2-Bromopropane

HCID 6358CAS 75-26-3

Basic information

Standard SMILES
CC(C)Br
InChIKey
NAMYKGVDVNBCFQ-UHFFFAOYSA-N
Molecular formula
C3H7Br
Average molar mass
122.99 g/mol
Monoisotopic mass
121.97311232

Overview

2-Bromopropane (2-BP) can cause cancer according to California Labor Code and the World Health Organization's International Agency for Research on Cancer (IARC). It can cause female reproductive toxicity and male reproductive toxicity according to The National Toxicology Program's Center for the Evaluation of Risks to Human Reproduction.

Names & identifiers

Preferred name
2-Bromopropane
IUPAC
2-bromopropane
English name
2-Bromopropane
Molecular formula
C3H7Br
Molecular weight
122.99

Names & synonyms

2-Bromopropane75-26-3ISOPROPYL BROMIDEPropane, 2-bromo-sec-Propyl bromide2-BROMO-PROPANEUN2344DTXSID7030197R651XOV97ZDTXCID5010197UN-2344RefChem:85898
Show more names
2-Brompropaniso-C3H7Br2-bromo-propanbromo-2propanepropane,2-bromo-bromo isopropane2-Propyl bromidePropylBromide~98%
200-855-1Isopropylbromide2-bromo propaneMFCD00000147BR1118CCRIS 7919HSDB 6232-Bromopropane, 99%

Database identifiers

CAS
75-26-3
PubChem CID
6358
DTXSID
DTXSID7030197
ChEMBL
CHEMBL451810
UNII
R651XOV97Z
EC Number
200-855-1
Nikkaji
J1.447H

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
4

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesCoriolis coupling
LogP · 2 items

log Kow = 2.14

2.1

Density · 2 items

1.31 at 20 °C/4 °C

1.31 @ 20°C

Viscosity1.0012X10-3 Pa.s (liquid) @ -23.15 °C

Physicochemical properties

Melting point
-89 °C · -89 °C (lit.)
Boiling point
59 °C · 59 °C (lit.)
Density
1.31 g/mL · 1.31 g/mL at 25 °C (lit.)
vapor pressure
224 hPa · 224 hPa (20 °C)
refractive index
20 · n20/D 1.425(lit.)
Flash point
67 °F · 67 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P203, P210, P233, P240, P241, P242, P243, P260, P280, P303+P361+P353, P318, P319, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.2% (1 of 85) of reports.

Danger

H225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 6 items

Chemical: Propane, 2-bromo-

Hazard Traits - Carcinogenicity; Developmental Toxicity; Reproductive Toxicity

Propane, 2-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-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: No longer Valid Update: 22-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1580

Propane, 2-bromo-: 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.)

Other Safety InformationIMAP assessments - Propane, 2-bromo-: Human health tier II assessment
Fire PotentialA very flammable liquid and dangerous fire hazard.
Hazards Summary · 1 item

In 1995, an outbreak was reported in Korean electronics workers using 2-BP to degrease switches. Adverse effects were amenorrhea and severe anemia in 17/25 females and oligospermia or azospermia in 6/8 males. The work area concentration was 12.4 ppm, and some workers had skin contact. In a Chinese plant manufacturing 2-BP, 25 workers were studied. Four females exposed at >10 ppm had amenorrhea or polymenorrhea. [ACGIH] See 1-Bromopropane.

DOT Emergency Guidelines · 5 items

/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.

Hazard Classes and Categories · 6 items

Flam. Liq. 2 (98.8%)

Flammable liquid - category 2

Flammable liquids - Category 2

Flammable liquids - Category 2

Flammable liquids - Category 2

Flammable agents - 3rd degree

Safety & protection

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/

Storage Conditions · 1 item

...Materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well ventilated place, out of the direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected. Incompatible materials should be isolated...

Disposal Methods · 1 item

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.

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/

Protective Action Criteria (PAC) · 3 items

3.0 [ppm]

230 [ppm]

1400 [ppm]

Personal Protective Equipment (PPE)Personnel Protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Bromopropanes/

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

2-Bromopropane is a strong lachrymator. Chronic exposure has been shown to have teratogenic effects in mouse and rat embryos. Very high chronic doses led to developmental toxicity which included an increase in the fetal deaths, a decrease in the litter size, and a reduction in the fetal body weight. In addition, an increase in the incidence of fetal external, visceral, and skeletal abnormalities was seen. Chronic exposure to 2-bromopropane depletes spermatogenic cells in male rats and oocytes in female rats. Humans exposed to 2-bromopropane exhibited oligospermia, amenorrhea and other reproductive toxic effects.

Environmental Fate · 3 items

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).

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

Organobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Alkylation of DNA by alkylbromides may also lead to mutations. 2-bromopropane triggers the mitochondrion-dependent apoptotic pathway via ROS (reactive oxygen species) generation. 2-bromopropane has also been shown to induce DNA damage, impair functional antioxidant cellular defenses, and enhance the lipid peroxidation in cultured Leydig cells.

Safety data

PPE
Eyeshields, Faceshields, Gloves
wgk
1
tsca
TSCA listed
rtecs
TX4111000
ridadr
UN 2344 3/PG 2
hs_code
29033036

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed)

Uses & manufacturing

Uses · 4 items

Used as a freon substitute; [ChemIDplus] Used in organic synthesis; [Hawley]

Metal Degreasing [Category: Clean]

Used in the synthesis of pharmaceuticals, dyes and other organics

2-Bromopropane is an industrial and laboratory chemical.

U.S. Production · 4 items

2023: 50,000 - <250,000 lb

(1994) 10 thousand - 500 thousand pounds

(1998) 10 thousand - 500 thousand pounds

(2002) >500 thousand - 1 million pounds

Industry UsesIntermediate
Methods of ManufacturingObtained by heating isopropyl alcohol with HBr.
General Manufacturing Information · 2 items

All Other Basic Inorganic Chemical Manufacturing

Propane, 2-bromo-: ACTIVE

Applications · 3 items

Description2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula CH3CHBrCH3. It is a colorless liquid. It is used for introducing the isopropyl functional group in organic synthesis. 2-Bromopropane is prepared by heating isopropanol with hydrobromic acid.

Uses2-Bromopropane is a general reagent used to introduce isopropyl group as in the case of the synthesis of various Buchwald ligands. It can also be used as a starting material in the total synthesis of lamellarin D, lamellarin H, ningalin B and (±)-dichroanal. It is sometimes used as an alternative to ozone-depleting cleaning solvents such as chlorofluorocarbons.

Uses2-Bromopropane serves as an alkylating agent in organic synthesis. It is also used as an intermediate to form alkylated amines and alkylated metallic compounds. Further, it acts as a solvent for industrial cleaning, degreasing, metal processing and finishing, electronics, aerospace and aviation, aerosols, textiles, adhesives and inks. In addition, it is used for introducing the isopropyl functional group in organic synthesis.

Preparation methods

Preparation2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine, or with phosphorus tribromide.

Related reactions

1,063 records

Linked notes

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