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(+-)-2,3-Dichloro-1-propanol

HCID 12018
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
616-23-9
Standard SMILES
OCC(Cl)CCl
InChIKey
ZXCYIJGIGSDJQQ-UHFFFAOYSA-N
Molecular formula
C3H6Cl2O
Average molar mass
128.98 g/mol
Monoisotopic mass
127.9795702

Overview

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

Names & identifiers

Preferred name
(+-)-2,3-Dichloro-1-propanol
IUPAC
2,3-dichloropropan-1-ol
English name
2,3-DICHLORO-1-PROPANOL
Molecular formula
C3H6Cl2O
Molecular weight
128.99

Names & synonyms

2,3-Dichloro-1-propanol616-23-91-Propanol, 2,3-dichloro-alpha,beta-Dichlorohydrin2,3-DICHLOROPROPANOL1,2-Dichloro-3-propanol2,3-Dichloropropyl alcoholGlycerol 1,2-dichlorohydrinGlycerol alpha,beta-dichlorohydrinbeta-DichlorohydrinDTXSID20240381,2-Dichloropropanol-3
Show more names
GLYCEROL-ALPHA2,3-DICHLORO-1-PROPAArotinolol impurity 62,3-dichloro-1-propano
DC1P88I7UKE7IMDTXCID504038BETA,GAMMA-DICHLOROHYDRINRefChem:81588(+-)-2,3-DICHLORO-1-PROPANOL210-470-02,3-Dichloropropan-1-ol

Database identifiers

CAS
616-23-9
PubChem CID
12018
DTXSID
DTXSID2024038
ChEMBL
CHEMBL1538584
UNII
88I7UKE7IM
EC Number
210-470-0
Nikkaji
J3.003A

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
6
Formal charge
0
Complexity
32

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Halogenated Alcohols
PesticidesPesticide -> EPA IRIS
Density · 2 items

1.3607 at 68 °F (NTP, 1992) - Denser than water; will sink

1.3607 @ 20 °C/4 °C

Color/FormVISCOUS LIQ
Solubility · 2 items

1 to 10 mg/mL at 76.1 °F (NTP, 1992)

Soluble in ethanol, ether, acetone

Flash Point196.5 °F (NTP, 1992)
Boiling Point · 2 items

361 to 365 °F at 760 mmHg (NTP, 1992)

183-185 °C

DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/.
Vapor Pressure0.18 [mmHg]
Refractive IndexINDEX OF REFRACTION: 1.4819 @ 20 °C/D

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 111 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H227: Combustible liquid [Warning Flammable liquids]

Hazard information

Regulatory Information · 3 items

Chemical: 1-Propanol, 2,3-dichloro-

1-Propanol, 2,3-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propanol, 2,3-dichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

2,3-Dichloro-1-propanol: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelPoison
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health Hazards · 1 item

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.

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used for the production of epichlorohydrin; [HSDB]

Production of epichlorohydrin

U.S. Production2023: 10,000,000 - <50,000,000 lb
Industry UsesIntermediate
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

1-Propanol, 2,3-dichloro-: ACTIVE

Applications · 3 items

Uses2,3-Dichloro-1-propanol may be employed as carbon and energy supplement for the growth of Pseudomonas putida strain (MC4).

UsesAn isomer of dichloropropanol; shows metabolite toxicity.

General DescriptionViscous colorless to amber liquid with an ethereal odor.

Upstream & downstream products

Upstream raw materials

1,3-dichloropropan-2-yl acetateAcetic acid 2,3-dichloropropyl ester2-chloropropane-1,3-diolAcetic acid 2-hydroxy-3-chloropropyl esterDIGLYCEROL3-Chloro-1,2-propanediol1,3-Dichloroacetone

Related reactions

2 records
New reaction record
HRID 247364 reaction equation
HRID 247364As reactantuspto-grants-1987_11
HRID 1383882 reaction equation
HRID 1383882As reactantuspto-grants-2001_07

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Physical Description · 3 items

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

Liquid

Colorless to amber liquid with an ethereal odor; [CAMEO]

Other Experimental Properties1 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

