2131-64-8

Basic information

• Product Name: 4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE
• Synonyms: N,N-Dimethyl-4-isothiocyanatoaniline;4-Isothiocyanato-N,N-dimethylaniline;Benzenamine, 4-isothiocyanato-N,N-dimethyl-;Isothiocyanic acid, p-(dimethylamino)phenyl ester;isothiocyanicacid,p-dimethylaminophenylester;p-(N,N-Dimethylamino)phenyl isothiocyanate;Phenylisothiocyanate, 4-dimethylamino;TL 1106
• CAS NO: 2131-64-8
• Molecular Formula: C₉H₁₀N₂S
• Molecular Weight: 178.25
• EINECS: 218-360-4
• Mol File: 2131-64-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 69 °C
• Boiling Point: 152 °C
• Flash Point: 152°C/6mm
• Appearance: /
• Density: 1.1355 (rough estimate)
• Vapor Pressure: 0.00108mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Keep Cold
• PKA: 3.88±0.12(Predicted)
• Water Solubility: 13.37mg/L(25 oC)
• Sensitive: Moisture Sensitive
• BRN: 388270
• CAS DataBase Reference: 4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE(2131-64-8)
• EPA Substance Registry System: 4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE(2131-64-8)

Safety Data

• Hazard Codes: Xi,T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45
• RIDADR: 2811
• RTECS: NX8500000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 2131-64-8(Hazardous Substances Data)

Usage

General Description

4-(dimethylamino)phenyl isothiocyanate is a chemical compound with the formula C10H11N3S. It is a derivative of isothiocyanate, which is known for its diverse biological activities, including anti-cancer, anti-inflammatory, and anti-microbial properties. 4-(dimethylamino)phenyl isothiocyanate is commonly used in organic synthesis to introduce isothiocyanate functional groups into various molecules. It also has potential applications in medicinal chemistry and drug development due to its ability to modify the properties of organic compounds. Additionally, it is known to exhibit fluorescence properties and is used as a fluorescent label in biochemical and immunological assays.

InChI:InChI=1/C9H10N2S/c1-11(2)9-5-3-8(4-6-9)10-7-12/h3-6H,1-2H3

Upstream product

• 13991-81-6 N,N'-bis-(4-dimethylamino-phenyl)-thiourea 
• 103-72-0 phenyl isothiocyanate 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 57-06-7 N-allyl isothiocyanate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 29647-71-0 o-phenyl [4-(dimethylamino)phenyl]carbamothioate 
• 1005-56-7 phenylcarbonochloridothioate 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 75-15-0 carbon disulfide 
• 2052-46-2 N,N-dimethyl-p-phenylenediamine hydrochloride 
• 463-71-8 thiophosgene 
• 75-44-5 phosgene 
• 200337-28-6 N,N-Dimethyl-N'-[1,3]thiazepan-(2Z)-ylidene-benzene-1,4-diamine 

Downstream Products

• 76609-49-9 4-(4'-(dimethylamino)phenyl)-3-thiosemicarbazide 
• 22283-43-8 1-(4-Dimethylaminophenyl)-thioharnstoff 
• 39123-63-2 3-(4-dimethylamino-phenyl)-2-thioxo-imidazolidin-4-one 
• 1383478-82-7 C₂₇H₃₁N₃OS 
• 148962-11-2 5-amino-4-cyano-3-(4-dimethylamino-phenylamino)-pyrazole 
• 196504-89-9 2-[(4-Dimethylamino-phenylamino)-methylsulfanyl-methylene]-malononitrile 
• 56610-80-1 1-(4-dimethylamino-phenyl)-1,4-dihydro-tetrazole-5-thione 
• 31979-44-9 N-(4-ethoxy-phenyl)-N'-(4-dimethylamino-phenyl)-thiourea 
• 15863-28-2 N-cyclohexyl-N'-p-dimethylaminophenyl-thiourea 
• 102158-43-0 N-(4-dimethylamino-phenyl)-N'-(4-[2]pyridyl-phenyl)-thiourea 
• 109437-39-0 piperidine-1-carbothioic acid-(4-dimethylamino-anilide) 

Relevant articles and documents

Fluorescence detection of iodide anion using a donor-acceptor (D-A) thiourea derivative

1-(4-acetyl-phenyl)-3-(4-N,N-dimethylaminophenyl)-thiourea is synthesized and characterized by NMR, IR, MS and elemental analysis. The probe exhibits the "turn-off" fluorescence response to iodide anion in THF/H2O (v/v = 9/1) pH = 7.4 Tris-HCl buffer solution, which is attributed to the intramolecular charge transfer (ICT). It is found that the probe has a detection limit of 0.336 μM. Such interesting results could be further supported by quantum chemical calculation, UV and 1H NMR titration. Moreover, the probe is applied to determine iodide in powdered milk and urine samples. This experiment shows a good agreement between added and detected concentration of the iodide in real samples.

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Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

Alkali-free green synthetic isothiocyanate method

The invention discloses an alkali-free green synthetic method for isothiocyanate, and relates to the field of organic chemical industry. The method includes the steps: (1) adding solvents into carbon sulfide reagents and primary amine serving as raw materials, performing organic reaction at the temperature of 100-150 DEG C for 10-30 hours; (2) cooling and spin-drying the raw materials after reaction, adding dichloromethane, extracting and separating organic phases by 10% of dilute hydrochloride acid, washing the organic phases, combining the organic phases into an organic layer, washing the organic layer with saturated salt water, drying the organic layer by anhydrous Na2SO4, and performing column chromatographic separation to obtain the isothiocyanate. The molar ratio of the carbon sulfide reagents to the primary amine is 1:1.2-3. Compared with a preparation method in the prior art, the method has the advantages that only heating reaction needs to be performed in the solvents, additional alkali is omitted, and the method is greener and more environmentally friendly and has better application values.