4044-65-9

Basic information

• Product Name: 1,4-PHENYLENE DIISOTHIOCYANATE
• Synonyms: 1,4-diisothiocyanato-benzen;1,4-diisothiocyanatobenzene[qr];1,4-phenylenedi-isothiocyanicaci;16842(uspddn)[qr];ai3-28258[qr];Benzene, 1,4-diisothiocyanato-;benzene,1,4-diisothiocyanato-[qr];Biscomate
• CAS NO: 4044-65-9
• Molecular Formula: C₈H₄N₂S₂
• Molecular Weight: 192.26
• EINECS: 223-741-3
• Product Categories: JONIT;reagent
• Mol File: 4044-65-9.mol

Chemical Properties

• Melting Point: 129-131 °C(lit.)
• Boiling Point: 339.4°C at 760 mmHg
• Flash Point: 167.2°C
• Appearance: white/powder
• Density: 1.3675 (rough estimate)
• Vapor Pressure: 0.000182mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: −20°C
• Solubility: chloroform: clear
• Water Solubility: Hydrolyzes in water.
• Sensitive: Moisture Sensitive
• Merck: 14,1308
• BRN: 2414340
• CAS DataBase Reference: 1,4-PHENYLENE DIISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-PHENYLENE DIISOTHIOCYANATE(4044-65-9)
• EPA Substance Registry System: 1,4-PHENYLENE DIISOTHIOCYANATE(4044-65-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-42
• Safety Statements: 22-26-36/37
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NX9150000
• F: 10-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 4044-65-9(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C8H4N2S2/c11-5-9-7-1-2-8(4-3-7)10-6-12/h1-4H

Synthetic route

N,N'-(1,4-Phenylene)bis(methyldithiocarbamate) (19972-69-1) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With ammonium hydroxide; mercury(II) oxide In N,N-dimethyl-formamide at 40℃; for 4h; also with other bis(dithiocarbamates) to form the corresponding p-arylenediisothiocyanates;	83%
With ammonium hydroxide; mercury(II) oxide In N,N-dimethyl-formamide at 40℃; for 4h;	83%

carbon disulfide (75-15-0) + 1,4-phenylenediamine (106-50-3) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
Stage #1: carbon disulfide; 1,4-phenylenediamine With triethylamine In tetrahydrofuran at 0 - 20℃; for 16h; Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 16h;	72%
Stage #1: carbon disulfide; 1,4-phenylenediamine With ammonium hydroxide at 0 - 5℃; Stage #2: With lead(II) nitrate
With ammonium hydroxide und Eintragen des Reaktionsloesung in wss.Eisen(III)-chlorid-Loesung;

carbon disulfide (75-15-0) + 4-nitro-aniline (100-01-6) → 1 ,4-phenylenediisothiocyanate (4044-65-9) + p-nitrophenyl isothiocyanate (2131-61-5)

Conditions	Yield
Stage #1: carbon disulfide; 4-nitro-aniline With potassium carbonate In water at 40℃; for 72h; Inert atmosphere; Stage #2: With 1,3,5-trichloro-2,4,6-triazine In dichloromethane; water; N,N-dimethyl-formamide at 0℃; Inert atmosphere; Stage #3: With sodium hydroxide In dichloromethane; water pH=11; Inert atmosphere;	A 50% B 13%

Langlois reagent (2926-29-6) + 1,4-phenylenediamine (106-50-3) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With copper(l) iodide; phosphonic acid diethyl ester In toluene at 110℃; for 16h; Schlenk technique; Green chemistry;	32%

thiophosgene (463-71-8) + chloroform (67-66-3) + 1,4-phenylenediamine (106-50-3) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

thiophosgene (463-71-8) + 1,4-phenylenediamine (106-50-3) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With chloroform
In acetone Ambient temperature;

thiophosgene (463-71-8) + p-phenylenediamine hydrochloride (540-24-9) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With sodium hydroxide

thiophosgene (463-71-8) + N-(p-aminophenyl)-N',N"-dicarbomethoxyguanidine (107167-58-8) → dimethyl N,N'-carbonylbis(carbamate) (17616-33-0) + 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
In 1,4-dioxane; water 1) 5 deg C, 2) r.t., overnight;

thiourea (17356-08-0) + C8H5ClN2OS → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With triethylamine In tetrahydrofuran Ambient temperature; Yield given;