Physicochemical properties

Melting point
-29.15 °C · -29.15°C
Boiling point
182 °C · 182 °C
Density
1.36 g/mL · 1.360 g/mL at 20 °C (lit.)
refractive index
1.4835 · 1.4835-1.4855
Flash point
93 °C · 93 °C
storage temp.
2 · Sealed in dry,2-8°C
solubility
1 · 1-10g/l
pka
13.75 · 13.75±0.10(Predicted)
form
Liquid
color
Clear colorless
optical activity
-0.1 ° · -0.1°(C=0.01 g/ml CHCL3)
BRN
1732060 · 1732060
Henry's Law Constant
7.8 · 7.8×100 mol/(m3Pa) at 25℃, Wang et al. (2017)
InChI
1S/C3H6Cl2O/c4-1-3(5)2-6/h3,6H,1-2H2
InChIKey
ZXCYIJGIGSDJQQ-UHFFFAOYSA-N
SMILES
OCC(Cl)CCl
CAS DataBase Reference
616 · 616-23-9(CAS DataBase Reference)
FDA UNII
88 I7UKE7IM · 88I7UKE7IM
EPA Substance Registry System
2 · 2,3-Dichloropropanol (616-23-9)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301-H310-H319
Precautionary statements
262 · P262-P280-P301+P310+P330-P302+P352+P310-P305+P351+P338
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
T
Risk Statements
20 · 20-24/25-41
Safety Statements
26 · 26-36/37/39-45
RIDADR
2810 · UN 2810 6.1/PG 2
WGK Germany
3 · 3
RTECS
1225000 · UB1225000
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29051990 · 29051990
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 DermalAcute · Acute Tox. 2 DermalAcute Tox. 3 OralEye Irrit. 2
Hazardous Substances Data
616 · 616-23-9(Hazardous Substances Data)
Hazards Summary · 1 item

Irritating to skin; Severely irritating to eyes; Poisonous by ingestion and skin contact; Moderately toxic by inhalation; 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. [HSDB] Toxic after ingestion or skin absorption; An irritant; May cause serious injury to eyes; [MSDSonline]

Reactive GroupAlcohols and Polyols
TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,3-dichloropropanol is included on this list.

Reactivity Profile2,3-DICHLORO-1-PROPANOL is incompatible with oxidizers, oxygen and peroxides. (NTP, 1992)
Air and Water ReactionsMay be sensitive to prolonged exposure to air. Slightly soluble in water.
Hazard Classes and Categories · 2 items

Acute Tox. 3 (100%)

Flammable liquids - Category 4

Skin, Eye, and Respiratory IrritationsA skin and severe eye irritant.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

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.

Nonfire Spill Response · 1 item

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.

Disposal Methods · 1 item

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.

Preventive Measures · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Personal Protective Equipment (PPE)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.

Toxicology

Target OrgansCardiovascular
Environmental Fate · 3 items

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).

Adverse EffectsOccupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.
Effluent Concentrations2,3-Dichloropropanol has been detected in 1 of 46 US industrial effluent samples(1).
EPA IRIS Information · 3 items

2,3-Dichloropropanol

Cardiovascular

3 x 10 ^-3 mg/kg-day

Soil Adsorption/Mobility · 1 item

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.

Human Toxicity Excerpts · 2 items

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.

Artificial Pollution Sources2,3-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).
Environmental Biodegradation · 1 item

Incubation of 1,200 and 750 mg/kg 2,3-dichloropropanol with soil samples from Texas and Mississippi that had not previously been exposed to chemical waste resulted in calculated biodegradation removal half-lives of 23.1 and 55.3 days, respectively(1).

Environmental Bioconcentration · 1 item

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.

Volatilization from Water/Soil · 1 item

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).

Non-Human Toxicity Excerpts · 2 items

2,3-DICHLOROPROPANOL-1 RATED 5 ON RABBIT EYES. ...TESTED EXTERNALLY ON EYES OF RABBITS...PAYING PARTICULAR ATTENTION TO CONDITION OF CORNEA. MOST SEVERE INJURIES HAVE BEEN RATED 10.

ALL PROPANOL DERIV TESTED, INCL 2,3-DICHLORO-1-PROPANOL, WERE MUTAGENIC FOR SALMONELLA TYPHIMURIUM.

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,3-dichloropropanol is included on this list.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
UB1225000
ridadr
UN 2810 6.1/PG 2
hs_code
29051990
risk_code
20-24/25-41
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T
safety_code
26-36/37/39-45
hazard_class
6.1
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
III
Hazard statements
H301-H310-H319
Hazard Classifications
Acute Tox. 2 DermalAcute Tox. 3 OralEye Irrit. 2
Precautionary statements
P262-P280-P301+P310+P330-P302+P352+P310-P305+P351+P338
Hazardous Substances Data
616-23-9(Hazardous Substances Data)
2,3-dichloropropyl acrylate
2,3-Dichloropropionaldehyde
1,2,3-Trichloropropane
Allyl chloride
Allyl alcohol

Downstream products

EpichlorohydrinGLYCIDYL METHYL ETHER2,3-Dimercapto-1-propanolTetrachloroethylene1-BROMO-2,3-DICHLOROPROPANE