1-Bromo-3-chloropropane

Log P = 2.18

2.18

1.5969 @ 20 °C/4 °C

Relative density (water = 1): 1.6

Very sol in alc, ether, chloroform

SOL IN METHANOL

Soluble in oxygenated and chlorinated solvents.

In water = 2240 mg/l at 25 °C.

Solubility in water, g/100ml at 25 °C: 0.224

57 °C

57 °C

143.3 °C @ 760 MM HG

143.3 °C

-58.90 °C

-58.9 °C

6.38 [mmHg]

Vapor pressure, kPa at 25 °C: 0.85

Danger

H226 (28.6%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 189 reports by companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Propane, 1-bromo-3-chloro-

Hazard Traits - Carcinogenicity

Propane, 1-bromo-3-chloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 1-bromo-3-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)

Status: Active Update: 12-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24661

1-Bromo-3-chloropropane: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

· Some of these materials may burn, but none ignite readily.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 57 °C explosive vapour/air mixtures may be formed.

Excerpt from ERG Guide 159 [Substances (Irritating)]:

· Inhalation of vapors or dust is extremely irritating.

May cause CNS effects and liver injury; [ICSC] No significant adverse gross or histopathological changes observed with regard to body weight, kidneys, or male reproductive organs in two week feeding study with rats; Emergency medical treatment: see Dibromochloropropane; [HSDB] A strong eye and respiratory tract irritant; [CAMEO] Observations in four hour inhalation study with rats include pulmonary hemorrhages, fatty degeneration of the liver and heart, albuminoid degeneration of the kidney, and edema and swelling of brain neural tissue; No gross or histopathological changes observed in another inhalation study; Classified as not irritating to skin and eyes of rabbits (some corneal opacity and conjunctival irritation/redness observed, but cleared by day 8 in all studies); Observations in 24 day study with rats include liver degeneration, increased frequency of chromosomal aberrations in bone marrow, and decrease in testicular weight coefficient and spermatozoa motility; Not mutagenic to various Salmonella typhimurium strains; No significant adverse effects to male reproductive system observed in five week feeding or two week gavage studies with rats; [IUCLID]

Halogenated aliphatic compounds, such as 1-BROMO-3-CHLOROPROPANE, are moderately or very reactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch or walk through spilled material.

Excerpt from ERG Guide 159 [Substances (Irritating)]:

General First Aid:

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.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Immediate precautionary measure

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 63(SRC), determined from a measured water solubility(2) and a regression-derived equation(3,SRC), indicates that 1-bromo-3-chloropropane will have high mobility in soil(SRC). Volatilization of 1-bromo-3-chloropropane may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.5X10-4 atm-cu m/mole(SRC), determined using a fragment constant estimation method(4). Volatilization from dry soil surfaces(SRC) is expected based on an extrapolated vapor pressure of 6.4 mm Hg(5,SRC). Based on limited data, this compound is expected to be resistant to aerobic biodegradation(SRC); 1-bromo-3-chloropropane, inoculated with effluent from a biological waste treatment plant, reached 3% of the theoretical BOD in 5 days(6).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 63(SRC), determined from a measured water solubility(2) and a regression-derived equation(1,SRC), indicates that 1-bromo-3-chloropropane should not adsorb to suspended solids and sediment in water(SRC). 1-Bromo-3-chloropropane should volatilize from water surfaces(1,SRC) given an estimated Henry's Law constant of 2.5X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 8 hours and 6 days, respectively(1,SRC). According to a classification scheme(5), an estimated BCF value of 27(1,SRC), from a measured log Kow(4), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited data, this compound is expected to be resistant to aerobic biodegradation(SRC); 1-bromo-3-chloropropane, inoculated with effluent from a biological waste treatment plant, reached 3% of the theoretical BOD in 5 days(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-bromo-3-chloropropane, which has an extrapolated vapor pressure of 6.4 mm Hg at 25 °C(2,SRC), will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-bromo-3-chloropropane 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 18 days(3,SRC).

Tremor. Drowsiness.

See Inhalation.

The Koc of 1-bromo-3-chloropropane is estimated as approximately 63(SRC), using a measured water solubility of 2240 mg/l at 25 °C(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1-bromo-3-chloropropane has high mobility in soil(SRC).

Toxicity of 1-chloro-3-bromopropane (CBP) with respect to testicular changes was evaluated in male albino Wistar rats (10/treated group, 20 in arachis oil vehicle control group) exposed orally to CBP by gavage at dosage levels of 40 or 160 mg/kg/day for 14 days. On day 15, the animals were sent for pathological examination. Significant differences between treated and control animals were not observed at any dose level. No significant differences between treated and control animals were observed in the following: body weights, body weight gain, testes weights, morphology, or detailed macroscopic and microscopic examination of the kidneys, testes, epididymides, ductuli efferentes, and vasa deferentes.

URBAN/SUBURBAN: Source-dominated air samples contained 1-bromo-3-chloropropane at a median concentration of 2 parts/trillion(1). Air samples collected from a geographic area associated with the bromine industry in Arkansas contained 1-bromo-3-chloropropane at unreported concentrations(2). Ambient concentrations of 1-bromo-3-chloropropane in air surrounding the Ethyl Corporation, Magnolia, AK in July 1977 ranged from trace levels to 1,688 ng/cu m(3). Ambient concentrations of 1-bromo-3-chloropropane in air surrounding the Great Lakes Corporation and the Michigan Chemical Corporation in El Dorado, AK in July 1977 ranged from not detected to trace levels and trace to 63 ng/cu m, respectively(3).

