1,2-Dibromopropane

HCID 6553CAS 78-75-1

Basic information

Standard SMILES
CC(Br)CBr
InChIKey
XFNJYAKDBJUJAJ-UHFFFAOYSA-N
Molecular formula
C3H6Br2
Average molar mass
201.89 g/mol
Monoisotopic mass
199.88362439

Overview

1,2-dibromopropane is a colorless liquid. (NTP, 1992)

Names & identifiers

Preferred name
1,2-Dibromopropane
IUPAC
1,2-dibromopropane
English name
1,2-Dibromopropane
Molecular formula
C3H6Br2
Molecular weight
201.89

Names & synonyms

1,2-DIBROMOPROPANE78-75-1Propylene dibromidePropane, 1,2-dibromo-2,3-DibromopropaneFGB8O5N903DTXSID60870403RefChem:71833DTXCID60818128201-139-1MFCD00000148Propylene Bromide
Show more names
1,2-Dobromopropane1,2-Dibromopropane98%1,2 - Propylene DibromideCH2BrCHBrCH31.2-DibroMopro1,2-Dibrompropan(RS)-Dibrompropan1,2-dibromo-propan
1,2-DIBROMOPROPANE-D6CCRIS 6710HSDB 7379EINECS 201-139-1BRN 1718884UNII-FGB8O5N903AI3-154051,2 dibromopropane

Database identifiers

CAS
78-75-1
PubChem CID
6553
DTXSID
DTXSID60870403
UNII
FGB8O5N903
EC Number
201-139-1
Nikkaji
J1.957G

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Halogenated Aliphatics, Saturated
Density · 2 items

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

1.9324 g/cu cm at 20 °C

Viscosity1.623 cP at 20 °C
Color/FormColorless liquid
Solubility · 2 items

In water, 1.43X10+3 mg/L at 25 °C

Soluble in ethanol, ether, and chloroform; slightly soluble in carbon tetrachloride.

Flash PointFlash point: <-75 °C

Physicochemical properties

Melting point
-55 °C · -55 °C
Boiling point
140 · 140-142 °C(lit.)
Density
1.937 g/mL · 1.937 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.519(lit.)
Flash point
35 °C · 35 °C
storage temp.
Flammables area

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (91.8%): Flammable liquid and vapor [Warning Flammable liquids]

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, P317, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 49 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelCombustible Liquid
Fire HazardsThis compound is considered non-flammable. (NTP, 1992)
Health HazardsSYMPTOMS: Irritant and narcotic in high conc.
Hazards Summary · 1 item

Increased liver enzymes in feeding studies of mice; Some evidence of mutagenicity; Emergency medical treatment: see 2-Bromopropane. [HSDB] High concentrations may have irritating and narcotic effects; [CAMEO] A mutagen; Effects in high-dose animal studies include fatty liver degeneration and acute renal failure; [RTECS]

Reactive GroupHalogenated Organic Compounds
Reactivity Profile · 1 item

Halogenated aliphatic compounds, such as 1,2-DIBROMOPROPANE, 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 may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. This compound is considered nonflammable. (NTP, 1992)

Safety & protection

Fire FightingThis material is considered to be non-flammable. (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.

Fire Fighting Procedures · 1 item

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/

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, 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 acetone followed by washing with a strong 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.

Preventive Measures · 2 items

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/

Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing. /Bromopropanes/

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Toxicology

Treatment · 1 item

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.

Health Effects · 1 item

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a water solubility of 1.43X10+3 mg/L(2) and a regression-derived equation(3), indicates that 1,2-dibromopropane is expected to have high mobility in soil(SRC). Volatilization of 1,2-dibromopropane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.46X10-3 atm-cu m/mole(SRC), calculated from a vapor pressure of 7.84 mm Hg(4) and water solubility of 1.43X10+3 mg/L(2). 1,2-Dibromopropane is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 80(SRC), determined from a water solubility of 1.43X10+3 mg/L(2) and a regression-derived equation(3), indicates that 1,2-dibromopropane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.46X10-3 atm-cu m/mole(SRC), calculated from its vapor pressure, 7.84 mm Hg(4), and water solubility, 1.43X10+3 mg/L(3). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 hours and 6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 10(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Using hydrolysis rates measured at elevated temperatures, a hydrolysis half-life of 320 days (rate constant = 2.5X10-8 per second) at 25 °C and pH 7 was calculated for 1,2-dibromopropane(7,8). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-dibromopropane, which has a vapor pressure of 7.84 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2-dibromopropane 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 37 days(SRC), calculated from its rate constant of 4.3X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,2-dibromopropane does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1 item

