HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Bromo-3-chloropropane
BROMOCHLOROPROPANE · 3-Chloro-1-bromopropane · 3-Bromo-1-chloropropane · TRIMETHYLENE CHLOROBROMIDE · I-BCP · 1,3-BCP · CHLOROBROMOPROPANE · 1-CHLORO-3-BROMOPROPANE
Identifiers & Physical Properties
| CAS No. | 109-70-6 |
|---|---|
| Molecular formula | C3H6BrCl |
| Average molar mass | 157.44 g/mol |
| Monoisotopic mass | 155.93413997 g/mol |
| SMILES | ClCCCBr |
| InChIKey | MFESCIUQSIBMSM-UHFFFAOYSA-N |
| PubChem CID | 8006 |
| ChEMBL | CHEMBL156560 |
| ChEBI | CHEBI:189106 |
| EC No. | 203-697-1 |
| DTXSID | DTXSID1051565 |
Chemical & Physical Properties
| XLogP | 1.9 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 2 |
| Heavy atoms | 5 |
| Formal charge | 0 |
| Complexity | 16.4 |
| Chemical classes | Other Classes -> Halogenated Aliphatics, Saturated |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (partition coefficient) | Log P = 2.18 |
| Density | 1.5969 @ 20 °C/4 °CRelative density (water = 1): 1.61.592 g/mL at 25 °C (lit.) |
| Color/Form | COLORLESS LIQUID |
| Solubility | Very sol in alc, ether, chloroformSOL IN METHANOLSoluble in oxygenated and chlorinated solvents.In water = 2240 mg/l at 25 °C.Solubility in water, g/100ml at 25 °C: 0.2242.24g/l insoluble |
| Flash point | 57 °C81 °C |
| Boiling point | 143.3 °C @ 760 MM HG144-145 °C (lit.) |
| Melting point | -58.90 °C-58.9 °C-59 °C |
| Vapor density | Relative vapor density (air = 1): 5.4 |
| Vapor pressure | 6.38 [mmHg]Vapor pressure, kPa at 25 °C: 0.857.5 hPa (20 °C) |
| Refractive index | INDEX OF REFRACTION: 1.4864 @ 20 °C/Dn20/D 1.486(lit.) |
| Storage conditions | room temp |
| Physical state | liquid |
| Color | Clear liquid |
| Explosive limits | 3.2-8.6%(V) |
| BRN | 605278 |
| Henry's law constant | 3.9×10-2 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability | Volatile |
| InChI | 1S/C3H6BrCl/c4-2-1-3-5/h1-3H2 |
| InChIKey | MFESCIUQSIBMSM-UHFFFAOYSA-N |
| SMILES | ClCCCBr |
| CAS DataBase Reference | 109-70-6(CAS DataBase Reference) |
| FDA UNII | KA4WR2LS00 |
| NIST Chemistry Reference | Propane, 1-bromo-3-chloro-(109-70-6) |
| IARC | 2B (Vol. 125) |
| EPA Substance Registry System | Propane, 1-bromo-3-chloro- (109-70-6) |
| UNSPSC Code | 41105515 |
| NACRES | NA.52 |
| GHS pictogram | GHS02,GHS06,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H331-H302-H313-H371-H373-H341-H412-H226 |
| GHS precautionary statements | P501-P273-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P308+P311-P303+P361+P353-P301+P312+P330-P304+P340+P311-P403+P233-P403+P235-P405 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn |
| Risk statements (R) | 10-22-36/37/38-20/21/22-20/22-68-52/53-37 |
| Safety statements (S) | 16-45-36/37/39-26 |
| UN transport number | UN 2688 |
| Water hazard class (WGK) | 3 |
| RTECS number | TX4113000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Muta. 2STOT SE 3 |
| Packing group | III |
| Customs code | 29034980 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazardous substances data | 109-70-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 1100 - 1200 mg/kg LD50 dermal Rat > 2000 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | DangerH226 (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.H226: Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatory information | Chemical: Propane, 1-bromo-3-chloro-Hazard Traits - CarcinogenicityPropane, 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/246611-Bromo-3-chloropropane: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| Other safety information | Evaluation - 1-bromo-3-chloropropane and 1,3-dibromopropane |
| DOT label | Poison |
| Fire hazards | 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. |
| Health hazards | Excerpt from ERG Guide 159 [Substances (Irritating)]:· Inhalation of vapors or dust is extremely irritating. |
| Hazards summary | 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 ratsEmergency 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 tissueNo gross or histopathological changes observed in another inhalation studyClassified 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 motilityNot mutagenic to various Salmonella typhimurium strainsNo significant adverse effects to male reproductive system observed in five week feeding or two week gavage studies with rats[IUCLID] |
| DOT ID and guide | 2688 159 |
| Reactive group | Halogenated Organic Compounds |
| UN classification | UN Hazard Class: 6.1UN Pack Group: III |
| Reactivity Profile | 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. |
| Chemical Dangers | Decomposes on burning. This produces toxic and corrosive gases including hydrogen bromide (see ICSC 0282) and hydrogen chloride (see ICSC 0163). |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| Fire fighting | 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. |
