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Home > Encyclopedia > 1-Chloro-2-propanol

1-Chloro-2-propanol

1-Chloro-2-propanol structure

1-Chloro-2-propanol 

structure
  • CAS No:

    127-00-4

  • Formula:

    C3H7ClO

  • Chemical Name:

    1-Chloro-2-propanol

  • Synonyms:

    2-Propanol,1-chloro-;1-Chloro-2-propanol;1-Chloroisopropyl alcohol;α-Propylene chlorohydrin;sec-Propylene chlorohydrin;1-Chloro-2-hydroxypropane;(±)-1-Chloro-2-propanol;NSC 77373;20008-07-5

  • Categories:

    Organic Chemistry  >  Alcohols, Phenols, Phenol Alcohols

Description

colourless to light yellow liquidClear colorless to light amber liquid with a mild non residual odor.


1-chloro-2-propanol is a clear colorless to light amber liquid with a mild non residual odor. (NTP, 1992)


1-chloro-2-propanol is a clear colorless to light amber liquid with a mild non residual odor. (NTP, 1992)|1-chloropropan-2-ol is a secondary alcohol that is isopropanol in which one of the methyl hydrogen atoms is substituted by chlorine. It is an organochlorine compound and a secondary alcohol. It derives from a hydride of a propane.

1-Chloro-2-propanol Basic Attributes

94.54

94.54

773653

204-819-6

77373

2611

DTXSID5020285

COLORLESS LIQUID

29055900

Characteristics

20.2

0.27

1-chloro-2-propanol is a clear colorless to light amber liquid with a mild non residual odor. (NTP, 1992)

1.115 g/cm3 @ Temp: 20 °C

126-127 °C

125 °F

n 20/D 1.439(lit.)

SOL IN ETHANOL, ETHER, CARBON TETRACHLORIDE

Flammables area

4.9 mmHg

3.3

Oral-Rat  LD50 300  mg/kg; Oral-Mouse LD50: 220 mg/kg

Open flame, high heat and flammable; heated to liberate toxic chloride gas; react with oxidant

Soluble in water.

Alcohols and Polyols

May be sensitive to prolonged exposure to light. Incompatible with strong oxidizing agents. (NTP, 1992)

Safety Information

II

6.1

UN 2611 6.1/PG 2

3

10-20-36/37/38

26-36/39

UA8942000

Xn

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Stable. Flammable. Incompatible with strong oxidizing agents.

Missing Phrase - N15.00950417-P210-P261-P304 + P340 + P312-P370 + P378-P403 + P233

H226-H301 + H331-H315-H319-H335

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.

Toxicology & Carcinogenesis Studies of 1-Chloro-2-propanol (Technical Grade) in F344/N Rats and B6C3F1 Mice (Drinking Water Studies) p.6 Technical Report Series No. 477 (1998) NIH Publication No. 98-3967 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709

This chemical is combustible. (NTP, 1992)|Mutagens, Flammable - 2nd degree

|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 69 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H226: Flammable liquid and vapor [Warning Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P303+P361+P353, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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)

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light. Keep it away from oxidizing materials and store it under refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: If this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, replace them at once. Glove Type Model Number Thickness Bkthru Time Nitrile Edmont 37-175 0.64 mm 190 min PVA Edmont 25-545 0.89 mm 480 min PVC Edmont 34-100 0.20 mm 100 min Viton North F-101 0.36 mm 480 min Butyl rubber North B-144 0.43 mm 480 min (NTP, 1992)

MODERATE, WHEN EXPOSED TO HEAT OR FLAME.

ALC FOAM, SPRAY, MIST, DRY CHEM.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

highly toxic

LC50 Rat inhalation 1000 ppm/4 hr|LD50 Rat oral 100 to 300 mg/kg, 381 mg/kg, and 0.22 mL/kg|LD50 Rabbit dermal is 480 mg/kg, 0.48 mL/kg, and 0.5 g/kg

