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Home > Encyclopedia > 2-Bromopropane

2-Bromopropane

2-Bromopropane structure

2-Bromopropane 

structure
  • CAS No:

    75-26-3

  • Formula:

    C3H7Br

  • Chemical Name:

    2-Bromopropane

  • Synonyms:

    Propane,2-bromo-;2-Bromopropane;Isopropyl bromide;sec-Propyl bromide

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

colourless liquid


Liquid|Colorless to slightly yellow flammable liquid.

2-Bromopropane Basic Attributes

122.99200

122.99

200-855-1

R651XOV97Z

2344

DTXSID7030197

Colorless liquid

2930909090

Characteristics

0

1.78970

Clear colorless to very light brown Liquid

1.31 g/cm3 @ Temp: 20 °C

-89.0 °C

59.38 °C @ Press: 760 Torr

1ºC

1.425-1.427

H2O: 0.3 g/100 mL

Flammables area

224 hPa (20 °C)

4.27 (Air=1)

8.80e-13 cm3/molecule*sec

Henry's Law constant = 0.011 atm-cu m/mol at 25 °C (est)

Liquid molar volume = 0.0959 cu meter/kmol|IG Heat of formation = -9.7069X10+7 J/kmol|Hydroxyl radical reaction rate constant = 8.8X10-13 cu cm/molec-sec at 25 °C

Safety Information

II

3

UN 2344

1

R11; R48/20; R60; R66

S16-S45-S53

TX4111000

F

Stable. Flammable. Incompatible with strong oxidizing agents.

P201-P210-P308 + P313

H225-H360F-H373

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.

Flammable - 3rd degree

|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P201, P202, P210, P233, P240, P241, P242, P243, P260, P280, P281, P303+P361+P353, P308+P313, P314, P370+P378, P403+P235, P405, and P501|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|Aggregated GHS information provided by 235 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P303+P361+P353, P305+P351+P338, P308+P313, P314, P337+P313, P370+P378, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P281, P303+P361+P353, P308+P313, P314, P332+P313, P370+P378, P403+P235, P405, and P501

Personnel Protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Bromopropanes/

A very flammable liquid and dangerous fire hazard.

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/

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/

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for 2-BROMOPROPANE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Toxicity

LD50 Mouse ip 4837 mg/kg|LD50 Rat oral >2000 mg/kg|LC50 Mouse (ICR) inhalation 31,171 ppm/4 hr

Isopropyl bromide's production and use in the synthesis of pharmaceuticals, dyes, and other organics(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow of 2.14(2) and a regression derived equation(3), indicates that isopropyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of isopropyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.011 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure of 216 mm Hg(4) and water solubility of 3180 mg/L(5). The potential for volatilization of isopropyl bromide from dry soil surfaces exists(SRC) based upon its extrapolated vapor pressure(4). No terrestrial biodegradation data were located for isopropyl bromide(SRC, 2005); however, an aqueous aerobic screening study using an activated sludge inoculum indicated that this compound is readily biodegradable(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow of 2.14(2) and a regression derived equation(3), indicates that isopropyl bromide 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 0.011 atm-cu m/mole(SRC), derived from an extrapolated vapor pressure of 216 mm Hg(4) and water solubility of 3180 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 hour and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 9(SRC), from a log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The hydrolysis half-life of isopropyl bromide was reported as 2.1 days at 25 °C(8). No aquatic biodegradation data were located for isopropyl bromide(SRC, 2005); however, an aqueous aerobic screening study using an activated sludge inoculum indicated that this compound is readily biodegradable(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl bromide, which has an extrapolated vapor pressure of 216 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropyl bromide 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 18 days(SRC), calculated from its rate constant of 8.8X10-13 cu cm/molecule-sec at 25 °C(3).

The rate constant for the vapor-phase reaction of isopropyl bromide with photochemically produced hydroxyl radicals has been measured as 8.8X10-13 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 18 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm. A hydrolysis half-life of about 2.1 days was reported for isopropyl bromide at 25 °C and pH 7(2). Isopropyl bromide is not expected to undergo direct photolysis in the environment since it lacks functional groups that absorb light at wavelengths greater than 290 nm(SRC).