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
TX8574000
ridadr
UN 1993 3/PG 3
hs_code
29033036

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

... The following four metabolites were identified in the liver at 12 h after treatment with 1,2-DBP, by liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI/MS): M1, 2-hydroxypropylglutathione; M2, 2-oxopropylglutathione; M3, N-acetyl-S-(2-hydroxypropyl)-L-cysteine; and M4, N-acetyl-S-(2-oxopropyl)-L-cysteine. Ions of individual conjugates were observed at m/z 366, 364, 222 and 220, respectively. Characteristic product ions at m/z 237, 217, 204 and 202 for the identification of M1, M2, M3 and M4 were observed, respectively. In the sera isolated from the same animals, only mercapturic acids (M3 and M4) were observed by LC-ESI/MS. When female BALB/c mice were treated orally with 1,2-DBP at doses of 150, 300 and 600 mg kg(-1) once for 12 h, the production of glutathione conjugates and mercapturic acids in liver was apparently dose dependent, as were the concentrations of them in sera. When the production of metabolites from 1,2-DBP was investigated in liver following oral treatment with 600 mg kg(-1) 1,2-DBP for 6, 12, 24 and 48 h, metabolite concentrations were greatest at the first time point (6 h).

1,2-Dibromopropane was administered orally in doses of 50-350 mg/kg to male Wistar rats. Four mercapturic acids were identified in urine by GC/MS, viz. N-acetyl-S-(2-oxopropyl)-L-cysteine (I), N-acetyl-S-(2-hydroxypropyl)-L-cysteine (II), N-acetyl-S-(1-carboxyethyl)-L-cysteine (III), and N-acetyl-S-(2-bromo-2-propenyl)-L-cysteine (IV). Mercapturic acid IV was a minor metabolite which could only be measured at doses of 200 mg/kg or higher. In 24 hr, urinary excretion of mercapturic acids amounted to about 36% of the dose (11% I, 21% II, 4% III, 0.2% IV). No dose dependency was found up to the highest dose.

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Uses & manufacturing

Uses · 2 items

Used as a research chemical; [HSDB]

Research chemical

Methods of ManufacturingPrepared from propyl bromide and Br in the presence of AlCl3 or AlBr3.
General Manufacturing InformationPropane, 1,2-dibromo-: ACTIVE
Applications · 2 items

Uses1,2-Dibromopropane is used in organic synthesis and solvent. It was used to study the effect of reductant concentration, reductant contact time and suspension pH on reductive dechlorination of carbon tetrachloride by soil manipulated with Fe(II) and HS-. It was used as internal standard during the determination of nitrogenous disinfection byproduct trichloronitromethane by gas chromatography mass spectrometry.

General Description1,2-dibromopropane is a colorless liquid. Prepared from propyl bromide and Br in the presence of AlCl3 or AlBr3. (NTP, 1992)

Preparation methods · 1 item

Preparation1,2-Dibromopropane is synthesized from bromopropane by bromination. First mix bromopropane and iron powder, heat to 40-50°C, slowly add bromine, and continue to reflux for 2h after adding. Then, the iron slag was filtered off, and the filtrate was washed several times with water, once with 5% sodium carbonate solution, and then with 5% sodium thiosulfate solution to remove free bromine. Dry with anhydrous calcium chloride. Fractional distillation, collecting 139-142 ℃ fraction is the finished product of 1,2-dibromopropane.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海毕合生物化学技术有限公司13816464724 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]

Related reactions

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1,2-Dibromopropane (HCID 6553)|Huagongshe