2698-41-1 Usage
Description
CS, or o-chlorobenzylidene malononitrile, is the current major
riot control agent (RCA) used by U.S. military forces. It was
originally synthesized in 1928 by Corson and Stoughton, and
the U.S. Army designated the compound ‘CS’ for the authors’
initials. CS replaced CN, chloroacetophenone, in 1959 as the
U.S. Army’s premier RCA due to its higher safety ratio over CN.
CS is more effective as an RCA, that is to say, more potent and
safer than its predecessor CN. CS can be disseminated pyrotechnically,
or in the cases of CS1 and CS2, in powder
formulations.
Chemical Properties
Different sources of media describe the Chemical Properties of 2698-41-1 differently. You can refer to the following data:
1. white crystalline solid with a peppery smell
2. o-Chlorobenzylidene malonitrile is a combustible, white crystalline solid. Pepper-like odor.
Uses
Different sources of media describe the Uses of 2698-41-1 differently. You can refer to the following data:
1. The defining component of tear gas (CS gas).
2. Riot control agent.
3. Active ingredient in tear gas
General Description
White crystalline solid or light beige powder. Odor of pepper.
Air & Water Reactions
The finely powdered nitrile is a significant dust explosion hazard. Slightly soluble in water.
Reactivity Profile
[(2-Chlorophenyl)methylene]malononitrile may react with strong oxidizers.
Hazard
Toxic by inhalation and skin contact. Strong
irritant to eyes and mucous membranes.
Health Hazard
o-Chlorobenzylidene malononitrile
(CS) aerosol is a potent lacrimator and
upper respiratory irritant.
Characteristic effects of CS exposure are
instantaneous conjunctivitis, blepharospasm,
burning, and pain.1 Prolonged exposure to high
concentrations in enclosed spaces may cause
pulmonary edema and severe bronchospasm.
Fire Hazard
Flash point data for [(2-Chlorophenyl)methylene]malononitrile are not available, but [(2-Chlorophenyl)methylene]malononitrile is probably combustible.
Safety Profile
Poison by ingestion,
intraperitoneal, and intravenous routes.
Moderately toxic by inhalation. Human
systemic effects by inhalation: conjunctiva
irritation, cough, and unspecified respiratory
system effects. A human skin and eye
irritant. Human exposure data suggest
relatively low systemic toxicity, but intense
irritation of eyes, skin, and mucous
membranes. Mutation data reported. A tear
gas used for riot control. When heated to
decomposition it emits very toxic fumes of
Cl-, NOx, and CN-. See also NITRILES.
Potential Exposure
CS tear gas is used as a riot control
agent and is also used as an agent in CS1, CS2, and CSX
riot control, and tear gases.
Carcinogenicity
o-Chlorobenzylidene malononitrile did
not cause a mutagenic response when tested in
a variety of assays that examined point mutations,
germinal gene mutations, chromosomal
breaks, and mitotic chromosome misdistribution.
5 Although limited, a study of the repeated
inhalation toxicity of CS in mice, rats, and
guinea pigs did not find a relationship between
tumors in a particular site and total dose of CS.6
F344N rats exposed at 0.075, 0.25, or 0.75mg/
m3 and B6C3F1 mice exposed at 0.75 or
1.5mg/m3 6 hours/day, 5 days/week for 2 years
had no compound-related incidences of neoplasm.
7 Nonneoplastic lesions occurred primarily in the nasal passages and included hyperplasia
and squamous metaplasia of the respiratory
epithelium.
Environmental fate
Chemical/Physical. Hydrolyzes in water forming 2-chlorobenzaldehyde and malononitrile
(quoted, Verschueren, 1983).
Shipping
UN2810 Toxic liquids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. Military driver shall be given full and
complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the
shipment of chemical agents. Shipments of agent will be
escorted in accordance with AR 740-32.
Toxicity evaluation
Tests conducted at Eglin Air Force Base near Ft. Walton Beach,
Florida, concluded that CS in soil has a ‘conservative’ half-life
of 3.9 days. Degradation of CS increases with soil and air
moisture, and with light exposure as it undergoes a slow
hydrolysis process. Olajos (2004) concluded that CS degrades
to o-chlorobenzaldehyde and malononitrile, the former of
which is ultimately converted to catechol under aerobic
conditions. Nitriles such as the malononitrile degradation
product of CS have a short half-life in soil and can be converted
readily to organic acids. Anaerobically, microalgae have
been reported to transform CS breakdown products into
benzoate. The U.S. Army Edgewood Research Development
and Engineering Center (USAERDEC) reports a solubility of
200 mg l-1. CS concentrations attenuate in the atmosphere through three
processes: reaction with hydroxyl radicals, hydrolysis reactions
with atmospheric humidity, and deposition of particulate CS. It
should be noted that vapor pressure increases with temperature,
as should be expected. At 20°C, CS vapor pressure is
3.5×10-5 mmHg, and at 60°C, it is 5–7 mmHg.
