3-Chloro-1,2-propanediol
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3-Chloro-1,2-propanediol
structure -
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CAS No:
96-24-2
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Formula:
C3H7ClO2
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Chemical Name:
3-Chloro-1,2-propanediol
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Synonyms:
1,2-Propanediol,3-chloro-;3-Chloro-1,2-propanediol;1-Chloro-2,3-dihydroxypropane;3-Chloro-1,2-dihydroxypropane;3-Chloropropylene glycol;Glycerin α-monochlorhydrin;Glycerol α-chlorohydrin;Glycerol α-monochlorohydrin;α-Chlorohydrin;1-Chloro-2,3-propanediol;Chloropropanediol;Glycerol 3-chlorohydrin;3-Chloropropanediol;Chlorohydrin;Glyceryl α-chlorohydrin;Glyceryl chloride;Glycerin epichlorohydrin;Glycerol monochlorohydrin;1,2-Dihydroxy-3-chloropropane;U 5897;α-Monochlorohydrin;3-Chloro-1,2-propylene glycol;1-Chloro-1-deoxyglycerol;Epibloc;Glycerin monochlorohydrin;dl-α-Chlorohydrin;(±)-2,3-Dihydroxychloropropane;(RS)-α-Chlorohydrin;(±)-3-Chloro-1,2-propanediol;(RS)-3-Chloro-1,2-propanediol;Ekorod A;3-Monochloro-1,2-propanediol;52340-46-2;69420-22-0
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CAS No:
Description
Clear pale yellow liquid
Glycerol alpha-monochlorohydrin appears as a colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.|Liquid|COLOURLESS-TO-PALE-YELLOW HYGROSCOPIC LIQUID.
Glycerol alpha-monochlorohydrin appears as a colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.|3-chloropropane-1,2-diol is a chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.|A chlorinated PROPANEDIOL with antifertility activity in males used as a chemosterilant in rodents.
3-Chloro-1,2-propanediol Basic Attributes
110.53900
110.54
202-492-4
1664
2689
DTXSID4020664
Colorless or pale yellow liquid|Heavy liquid
2905590090
Characteristics
40.46000
-0.42160
Glycerol alpha-monochlorohydrin appears as a colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
1.3218 g/cm3 @ Temp: 20 °C
34.4 °C
116 °C
135ºC
1.479-1.481
H2O: soluble
2-8ºC
Vapour pressure, Pa at 20°C: 27
Relative vapour density (air = 1): 3.8
LD50 in mice, rats (g/kg): 0.16, 0.15 orally (Hine)
SWEETISH TASTE
Tendency to turn straw color|Unstable; hygroscopic; BP = 213 (decomposes); wt/gal 11.102 lb.|114-120 °C @ 14 mm Hg
Soluble in water. Hygroscopic.
Alcohols and Polyols
GLYCEROL ALPHA-MONOCHLOROHYDRIN is hygroscopic and may be sensitive to prolonged exposure to air. Glycols and their ethers undergo violent decomposition in contact with approximately 70% perchloric acid. (NTP, 1992).
Safety Information
III
6.1
UN 2689
3
R23/24/25; R36; R39; R60
S26-S28-S36/37/39-S38-S45-S53
TY4025000
T
Dry. Well closed. Separated from strong oxidants and food and feedstuffs.
TENDENCY TO TURN STRAW COLOR
P201-P261-P264-P280-P301 + P310-P305 + P351 + P338
H300-H312-H318-H331-H351-H360
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.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)|Combustible. Risk of explosion on contact with strong oxidants.
|Danger|H300 (86.39%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P311, P312, P314, P320, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 169 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P264, P270, P271, P280, P281, P284, P301+P310, P304+P340, P305+P351+P338, P308+P313, P310, P314, P320, P321, P330, P403+P233, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P310, P312, P314, P320, P321, P322, P330, P337+P313, P363, P403+P233, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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)|Use alcohol-resistant foam, dry powder, carbon dioxide.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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 153 [Substances - Toxic and/or Corrosive (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)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)
FIRE HAZARD: SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Dry. Well closed. Separated from strong oxidants and food and feedstuffs.
A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
The substance is irritating to the eyes and respiratory tract. The substance may cause effects on the central nervous system.
The substance may have effects on the kidneys. This may result in kidney impairment. Tumours have been detected in experimental animals but may not be relevant to humans. Animal tests show that this substance possibly causes toxicity to human reproduction or development.