... Groups of 50 male and 50 female F344/N rats were admin drinking water containing 0, 150, 325 or 650 ppm 1-chloro-2-propanol (equivalent to average daily doses of approx 15, 30 or 65 mg/kg during the first several months of the study and 8, 17 or 34 mg/kg for the remainder of the 2 yr study) for up to 105 wk. ... Groups of 50 male and 50 female B6C3F1 mice were admin drinking water containing 0, 250, 500 or 1,000 ppm 1-chloro-2-propanol (equivalent to average daily doses of approx 45, 75 or 150 mg/kg for the males and 60, 105 or 210 mg/kg to females during the first several months of the study and 25, 50 or 100 mg/kg for the remainder of the 2 yr study for up to 105 wk). CONCLUSIONS: Under the conclusions of these 2 yr drinking water studies, there was no evidence of carcinogenic activity of technical grade 1-chloro-2-propanol in male or female F344/N rats exposed to 150, 325 or 650 ppm. There was no evidence of carcinogenic activity of technical grade 1-chloro-2-propanol in male or female B6C3F1 mice exposed to 250, 500 or 1,000 ppm.|1-Chloro-2-propanol (1CP) ... was tested for its effects on reproduction & fertility in Sprague-Dawley rats using the RACB protocol. This was stimulated by preliminary reproductive data that showed a decr in epididymal weight, an incr in sperm abnormalities, & a change in estrous cycle in rats dose for 90 days with 1CP. Data from a 2 wk dose-range-finding study (Task 1) were used to set exposure concns for the Task 2 continuous cohabitation study at 0.0, 0.03, 0.065, & 0.13% in drinking water. These concns produced estimated exposures of nearly equal to 30, 65, & 100 mg/kg/d. In the F0 animals in Task 2, 1 control, 1 low dose, & 1 high dose female died; 2 from kidney problems, & the remaining cause of death was undetermined. There was no change in the number of litters/pair, or the number or weight of live pups/litter. The high dose females took 2 days longer than controls to deliver their last litter; the biological significance of 116 days (control) vs. 118 days is questionable. Post-partum dam weights were reduced for the middle dose (by nearly =7%) & high dose females (by nearly =15%); low dose females were reduced, but not significantly so. Sire weights were reduced only at the high dose (by nearly =7%). This is consistent with the 10% & 30% reduction in water consumption measured for the middle & high dose animals, respectively. The last litter from all groups was reared by the dams until weaning at pnd 21. While pup viability was unaffected by 1CP consumption, pup weight was reduced by nearly =9% & nearly =20% at the middle & high dose levels, respectively. No F0 crossover test was conducted since no reproductive changes were observed for the first generation rats. Task 4 was conducted with the control & high dose rats. At the time of mating, body weights were reduced by 14% for males & 11% for females. Despite this difference, there were no differences between the 2 groups in reproductive parameters: both groups delivered equivalent number of litters, numbers of live pups/litter, & the viability & weight of those pups was unchanged by 1CP exposure. After the F2 pups were evaluated & removed, the F1 control & high dose adults were killed & necropsied. For males, body weight was reduced (see above), relative kidney weights increased by 7% in males. Absolute testis weight was 8% lower in 1CP-treated males while relative epididymis weight was increased by 8%. The proportion of abnormal sperm in control rats was 0.78% & the exposed value was 2.4%, a significant incr, but within the historical range. Female body weight was reduced by nearly =11%, relative kidney weight was increased by nearly =8%, & estrous cycle length was unchanged. These data show that even in the presence of 1CP sufficient to limit water consumption by approx 30% & to produce significant differences in body weight, 1CP caused no adverse effects on fertility in either generation. The statistically significant effects on testis weights & sperm abnormalities may indicate very slight reproductive toxicity. No effects were observed in females.

1-Chloro-2-propanol's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-propanol is expected to have very high mobility in soil(SRC). Volatilization of 1-chloro-2-propanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-6 atm-cu m/mole(SRC), obtained using a fragment constant estimation method(3). The potential for volatilization of 1-chloro-2-propanol from dry soil surfaces may exist(SRC) based upon a vapor pressure of 4.9 mm Hg(4). The importance of biodegradation of 1-chloro-2-propanol in soil is unknown(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-propanol is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.7X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 150 days and 3 years, respectively(SRC), using an estimation method(3). According to a classification scheme(5), an estimated BCF of 3(3,SRC), from an estimated log Kow(6,SRC), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A neutral first-order hydrolysis rate constant of 1.1X10-8 1/s for 1-chloro-2-propanol corresponds to a half-life of 2 years a pH 7(7), the half-life for hydrolysis at pH 8 is expected to be approximately 1 month by analogy to 1,3-dichloro-2-propanol(SRC). The importance of biodegradation of 1-chloro-2-propanol in water is unknown(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-2-propanol, which has a vapor pressure of 4.9 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-2-propanol 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 5 days(SRC) from its estimated rate constant of 3.19X10-12 cu cm/molecule-sec at 25 °C(3).

The rate constant for the vapor-phase reaction of 1-chloro-2-propanol with photochemically-produced hydroxyl radicals has been estimated as 3.19X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A neutral first-order hydrolysis rate constant of 1.1X10-8 1/s corresponds to a half-life of 2 years a pH 7(2). By analogy to 1,3-dichloro-2-propanol which has a base-catalyzed second-order hydrolysis rate constant of 850 L/mole-hour(3), 1-chloro-2-propanol is expected to have a half-live of approximately 1 month at pH 8(4,SRC). 1-Chloro-2-propanol is not expected to directly photolyze due to the lack of absorption in the environmental spectrum(5).