1,4-phenylenediamine (106-50-3) + CS2 → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With ammonium hydroxide Behandeln des Reaktionsprodukts mit Natrium-chloracetat und ZnCl2 in H2O bei pH 7;

acetic anhydride (108-24-7) + polymer(ic) p-phenylenethiourea → 1 ,4-phenylenediisothiocyanate (4044-65-9)

4-Isothiocyanato-benzaldehyde oxime → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-chlorosuccinimide / dimethylformamide; H2O / 0.5 h / Ambient temperature 2: triethylamine / tetrahydrofuran / Ambient temperature View Scheme

1,4-phenylenediamine (106-50-3) + KHCO3 → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: p-toluenesulphonic acid / methanol / 3 h / Heating 2: dioxane; H2O / 1) 5 deg C, 2) r.t., overnight View Scheme

1,4-phenylenediamine (106-50-3) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 0.5 h / 20 °C 2: di-tert-butyl dicarbonate; dmap / 20 °C / Cooling with ice View Scheme

1,4-dithiocarbamatobenzene (46350-14-5) → 1 ,4-phenylenediisothiocyanate (4044-65-9)

Conditions	Yield
With dmap; di-tert-butyl dicarbonate at 20℃; Cooling with ice;

1 ,4-phenylenediisothiocyanate (4044-65-9) + dimethyl amine (124-40-3) → 3-[4-(3,3-dimethyl-thioureido)-phenyl]-1,1-dimethyl-thiourea (16349-56-7)

Conditions	Yield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;	100%

1 ,4-phenylenediisothiocyanate (4044-65-9) + methylamine (74-89-5) → 1-methyl-3-[4-(3-methyl-thioureido)-phenyl]-thiourea (16349-55-6)

Conditions	Yield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;	100%

(S)-valinol (2026-48-4) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → C18H30N4O2S2 (1355364-01-0)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.583333h; Inert atmosphere;	98%

(η3-allyl)Pd(N3)(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → [(η3-allyl)Pd{SCN4-}(3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)]2(μ-C6H4)

Conditions	Yield
In tetrahydrofuran for 3h;	98%

(η3-2-methylallyl)Pd(N3)(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → [(η3-2-methylallyl)Pd{SCN4-}(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)]2(μ-C6H4)

Conditions	Yield
In tetrahydrofuran for 3h;	97%

bis(trichloromethyl) carbonate + 1 ,4-phenylenediisothiocyanate (4044-65-9) → C10H4F8N2O2

Conditions	Yield
With silver fluoride In acetonitrile at 20℃;	96%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-methoxy-aniline (104-94-9) → N1,N2-bis[N-(4-methoxyphenyl)thiocarbamoyl]-1,4-diaminobenzene

Conditions	Yield
With triethylamine In 1,4-dioxane for 6h; Heating;	95%
at 60℃; for 0.05h; Neat (no solvent); Microwave irradiation;	92%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-Ethoxyaniline (156-43-4) → 1,4-phenylene-bis[3-(4'-ethoxylphenyl)thiourea]

Conditions	Yield
With triethylamine In 1,4-dioxane for 6h; Heating;	95%
at 60℃; for 0.0333333h; Neat (no solvent); Microwave irradiation;	91%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-amino-o-xylene (95-64-7) → 1,4-phenylene-bis[3-(3',4'-dimethylphenyl)thiourea] (479054-96-1)

Conditions	Yield
at 60℃; for 0.0166667h; Neat (no solvent); Microwave irradiation;	94%

1 ,4-phenylenediisothiocyanate (4044-65-9) + p-toluidine (106-49-0) → 1,4-phenylene-bis[3-(4'-methylphenyl)thiourea]

