4044-65-9 Usage
Description
1,4-PHENYLENE DIISOTHIOCYANATE is an organic compound with the chemical formula C8H4N2S2. It is a diisothiocyanate derivative of benzene, featuring two isothiocyanate groups attached to the 1,4-positions of the benzene ring. 1,4-PHENYLENE DIISOTHIOCYANATE is known for its reactivity and is commonly used in various applications due to its unique chemical properties.
Uses
Used in Pharmaceutical Industry:
1,4-PHENYLENE DIISOTHIOCYANATE is used as an anthelmintic agent for the treatment of hookworm infections. It works by paralyzing the worms and causing their expulsion from the body.
Used in Chemical Synthesis:
1,4-PHENYLENE DIISOTHIOCYANATE is used as a reagent in solid-phase sequencing, a technique employed in the determination of the nucleotide sequence of DNA or RNA molecules. Its reactive isothiocyanate groups facilitate the attachment of nucleotides to the solid support during the sequencing process.
Used in Chemical Research:
1,4-PHENYLENE DIISOTHIOCYANATE is utilized in various chemical research applications due to its reactivity and ability to form stable conjugates with other molecules. This makes it a valuable tool in the development of new compounds and materials.
Reactivity Profile
1,4-PHENYLENE DIISOTHIOCYANATE reacts readily with amines [Noller]. These reactions may generate significant amounts of heat . Emits very toxic fumes of nitrogen oxides and sulfur oxides when heated to decomposition [EPA, 1998].
Health Hazard
1,4-PHENYLENE DIISOTHIOCYANATE is highly toxic if ingested. It is a central nervous system and gastrointestinal toxin in humans.
Fire Hazard
When heated to decomposition, 1,4-PHENYLENE DIISOTHIOCYANATE emits very toxic fumes of nitrogen oxides and sulfur oxides.
Safety Profile
Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: hallucinations, nausea. When heated to decomposition it emits very toxic fumes of NOx,CN,and SOx.See also THIOCYANATES
Potential Exposure
Those engaged in the manufacture,
formulation and application of this anthelmintic
compound.
Incompatibilities: In general, keep away from strong oxidizers,
moisture, strong acids, strong bases. This is a thiocyanate
compound. Violent reactions may occur upon contact
with chlorates (potassium chlorate, sodium chlorate),
nitrates, nitric acid; organic peroxides.
Shipping
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1—Poisonous materials, Technical
Name Required.
Purification Methods
Purify bitoscanate by recrystallisation from AcOH, pet ether (b 40-60o), Me2CO or aqueous Me2CO. [van der Kerk et al. Recl Trav Chim Pays-Bas 74 1262 1955, Leiber & Slutkin J Org Chem 27 2214 1962, Beilstein 13 IV 174.]
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides.
Check Digit Verification of cas no
The CAS Registry Mumber 4044-65-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,4 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4044-65:
(6*4)+(5*0)+(4*4)+(3*4)+(2*6)+(1*5)=69
69 % 10 = 9
So 4044-65-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H4N2S2/c11-5-9-7-1-2-8(4-3-7)10-6-12/h1-4H
4044-65-9Relevant articles and documents
NSCLC structure-activity relationship (sar) study of diisothiocyanates for antiproliferative activity on A549 Human non-small cell lung carcinoma (NSCLC)
Chatwichien, Jaruwan,Prachavna, Buntarika,Suntivich, Rinrada,Kumphune, Sarawut
, p. 569 - 574 (2019/08/07)
Isothiocyanate functional group (-N=C=S) is widely accepted as an important moiety for anti-cancer effects of naturally occurring isothiocyanate compounds (ITCs). Herein, a series of diisothiocyanate (diITCs) derivatives were synthesized and evaluated in antiproliferative assays on A549 human non-small cell lung cancer and IMR90 human foetal lung cell lines for structure-activity relationship (SAR) and cancer cell selectivity studies. Results showed that aliphatic and benzylic diITCs were more cytotoxic to A549 cells than natural ITCs; benzyl isothiocyanate (BITC) and phenyl isothiocyanate (PITC), and a currently available anticancer drug; etoposide. Aromatic diITCs were not as active. Notably, most of the diITCs reported in this work were significantly more selective than etoposide to inhibit proliferation of the cancer cells (A549) over the normal cells (IMR90). This study demonstrated a guideline to modify chemical structures of diITCs for anti-NSCLC agents.
New insights into dihydrogenphosphate recognition with dirhenium(i) tricarbonyl complexes bridged by a thiourea moiety
Blackburn, Anna L.,Baker, Naomi C. A.,Fletcher, Nicholas C.
, p. 18442 - 18452 (2014/05/20)
Three thiourea bridged 2,2′-bipyridine ligands bearing either a single thiourea group (L1), or two units separated by either a para (L2) or meta-substituted (L3) aromatic spacer, along with the corresponding bis(fac-tricarbonylrhenium(i)) complexes are reported. The three ligands all show the anticipated binding to acetate. However 1H NMR titrations reveal an unusual cooperative binding to, and selectivity for, two dihydrogenphosphate ions. The rhenium(i) complexes similarly demonstrate unusual sigmoidal titration curves, and in the case of {Re(CO)3Br} 2(μ-L1) a surprisingly strong interaction to two anions. These were further exemplified in the emissive behaviour leading to the conclusion that there is an unusual interaction with dihydrogenphosphate, giving an initial increase in the emission, followed by a decrease and a blue shift in wavelength possibly as a result of partial deprotonation. It appears that dihydrogenphosphate binds cooperatively, with the addition of a second anion enhancing the interaction of the first, probably by proton transfer; this could explain the remarkable selectivity for phosphate seen with many reported anion receptors.
Synthesis and antifungal activities of phenylenedithioureas
Phuong, Truong,Khac-Minh, Thai,Van Ha, Nguyen Thi,Ngoc Phuong, Huynh Thi
, p. 653 - 656 (2007/10/03)
A total of 20 new phenylenedithiourea derivatives was synthesized by reaction of phenylenediisothiocyanates with aromatic amines as aminobenzoic, aminosalicylic acid and their derivatives. Their chemical structures were confirmed by elemental analysis, IR spectrometry and 1H NMR. The compounds were screened for in vitro antifungal, antibacterial activities and some of them have strong antifungal activities comparable to the activity observed for ketoconazole.