NO open flames.
PREVENT GENERATION OF MISTS!
Avoid inhalation of mist.
Protective gloves.
Wear safety goggles.
Toxicity
EFFECT OF SODIUM NITRITE ON ALPHA-CHLOROHYDRIN-INDUCED LESION OF TESTIS-EPIDIDYMIS COMPLEX IN RAT.
3-Chloro-1,2-dihydroxypropane's production and use in dynamite, in the manufacture of dye intermediates, as a rodent chemosterilant(1), a solvent and a chemical intermediate(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 3-chloro-1,2-dihydroxypropane will have very high mobility in soil(SRC). Volatilization of 3-chloro-1,2-dihydroxypropane is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Data regarding the aerobic biodegradation of 3-chloro-1,2-dihydroxypropane in soil are variable; in screening tests, this compound reached 0(4) to 1%(5) of the theoretical BOD in 5 days and 68% of the theoretical BOD in 14 days(6). Under anaerobic conditions, 3-chloro-1,2-dihydroxypropane may be resistant to biodegradation; using an acclimated culture, only 26% of the initial 3-chloro-1,2-dihydroxypropane concentration was utilized in 90 days(7).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1(SRC), determined from structure estimation method(2), indicates that 3-chloro-1,2-dihydroxypropane should not adsorb to suspended solids and sediment in water(SRC). 3-Chloro-1,2-dihydroxypropane is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 6.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF value of 0.2(1,SRC), from an estimated log Kow(9,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Data regarding the aerobic biodegradation of 3-chloro-1,2-dihydroxypropane in water are inconclusive; in screening tests, this compound reached 0(5) to 1%(6) of the theoretical BOD in 5 days and 68% of the theoretical BOD in 14 days(7). Under anaerobic conditions, 3-chloro-1,2-dihydroxypropane may be resistant to biodegradation; using an acclimated culture, only 26% of the initial 3-chloro-1,2-dihydroxypropane concentration was utilized in 90 days(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-chloro-1,2-dihydroxypropane, which has a measured vapor pressure of 0.2 mm Hg at 20 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-chloro-1,2-dihydroxypropane is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 2 days(3,SRC).
The rate constant for the vapor-phase reaction of 3-chloro-1,2-dihydroxypropane with photochemically-produced hydroxyl radicals has been estimated as 7.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
An estimated BCF value of 0.2 was calculated for 3-chloro-1,2-dihydroxypropane(SRC), using an estimated log Kow of -0.53(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 3-chloro-1,2-dihydroxypropane can be estimated to be about 1(SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 3-chloro-1,2-dihydroxypropane has very high mobility in soil(SRC).
The Henry's Law constant for 3-chloro-1,2-dihydroxypropane is estimated as 6.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 3-chloro-1,2-dihydroxypropane will be essentially nonvolatile from water surfaces(2,SRC). Its estimated value for the Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces should not occur(SRC).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 2917 workers are potentially exposed to 3-chloro-1,2-dihydroxypropane in the US(1). Occupational exposure may be through inhalation and dermal contact at workplaces where 3-chloro-1,2-dihydroxypropane is produced or used(SRC). The general population may be exposed to 3-chloro-1,2-dihydroxypropane via inhalation of ambient air and dermal contact with vapors and other products containing 3-chloro-1,2-dihydroxypropane(SRC).
Drug Information
Compounds that cause reproductive sterility in organisms. They are sometimes used to control pest populations by sterilizing males within the population. (See all compounds classified as Chemosterilants.)
FOLLOWING ADMIN OF ALPHA-CHLOROHYDRIN (100 MG/KG, IP) TO MALE RATS, BETA-CHLOROLACTIC ACID & OXALIC ACID WERE ISOLATED FROM URINE.