Mortality rates in workers exposed to brominated chemicals in manufacturing research facilities from 1935 to 1976 were investigated epidemiologically. These workers were potentially exposed to 1,2-dibromo-3-chloropropane, polybrominated biphenyls, tris(2,3-dibromopropyl)phosphate, trimethylene chlorobromide, and DDT as well as various organic and inorganic bromides. Data was collected from personnel records and death certificates. Standardized mortality ratios were calculated for comparison against rates for American white males. In all, 2,806 male workers were identified as living, 578 workers were identified as deceased. Almost half of the cohort had worked less than 6 mo. The average term of employment was 3 yr 9 mo. Overall, the standardized mortality ratio for workers was lower than that of American white males. Deaths from diabetes mellitus occurred more frequently in these workers, with rates more than twice the number expected. Overall cancer death rates were comparable among the workers and the comparison population. Stomach cancer rates were lower among workers than expected; otherwise, differences in site specific cancer deaths were not statistically significant. The workers showed lower than expected death rates for diseases of the circulatory and digestive systems and pneumonia. There was no incr trend in mortality with length of employment. /Results indicate/ that this study has identified a number of potential health problems and should be continued with a longer observation period to establish mortality trends.

A historical prospective mortality study was conducted for 3579 white male workers employed between 1935 and 1976 at four Vesicol Chemical Corporation facilities. The members of the study cohort were potentially exposed to brominated compounds including 1,2-dibromo-3-chloropropane (DBCP), tris(2,3-dibromopropyl)phosphate, trimethylene chlorobromide. Some were exposed to DDT, polybrominated biphenyls (PBB) and others to radiation from rare earths process. Overall mortality was lower than expected, particularly in diseases of the circulatory system, nonmalignant respiratory diseases and diseases of the digestive system. No significant overall or cause specific mortality excess was noted among those potentially exposed to either TRIS or DDT. No cancer death was noted among the rare earth employees. Mortality from diabetes mellitus was significantly elevated among the maintenance workers hired in the early 1940's. A significant mortality excess due to diseases of the circulatory system was observed among workers potentially exposed to DBCP and or rare earth process. Mortality from testicular cancer was significantly higher in those exposed to organic bromides. The common potential exposure of the testicular cancer decedents was methyl bromide. A number of other cause specific mortality excesses were also noted.

1-Bromo-3-chloropropane

Group 2B: Possibly carcinogenic to humans

Volume 125: (2020) Some Industrial Chemical Intermediates and Solvents

2020 online

2019

The present study examines how variations in position, number, and type of halogen substituents affect renal and testicular necrosis, renal and testicular DNA damage, and the tissue distribution of the halogenated propanes. Groups of five male MOL:WIST rats were given single ip injections, ranging from 85 to 3000 um/kg of 1,2-dibromo-3-chloropropane (DBCP), 1,2,3-tribromopropane (TBP), 1,3-dichloro-2-bromopropane (DB2CP), or 1-bromo-2,3-dichloropropane (B2,3DCP), 1,3-dibromopropane, 1,2-dibromopropane, 1,2,3-trichloropropane or 1-bromo-3-chloropropane. The most potent in causing organ damage in both kidney and testes were DBCP and TBP. DB2CP was less organ toxic than DBCP or TBP, but induced more organ damage than B2,3DCP and DC2BP. The ability of the halogenated propanes to induce DNA damage in vivo correlated well with their ability to induce organ damage. However, DNA damage occurred at lower doses and after a shorter period of exposure. DNA damage may be an initial event in the development of organ necrosis by halogenated propanes in general. Testicular DNA damage induced by the halogenated propanes in vivo correlated well with the DNA damage observed in isolated testicular cells in vitro, showing that toxicity was due to in situ activation. The findings established a good relationship between in vivo organ necrogenic effects and DNA damage for a series of halogenated propanes. Both the type, the number, and the position of the halogens affected the toxic potential. The most toxic of the halogenated propanes contained three halogens with at least two vicinal bromines.

Used as a chemical intermediate for organic synthesis (i.e. pharmaceuticals); [HSDB]

IN ORGANIC SYNTHESIS; IN PHARMACEUTICALS

CHEM INT FOR PHARMACEUTICALS-EG, ACETOPHENAZINE MALEATE

CHEM INT FOR ORG SYNTH, EG, DIALKYLAMINOPROPYL CHLORIDES

Used as a chemical intermediate for the synthesis of cyclomethycaine; fluphenazine; opipramol; pentoxifylline; perphenazine; piperocaine; prochlorperazine; propentofylline; reproterol; trazodone; trifluoperazine; urapidil; verapamil.

1-Bromo-3-chloropropane is a useful reaction intermediate to prepare gamma-chloropropyl derivatives...for example, the cyanide displacement of 1-bromo-3-chloropropane forms gamma-chlorobutyronitrile, an intermediate used for the production of herbicides, pesticides, pharmaceuticals, and other commercial products.

2023: <50,000 lb

(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS

1-Bromo-3-chloropropane is virtually always produced by the free-radical addition of anhydrous hydrogen bromide to allyl chloride.

1-Bromo-3-chloropropane can be made from ethylene and methylene chlorobromide.

All Other Basic Organic Chemical Manufacturing

Propane, 1-bromo-3-chloro-: ACTIVE

The yield of crude product, which typically consists of 95% primary and 5% secondary bromochloropropanes, is about 95% based on converted allyl chloride. The minor isomer can easily be separated by distillation if product specifications call for higher purity.