Conditions	Yield
at 60℃; for 0.0333333h; Neat (no solvent); Microwave irradiation;	93%
With triethylamine In 1,4-dioxane for 6h; Heating;	90%

1 ,4-phenylenediisothiocyanate (4044-65-9) + p-aminoiodobenzene (540-37-4) → 1,4-phenylene-bis[3-(4'-iodophenyl)thiourea] (77006-86-1)

Conditions	Yield
at 60℃; for 0.0333333h; Neat (no solvent); Microwave irradiation;	93%

methyl 2-chloroacetoacetate (4755-81-1) + 1 ,4-phenylenediisothiocyanate (4044-65-9) + para-methylbenzylamine (104-84-7) → dimethyl 3,3'-(1,4-phenylene)-bis-[2-(4-methylbenzylimino)-4-methyl-2,3-dihydrothiazole-5-carboxylate]

Conditions	Yield
Stage #1: 1 ,4-phenylenediisothiocyanate; para-methylbenzylamine at 20℃; for 1h; Green chemistry; Stage #2: methyl 2-chloroacetoacetate at 20℃; Green chemistry; regioselective reaction;	93%

methanol (67-56-1) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → N,N'-(1,4-Phenylen)bis(methylthionocarbamat) (19972-59-9)

Conditions	Yield
With sodium hydroxide	93%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 3-methyl-2-methylene-1,3-thiazolidine (734510-89-5) → 2-(3-methyl-thiazolidin-2-ylidene)-N-{4-[2-(3-methyl-thiazolidin-2-ylidene)-thioacetylamino]-phenyl}-thioacetamide

Conditions	Yield
In tetrahydrofuran at 20 - 25℃;	92%

1 ,4-phenylenediisothiocyanate (4044-65-9) + o-toluidine (95-53-4) → 1,4-phenylene-bis[3-(2'-methylphenyl)thiourea] (150660-38-1)

Conditions	Yield
at 60℃; for 0.0333333h; Neat (no solvent); Microwave irradiation;	92%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-bromo-aniline (106-40-1) → 1,4-phenylene-bis[3-(4'-bromophenyl)thiourea] (77006-85-0)

Conditions	Yield
at 60℃; for 0.05h; Neat (no solvent); Microwave irradiation;	92%

1 ,4-phenylenediisothiocyanate (4044-65-9) + α-bromoacetophenone (70-11-1) + 4-Ethoxyaniline (156-43-4) → 2,2′-(1,4-phenylene)-bis-[3-(4'-ethoxyphenyl)-2-imino-4-phenyl-3H-thiazole]

Conditions	Yield
With polyvinyl pyridine (PVP) In ethanol at 20℃; for 18h; regioselective reaction;	92%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 1,3,5-tris(4-aminophenyl)benzene (118727-34-7) → 1,3,5-tris[4-(1,3-diphenylthiourea)]benzene

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	92%

hexane (110-54-3) + [(C5H5)Ru(P(C6H5)3)2(SSi(CH(CH3)2)3)] (266342-85-2) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → 1,4-[CpRu(PPh3)S2CN(Si(i)Pr3)]2C6H4*1.6(hexane)

Conditions	Yield
In tetrahydrofuran; acetone byproducts: PPh3; (N2 or Ar); mixed at room temp., stirred overnight; solvent-removed (vac.), residue dissolved in CH2Cl2, filtered (Celite), concd. (vac.), layered with hexane, crystd. at room temp., filtered, dried; elem. anal.;	91%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-chloro-aniline (106-47-8) → 1,4-phenylene-bis[3-(4'-chlorophenyl)thiourea] (77006-84-9)

Conditions	Yield
at 60℃; for 0.0666667h; Neat (no solvent); Microwave irradiation;	91%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-methoxy-benzylamine (2393-23-9) + ethyl 2-chloro-3-oxo-butyrate (609-15-4) → diethyl 3,3'-(1,4-phenylene)-bis-[2-(4-methoxybenzylimino)-4-methyl-2,3-dihydrothiazole-5-carboxylate]

