542-88-1 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 542-88-1 differently. You can refer to the following data:
1. colorless liquid
2. Bis(chloromethyl) ether is a clear liquid with a strong unpleasant odor. It does not
occur naturally. It dissolves easily in water, but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types
of polymers, resins, and textiles, but its use is now highly restricted. Only small
quantities of bis(chloromethyl) ether are produced in the United States. The small quantities produced are only used in enclosed systems to make other chemicals.
However, small quantities of bis(chloromethyl) ether may be formed as an impurity
during the production of chloromethyl methyl ether. Along with other chemicals, rain,
and sunlight, it undergoes chemical reactions and breaks down as formaldehyde and
hydrochloric acid
3. Bis(chloromethyl)ether is a colorless, volatile
liquid with a suffocating odor.
Uses
Different sources of media describe the Uses of 542-88-1 differently. You can refer to the following data:
1. Bis(chloromethyl)ether (BCME) is used asan intermediate in anion-exchange quater nary resins. Its use as a chloromethylationreagent in industry is being discontinuedbecause of its high carcinogenic properties.Exposure risks associated with this com pound can arise during the use or productionof chloromethyl methyl ether when the lat ter compound comes in contact with tracesof water in the presence of hydrogen orhydroxyl ions. It may occur in trace amountsin chloromethyl methyl ether.
2. Bis(chloromethyl) ether is a clear liquid with a strong unpleasant odour. It does not occur naturally. It dissolves easily in water but degrades rapidly and readily evaporates into air. During earlier years, bis(chloromethyl) was used to make several types of polymers, resins, and textiles, but its use is now highly restricted. Only small quantities of bis(chloromethyl) ether are produced in the United States. The small quantities that are produced are only used in enclosed systems to make other chemicals.
3. Reagent used in the formation of ether linked dimers
General Description
A colorless volatile liquid with a chloroform-like odor. Toxic by inhalation, skin absorption and ingestion. Dangerous fire risk - flash point below 0°F. Vapors much denser than air. Insoluble in water and denser than water. Used to make paints and varnish, and as a solvent.
Air & Water Reactions
Highly flammable. Insoluble in water. Reacts with water to form hydrochloric acid & formaldehyde.
Reactivity Profile
DICHLORODIMETHYL ETHER is incompatible with the following: Acids, water [Note: Reacts with water to form hydrochloric acid & formaldehyde.] .
Hazard
A carcinogen. Toxic by ingestion.
Health Hazard
Different sources of media describe the Health Hazard of 542-88-1 differently. You can refer to the following data:
1. BCME is a highly toxic and carcinogeniccompound. The inhalation toxicity and car cinogenicity of this compound are greatestamong the haloethersExposure to its vapors can cause irritationof the eyes, nose, and throat in humans. Theprimary target organ is the lungs. Inhalationof 100 ppm of this compound in air for afew minutes can cause death to humans.Irritation of the eyes can be moderate tosevere and conjunctival. The acute oral anddermal toxicity of this compound, however,is moderate and comparable to that of bis(2-chloroethyl)etherLC50 value, inhalation (rats): 33 mg (7ppm)/m3/7 hrLD50 value, oral (rats): 210 mg/kg (NIOSH1986)Tests on animals have confirmed the car cinogenic action of BCME. It is carcinogenicby inhalation and by subcutaneous and skinapplications. In humans it can produce lungcancer — a fact that is now well established.Tests on rats indicate that exposure to 0.1-ppm concentrations in air for 6 hours per dayfor 6 months produced tumors in the noseand lungs. Subcutaneous and skin applicationsproduced tumors at the site of application.
2. Acute toxicity is high by ingestion, inhalation, and skin irritation. Small quantities may cause death or permanent injury after very short exposure. Chloromethyl ether is an alkylating agent which is a recognized human carcinogen. There is a strong association between industrial exposure and excess lung cancer.
3. Exposures to bis(chloromethyl) ether cause irritation to the skin, eyes, throat, and
lungs, and in cases of severe exposures cause damage to the lungs (swelling and bleeding) and death. Breathing low concentrations will cause coughing and nose and throat
irritation.
Fire Hazard
Container may explode in heat of fire. When heated to decomposition, BIS(CHLOROMETHYL)ETHER emits very toxic fumes of chlorides. Decomposed by water to hydrochloric acid and formaldehyde. Avoid water: hydrolyzes very rapidly (half life 10-40 seconds) on contact with water. Avoid decomposing heat, powerful oxidizers, areas of high fire hazard and moist air.
Potential Exposure
Exposure to bis(chloromethyl)ether
may occur in industry and in the laboratory. This substance
can form spontaneously in warm moist air by the combination
of formaldehyde and hydrogen chloride. This compound
is used as an alkylating agent in the manufacture of
polymers; as a solvent for polymerization reactions; in the
preparation of ion exchange resins; and as an intermediate
for organic synthesis. Haloethers, primarily α-chloromethyl
ethers, represent a category of alkylating agents of increasing
concern due to the establishment of a causal relationship
between occupational exposure to two agents of this
class and lung cancer in the United States and abroad. The
cancers are mainly oat cell carcinomas. Potential sources of
human exposure to BCME appear to exist primarily in
areas including: (1) its use in chloromethylating (crosslinking)
reaction mixtures in anion-exchange resin production;
(2) segments of the textile industry using formaldehydecontaining
reactants and resins in the finishing of fabric
and as adhesive in the laminating and flocking of fabrics;
and (3) the nonwoven industry which uses as binders, thermosetting
acrylic emulsion polymers comprising methylol
acrylamide, since a finite amount of formaldehyde is
liberated on the drying and curing of these bonding agents.