Incompatibilities
Contact with strong oxidizers may cause
fire and explosion. May be explosive if dust mixes with air.
Check Digit Verification of cas no
The CAS Registry Mumber 2698-41-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,9 and 8 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2698-41:
(6*2)+(5*6)+(4*9)+(3*8)+(2*4)+(1*1)=111
111 % 10 = 1
So 2698-41-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H
2698-41-1Relevant articles and documents
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, p. 14971 - 14974 (2019)
The fine-tuning of metal-based molecular building blocks in Zn-MOF-74 through post-synthetic cation exchange with Ca2+ significantly enhances its basicity and corresponding catalytic performance. The resulting material, exemplified by Ca/Zn-MOF-74, is sho
Design and Development of Amine Functionalized Mesoporous Cubic Silica Particles: A Recyclable Catalyst for Knoevenagel Condensation
Gupta, Padmini,Kumar, Lalita S.,Kumar, Yogesh,Shabir, Javaid
, (2021)
Abstract: The amine functionalized cubic mesoporous silica nanoparticles (cSiO2-NH2) were successfully synthesized through biphasic stratification approach. The synthesized material was characterised by various spectroscopic and phys
Janus Interphase Organic-Inorganic Hybrid Materials: Novel Water-Friendly Heterogeneous Catalysts
Vafaeezadeh, Majid,Breuninger, Paul,L?sch, Philipp,Wilhelm, Christian,Ernst, Stefan,Antonyuk, Sergiy,Thiel, Werner R.
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In this work, amphiphilic silica-based Janus-type acid and base catalysts are introduced as heterogeneous analogues of surfactants. The new interphase organic-inorganic hybrid catalysts comprise of two different groups (?C8H17, ?Csu
An efficient and environment friendly procedure for the synthesis of arylmethylenemalononitrile catalyzed by strong base anion-exchange resin in water
Jin, Tong-Shou,Zhang, Jian-She,Wang, Ai-Qing,Li, Tong-Shuang
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Knoevenagel condensation of malononitrile with aromatic aldehydes catalyzed by strong base anion-exchange resin in water results aryl- methylenemalononitrile in 74-98% yield at room temperature.
New facile, eco-friendly and rapid synthesis of trisubstituted alkenes using bismuth nitrate as lewis acid
Muhammad, Munira T.,Khan, Khalid M.,Taha, Muhammad,Khan, Tariq,Hussain, Shafqat,Fakhri, Muhammad I.,Perveen, Shahnaz,Voelter, Wolfgang
, p. 231 - 235 (2016)
Background: For the synthesis of tri and tetra-substituted alkenes, Knoevenagel condensations have previously been performed in solvents like dichloromethane, DMF, toluene, acetonitrile, DMSO etc. These conditions suffer from certain limitations like long
Synthesis and characterization of Al2O3-SiO2-MgO nanocomposite prepared by sol-gel process as an efficient catalyst for the Knoevenagel condensation of aldehydes with malononitrile
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, p. 6625 - 6633 (2015)
Abstract The composite of Al2O3-SiO2 and Al2O3-SiO2-MgO nanocomposite were synthesized by sol-gel method and FT-IR, XRD, FE-SEM, EDAX, TEM, and BET surface area analysis were used to charac
Supported copper on a diamide-diacid-bridged PMO: an efficient hybrid catalyst for the cascade oxidation of benzyl alcohols/Knoevenagel condensation
Dekamin, Mohammad G.,Valiey, Ehsan
, p. 437 - 450 (2022/01/20)
In this study, a novel periodic mesoporous organosilica (PMO) containing diamide-diacid bridges was conveniently prepared using ethylenediaminetetraacetic dianhydride to support Cu(ii) species and affording supramolecular Cu@EDTAD-PMO nanoparticles efficiently. Fourier transform infrared (FT-IR) and energy dispersive X-ray (EDX) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), Brunauer-Emmett-Teller (BET) analysis, and high-resolution transmission electron microscopy (HRTEM) results confirmed the successful synthesis of Cu@EDTAD-PMO. The stabilized Cu(ii) nanoparticles inside the mesochannels of the new PMO provided appropriate sites for selective oxidation of different benzyl alcohol derivatives to their corresponding benzaldehydes and subsequent Knoevenagel condensation with malononitrile. Therefore, Cu@EDTAD-PMO can be considered as a multifunctional heterogeneous catalyst, which is prepared easily through a green procedure and demonstrates appropriate stability with almost no leaching of the Cu(ii) nanoparticles into the reaction medium, and easy recovery through simple filtration. The recycled Cu@EDTAD-PMO was reused up to five times without significant loss of its catalytic activity. The stability, recoverability, and reusability of the designed heterogeneous catalyst were also studied under various reaction conditions.
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