Glycidol ... an industrial chemical, has been showed to be a reproductive toxicant in short term studies and a carcinogen in rats and mice in /carcinogenicity/ studies. The reproductive toxicity of glycidol was believed to result from its conversion to alpha-chlorohydrin by the action of hydrochloric acid in the stomach. The comparative disposition of glycidol was investigated in rats following oral or iv admin at doses of 37.5 and 75 mg/kg. ... Approx 87-92% of the dose was absorbed from the gastrointestinal tract of the rat. (14)C-Glycidol equivalents were eliminated in urine (40-48% of the dose in 72 hr), feces (5-12%), and exhaled as CO2 (26-32%). At both doses, 9-12% and 7-8% (estimated) of the dose remained in tissues at 24 or 72 hr following dosing, respectively. In general, the concn of glycidol equivalents in tissues were proportional to the dose. The highest concn of radioactivity were /noted/ in the blood cells, thyroid, liver, kidney, spleen, and the lowest in adipose tissue, skeletal muscle, and plasma. The pattern of distribution of radioactivity in tissues was similar for both the iv and oral routes. The total recovery of radioactivity ranged from 87 to 91% of the dose. Urinary radioactivity was resolved by HPLC analysis into 15 metabolites. There were one major (14-21% of the dose) and four lesser metabolites (each representing 2-8%); the others were minor, each representing 1% or less of the dose. In general, the urinary metabolic profile was similar to iv or oral admin of the two doses studied. ...|The ultrastructural changes of each epididymal segment of the rat were brought about by alpha-chlorohydrin (20 mg/kg/day, for successive five times). The alteration appeared in proper order from initial segment to caudal segment, and the digression in profundity and range got less serious as the distance to the testis increased. This alteration disappeared gradually as the time went by. The recovery process also began at initial segment but its cycle was shortened gradually from initial segment to caudal segment. These results showed the factor that caused the above mentioned processes stemmed from the testis chiefly and was in epididymal plasma. It affected each epididymal segment along the epididymal lumen and to the injury of the epididymal epithelium; at the same time, the concentration of the factor became more decreased. The relationship between the antifertility effect of alpha-chlorohydrin and the ... ultrastructural changes of the epididymis and the mechanism of the double effects depending on dose of alpha-chlorohydrin were discussed.|An acute phase of severe hepatic necrosis induced by dichloropropanol was examined immunohistochemically and ultrastructurally, in order to study chronological changes of sinusoidal morphology during acute hepatic injury. Male wistar rats were injected with 1,3-dichloro-2-propanol (DC2P) and sacrificed at various intervals after the injections. DC2P injected rats showed zonal necrosis of the centrilobular space with a peak from 24 to 48 hr after the injection. Destruction of sinusoidal linings appeared at 4 hr, and was gradually aggravated along the advancing hepatocytic necrosis. Monocytic influx into the necrotic areas was initiated at 6 hr. At 48 hr, collapsed centrilobular spaces showed a loss of most sinusoidal structures with active phagocytosis of macrophages, proliferation of perisinusoidal cells and accumulation of collagen fibrils. At 72 hr, there were many regenerating sinusoidal structures, which were composed of rather thick and less fenestrated endothelium and underlying multilayered processes of mesenchymal cells, along the regenerating hepatocytes. In these areas, occasional junctions between regenerating hepatocytes and mesenchymal cells were /observed/. Reconstruction of sinusoidal linings was closely related to the hepatocytic regeneration, and a hepatocytic mesenchymal interaction might participate in this morphodynamic course of the sinusoidal reconstruction.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.
A 34 yr old man suffered from fumigant hepatitis after cleaning a tank in which there were traces of dichlorohydrin. In spite of daily plasma exchanges he /expired/ 10 days after exposure. A 27 yr old man with much lighter exposure showed only slight /hepatic/ dysfunction. ... /Dichlorohydrin/
3 Chloro 1,2 propanediol
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Cough. Sore throat. Further see Ingestion.
See Ingestion.
Redness. Pain.
3-Chloro-1,2-propanediol Use and Manufacturing
By passing hydrogen chloride gas into glycerol containing 2% acetic acid.|Production: from allyl alcohol via hypochlorination|Production: from epichlorohydrin via dehydrochlorination
A metabolite of Dichloropropanols
Intermediates
Personal care products
Technical
All other chemical product and preparation manufacturing|1,2-Propanediol, 3-chloro-: ACTIVE|The commercial grade is a mixture of the two isomers, alpha and beta, of which alpha is in a greater proportion.
Food Contaminant -> CONTAMINANT; -> JECFA Functional Classes
Food Contaminant -> CONTAMINANT;
Computed Properties
Molecular Weight:110.54
XLogP3:-0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:110.0134572
Monoisotopic Mass:110.0134572
Topological Polar Surface Area:40.5
Heavy Atom Count:6
Complexity:32
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
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