NIOSH has confirmed the spontaneous formation of BCME
from the reaction of formaldehyde and hydrochloric acid in
some textile plants and is now investigating the extent of
possible worker exposure to the carcinogen. However, this
finding has been disputed by industrial tests in which
BCME was not formed in air by the reaction of textile systems
employing hydrochloric acid and formaldehyde.
Carcinogenicity
Bis(chloromethyl) ether (BCME) is known to be human carcinogens based on sufficient evidence of carcinogenicity from studies in humans.
Source
sym-Dichloromethyl ether may form as an intermediate by-product when form-aldehyde
reacts with chloride ions under acidic conditions (Frankel et al., 1974; Tou and Kallos, 1974a;
Travenius, 1982). Tou and Kallos (1974) reported that the reactants (formaldehyde and chloride
ions) must be in concentrations of mg/L to form sym-dichloromethyl ether at concentrations of
μg/L.
Chloromethyl methyl ether may contain 1 to 8% sym-dichloromethyl ether as an impurity
(Environment Canada, 1993a).
Environmental fate
Chemical/Physical. Reacts rapidly with water forming HCl and formaldehyde (Fishbein, 1979;
Tou et al., 1974). Tou et al. (1974) reported a hydrolysis half-life of 38 sec for sym-dichloromethyl
ether at 20 °C.
Anticipated products from the reaction of sym-dichloromethyl ether with ozone or OH radicals
in the atmosphere, excluding the decomposition products formaldehyde and HCl, are chloromethyl
formate and formyl chloride (Cupitt, 1980).
Shipping
UN2249 Dichlorodimethyl ether, symmetrical,
Hazard class: 6.1; Labels: 6.1—Poisonous materials, 3—
Flammable liquid.
Toxicity evaluation
No information is available on the transport and partitioning
of BCME in the environment. Due to the relatively short
half-life in both air and water, it is unlikely that significant
partitioning between media or transport occurs. Primary
process for BCME degradation in air is believed to be reaction
with photochemically generated hydroxyl radicals to yield
chloromethyl formate ClCHO, formaldehyde, and HCl.
Atmospheric half-life due to reaction with hydroxyl radicals is
estimated to be 1.36 h. Hydrolysis in the vapor phase is found
to be slower with an estimated half-life of 25 h.
BCME is rapidly hydrolyzed in water to yield formaldehyde
and HCl, and the hydrolysis rate constant is estimated to be
0.018 s-1at 20°C, which is equal to a half-life of ～35 s.
No information is available on the fate of BCME in soil. It is
probable that BCME would rapidly degrade upon contact with
moisture in soil. Due to its high volatile nature, it is not
expected that BCME would persist in soil for significant
periods.
Incompatibilities
May form explosive mixture with air.
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. Decomposes on contact with water, moist
air, and heat, forming corrosive hydrochloric acid, hydrogen
chloride, and formaldehyde vapors. May form shocksensitive
compounds on contact with oxidizers, peroxides,
and sunlight. Attacks many plastics.
Waste Disposal
Incineration, preferably after
mixing with another combustible fuel. Care must be exercised
to assure complete combustion to prevent the formation
of phosgene. An acid scrubber is necessary to remove
the halo acids produced.
Check Digit Verification of cas no
The CAS Registry Mumber 542-88-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 2 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 542-88:
(5*5)+(4*4)+(3*2)+(2*8)+(1*8)=71
71 % 10 = 1
So 542-88-1 is a valid CAS Registry Number.
InChI:InChI=1/C2H2Cl4O/c3-1(4)7-2(5)6/h1-2H
542-88-1Relevant articles and documents
ADENOSINE RECEPTOR ANTAGONISTS AND USES THEREOF
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Paragraph 00307; 00308, (2019/10/01)
Disclosed herein are compounds, compositions, formulations, and methods for modulating the A2B adenosine receptor.
GLYCOSIDE COMPOUND, METHOD FOR PRODUCING THIOETHER, ETHER, METHOD FOR PRODUCING ETHER, METHOD FOR PRODUCING GLYCOSIDE COMPOUND, METHOD FOR PRODUCING NUCLEIC ACID
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Paragraph 0154; 0155; 0156, (2014/07/09)
Provided is a glucoside compound, which is capable of providing a phosphoramidite, which can be produced at a low cost and can produce a nucleic acid in a high yield and with high purity. A glycoside compound represented by the following chemical formula (1). In the chemical formula (1), B is an atomic group having a nucleic acid base skeleton, and optionally having a protecting group, R1 and R2 are each a hydrogen atom or a protecting group, or R1 and R2 in conjunction optionally form an atomic group represented by the following chemical formula (R1R2A) or (R1R2B): each R1a is a hydrogen atom, a straight chain or branched alkyl group and the like, L1 is an unsubstituted or alkyl-substituted ethylene group, R3 is a group represented by the following chemical formula (R3): in the chemical formula (R3), n is a positive integer, and [D1] is an electron-withdrawing group.
