; Rate constant; pD 9; without cyclophanes; |
dimethylphenyl sulfonium tetrafluoroborate
A
methyl thiocyanate
B
methyl-phenyl-thioether
Conditions | Yield |
---|---|
With cyclophane (1); HPLC buffer; potassium thioacyanate at 45.9℃; Rate constant; pD 9; without cyclophanes; |
methyl phosphorodiisothiocyanatidite
Phosphoric acid dimethyl ester 2,2,2-trichloro-ethyl ester
methyl thiocyanate
Conditions | Yield |
---|---|
Product distribution; |
Conditions | Yield |
---|---|
With cyclophane (1); HPLC buffer; potassium thioacyanate at 45.9℃; Rate constant; pD 9; without cyclophanes; |
Conditions | Yield |
---|---|
With cyclophane (1); HPLC buffer; potassium thioacyanate at 45.9℃; Rate constant; pD 9; without cyclophanes; |
methyl thiocyanate
ethyl 2-amino-6-cyanoindole-3-carboxylate
ethyl 5-cyano-2-(methylsulfanylimidoylamino)-1H-indole-3-carboxylate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 20 - 60℃; | 100% |
methyl thiocyanate
C13H21NO
2-cyclohexyl-4-(methylthio)-5,6,7,8-tetrahydroquinazoline
Conditions | Yield |
---|---|
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 23℃; Inert atmosphere; | 100% |
methyl thiocyanate
terephthaloyl chloride
2,2'-(1,4-Phenylen)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane at 0℃; for 1h; | 97% |
methyl thiocyanate
benzene-1,3-dicarbonyl dichloride
2,2'-(1,3-Phenylen)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature; | 97% |
methyl thiocyanate
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienenitrile
3-methyl-2-thiomethyl-5-(2',6',6'-trimethyl-1'-cyclohexen-1'-yl)-2,4-pentadienenitrile
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -85℃; | 97% |
methyl thiocyanate
1-(p-methoxyphenyl)-2-methylpropan-1-ol
Conditions | Yield |
---|---|
With sulfuric acid In toluene Ritter reaction; | 97% |
methyl thiocyanate
9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -85℃; | 96% |
methyl thiocyanate
1-[(1-chloro-1-methylethyl)azo]-2,4,6-trichlorobenzene
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at -60 - 23℃; | 95% |
methyl thiocyanate
potassium O,O-diisopropyl phoshorodithioate
O,O-diisopropyl S-methyl phosphorothioate
Conditions | Yield |
---|---|
at 90 - 100℃; for 2.5h; | 95% |
methyl thiocyanate
diisopropyl monothiophosphoric acid, sodium salt
O,O-diisopropyl S-methyl phosphorothioate
Conditions | Yield |
---|---|
at 90 - 100℃; for 2.5h; | 95% |
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane at 0℃; for 1h; | 95% |
methyl thiocyanate
O,O-diisopropyl hydrogen phosphorodithioate
diisopropoxythiophosphoryl isothiocyanate
Conditions | Yield |
---|---|
at 100℃; for 3h; | 95% |
methyl thiocyanate
O.O-Dipropyl-dithyophosphat
O,O-dipropyl phosphoroisothiocyanatidothioate
Conditions | Yield |
---|---|
at 100℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In chloroform for 0.25h; Reagent/catalyst; Ritter Amidation; Reflux; | 95% |
methyl thiocyanate
4-amino-5-methyl-2,4-dihydro-[1,2,4]triazole-3-thione
3-methyl-6-methylsulfanyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
Conditions | Yield |
---|---|
With PPA for 6h; boiling water bath; | 94% |
methyl thiocyanate
Methyl 3-aminothiophene-2-carboxylate
2-(methylthio)thieno[3,2-d]pyrimidin-4(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 90℃; for 24h; Sealed tube; | 94% |
methyl thiocyanate
dimethyl 2-(3-phenyl-3-butenyl)-2-(2-propynyl)malonate
Conditions | Yield |
---|---|
Stage #1: dimethyl 2-(3-phenyl-3-butenyl)-2-(2-propynyl)malonate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: methyl thiocyanate In tetrahydrofuran; hexane at -78 - 20℃; for 17h; | 93.4% |
methyl thiocyanate
gloutaric dichloride
2,2'-(1,3-Propandiyl)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature; | 93% |
methyl thiocyanate
potassium O,O-diethyldithiophosphate
O,O-diethyl S-methyl phosphorodithioate
Conditions | Yield |
---|---|
at 100 - 130℃; for 3h; | 93% |
methyl thiocyanate
N-(p-methoxyphenyl)benzamide
6-methoxy-4-(methylthio)-2-phenylquinazoline
Conditions | Yield |
---|---|
With 2-chloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at -78 - 140℃; for 0.35h; Inert atmosphere; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane at 0℃; for 1h; | 92% |
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2.5h; | 92% |
methyl thiocyanate
nickel diacetate
methyl 2-(5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)acetate
Conditions | Yield |
---|---|
In methanol for 3h; Reflux; | 92% |
methyl thiocyanate
5-methylsulfanyl-1H-tetrazole
Conditions | Yield |
---|---|
With sodium azide; titanium(IV) dioxide In N,N-dimethyl-formamide at 110℃; for 20h; regiospecific reaction; | 91% |
Stage #1: methyl thiocyanate With sodium azide In water at 20℃; for 0.5h; Stage #2: With hydrogen bromide In water pH=1-2; | 88% |
With ammonium azide; N,N-dimethyl-formamide; lithium chloride | |
With azide(1-) |
methyl thiocyanate
fumaryl dichloride
2,2'-(1,2-Ethendiyl)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 0℃; | A 4% B 91% |
methyl thiocyanate
N-(But-3-ynyl)-N-(4-methylpenta-2,3-dienyl)-4-methylbenzenesulfonamide
N-(4-Methythiobut-3-ynyl)-N-(4-methylpenta-2,3-dienyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-(But-3-ynyl)-N-(4-methylpenta-2,3-dienyl)-4-methylbenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Metallation; Stage #2: methyl thiocyanate In tetrahydrofuran; hexane at -78℃; for 0.5h; Substitution; | 91% |
methyl thiocyanate
2-Methyl-1-phenyl-2-propanol
1-methylsulfanyl-3,3-dimethyl-3,4-dihydroisoquinoline
Conditions | Yield |
---|---|
With sulfuric acid | 90% |
methyl thiocyanate
Adipic acid dichloride
2,2'-(1,4-Butandiyl)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)
Conditions | Yield |
---|---|
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature; | 90% |
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 (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.
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.
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. |
Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.
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: T
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 (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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