19009-45-1

Basic information

• Product Name: N-METHYL-N-PHENYLTHIOCARBAMOYL CHLORIDE
• Synonyms: N-METHYL-N-PHENYLTHIOCARBAMOYL CHLORIDE
• CAS NO: 19009-45-1
• Molecular Formula: C₈H₈ClNS
• Molecular Weight: 185.67
• Mol File: 19009-45-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 31 °C
• Boiling Point: 245.5±23.0 °C(Predicted)
• Appearance: /
• Density: 1.291±0.06 g/cm3(Predicted)
• PKA: -1.43±0.50(Predicted)
• CAS DataBase Reference: N-METHYL-N-PHENYLTHIOCARBAMOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-N-PHENYLTHIOCARBAMOYL CHLORIDE(19009-45-1)
• EPA Substance Registry System: N-METHYL-N-PHENYLTHIOCARBAMOYL CHLORIDE(19009-45-1)

Safety Data

• Hazardous Substances Data: 19009-45-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 36, p. 539, 1980 DOI: 10.1016/0040-4020(80)80032-9

Upstream product

• 463-71-8 thiophosgene 
• 100-61-8 N-methylaniline 
• 67-66-3 chloroform 
• 2739-12-0 N-methylaniline hydrochloride 
• 7732-18-5 water 
• 17890-34-5 N-(trimethylsilyl)phenyl(methyl)amine 
• 36325-39-0 N-phenylthioacetamide 

Downstream Products

• 87463-11-4 O-methyl N-methyl-N-phenylcarbamothioate 
• 5076-39-1 N,N'-Dimethyl-N,N'-diphenylthioharnstoff 
• 38930-57-3 C₉H₁₁NO₂S₂ 
• 38930-63-1 C₁₄H₁₃NO₂S₂ 
• 38930-59-5 C₁₈H₂₃NO₂S₂ 
• 34551-25-2 methyl-phenyl-[1,2,3,4]thiatriazol-5-yl-amine 
• 100449-45-4 Tetrahydro-N-methyl-N-phenyl-2-thioxo-2H-1,3-thiazin-3-carboxamid 
• 100449-46-5 Tetrahydro-N-methyl-N-phenyl-2-oxo-2H-1,3-thiazin-3-thiocarboxamid 
• 100449-39-6 Tetrahydro-N-methyl-N-phenyl-2-thioxo-2H-1,3-thiazin-3-thiocarboxamid 
• 21076-09-5 2-methyl-4-phenyl-3-thiosemicarbazide 
• 219646-02-3 C₁₇H₁₄N₂O 
• 1558811-66-7 S-2-phenylbut-3-en-2-yl methylcarbamothioate 
• 1415351-67-5 S-but-3-en-2-yl methyl(phenyl)carbamothioate 
• 1415351-59-5 (E)-O-but-2-enyl methyl(phenyl)carbamothioate 

Relevant articles and documents

Tertiary thiols from allylic thiocarbamates by tandem enantioselective [3,3]-sigmatropic rearrangement and stereospecific arylation

The synthesis of tertiary thiols in enantiomerically enriched form is accomplished by lithiation of enantiomerically enriched N-aryl allylic thiocarbamates. Formation of an allyllithium derivative promotes intramolecular N to C aryl migration to the posit

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.

Novel [2-(4-piperidinyl)ethyl](thio)ureas: Synthesis and antiacetylcholinesterase activity

A series of 1-ar(o)yl-3-[2-(1-benzyl-4-piperidinyl)ethyl](thio)urea derivatives was synthesized and evaluated for antiacetylcholinesterase activity. Most aroyl(thio)urea derivatives showed potent inhibitory activity in the sub-micromolar range. A comparable potency was obtained with the aryl(thio)urea analogues by replacing the phenyl with a 2-pyridyl group. The substituted guanidine variations proved to be almost inactive whereas the nitroethylene analogues appeared to be quite efficient. These results were interpreted in terms of the preferential cis-trans conformation of the aroyl(thio)urea and 2-pyridyl(thio)urea moieties involving the existence of hydrogen bonding. In vivo experiments showed that compound 7m had maximal antiamnestic activity at 0.03 mg/kg with a therapeutic ratio greater than 1000, while cholinergic side effects were only seen at doses 100-fold the maximally effective antiamnestic dose. Compound 7m represents a potentially interesting antidementia agent.