1-Bromopropane

HCID 7840CAS 106-94-5

기본 정보

표준 SMILES
CCCBr
InChIKey
CYNYIHKIEHGYOZ-UHFFFAOYSA-N
분자식
C3H7Br
평균 분자량
122.99 g/mol
단동위원소 질량
121.97311232

개요

1-Bromopropane is a colorless liquid. Commercial 1-bromopropane includes not only 1-bromopropane, but also additives that improve its performance in the desired application and stabilizers to inhibit decomposition. 1-Bromopropane was originally used in the production of pesticides, flavors and fragrances, pharmaceuticals, and other chemicals.

이름 및 식별자

우선 이름
1-Bromopropane
IUPAC
1-bromopropane
영어명
1-bromopropane
분자식
C3H7Br
분자량
122.99

이름 및 동의어

1-BROMOPROPANE106-94-5N-Propyl bromidePropyl bromidePropane, 1-bromo-1-BROMO-PROPANEpropylbromiden-propylbromideDTXSID6021874CCRIS 30Y9746DNE68DTXCID401874
이름 더 보기
CHEBI:471051-BP, propaneRefChem:430780203-445-0Propane, bromo-BROMOPROPANE1-Propyl bromideMFCD00000254

데이터베이스 식별자

CAS
106-94-5、26446-77-5
PubChem CID
7840
DTXSID
DTXSID6021874
ChEMBL
CHEMBL1230095
ChEBI
CHEBI:47105
UNII
Y9746DNE68
EC Number
203-445-0
Nikkaji
J4.039H

물성

구조 계산 물성

XLogP
2.1
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
1
무거운 원자 수
4

실험 및 물리화학적 성질

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesSchoenflies notation
LogP · 3건

log Kow = 2.10

2.1

2.1

OdorSweet odor
Density · 5건

1.3537 at 68 °F (USCG, 1999) - Denser than water; will sink

1.353 at 20 °C/20 °C

Relative density (water = 1): 1.35

1.3537

1.35 @ 20°C

물리화학적 성질

EPA
Propane, bromo- (26446-77-5)

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 6건

Chemical: Propane, 1-bromo-

Hazard Traits - Carcinogenicity; Developmental Toxicity; Neurotoxicity; Reproductive Toxicity

Propane, 1-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 1-bromo- 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: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15004

Substance: 1-bromopropane (n-propyl bromide)

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

Other Safety InformationIMAP assessments - Propane, 1-bromo-: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 2건

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire Potential · 2건

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Dangerous fire hazard when heated or exposed to flame or oxidizers.

Health HazardsIrritating to the eyes, nose, throat, upper respiratory tract, and skin. (USCG, 1999)

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

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

First Aid Measures · 4건

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Seek medical attention if you feel unwell.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

First AidCall a physician.
Safe StorageFireproof. Well closed. Separated from strong oxidants and strong bases. Store in an area without drain or sewer access. Ventilation along the floor.
Fire Fighting Procedures · 5건

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use "alcohol" foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Bromopropanes/

To fight fire, use water, foam, CO2, dry chemical.

Storage Conditions · 3건

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

Fireproof. Separated from strong oxidants, strong bases.

독성 정보

Toxicological InformationCDC-ATSDR Toxicological Profile
Treatment · 1건

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Interactions · 3건

1-Bromopropane (1-BP) has been used as an alternative for fluoride compounds and 1-BP intoxication may involve lung, liver, and central neural system (CNS). Our previous studies showed that 1-BP impaired memory ability by compromising antioxidant cellular defenses. Melatonin is a powerful endogenous antioxidant, and the objective of this study was to explore the therapeutic role of melatonin in the treatment of 1-BP intoxication. Rats were intragastrically treated with 1-BP with or without melatonin, and then sacrificed on 27th day after 1-BP administration. The Morris water maze (MWM) test was used to evaluate the spatial learning and memory ability of the experimental animals, and NeuN staining was performed to assess neuron loss in hippocampus. We found that rats treated with 1-BP spent more time and swam longer distance before landing on the hidden platform with a comparable swimming speed, which was markedly mitigated by the pretreatment with melatonin in a concentration-dependent manner. In addition, 1-BP-induced notable decrease in neuron population in hippocampus by promoting apoptosis, and melatonin pretreatment attenuated those changes in brain. The GSH/GSSG ratio was proportionately decreased and heme oxygenase 1 was increased in the rats exposed to 1-BP, and administration of melatonin restored them. Meanwhile, MDA, the level of lipid peroxidation product, was significantly increased upon exposed to 1-BP, which was significantly attenuated by melatonin pretreatment, indicating that administration of 1-BP could interfere with redox homeostasis of brain in rat, and such 1-BP-induced biomedical changes were reversed by treatment with melatonin. We conclude that treatment with melatonin attenuates 1-BP-induced CNS toxicity through its ROS scavenging effect.