Conditions	Yield
Stage #1: 1 ,4-phenylenediisothiocyanate; 4-methoxy-benzylamine at 20℃; for 1h; Green chemistry; Stage #2: ethyl 2-chloro-3-oxo-butyrate at 20℃; Green chemistry; regioselective reaction;	91%

1 ,4-phenylenediisothiocyanate (4044-65-9) + N-[2-(2-Amino-acetylamino)-ethyl]-2-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxy]-acetamide; compound with trifluoro-acetic acid → 2-[4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-phenoxy]-N-(2-{2-[3-(4-isothiocyanato-phenyl)-thioureido]-acetylamino}-ethyl)-acetamide

Conditions	Yield
In N,N-dimethyl-formamide	90%

1 ,4-phenylenediisothiocyanate (4044-65-9) + potassium cyanide (151-50-8) → 1,4-bis(cyanothioformamido)benzene (625855-55-2)

Conditions	Yield
at 20℃;	90%

3,4,4-trimethyl-2-methyleneoxazolidine (159064-15-0) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → 2-(3,4,4-trimethyl-oxazolidin-2-ylidene)-N-{4-[2-(3,4,4-trimethyl-oxazolidin-2-ylidene)-thioacetylamino]-phenyl}-thioacetamide

Conditions	Yield
In tetrahydrofuran at 20 - 25℃;	90%

[(η5-trimethylsilylcyclopentadienyl)2Nb(III)(CO)(diphenylphosphanido)] (880870-87-1) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → [(η5-C5H4SiMe3)2(CO)niobium(III)]2(μ-(κ1-S-1,4-SC(diphenylphosphanyl)N)2(C6H4))

Conditions	Yield
In toluene Nb complex treated with 0.5 equiv. of Ph(NCS)2 in dry toluene at room temp. for 15 min; filtered, washed (dry hexane) at 0°C, elem. anal.;	90%

(η5-C5H4SiMe3)2(diphenylphosphanyl)niobium(II)(CNXylyl) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → [(η5-C5H4SiMe3)2(CNXylyl)niobium(III)]2(μ-(κ1-S-1,4-SC(diphenylphosphanyl)N)2(C6H4))

Conditions	Yield
In toluene Nb complex treated with 0.5 equiv. of Ph(NCS)2 in dry toluene at room temp. for 30 min; filtered, washed (dry hexane) at 0°C, elem. anal.;	90%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 2-Chloroaniline (95-51-2) → 1,4-phenylene-bis[3-(2'-chlorophenyl)thiourea] (105169-81-1)

Conditions	Yield
at 60℃; for 0.05h; Neat (no solvent); Microwave irradiation;	90%

1,2-distearoyl-sn-glycero-3-phosphoethanolamine (1069-79-0) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → C49H86N3O8PS2

Conditions	Yield
With triethylamine In methanol; chloroform for 5h;	90%

N-(Rhodamine-B) lactam-hydrazine (188944-67-4) + 1 ,4-phenylenediisothiocyanate (4044-65-9) → C36H36N6O2S2 (1033581-68-8)

Conditions	Yield
In tetrahydrofuran at 20℃; for 5h;	89%

1 ,4-phenylenediisothiocyanate (4044-65-9) + 4-fluoroaniline (371-40-4) → 1,4-phenylene-bis[3-(4'-fluorophenyl)thiourea] (349640-45-5)

Conditions	Yield
at 60℃; for 0.133333h; Neat (no solvent); Microwave irradiation;	89%

Upstream product

• 75-15-0 carbon disulfide 
• 106-50-3 1,4-phenylenediamine 
• 463-71-8 thiophosgene 
• 67-66-3 chloroform 
• 540-24-9 p-phenylenediamine hydrochloride 
• 107167-58-8 N-(p-aminophenyl)-N',N-dicarbomethoxyguanidine 
• 19972-69-1 N,N'-(1,4-Phenylene)bis(methyldithiocarbamate) 
• 17356-08-0 thiourea 
• 108-24-7 acetic anhydride 
• 100-01-6 4-nitro-aniline 
• 2926-29-6 Langlois reagent 
• 46350-14-5 1,4-dithiocarbamatobenzene 

