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Home > Encyclopedia > p-Phenylene diisothiocyanate

p-Phenylene diisothiocyanate

p-Phenylene diisothiocyanate structure

p-Phenylene diisothiocyanate 

structure
  • CAS No:

    4044-65-9

  • Formula:

    C8H4N2S2

  • Chemical Name:

    p-Phenylene diisothiocyanate

  • Synonyms:

    Benzene,1,4-diisothiocyanato-;Isothiocyanic acid,p-phenylene ester;1,4-Diisothiocyanatobenzene;Bitoscanate;WM 842;Jonit;Phenylene-1,4-diisothiocyanate;p-Phenylene diisothiocyanate;p-Phenylene bisisothiocyanate;Bitoscanat;PDITC;1,4-phenylenediisothiocyanate

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

Bitoscanate (p-Phenylene diisothiocyanate) is an organic chemical compound used in the treatment of hookworms.


Bitoscanate appears as odorless colorless crystals. Melting point 132°C.


Bitoscanate appears as odorless colorless crystals. Melting point 132°C.|Bitoscanate is a member of benzenes.

p-Phenylene diisothiocyanate Basic Attributes

192.26

192.26

2414340

223-741-3

6D1R3P86GX

758884

2928

DTXSID3046532

Colorless needles|Yellowish-white, crystalline powder

2930909090

Characteristics

88.9

4.67 (est)

white powder

1.2g/cm3

132 °C

339.4ºC at 760 mmHg

167.2ºC

1.641

Hydrolyzes in water.chloroform: clear

−20°C

6.2X10-5 mm Hg at 25 deg C /Estimated/

LD50 oral in mouse: 230mg/kg

Odorless

Tasteless

Henry's Law constant = 1.13X10-4 atm-cu m/mole at 25 °C /Estimated/

Hydroxyl radical reaction rate constant = 1.3X10-12 cu cm/molec-sec at 25 °C /Estimated/

No rapid reaction with air. No rapid reaction with water.

Isocyanates and Isothiocyanates

BITOSCANATE 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].

Safety Information

II

6.1

UN 2811 6.1/PG 3

3

22-36/37/38-42

22-26-36/37

NX9150000

Xn,Xi

Irritant

P261-P301 + P310-P305 + P351 + P338-P342 + P311

H301-H315-H319-H334-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

USEPA; Chemical Profile: Bitoscanate (1985) http://yosemite.epa.gov/oswer/CeppoEHS.nsf/Profiles/4044-65-9?OpenDocument

When heated to decomposition, it emits very toxic fumes of nitrogen oxides and sulfur oxides. (EPA, 1998)|Reactive - 1st degree

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P285, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Bitoscanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Toxicity

LD50 Mouse ip 21 mg/kg|LD50 Mouse oral 230 mg/kg|LD50 Rat oral 21 mg/kg

Bitoscanate may decompose upon exposure to water or moist air(1).

Drug Information

Antinematodal Agents|As an anthelmintic in the treatment of hookworms. It has been given in 3 doses of 100 mg at 12-hourly intervals or as a single dose of 150 mg. It is recommended that 8 weeks should elapse before a course is repeated.|In a survey of 1395 patients with mixed infection treated with bitoscanate the cure-rate for those with hookworms was highest for patients aged 10-14 years who received the total dose of 300 mg. Bitoscanate was effective also against giardiasis and against the dwarf tapeworm Hymenolepis nana.|In a survey including 1714 persons, a single dose of bitoscanate 150 mg was considered to be of value for large-scale eradication of hookworms (Ancylostoma and Necator).|Bitoscanate (Jonit) was examined for clinical efficacy and safety in 30 hospitalized patients with hookworm infection due to Necator americanus. With 2 doses of 100 mg., each administered 12 hours apart after food, cure was obtained in 16 out of 30 patients. Egg reduction of over 95% occurred in 90% of the patients. The untoward effects observed were mild and limited to the gastrointestinal tract. There was no significant alteration of any of the laboratory tests performed.

After oral administration of the anthelmintic, (14)C-bitoscanate to dogs, renal elimination ... and fall-off of blood concentrations ... of (14)C- were biphasic. Similar results were obtained in man except that urinary excretion was more delayed, and more (14)C- was excreted renally. Much of the (14)C- had been excreted within 5 days from both species, but excretion of the remainder was protracted. Thus after 3 weeks, the dog had excreted 80% in the feces, and 12% in the urine, and after 5 weeks, man had excreted respectively 55 and 28% by these routes; 3% still circulated in the blood. Fetuses contained 3% of the dose, 16 hr after admin of (14)C-bitoscanate to a pregnant dog. The data indicated that part of the (14)C binding to the tissues was only slowly excreted, possibly because (14)C-bitoscanate was irreversibly bound to biological macromolecules through its isothiocyanate groups. ... final rates of excretion of (14)C reflected rates of metabolism and excretion of the endogenous macromolecules to which bitoscanate was bound.|Bitoscanate is partly absorbed from the gastro-intestinal tract and slowly excreted ...

Half-life of 0.5 and 8 days in renal elimination and fall-off of blood concentrations of half-life of 0.8 and 12 days /occurred after oral admin of bitoscanate to dogs/. /Similar results were obtained in man except that urinary excretion was more delayed, and more (14)C-bitoscanate was excreted renally/.|... a half-life of 26 days has been reported /in humans/.

This material is highly toxic if ingested. It is a central nervous system and gastrointestinal toxin in humans. (EPA, 1998)

Warning: Fatalities have occurred with ingestion of as little as 300 mg of bitoscanate. Effects may be delayed. Signs and Symptoms of Bitoscanate Exposure: Signs and symptoms of acute exposure to bitoscanate may include muscle weakness (especially in the arms and legs), irritability, confusion, delirium, convulsions, visual and auditory hallucinations, apnea (cessation of breathing), and coma. Nystagmus (involuntary, rapid movement of the eye), coryza (nasal inflammation and discharge), skin rashes, and dermatitis have also been reported. Nausea, vomiting, abdominal cramping, and diarrhea are also possible signs of acute exposure. Emergency Life-Support Procedures: Acute exposure to bitoscanate may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to bitoscanate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 4. Rush to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self-exposure to bitoscanate. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Wash exposed skin areas thoroughly with soap and water. Speed in removing material from skin is of extreme importance. 6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures. 7. Rush to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer 100% humidified oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of bitoscanate is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4. Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of bitoscanate may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Rush to a health care facility. (EPA, 1998)

/SIGNS AND SYMPTOMS/ Transient mild to moderate side effects may occur in up to half of the patients treated. They include nausea and vomiting, anorexia, abdominal pain, diarrhea, headache, and dizziness.

1,4-phenylenediisothiocyanate

p-Phenylene diisothiocyanate Use and Manufacturing

Methods of Manufacturing

Preparation and use as anthelmintic: FR M1652 and GB 1001314 (1963, 1965 to Hoechst).|Purification: Soeder, Laemmer, DE 1172664 (1964 to Hoechst).

Uses

anthelmintic

Benzene, 1,4-diisothiocyanato-: ACTIVE

Fire Hazards -> Reactive - 1st degree

Computed Properties

Molecular Weight:192.3
XLogP3:4.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:191.98159048
Monoisotopic Mass:191.98159048
Topological Polar Surface Area:88.9
Heavy Atom Count:12
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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