Neurotoxicity of 1-bromopropane (1-BP) has been reported in both human cases and animal studies. To date, neurotoxicity of 1-BP has been induced in rats but not in mice due to the lethal hepatotoxicity of 1-BP. Oxidization by cytochromes P450 and conjugation with glutathione (GSH) are two critical metabolism pathways of 1-BP and play important roles in toxicity of 1-BP. The aim of the present study was to establish a murine model of 1-BP neurotoxicity, by reducing the hepatotoxicity of 1-BP with 1-aminobenzotriazole (1-ABT); a commonly used nonspecific P450s inhibitor. The results showed that subcutaneous or intraperitoneal injection of 1-ABT at 50 mg/kg body weight BID (100 mg/kg BW/day) for 3 days, inhibited about 92-96% of hepatic microsomal CYP2E1 activity, but only inhibited about 62-64% of CYP2E1 activity in brain microsomes. Mice treated with 1-ABT survived even after exposure to 1200 ppm 1-BP for 4 weeks and histopathological studies showed that treatment with 1-ABT protected mice from 1-BP-induced hepatic necrosis, hepatocyte degeneration, and hemorrhage. After 4-week exposure to 1-BP, the brain weight of 1-ABT(+)/1200ppm 1-BP group was decreased significantly. In 1-ABT-treated groups, expression of hippocampal Ran protein and cerebral cortical GRP78 was dose-dependently increased by exposure to 1-BP. We conclude that the control of hepatic P450 activity allows the observation of effects of 1-BP on the murine brain at a higher concentration by reduction of hepatotoxicity. The study suggests that further experiments with liver-specific control of P450 activity using gene technology might provide better murine models for 1-bromopropane-induced neurotoxicity.

OBJECTIVE: To investigate the protective effects of docosahexaenoic acid (DHA) and nervonic acid (NA) on the learning and memory abilities in rats exposed to 1-bromopropane (1-BP) and their action mechanisms. METHODS: Forty male Wistar rats (specific pathogen-free) were randomly divided into 4 groups (n = 10 for each), i.e., solvent control group, 1-BP (800 mg/kg) group, NA (150 mg/kg) + 1-BP (800 mg/kg) group, and DHA (500 mg/kg) + 1-BP (800 mg/kg) group. The rats were given respective test substances by gavage for 7 d. The Morris water maze (MWM) test was performed from days 8 to 12 to evaluate the rats' learning and memory abilities. After MWM test, rats were sacrificed in the next day, and cerebral cortex was quickly dissected and homogenized in an ice bath. The supernatant of the obtained homogenate was collected to measure the content of glutathione (GSH) and malondialdehyde (MDA) and the activities of glutathione reductase (GR) and gamma-glutamate cysteine ligase (gamma-GCL). RESULTS: The MWM spatial navigation test showed that the 1-BP group had significantly longer escape latency and significantly longer total swimming distance compared with the control group (P<0.05), while the DHA+1-BP group had significant decreases in escape latency and total swimming distance compared with the 1-BP group (P<0.05). The spatial probe test showed that the number of platform crossings was significantly greater in the DHA+1-BP group and NA+1-BP group than in the 1-BP group (P<0.05); compared with the control group, the 1-BP group had a significantly lower ratio of time spent in the zone around the platform to total time (P < 0.05), and the ratio was significantly higher in the DHA+1-BP group than in the 1-BP group (P < 0.05). Compared with the control group, the 1-BP group had a 18.1% decrease in GSH content, and DHA could significantly reverse 1-BP-induced decrease in GSH content (P < 0.05). Compared with the 1-BP group, the DHA+1-BP group and NA+1-BP group had significantly decreased MDA content (P < 0.05), the DHA+1-BP group had significantly increased GR activity (P < 0.05), and the NA+1-BP group had significantly increased gamma-GCL activity (P < 0.05). CONCLUSION: The rats exposed to 1-BP have oxidative stress in the brain and impaired cognitive function. DHA and NA can reduce 1-BP-induced cognitive function impairment in rats, possibly by increasing the activities of GR and gamma-GCL and the content of GSH in the brain.

Target OrgansCancer, Neurological (Nervous System)
Health Effects · 1건

Skin irritation if contacts skin, redness and itching of skin and eyes. Acute exposure may lead to coughing, shortness of breath, headache, nausea, vomiting. Chronic exposure can lead to damage of the blood, liver and CNS. Neurotoxicity can arise due to chronic exposure through inhalation or skin. Human cases of 1-bromopropane (1-BP) toxicity exhibit ataxic gait and cognitive dysfunction, whereas rat studies showed pyknotic shrinkage in cerebellar Purkinje cells and electrophysiological changes in the hippocampus. Inhalation exposure to 1-bromopropane causes skin tumors in male rats, large intestine tumors in female and male rats, and lung tumors in female mice. 1-bromopropane, either directly or via reactive metabolites, can cause molecular alterations that typically are associated with carcinogenesis, including genotoxicity, oxidative stress, and glutathione depletion. Hepatotoxicity and reproductive toxicity have been noted in rodent studies.

