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1-Chlorooctane

HCID 8142
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Basic information

CAS
111-85-3
Standard SMILES
CCCCCCCCCl
InChIKey
CNDHHGUSRIZDSL-UHFFFAOYSA-N
Molecular formula
C8H17Cl
Average molar mass
148.67 g/mol
Monoisotopic mass
148.1018782

Names & identifiers

Preferred name
1-Chlorooctane
IUPAC
1-chlorooctane
English name
Octylchloride
Molecular formula
C8H17Cl
Molecular weight
148.67

Names & synonyms

1-CHLOROOCTANE111-85-3Octyl chloriden-Octyl chlorideOctane, 1-chloro-Capryl chloride1-Octyl chlorideDTXSID0021543HSDB 5551NSC 5406NSC-5406EINECS 203-915-5
Show more names
E1047328LO1-CHLOROOCTANE [HSDB]DTXCID501543EC 203-915-5nOctyl chloride1Octyl chlorideOctane, 1chloroRefChem:431503

Database identifiers

CAS
111-85-3、57214-71-8
PubChem CID
8142
DTXSID
DTXSID0021543
ChEMBL
CHEMBL158445
UNII
E1047328LO
EC Number
203-915-5
Nikkaji
J1.990I

Properties

Computed structural properties

XLogP
4.7
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
6
Heavy atoms
9
Formal charge
0
Complexity
43.8

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Halogenated Aliphatics, Saturated
SpringerMaterials PropertiesBoiling point
LogP · 2 items

Log P= 4.73

4.73

Density0.8738 @ 20 °C/4 °C
Color/FormCOLORLESS LIQUID
Solubility · 2 items

INSOL IN WATER; VERY SOL IN ALCOHOL, ETHER; SLIGHTLY SOLUBLE IN CARBON TETRACHLORIDE

SOL IN MOST ORG SOLVENTS

Flash Point · 2 items

70 °C

158 °F

Boiling Point181.5 °C @ 760 MM HG
Melting Point-57.8 °C
Vapor Pressure · 2 items

0.95 [mmHg]

0.95 mm Hg at 25 °C

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

H304 (56.6%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

P273, P301+P316, P331, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 198 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H227: Combustible liquid [Warning Flammable liquids]

Hazard information

Regulatory Information · 4 items

Chemical: Octane, 1-chloro-

Octane, 1-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Octane, 1-chloro- 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)

REACH registered substance: 1-chlorooctane (EC: 203-915-5)

1-Chlorooctane: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Octane, 1-chloro-: Human health tier I assessment
Hazards SummaryEmergency medical treatment: see Hydrocarbons; [HSDB] An irritant; [MSDSonline]
DOT Hazard Classification · 2 items

1-Chlorooctane

Marine pollutant

Hazard Classes and Categories · 2 items

Asp. Tox. 1 (56.6%)

Flammable liquids - Category 4

Safety & protection

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used to make organometallics, as an alkylating agent in organic synthesis, and as a stabilizer for dibutylmagnesium; [HSDB]

CHEMICAL INT; IN MFR OF ORGANOMETALLICS

CHEM INT FOR OCTYLDIALKYLAMINES & OCTYL QUATERNARY AMINES

ALKYLATING AGENT IN ORG SYNTH

Used as a chemical intermediate for the synthesis of dimethyldioctylammonium chloride; tetra-n-octyltin.

1-Chlorooctane is used as a stabilizer for dibutylmagnesium (or n-butyl-sec-butylmagnesium).

U.S. Production · 3 items

2023: 58,520 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Industry UsesIntermediate
Methods of Manufacturingn-Octanol + hydrogen chloride, anhydrous (alcohol chlorination)
Formulations/PreparationsCommercial products have 95% C8 content.
General Manufacturing Information · 3 items

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Octane, 1-chloro-: ACTIVE

CMPD CONTAINING THE MONO- OR DICHLOROHYDROCARBONS AS ACTIVE INGREDIENTS ARE EFFECTIVE IN CONTROLLING COCCIDIOSIS IN DOMESTIC FOWLS. THUS, 1-CHLOROOCTANE 70 AND SURFACTANTS 30 PARTS WERE MIXED TO GIVE AN EMULSION PREPN. PREPN WAS DILUTED TO 40-100-FOLD & APPLIED TO CHICKEN HOUSES.

Related reactions

40 records
New reaction record
HRID 2535 reaction equation
HRID 2535As reactantuspto-grants-1998_03
HRID 26171 reaction equation
HRID 26171As reactantuspto-grants-1979_04
HRID 26172 reaction equation
HRID 26172As reactantuspto-grants-1979_04
HRID 46588 reaction equation
HRID 46588As reactantuspto-grants-1979_11
HRID 52765 reaction equation
HRID 52765As reactantuspto-grants-1997_04
HRID 96158 reaction equation
HRID 96158As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 120782 reaction equation
HRID 120782As productTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 154103 reaction equation
HRID 154103As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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Surface Tension
27.65 dyne/cm at 20 °C
Refractive IndexINDEX OF REFRACTION: 1.4305 @ 20 °C/D
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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 8900(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 1-chlorooctane will be immobile in soil(SRC). Volatilization of 1-chlorooctane may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.0X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The rate of this process may be attenuated based on the Koc value estimated for this compound(SRC). Volatilization from dry soil surfaces(SRC) is expected based on a measured vapor pressure of 0.95 mm Hg(5). Based on limited data, 1-chlorooctane is expected to readily biodegrade in soil under aerobic conditions(SRC). In an aerobic aqueous screening test, 1-chlorooctane, incubated with a sludge inoculum, reached 74-81% of the theoretical BOD in 4 weeks(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4.73(SRC), determined from a measured log Kow(2,SRC) and a recommended regression-derived equation(1), indicates that 1-chlorooctane should adsorb to suspended solids and sediment in water(SRC). 1-Chlorooctane may volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 6.0X10-2 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 4 hours and 5 days, respectively(1,SRC). Adsorption to sediment and particulate matter may attenuate the rate of this process(SRC). According to a classification scheme(4), an estimated BCF value of 2300(1,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is very high(SRC). Based on limited data, 1-chlorooctane is expected to readily biodegrade in water under aerobic conditions(SRC). In an aerobic aqueous screening test, 1-chlorooctane, incubated with a sludge inoculum, reached 74-81% of the theoretical BOD in 4 weeks(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chlorooctane, which has a measured vapor pressure of 0.95 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chlorooctane 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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1 item