| First aid measures | 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 . |
| Accidental release measures | · 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. |
| First aid | Excerpt from ERG Guide 159 [Substances (Irritating)]:General First Aid: |
| Safe storage | Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Nonfire spill response | Excerpt from ERG Guide 159 [Substances (Irritating)]: |
| Disposal methods | 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. |
| Spillage disposal | 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. |
| Preventive Measures | AVOID INHALATION OF FUMES. |
| Isolation and Evacuation | Excerpt from ERG Guide 159 [Substances (Irritating)]:Immediate precautionary measure |
| Eye Prevention | Wear safety spectacles. |
| Environmental fate | 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)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). |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| Exposure routes | The substance can be absorbed into the body by inhalation of its vapour and by ingestion. |
| Signs and Symptoms | Tremor. Drowsiness.See Inhalation. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | 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). |
| TSCA Test Submissions | 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. |
| Atmospheric Concentrations | 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). |
| Human Toxicity Excerpts | 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 expectedotherwise, 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. |
| Artificial Pollution Sources | 1-Bromo-3-chloropropane's production and use in organic syntheses and in the production of pharmaceuticals(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | 1-Bromo-3-chloropropane, inoculated with effluent from a biological waste treatment plant, reached 3% of the theoretical BOD in 5 days(1). |
| Carcinogen Classification | 1-Bromo-3-chloropropaneGroup 2B: Possibly carcinogenic to humansVolume 125: (2020) Some Industrial Chemical Intermediates and Solvents2020 online2019 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | TX4113000 |
| UN transport number | UN 2688 |
| Customs code | 29034980 |
| Toxicity | LD50 orally in Rabbit: 1100 - 1200 mg/kg LD50 dermal Rat > 2000 mg/kg |
| Risk statements (R) | 10-22-36/37/38-20/21/22-20/22-68-52/53-37 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS06,GHS08 |
| Hazard symbols | Xn |
| Safety statements (S) | 16-45-36/37/39-26 |
| Hazard class | 6.1Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Chronic 3Muta. 2STOT SE 3 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Packing group | III |
| Target organs | Respiratory system |
| GHS hazard statements | H331-H302-H313-H371-H373-H341-H412-H226 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P501-P273-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P308+P311-P303+P361+P353-P301+P312+P330-P304+P340+P311-P403+P233-P403+P235-P405 |
| Hazardous substances data | 109-70-6(Hazardous Substances Data) |
Applications & Uses
Description
1-Bromo-3-chloropropane is a halogenated alkane compound containing one bromine atom and one chlorine atom in its structure. Due to the high electronegativity of halogens, the molecule of 1-Bromo-3-chloropropane is highly electrophilic and is easily attacked by electrophilic reagents such as nucleophilic reagents, Lewis acid, etc., which undergoes nucleophilic substitution reactions. The compound is relatively stable at room temperature, but is susceptible to elimination reactions at high temperatures or in the presence of strong acids or bases. In addition, prolonged exposure to air should be avoided because 1-Bromo-3-chloropropane molecules contain halogen atoms that are susceptible to reaction by oxygen and moisture in the air to produce products such as alcohols and aldehydes.
Uses
1-Bromo-3-chloropropane is used in the preparation active pharmaceutical ingredient intermediate such as gemfibrozil and reproterol. It is also involved in the preparation of cardiovascular diseases and analgesic drugs materials. It is utilized as a phase separation reagent for the isolation of ribonucleic acid (RNA) in high quality. It is considered as a replacement of chloroform in nucleic acid separations.
General Description
1-bromo-3-chloropropane appears as a colorless liquid. Insoluble in water and denser than water. May be toxic by inhalation, ingestion or skin absorption. Used to make pharmaceuticals and other chemicals.
Preparation & Synthesis
Preparation
The most common method for producing 1-Bromo-3-chloropropane is through the free-radical addition of anhydrous hydrogen bromide to allyl chloride. Alternatively, it can be prepared by reacting ethylene with methylene chlorobromide.