Ecotoxicity ValuesLC50; Species: Pimephales promelas (Fathead minnow) age 30 days; Conditions: freshwater, flow through; Concentration: 67300 ug/L for 96 hr /99% purity/

화학 및 산업

약리 정보

Mechanism of Action · 1건

1-Bromopropane, either directly or via reactive metabolites, causes molecular alterations that typically are associated with carcinogenesis, including genotoxicity, oxidative stress, and glutathione depletion. These alterations, observed mainly in vitro and in toxicity studies in rodents, are relevant to possible mechanisms of human carcinogenicity and support the relevance of the cancer studies in experimental animals to human carcinogenicity.

Biological Half-Life · 1건

Wistar male rats were exposed to 1-bromopromane (1-BP) vapor for 6 hr a day, 5 days a week, for 3 and 4 weeks (1500 ppm) and 1 day, and 4 and 12 weeks (700 ppm). ... 1-BP in blood decreased rapidly to the detection limit within 0.7 hr. On the other hand, bromide ion persisted longer in both blood and urine; the biological half-life of bromide ion was 4.7-15.0 days in blood and 5.0-7.5 days in urine. ...

Metabolism/Metabolites · 6건

... Six workers, 1 male and 5 female, were exposed to high ambient 1-Bromopropane (1-BP) concentrations while employed in a golf club cleaning factory. 1-BP was identified in the bulk solvent sample used by the workers and confirmed the workers' daily occupational exposure to 1-BP for 3-10 months. The major presenting symptoms were tingling pain, soreness in lower extremities, and paresthesia. N-acetyl-S-(n-propyl)-L-cysteine (AcPrCys), a 1-BP metabolite, was identified by LC/MS/MS in the urine (0.171-1.74 mg/g-Cr) of these workers 5-26 days following 1-BP exposure. ...

... In this study, the factors influencing the disposition and biotransformation of 1-bromopropane (1-BrP) were examined in male F344 rats and B6C3F1 mice following inhalation exposure (800 ppm) or intravenous administration (5, 20, and 100 mg/kg). (1,2,3-(13)C)1-BrP and (1-(14)C)1-BrP were administered to enable characterization of urinary metabolites using NMR spectroscopy, LC-MS/MS, and HPLC coupled radiochromatography. ... Metabolites characterized in urine of rats and mice include N-acetyl-S-propylcysteine, N-acetyl-3-(propylsulfinyl)alanine, N-acetyl-S-(2-hydroxypropyl)cysteine, 1-bromo-2-hydroxypropane-O-glucuronide, N-acetyl-S-(2-oxopropyl)cysteine, and N-acetyl-3-[(2-oxopropyl)sulfinyl]alanine. These metabolites may be formed following oxidation of 1-bromopropane to 1-bromo-2-propanol and bromoacetone and following subsequent glutathione conjugation with either of these compounds. ...

Three metabolites of 1-bromopropane (1-BP) were measured in urine samples collected from 30 workers exposed to 1-BP at two facilities making furniture seat cushions and evaluated for use as biomarkers of exposure. The mercapturic acid metabolite, N-acetyl-S-(n-propyl)-l-cysteine (AcPrCys), 3-bromopropionic acid (3-BPA), and bromide ion levels (Br(-)) were quantitated for this evaluation. ...

Glutathione S-alkyl transferase catalyzes the conjugation of alkyl halides and nitroalkanes in which halogen or nitro group is replaced. Further metabolism of conjugates of this group to alkylmercapturic acid sulfoxides has been reported for...1-bromopropane.

For more Metabolism/Metabolites (Complete) data for 1-Bromopropane (13 total), please visit the HSDB record page.

1-bromopropane is metabolized rapidly in the liver. Three mercapturic acids are produced: N-acetyl-S-propyl cysteine, N-acetyl-S-propyl cysteine-S-oxide and N-acetyl-S-(2-hydroxypropyl)cysteine. 1-bromopropoane also reacts rapidly with glutathione and can form glutathione conjugates.

