1-Bromopropane

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1-Bromopropane
Skeletal formula of n-propyl bromide
Spacefill model of 1-Bromopropane
Names
Preferred IUPAC name
1-Bromopropane[1]
Other names
  • Bromopropane, 1-propyl bromide, 1-bromopropane, n-propyl bromide
Identifiers
3D model (
JSmol
)
Abbreviations n-PB[citation needed]
505936
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.003.133 Edit this at Wikidata
EC Number
  • 203-445-0
MeSH 1-bromopropane
RTECS number
  • TX4110000
UNII
UN number 2344
  • InChI=1S/C3H7Br/c1-2-3-4/h2-3H2,1H3 ☒N
    Key: CYNYIHKIEHGYOZ-UHFFFAOYSA-N ☒N
  • CCCBr
Properties
C3H7Br
Molar mass 122.993 g·mol−1
Appearance Colorless liquid
Density 1.354 g mL−1
Melting point −110.5 °C; −166.8 °F; 162.7 K
Boiling point 70.3 to 71.3 °C; 158.4 to 160.2 °F; 343.4 to 344.4 K
2.5 g L−1 (at 20 °C)
Solubility in ethanol Miscible
Solubility in diethyl ether Miscible
log P 2.319
Vapor pressure 19.5 kPa (at 20 °C)
1.4 μmol Pa−1 kg−1
1.43414
Viscosity 5.241 mPa s (at 20 °C)
Thermochemistry
134.6 J K−1 mol−1
Std enthalpy of
formation
(ΔfH⦵298)
 −125.8 to −123.0 kJ mol−1
Std enthalpy of
combustion
(ΔcH⦵298)
 −2.0580 to −2.0552 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark GHS08: Health hazard
Danger
H225, H315, H319, H335, H336, H360, H373
P201, P210, P261, P305+P351+P338, P308+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 22 °C (72 °F; 295 K)
490 °C (914 °F; 763 K)
Explosive limits
 4.6–?%
Lethal dose or concentration (LD, LC):
2.950 mg kg−1 (intraperitoneal, rat)
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1-Bromopropane (n-propylbromide or nPB) is an

chloro­alkanes such as 1,1,1-Trichloro­ethane under the Montreal Protocol
.

Preparation

Industrial routes to 1-bromopropane involve free-radical additions to the corresponding alkenes. In this way, the anti-Markovnikov product is obtained.[2]

A laboratory synthesis involves treating propanol with a mixture of hydrobromic and sulfuric acids:

CH3CH2CH2OH + HBr → CH3CH2CH2Br + H2O

Alternate synthetic routes include treating propanol with phosphorus tribromide[3] or via a Hunsdiecker reaction with butyric acid.[4]

Applications

Like many other liquid halocarbons, 1-bromopropane finds use as a liquid or gaseous solvent. It is a solvent for adhesives in aerosol glues that glue foam cushions together.[5] It is a solvent in asphalt production, in the aviation industry for maintenance, and in synthetic fiber production.[6] It is a solvent for degreasing plastics, optics and on metal surfaces, to remove soldering residues from electronic circuit boards.[7] It is an aggressive solvent with a Kauri-butanol value of 129 which is similar to 1,1,1-Trichloroethane[8]

Its increasing use in the 21st century resulted from the need for a substitute for

perchloroethylene (tetrachloroethylene) as a dry cleaning solvent,[9] however its use in dry cleaning has been steadily declining and by 2020, its use for dry cleaning is nearly obsolete.[10]

Regulation

In the EU, 1-bromopropane has been classified as reproductive toxicant per Registration, Evaluation, Authorisation and Restriction of Chemicals, which makes it a "substance of very high concern".[11]

As of January 5, 2022, 1-bromopropane has been added to the United States Clean Air Act list of Hazardous Air Pollutants (HAP).[12]

Since 2007, it has been approved for use under the U.S. EPA's Significant New Alternatives Policy (SNAP) as a suitable replacement for ozone depleting chemicals.[13] The U.S. EPA announced that, based on a work plan developed under the Toxic Substances Control Act of 1976, in 2013 it will begin a full risk assessment of 1-Bromopropane.[14]

The North Carolina Department of Labor’s Occupational Safety and Health Division issued a Hazard Alert in 6/2014, as it "is not regulated to protect workers, consumers or the environment".[15]

Safety

In 2003, the

California Occupational Safety and Health Administration set the permissible exposure limit at 5 ppm in 2010. Though symptoms of overexposure can begin within 2 days of exposure, typically long-term exposure is more harmful.[7]

In 2008, the U.S. CDC recommended that use of 1-bromopropane as a replacement for perchloroethylene may require adjustment and modification of equipment, improved ventilation, and use of personal protective equipment.[9]

In 2013, a peer-review panel convened by the U.S. National Toxicology Program unanimously recommended that 1-bromopropane, be classified as reasonably anticipated human carcinogens.[16]

Extended occupational exposure to 1-bromopropane in higher concentrations than recommended has resulted in significant injury to workers in the United States.