The Koc of 1-chlorooctane is estimated as approximately 8900(SRC), using a measured log Kow of 4.73(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1-chlorooctane will be immobile in soil(SRC).

Human Toxicity Excerpts · 5 items

LIQUID FRACTIONS ARE...CENTRAL NERVOUS DEPRESSANTS WHEN ABSORBED FROM ALIMENTARY TRACT, OR SEVERE PULMONARY IRRITANTS WHEN ASPIRATED. /ALIPHATIC HYDROCARBONS/

LIQUIDS, AS FAT SOLVENTS, EXTRACT SEBUM FROM SKIN LEAVING DRY IRRITATED SURFACE PRONE TO CRACKING & BACTERIAL INFECTION. /ALIPHATIC HYDROCARBONS/

A. ACUTE POISONING: (FROM INHALATION OR INGESTION). NAUSEA, VOMITING, COUGH, & PULMONARY...EDEMA, BLOODY SPUTUM, & BRONCHIAL PNEUMONIA WITH FEVER & COUGH. PNEUMOTHORAX & EMPHYSEMA MAY COMPLICATE RECOVERY. /ALIPHATIC HYDROCARBONS/

IF LARGE AMT (OVER 1 ML/KG) IS INGESTED & RETAINED, SYMPTOMS...INCL...SLOW & SHALLOW RESPIRATION, UNCONSCIOUSNESS, & CONVULSIONS. VENTRICULAR FIBRILLATION CAN OCCUR AFTER INGESTION OR INHALATION. /ALIPHATIC HYDROCARBONS/

B. CHRONIC POISONING: (FROM INHALATION) DIZZINESS, WEAKNESS, WT LOSS, ANEMIA, NERVOUSNESS, PAINS IN LIMBS, PERIPHERAL NUMBNESS, & PARESTHESIAS. /ALIPHATIC HYDROCARBONS/

Artificial Pollution Sources · 1 item

1-Chlorooctane's production and use in the manufacture of organometallics, as a chemical intermediate(1), and as a stabilizer(2) may result in its release to the environment through various waste streams(SRC). 1-Chlorooctane is formed during the chlorination process in the treatment of drinking water(3).

Environmental Biodegradation · 1 item

In an aerobic aqueous screening test, 1-chlorooctane at 100 mg/l was incubated with a sludge inoculum; 74-81% of the theoretical BOD was measured at 4 weeks(1). 1-Chlorooctane at 1 mg/l was readily biodegraded by a sludge inoculum with the utilization of 900 ug/L oxygen within 1.7 days; complete degradation was reported in 3 days with the formation of a metabolite containing a carbonyl oxygen(2). A pure culture of Corynebacterium sp. was shown to degrade 1-chlorooctane(3).

Environmental Bioconcentration · 1 item

An estimated BCF value of 2300 was calculated for 1-chlorooctane(SRC), using a measured log Kow of 4.73(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is very high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 1-chlorooctane is estimated as 6.0X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1-chlorooctane will volatilize rapidly from water surfaces(2,SRC). 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) is estimated as approximately 4 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 5 days(2,SRC). The rate of this process may be attenuated somewhat by adsorption to suspended solids and sediment based on the Koc value estimated for this compound(SRC). 1-Chlorooctane's values for vapor pressure, 0.95 mm Hg(3) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil surfaces may occur(SRC).

Non-Human Toxicity ExcerptsEXTREMELY HIGH LEVELS OF /C5 TO C8 HYDROCARBON VAPOR/...MAY PRODUCE DEATH IN EXPERIMENTAL ANIMALS... /ALIPHATIC HYDROCARBONS/
Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 1-chlorooctane with photochemically-produced hydroxyl radicals has been estimated as 7.8X10-12 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).

Probable Routes of Human Exposure · 1 item

NIOSH (NOES Survey 1981-1983) has statistically estimated that 28 workers are potentially exposed to 1-chlorooctane in the USA(1). Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where 1-chlorooctane is produced or used. The general population will be exposed to 1-chlorooctane via ingestion of drinking water and dermal contact with vapors, water, and other products containing 1-chlorooctane(SRC).

Environmental Water Concentrations · 2 items

SURFACE WATER: 1-Chlorooctane was detected in the water of the Black Warrior River in Tuscaloosa, AL at unreported concentrations(1).

DRINKING WATER: 1-Chlorooctane was detected in drinking water at an unreported location and concentration(1). Drinking water sampled from the District of Columbia water supply contained 1-chlorooctane at 0.001 ppm(2).