Absorption, Distribution and Excretion · 5건

... In this study, the factors influencing the disposition and biotransformation of 1-bromopropane (1-BrP) were examined in male F344 rats and B6C3F1 mice following inhalation exposure (800 ppm) or intravenous administration (5, 20, and 100 mg/kg). (1,2,3-(13)C)1-BrP and (1-(14)C)1-BrP were administered to enable characterization of urinary metabolites using NMR spectroscopy, LC-MS/MS, and HPLC coupled radiochromatography. Exhaled breath volatile organic chemicals (VOC), exhaled CO(2), urine, feces, and tissues were collected for up to 48 h post-administration for determination of radioactivity distribution. Rats and mice exhaled a majority of the administered dose as either VOC (40-72%) or (14)CO(2) (10-30%). For rats, but not mice, the percentage of the dose exhaled as VOC increased between the mid ( approximately 50%) and high ( approximately 71%) dose groups; while the percentage of the dose exhaled as (14)CO(2) decreased (19 to 10%). The molar ratio of exhaled (14)CO(2) to total released bromide, which decreased as dose increased, demonstrated that the proportion of 1-BrP metabolized via oxidation relative to pathways dependent on glutathione conjugation is inversely proportional to dose in the rat. ((14)C)1-BrP equivalents were recovered in urine (13-17%, rats; 14-23% mice), feces (<2%), or retained in the tissues and carcass (<6%) of rats and mice administered i.v. 5 to 100 mg/kg ((14)C)1-BrP. ... Rats pretreated with 1-aminobenzotriazole (ABT), a potent inhibitor of P450 excreted less in urine (down 30%), exhaled as (14)CO2 (down 80%), or retained in liver (down 90%), with a concomitant increase in radioactivity expired as VOC (up 52%). Following ABT pretreatment, rat urinary metabolites were reduced in number from 10 to 1, N-acetyl-S-propylcysteine, which accounted for >90% of the total urinary radioactivity in ABT pretreated rats. Together, these data demonstrate a role for cytochrome P450 and glutathione in the dose-dependent metabolism and disposition of 1-BrP in the rat.

.../It is/ reported that orally administered 1-bromopropane is excreted in expired air.

Parent compound and metabolites are excreted in urine as mercapturic acids.

/Investigators/ injected Sprague-Dawley rats intraperitoneally with 200 mg/kg 1-BP and observed a rapid excretion of greater than half of the administered dose in expired air. By hour 100, 25% of the 1-BP dose was excreted in the urine.

For more Absorption, Distribution and Excretion (Complete) data for 1-Bromopropane (7 total), please visit the HSDB record page.

용도 및 제조

Uses · 6건

Used as a solvent substitute to clean metals and electronics, in adhesive and coating applications, and in aerosol propellant applications. Has also been used to replace perchloroethylene in dry cleaning; [ACGIH]

Metal Degreasing [Category: Clean]

Solvent for fats, waxes and resins; intermediate in synthesis of pharmaceuticals, insecticides and other compounds; in spray adhesives; degreaser; cleaner for metal and precision electronic components.

Production of penconazole, valproic acid /From table/

In the early to mid 1990s, 1-bromopropane was used primarily as an intermediate in the production of pesticides, quaternary ammonium compounds, flavors and fragrances, pharmaceuticals, and other chemicals in well-controlled, closed processes. In the mid to late 1990s, it was introduced as a less toxic replacement for methylene chloride in emissive applications such as vapor and immersion degreasing operations and critical cleaning of electronics and metals. 1-Bromopropane was also introduced as a nonflammable, nontoxic, fast-drying, and inexpensive solvent for adhesive resins, and has been marketed as a replacement for ozone depleting refrigerants.

1-Bromopropane is used primarily as a solvent cleaner in vapor and immersion degreasing operations to clean optics, electronics, and metals and as a solvent vehicle in industries using aerosol-applied adhesives, such as foam cushion manufacturing. ...1-Bromopropane also has potential for use as a spot remover in the textile industry... In the past, 1-bromopropane was used primarily as a solvent for fats, waxes, and resins and as an intermediate in the synthesis of pharmaceuticals, insecticides, quaternary ammonium compounds, flavors, and fragrances in generally well-controlled, closed processes.

Impurities2-Bromopropane (75-26-3) is present as a contaminant in commercial grade bromopropane at 0.1% to 0.2%. 2-BP is also known as isopropylbromide; 2-propylbromide; and sec-propylbromide.
U.S. Production · 4건

2023: 10,000,000 - <50,000,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#2796]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Propane, 1-bromo-. Aggregated National Production Volume: 1 to < 10 million pounds.

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1-Bromopropane:

Industry UsesCleaning agent
Methods of Manufacturing · 1건

Treatment of the parent hydroxyl compound with a bromide and sulfuric acid, as in the preparation of methyl bromide. If the parent compound is unstable toward sulfuric acid, hydrobromic acid is passed in and alkyl bromide is flashed over from the hot mixture. The product is condensed, neutralized, and fractionated. In modifications of these procedures, bromine may be used along with a reducing agent such as sulfur, sulfur dioxide, phosphorus, or sodium borohydride.

Household ProductsInformation on 2 consumer products that contain 1-bromopropane in the following categories is provided:

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