An estimated BCF of 9 was calculated for isopropyl bromide (SRC), using a measured log Kow of 2.14(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of isopropyl bromide is estimated as 350(SRC), using a measured log Kow of 2.14(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that isopropyl bromide is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for isopropyl bromide is estimated as 0.011 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 216 mm Hg(1), and water solubility, 3180 mg/L(2). This Henry's Law constant indicates that isopropyl bromide is expected to volatilize rapidly from water surfaces(3). 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)(3) is estimated as 1 hour(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 4 days(SRC). Isopropyl bromide's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of isopropyl bromide from dry soil surfaces may exist(SRC) based upon its extrapolated vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,583 workers (323 of these are female) are potentially exposed to isopropyl bromide in the USA(1). Occupational exposure to isopropyl bromide may occur through inhalation and dermal contact with this compound at workplaces where isopropyl bromide is produced or used(SRC).

Drug Information

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)|Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant and Hackh's Chemical Dictionary, 5th ed) (See all compounds classified as Solvents.)

/HUMAN EXPOSURE STUDIES/ An outbreak of reproductive and hematopoietic toxicities occurred in Korean electronics workers in 1995 exposed to solvents containing 2-BP that were used as alternatives to chlorofluorocarbons for cleaning tactile switches. Seventeen of 25 female workers showed ovarian dysfunction accompanied by amenorrhea and severe anemia, and 6 of 8 male workers had oligospermia or azospermia. The mean ambient 2-BP concentration in the work area was 12.4 ppm, and the 2-BP concentration inside the hood of the cleaning baths was 4141 ppm. Some workers had skin contact with 2-BP. Two of the affected female workers regained normal ovarian function within 2 years following exposure.|/HUMAN EXPOSURE STUDIES/ Sixteen Korean female laborers who had been exposed to a cleaning solvent composed mainly of 2-bromopropane developed primary ovarian failure. Histologic findings from these patients' ovaries were similar to those observed in ovarian failure caused by radiation or chemotherapy, i.e., reduced number and developmental arrest of primary follicles, interstitial fibrosis and hyalinization of blood vessels. We followed their clinical course for 2 years and found that two patients recovered normal ovarian function spontaneously: one became pregnant and delivered a normal full-term baby, and the other resumed regular menstrual periods with normal hormonal values. Our observations support the idea that the increasing prevalence of ovarian failure in recent years might be due to an increase in presently unidentified environmental toxic agents.|/HUMAN EXPOSURE STUDIES/ A study of 25 workers in a Chinese 2-BP manufacturing plant found amenorrhea or polymenorrhea in 4 female workers exposed at >10 ppm (TWA) 2-BP.

2-bromopropane

2-Bromopropane Use and Manufacturing

Methods of Manufacturing

Obtained by heating isopropyl alcohol with HBr.

Uses

This product can be used in the manufacture of medicines, pesticides (Napropamide), etc. 2-Bromopropane is an intermediate of the insecticides fenvalerate, flufenvalerate, propoxur, the fungicide meprosamine, fluoxamide, and the herbicides tetrachloride and saraphos. Used in organic synthesis and pharmaceutical industry


Intermediates

Production

(1994) 10 thousand - 500 thousand pounds|(1998) 10 thousand - 500 thousand pounds|(2002) >500 thousand - 1 million pounds

All other basic inorganic chemical manufacturing|Propane, 2-bromo-: ACTIVE

Method: NIOSH 1025; Procedure: Gas chromatography with flame ionization detector; Analyte: 2-bromopropane; Matrix: air; Detection Limit: 1.0 ug/sample.|Method: OSHA PV2062; Procedure: Gas chromatography using flame ionization detector; Analyte: 2-bromopropane; Matrix: air; Detection Limit: 0.004 ppm (0.020 mg/ cu m).

Fire Hazards -> Flammable - 3rd degree

Computed Properties

Molecular Weight:122.99
XLogP3:1.8
Exact Mass:121.97311
Monoisotopic Mass:121.97311
Heavy Atom Count:4
Complexity:10.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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