An estimated BCF of 3 was calculated for 1-chloro-2-propanol(SRC), using an estimated log Kow of 0.53(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1-chloro-2-propanol can be estimated to be about 2(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-chloro-2-propanol is expected to have very high mobility in soil.

The Henry's Law constant for 1-chloro-2-propanol is estimated as 1.7X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-chloro-2-propanol is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 150 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 3 years(SRC). 1-Chloro-2-propanol's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1-chloro-2-propanol from dry soil surfaces may exist(SRC) based upon a vapor pressure of 4.9 mm Hg(3).

1-chloro-2-propanol was qualitatively detected as a volatile component of meat(1). 1-Chloro-2-propanol may be formed in foods (e.g., flour, pepper, cocoa, walnut meat, tapioca starch, glazed cherries, glazed citron, and dehydrated potato granules) fumigated with propylene oxide(2).

Occupational exposure to 1-chloro-2-propanol may occur through inhalation and dermal contact with this compound at workplaces where 1-chloro-2-propanol is produced or used(SRC). The general population may be exposed to 1-chloro-2-propanol via food fumigated with propylene oxide(1).

Drug Information

Propylene chlorohydrin is absorbed, widely distributed, and rapidly metabolized and eliminated.

SYMPTOMS: This compound causes skin and eye irritation. It may also be irritating to the mucous membranes and upper respiratory tract. Other symptoms include nasal irritation, nausea, vomiting, giddiness, dizziness, incoordination, visual disturbances and coma. It may also cause hemolysis, central nervous system effects and liver and kidney damage. Coughing, confusion and unconsciousness have also been reported. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. The vapor or mist is irritating to the skin, eyes, mucous membranes and upper respiratory tract. It may be absorbed through the skin. When heated to decomposition it emits toxic fumes of chlorine, carbon monoxide carbon dioxide and hydrogen chloride gas. (NTP, 1992)

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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: DO NOT INDUCE VOMITING. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (> 3 carbons) and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or has severe pulmonary edema. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W TKO /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam (Valium) ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Consider drug therapy for pulmonary edema ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (> 3 carbons) and related compounds/

1-chloro-2-propanol

1-Chloro-2-propanol Use and Manufacturing

Methods of Manufacturing

(1) Obtained by hypochlorous acidification of propylene. Propylene, chlorine and water are fed into the hypochlorous acidification reaction tower in a certain proportion. Generally, when the propylene is excessive so that there is no free chlorine in the reaction liquid and tail gas and the chlorohydrin concentration in the reaction liquid of the tower is lower than 5%, the chloropropane The selectivity of alcohol can reach 90%. The tail gas is partially vented after washing with water and alkali to prevent the accumulation of inert gas, and the rest is compressed and mixed with fresh propylene to return to the reaction system. When the reaction tower temperature is 45-60℃, about 0.12-0.13MPa and excess propylene, the propylene conversion rate is 97%. Among them, 93.5% is chloropropanol, 4.5% is dichloropropane, 1.7% is 2.2'-dichlorodiisopropyl ether, and 0.3% is propionaldehyde, acetone and other by-products. In the obtained chloropropanol, 1-chloro-2-propanol accounts for about 90%, and 2-chloropropanol accounts for about 10%. (2) It is derived from the action of chloropropene and sulfuric acid. At low temperature, sulfuric acid was added dropwise to chloropropene and the reaction was stirred. The reaction liquid was slowly added to ice water, and then the finished product was obtained by distillation. The yield was 86.5%. In addition, the reaction of propylene oxide and hydrogen chloride can also produce 1-chloro-2-propanol.

Uses

Mainly used in the production of propylene oxide and in medicine for the synthesis of chlorpromazine

ESSENTIALLY 100% AS CHEMICAL INTERMEDIATE

2-Propanol, 1-chloro-: ACTIVE|2-Propanol, 1-chloro-, 3-(C6-12-alkyloxy) derivs.: INACTIVE|2-Propanol, 1-chloro-, 3-(C6-10-alkyloxy) derivs.: ACTIVE|2-Propanol, 1-chloro-, 3-(C12-18-alkyloxy) derivs.: INACTIVE|2-Propanol, 1-chloro-, 3-(C12-15-alkyloxy) derivs.: ACTIVE

METHOD INVOLVING GAS CHROMATOGRAPHY & FLAME IONIZATION DETECTION FOR DETERMINATION OF...PROPYLENE /CHLOROHYDRIN/...DESCRIBED BY GRIFFITH LAB. LATTER...APPLIED VOLHARD METHOD FOR CHLORINE TO STEAM DISTILLATE OF SLURRY OF TREATED FOOD.

Fire Hazards -> Mutagens, Flammable - 2nd degree

Computed Properties

Molecular Weight:94.54
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:94.0185425
Monoisotopic Mass:94.0185425
Topological Polar Surface Area:20.2
Heavy Atom Count:5
Complexity:22.9
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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