Downstream Products

• 1519-70-6 N,N'-bis(thiocarbamoyl)-1,4-phenylenediamine 
• 10374-64-8 N,N'-p-phenylene-bis-thioacetamide 
• 111102-50-2 1,4-bis-(4-methoxy-thiobenzoylamino)-benzene 
• 16349-61-4 3,3'-dipropyl-1,1'-p-phenylene-bis-thiourea 
• 16349-66-9 1,4-Bis-benzol 
• 16349-63-6 1,4-Bis-(N',N'-diheptlthioureido)benzol 
• 21557-43-7 (4-m-Tolylsulfanylthiocarbonylamino-phenyl)-dithiocarbamic acid m-tolyl ester 
• 1986-09-0 N,N'-<1,4>Phenylen-bis-(S-chlor-isothiocarbamoylchlorid) 
• 1728-67-2 benzene-1,4-dithiosemicarbazide 
• 21557-41-5 (4-Phenylsulfanylthiocarbonylamino-phenyl)-dithiocarbamic acid phenyl ester 
• 16349-56-7 3-[4-(3,3-dimethyl-thioureido)-phenyl]-1,1-dimethyl-thiourea 
• 16349-62-5 3,3'-diisopropyl-1,1'-p-phenylene-bis-thiourea 
• 16349-65-8 3,3'-bis-(2-diethylamino-ethyl)-1,1'-p-phenylene-bis-thiourea 
• 21557-42-6 (4-o-Tolylsulfanylthiocarbonylamino-phenyl)-dithiocarbamic acid o-tolyl ester 

Relevant articles and documents

NSCLC structure-activity relationship (sar) study of diisothiocyanates for antiproliferative activity on A549 Human non-small cell lung carcinoma (NSCLC)

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.

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

New insights into dihydrogenphosphate recognition with dirhenium(i) tricarbonyl complexes bridged by a thiourea moiety

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.

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

A general and facile one-pot protocol for the preparation of a broad range of alkyl and aryl isothiocyanates has been developed from their corresponding primary amines under aqueous conditions. This synthetic process involves an in situ generation of a dithiocarbamate salt from the amine substrate by reacting with CS2 followed by elimination to form the isothiocyanate product with cyanuric acid as the desulfurylation reagent. The choice of solvent is of decisive importance for the successful formation of the dithiocarbamate salt particularly for highly electron-deficient substrates. This novel and economical method is suitable for scale-up activities.

Synthesis and antifungal activities of phenylenedithioureas

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.

A facile one-pot preparation of isothiocyanates from aldoximes

Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.

A FACILE NEW METHOD FOR THE PREPARATION OF AROMATIC DIISOTHIOCYANATES

In the present communication we describe a new facile method for the preparation of aromatic diisothiocyanates.The main advantage of this method is a one-pot procedure from bis(dithiocarbamates) compared with the methods described in the literature.

Fragmentation of N-aryl- and N-Aralkyl-N',N"-dicarbomethoxyguanidines with Thiophosgene

N-Aryl- and N-aralkyl-N',N"-dicarbomethoxyguanidines (3) on treatment with thiophosgene undergo fragmentation to yield N,N'-dicarbomethoxyurea (5) and the isothiocyanates.

Synthesis of Substituted Thiocarboxamides, Carboxamides and Thioureas as Potential Anthelmintic and Antimicrobial Agents

A series of substituted thiocarboxamides (6-26), carboxamides (27-32), thioureas (33-37) and urea (38) have been synthesized starting from various aryl isothiocyanates (1-5).Their anthelmintic and antimicrobial activities are reported.Of these 8 and 9 show 60-70percent reduction in worms at a dose of 100-250 mg/kg given for three days.