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Home > Encyclopedia > (±)-2,3-Dichloro-1-propanol

(±)-2,3-Dichloro-1-propanol

(±)-2,3-Dichloro-1-propanol structure

(±)-2,3-Dichloro-1-propanol 

structure
  • CAS No:

    616-23-9

  • Formula:

    C3H6Cl2O

  • Chemical Name:

    (±)-2,3-Dichloro-1-propanol

  • Synonyms:

    1-Propanol,2,3-dichloro-;2,3-Dichloro-1-propanol;Glycerol α,β-dichlorohydrin;α,β-Dichlorohydrin;β-Dichlorohydrin;Glycerol 1,2-dichlorohydrin;2,3-Dichloropropyl alcohol;β,γ-Dichlorohydrin;(±)-2,3-Dichloro-1-propanol;(RS)-2,3-Dichloro-1-propanol;2,3-Dichlorohydrin;1,2-Dichlorohydrin;82890-22-0

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

CLEAR COLORLESS LIQUID There are 4 isomers of dichloropropanols 1,3- dichloro-2-propanol (96-23-1) and “dichloropropanols” (26545-73-3) are citations in environmental regulations: C3H6OCl2 is a colorless viscous liquid with a chloroformlike odor. Slightly soluble in water. 1,3-Dichloro-2- propanol:


2,3-dichloro-1-propanol is a viscous colorless to amber liquid with an ethereal odor. (NTP, 1992)|Liquid


2,3-dichloro-1-propanol is a viscous colorless to amber liquid with an ethereal odor. (NTP, 1992)

(±)-2,3-Dichloro-1-propanol Basic Attributes

128.98

128.99

210-470-0

2810

DTXSID2024038

VISCOUS LIQ

29051990

Characteristics

20.2

0.65

2,3-dichloro-1-propanol is a viscous colorless to amber liquid with an ethereal odor. (NTP, 1992)

1.3607 g/cm3 @ Temp: 20 °C

-29.15°C

183-185 °C

196.5° F (NTP, 1992)

1.462

soluble in ethanol, ether, acetone

1 MG/L IS EQUIV TO 189.5 PPM @ 25 °C & 760 MM HG; 1 PPM IS EQUIV TO 5.28 MG/CU M @ 25 °C & 760 MM HG

May be sensitive to prolonged exposure to air. Slightly soluble in water.

Alcohols and Polyols

2,3-DICHLORO-1-PROPANOL is incompatible with oxidizers, oxygen and peroxides. (NTP, 1992)

Safety Information

III

6.1

UN 2810 6.1/PG 2

3

R20;R24/25;R41

S26-S36/37/39-S45

UB1225000

T:Toxic;

P280-P302 + P350-P305 + P351 + P338-P310

H301-H310-H318-H332

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.

This chemical is combustible. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P262, P264, P270, P271, P280, P301+P310, P302+P350, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P405, and P501|Aggregated GHS information provided by 67 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P262, P264, P270, P280, P301+P310, P302+P350, P305+P351+P338, P309+P311, P310, P314, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P235, P405, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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 keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

A skin and severe eye irritant.

2,3-Dichloropropanol has been detected in 1 of 46 US industrial effluent samples(1).

Toxicity

LD50 Rat oral 90 mg/kg|LD50 Rabbit skin 200 mg/kg

2,3-Dichloropropanol's production and use in the production of epichlorohydrin(1) may result in it's release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a structure estimation method(2), indicates that 2,3-dichloropropanol is expected to have very high mobility in soil(SRC). Volatilization of 2,3-dichloropropanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4X10-9 atm-cu m/mole(SRC), obtained using a fragment constant estimation method(3). 2,3-Dichloropropanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.18 mm Hg(SRC), determined from a fragment constant method(4). The half-life for the biodegradation of 2,3-dichloropropanol in two different soils was 23.1 and 55.3 days(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a structure estimation method(2), indicates that 2,3-dichloropropanol 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 4X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). 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). 2,3-Dichloropropanol has a neutral first-order hydrolysis rate constant of 5.3X10-5 1/s and base-catalyzed second-order hydrolysis rate constant of 20.6 L/mole-hour(7) and, based on these values, is expected to have a hydrolysis half-life of approximately 1.4 years at pH 7 and 140 days at pH 8(7,SRC). Limited data indicate that 2,3-dichloropropanol may slowly biodegrade under aerobic conditions(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-dichloropropanol, which has an estimated vapor pressure of 0.18 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-dichloropropanol 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 9 days(SRC) from its estimated rate constant of 1.77X10-12 atm cu m/mol(3).

The rate constant for the vapor-phase reaction of 2,3-dichloropropanol with photochemically-produced hydroxyl radicals has been estimated as 1.77X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 9 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3-Dichloropropanol has a neutral first-order hydrolysis rate constant of 5.3X10-5 1/s and base-catalyzed second-order hydrolysis rate constant of 20.6 L/mole-hour(2), and, based on these values, is expected to have a hydrolysis half-life of approximately 1.4 years at pH 7 and 140 days at pH 8(2,SRC). 2,3-Dichloropropanol is not expected to directly photolyze due to the lack of absorption in the environmental spectrum(3).

An estimated BCF of 3 was calculated for 2,3-dichloropropanol(SRC), using an estimated log Kow of 0.78(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 2,3-dichloropropanol can be estimated to be about 4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,3-dichloropropanol is expected to have very high mobility in soil.

The Henry's Law constant for 2,3-dichloropropanol is estimated as 3X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3-dichloropropanol is expected to be essentially nonvolatile(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 >10,000 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 >80,000 days(SRC). 2,3-Dichloropropanol's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 2,3-Dichloropropanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.18 mm Hg(SRC) determined from a fragment constant method(3).

Occupational exposure to 2,3-dichloropropanol may occur through inhalation and dermal contact with this compound at workplaces where 2,3-dichloropropanol is produced or used. (SRC)

Drug Information

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the eyes, skin, mucous membranes and respiratory tract; abdominal pain, dyspnea, coughing, hemolytic anemia, cerebral hemorrhage, toxic hepatitis, gastrointestinal hemorrhage, nephritis, respiratory edema, headache, nausea, vomiting, somnolence, vertigo, diarrhea, abdominal pain, decreased urinary output, jaundice, death by renal failure, comatose, central nervous system depression and damage to the kidney and liver. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. This compound can cause irritation of the skin, eyes and mucous membranes. (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. 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)

Two middle aged men developed severe hepatic injury just after cleaning a dichloropropanol tank at a plant producing dichloropropanol. They died from hepatic failure 4 and 11 days respectively, after carrying out the work. Liver specimens taken at autopsy from one of the cases showed submassive hepatic necrosis. /Dichloropropanol/|Poison by ingestion and skin contact. Moderately toxic by inhalation.

1-propanol, 2,3-dichloro-

(±)-2,3-Dichloro-1-propanol Use and Manufacturing

Uses

An isomer of dichloropropanol; shows metabolite toxicity.


Intermediates

All other basic organic chemical manufacturing|1-Propanol, 2,3-dichloro-: ACTIVE

Computed Properties

Molecular Weight:128.98
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:127.9795702
Monoisotopic Mass:127.9795702
Topological Polar Surface Area:20.2
Heavy Atom Count:6
Complexity:32
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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