mucous membranes, eyes, upper respiratory tract, and skin, as well as transient loss of consciousness.[7] Loss of feeling in the feet, an example of paresthesia, is colloquially called "dead foot" by workers who suffer from it.[5] Of nationwide "more than 140 cushion workers nationwide, mostly from plants in Utah, Mississippi and North Carolina,[...] that had been exposed to dangerous levels of the chemical, many of them sickened and [are] unable to walk".[5] One worker's long-term exposure resulting in neurological damage was covered in the NY Times.[5] Air sampling for the level of 1-bromopropane and monitoring workers' urine for metabolites are both effective at measuring workers' exposure.[7]

Occupational exposure to 1-bromopropane typically occurs through breathing or skin contact; it is easily absorbed into the blood via the skin. Replacing 1-bromopropane with water or acetone-based adhesives is the preferred NIOSH option for controlling occupational exposure, but other options include

administrative controls, and PPE that includes respiratory and skin protection.[7] 1-Bromopropane can penetrate most gloves, but not those made of polyvinyl alcohol or laminates.[6]

Animal studies

Animal studies of 1-bromopropane have showed that it is a carcinogen in those models.

colon, and skin cancer at higher rates.[6]

Environmental impact

Stratospheric ozone layer damage

Although 1-bromopropane is naturally produced,[citation needed] it is one of the very short-lived substances that depletes ozone. Because 1-bromopropane is so short-lived, its ozone depletion potential (ODP) is dependent on the latitude where it is released.[18][19] According to the United States Environmental Protection Agency, the ODP is 0.013-0.018 in U.S. latitudes and 0.071-0.100 in tropical latitudes.[18]

References

  1. ^ "1-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
  2. doi:10.1002/0471238961.0218151325150606.a01
    .
  3. ^ Oliver Kamm and C. S. Marvel (1941). "Alkyl and alkylene bromides" (PDF). Organic Syntheses; Collected Volumes, vol. 1, p. 25.
  4. ISBN 9780471007265
    . Retrieved 3 September 2014.
  5. ^ a b c d e Ian Urbina (March 30, 2013). "As OSHA Emphasizes Safety, Long-Term Health Risks Fester". The New York Times. Retrieved March 31, 2013.
  6. ^ a b c "Hazard Alert: 1-Bromopropane" (PDF). DHHS (NIOSH) Publication Number 2013-150. National Institute for Occupational Safety and Health. July 2013. Retrieved 17 January 2015.
  7. ^ a b c d e f Trout, Doug; Hudson, Naomi; Dotson, Scott; Hanley, Kevin (1 August 2013). "1-Bromopropane". National Institute for Occupational Safety and Health. Retrieved 16 January 2015.
  8. ISBN 978-1-4200-3982-5
    .
  9. ^ a b c "Neurologic Illness Associated with Occupational Exposure to the Solvent 1-Bromopropane --- New Jersey and Pennsylvania, 2007--2008". Centers for Disease Control. December 5, 2008. Retrieved March 31, 2013.
  10. S2CID 228978817
    .
  11. ^ "AGREEMENT OF THE MEMBER STATE COMMITTEE ON THE IDENTIFICATION OF 1-BROMOPROPANE [n-PROPYL BROMIDE] AS A SUBSTANCE OF VERY HIGH CONCERN According to Articles 57 and 59 of Regulation (EC) 1907/20061" (PDF). European Union. 29 November 2012. Retrieved 6 August 2014.
  12. ^ 87 FR 396, https://www.govinfo.gov/content/pkg/FR-2022-01-05/pdf/2021-28315.pdf
  13. ^ "Protection of Stratospheric Ozone: Listing of Substitutes for Ozone- Depleting Substances-n-Propyl Bromide in Solvent Cleaning" (PDF). Federal Register. U.S. Environmental Protection Agency. May 30, 2007. Retrieved March 31, 2013. This final rule lists n-propyl bromide (nPB) as an acceptable substitute when used as a solvent in industrial equipment for metals cleaning, electronics cleaning, or precision cleaning. General metals, precision, and electronics cleaning includes cleaning with industrial cleaning equipment such as vapor degreasers, in-line cleaning systems, or automated equipment used for cleaning below the boiling point.
  14. ^ United States Environmental Protection Agency. "List of Chemicals for Assessment". Retrieved 23 April 2013.
  15. ^ North Carolina Department of Labor (June 2014). "Hazard Alert" (PDF). State of North Carolina. Retrieved 6 August 2014.
  16. ^ "Report on Carcinogens Monograph on 1-Bromopropane" (PDF). National Toxicology Program. 21 March 2013. Retrieved 6 August 2014.
  17. ^ "1-BROMOPROPANE: Human Health Effects". Hazardous Substances Data Bank. Retrieved March 31, 2013.
  18. ^ a b "Q and A 2007 Final and Proposed Regulations for n Propyl Bromide (nPB)" (PDF). US EPA. 2007.
  19. ISSN 0148-0227
    .

Further reading
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