1-Bromopropane

changed changed 400503207 1-Bromopropane 1-bromopropane.svg correct ?? 150 Skeletal formula of n-propyl bromide skin-invert N-propylBromide.png correct ?? 120 Spacefill model of 1-Bromopropane bg-transparent 1-Bromopropane1-bromopropane - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/7840 PubChem Compound National Center for Biotechnology Information 15 June 2012 USA 27 March 2005 Identification Bromopropane, 1-propyl bromide, 1-bromopropane, n-propyl Bromide, DrySolv, FabriSolv n-PB June 2012PrBrn-PrBrnPrBrnPrBr 106-94-5 correct CAS correct FDA Y9746DNE68 7840 7552 changed chemspider 203-445-0 2344 1-bromopropane changed EBI 47105 1230095 changed EBI TX4110000 505936 CCCBr 1S/C3H7Br/c1-2-3-4/h2-3H2,1H3 changed chemspider CYNYIHKIEHGYOZ-UHFFFAOYSA-N changed chemspider 3 7 1 Colorless liquid 1.354 g mL−1 162.7 343.4 to 344.4 2.5 g L−1 (at 20 °C) ethanol Miscible diethyl ether Miscible 2.319 19.5 kPa (at 20 °C) 1.4 μmol Pa−1 kg−1 1.43414 5.241 mPa s (at 20 °C) −125.8 to −123.0 kJ mol−1 −2.0580 to −2.0552 MJ mol−1 134.6 J K−1 mol−1 flame exclamation mark health hazard DANGER 225 315 319 335 336 360 373 201 210 261 305+351+338 308+313 2 3 0 22 490 4.6–?% 2.950 mg kg−1 (intraperitoneal, rat) alkanes Bromoethane 2-Bromopropane tert-Butyl bromide 1-Bromobutane 2-Bromobutane 1-Bromopropane (also known as n-propyl bromide or nPB) is a bromoalkane with the chemical formula C3H7Br 1 or CH3CH2CH2Br. It is a colorless, flammable liquid that is used as a solvent. It has a characteristic hydrocarbon odor. Its industrial applications increased dramatically in the 21st century due to the phasing out of chlorofluorocarbons and chloroalkanes such as 1,1,1-trichloroethane under the Montreal Protocol. It was also used as a dry cleaning solvent as a substitute for perchloroethylene for a short time in the United States. 1-Bromopropane is highly neurotoxic to humans. Preparation Industrial routes to 1-bromopropane involve free-radical additions to the corresponding alkenes. In this way, the anti-Markovnikov product is obtained.David Ioffe, Arieh Kampf "Bromine, Organic Compounds" in Kirk-Othmer Encyclopedia of Chemical Technology 2002 by John Wiley & Sons. 10.1002/0471238961.0218151325150606.a01. Alternatively, npropanol may be substitutively brominated. 10.1002/14356007.a22_157.pub3 Propanal 2018 Hensel A. 978-3527306732 5 The latter reaction is also viable laboratory synthesis. One laboratory technique for substitutive bromination treats propanol with a mixture of hydrobromic and sulfuric acids: CH3CH2CH2OH + HBr → CH3CH2CH2Br + H2O Alternate synthetic routes include treating propanol with phosphorus tribromide Alkyl and alkylene bromides Oliver Kamm and C. S. Marvel 1 25 1941 http://www.orgsyn.org/Content/pdfs/procedures/CV1P0025.pdf or via a Hunsdiecker reaction with butyric acid.Adams Rodger Organic Reactions Volume IX 1957 John Wiley and Sons, Inc. New York 978-0-471-00726-5 356 https://books.google.com/books?id=8epyngEACAAJ&q=9780471007265 3 September 2014 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. It is a solvent in asphalt production, in the aviation industry for maintenance, and in synthetic fiber production. https://www.cdc.gov/niosh/docs/2013-150/pdfs/2013-150.pdf Hazard Alert: 1-Bromopropane National Institute for Occupational Safety and Health 17 January 2015 July 2013 DHHS (NIOSH) Publication Number 2013-150 It is a solvent for degreasing plastics, optics and on metal surfaces, to remove soldering residues from electronic circuit boards. https://www.cdc.gov/niosh/blogs/2013/1-bromopropane.html 1-Bromopropane Doug Trout Naomi Hudson Scott Dotson Kevin Hanley 1 August 2013 16 January 2015 National Institute for Occupational Safety and Health It is an aggressive solvent with a Kauri-butanol value of 129 which is similar to 1,1,1-trichloroethane.Kanegsberg Barbara https://books.google.com/books?id=lPPLBQAAQBAJ&pg=PA72 Handbook for Critical Cleaning Kanegsberg Edward 2000-12-26 CRC Press 978-1-4200-3982-5 en It was used in dry-cleaning in the United States, introduced in 2006. It was represented by the FabriSolv and DrySolv products. Its increasing use in the 21st century resulted from the need for a substitute for chlorofluorocarbons (such as CFC-113) and perchloroethylene as a dry cleaning solvent, however its use in dry cleaning has been steadily declining and by 2020, its use for dry cleaning is nearly obsoleteSmith Carr J Perfetti Thomas A Morford Richard G 2020-01-01 Use of 1-bromopropane (N-propyl bromide) in dry cleaning is rare and rapidly declining toward obsolescence Toxicology Research and Application en 4 2397847320966961 10.1177/2397847320966961 2397-8473 free 228978817 while perchloroethylene remained the most common solvent in dry cleaning as of 2024. Dry cleaning machines used with 1-Bromopropane were converted PERC machines. Regulation In the European Union, 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".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 http://echa.europa.eu/documents/10162/7183371/agreement_1-bromopropane_en.pdf European Union 6 August 2014 29 November 2012 10 August 2014 https://web.archive.org/web/20140810204341/http://echa.europa.eu/documents/10162/7183371/agreement_1-bromopropane_en.pdf dead As of January 5, 2022, 1-bromopropane has been added to the United States Clean Air Act list of Hazardous Air Pollutants (HAP).87 FR 396, https://www.govinfo.gov/content/pkg/FR-2022-01-05/pdf/2021-28315.pdf 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.Protection of Stratospheric Ozone: Listing of Substitutes for Ozone- Depleting Substances-n-Propyl Bromide in Solvent Cleaning http://www.epa.gov/fedrgstr/EPA-AIR/2007/May/Day-30/a9707.pdf https://web.archive.org/web/20081026153845/http://www.epa.gov/fedrgstr/EPA-AIR/2007/May/Day-30/a9707.pdf October 26, 2008 Federal Register U.S. Environmental Protection Agency March 31, 2013 May 30, 2007 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. In 2013, the U.S. EPA announced that, based on a work plan developed under the Toxic Substances Control Act of 1976, it would begin a full risk assessment of 1-Bromopropane.United States Environmental Protection Agency List of Chemicals for Assessment http://www.epa.gov/oppt/existingchemicals/pubs/assessment_chemicals_list.html 23 April 2013 https://web.archive.org/web/20131018010457/http://www.epa.gov/oppt/existingchemicals/pubs/assessment_chemicals_list.html 2013-10-18 In December 2022, the U.S. EPA released a revised risk determination from the August 2020 risk evaluation, used to form a proposed risk management rule in July 2024.United States Environmental Protection Agency Risk Evaluation for 1-Bromopropane (1-BP) https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-evaluation-1-bromopropane-1-bp 28 August 2024 https://web.archive.org/web/20240709191050/https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-evaluation-1-bromopropane-1-bp 2024-07-09 liveUnited States Environmental Protection Agency Risk Management for 1-Bromopropane (1-BP) https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-1-bromopropane-1-bp 28 August 2024 https://web.archive.org/web/20240815211415/https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-1-bromopropane-1-bp 2024-08-15 live 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".North Carolina Department of Labor Hazard Alert http://www.nclabor.com/osha/etta/hazard_alerts/1-Bromopropane.pdf State of North Carolina 6 August 2014 June 2014 Safety In 2003, the American Conference of Governmental Industrial Hygienists (ACGIH) set the time-weighted average threshold limit value for an 8-hour exposure at 10 parts per million (ppm). In 2014, the ACGIH adopted a lower threshold limit value of 0.1 ppm as an 8-hour time-weighted average. 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. 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. 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.https://ntp.niehs.nih.gov/sites/default/files/ntp/about_ntp/monopeerrvw/2013/march/draftroc1bpmonograph_508.pdf National Toxicology Program 6 August 2014 21 March 2013 Report on Carcinogens Monograph on 1-Bromopropane Extended occupational exposure to 1-bromopropane in higher concentrations than recommended has resulted in significant injury to workers in the United States.1-BROMOPROPANE: Human Health Effects http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+106-94-5 https://web.archive.org/web/20170122231338/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+106-94-5 January 22, 2017 Hazardous Substances Data Bank March 31, 2013 Its use as a solvent in aerosol glues used to glue foam cushions has been especially controversial. Reported symptoms of overexposure affect the nervous system and include confusion, slurred speech, dizziness, paresthesias, and difficulty walking, unusual fatigue and headaches, development of arthralgias, visual disturbances (difficulty focusing), and muscle twitching. Symptoms may persist over one year.Neurologic Illness Associated with Occupational Exposure to the Solvent 1-Bromopropane --- New Jersey and Pennsylvania, 2007--2008 https://www.cdc.gov/mmwr/preview/mmwrhtml/mm5748a2.htm Centers for Disease Control March 31, 2013 December 5, 2008 Other symptoms include irritation of mucous membranes, eyes, upper respiratory tract, and skin, as well as transient loss of consciousness. Loss of feeling in the feet, an example of paresthesia, is colloquially called "dead foot" by workers who suffer from it. 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".As OSHA Emphasizes Safety, Long-Term Health Risks Fester https://www.nytimes.com/2013/03/31/us/osha-emphasizes-safety-health-risks-fester.html March 31, 2013 The New York Times March 30, 2013 Ian Urbina One worker's long-term exposure resulting in neurological damage was covered in the NY Times. Air sampling for the level of 1-bromopropane and monitoring workers' urine for metabolites are both effective at measuring workers' exposure. 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 engineering controls like isolation and ventilation, administrative controls, and PPE that includes respiratory and skin protection. 1-Bromopropane can penetrate most gloves, but not those made of polyvinyl alcohol or laminates. Animal studies Animal studies of 1-bromopropane have shown that it is a carcinogen in those models. Rodents exposed to 1-bromopropane developed lung, colon, and skin cancer at higher rates. Environmental impact Stratospheric ozone layer damage Although 1-bromopropane is naturally produced,March 2021 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.2007 Q and A 2007 Final and Proposed Regulations for n Propyl Bromide (nPB) https://www.epa.gov/sites/default/files/2014-11/documents/qandacln5-1-07_0.pdf US EPAWuebbles Donald J. Patten Kenneth O. Johnson Matthew T. Kotamarthi Rao 2001-07-01 New methodology for Ozone Depletion Potentials of short-lived compounds: n-Propyl bromide as an example Journal of Geophysical Research 106 D13 14 10.1029/2001JD900008 2001JGR...10614551W 0148-0227 free 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. References Further reading OSHA/NIOSH Hazard Alert: 1-Bromopropane Category:Bromoalkanes Category:Dry cleaning Category:Halogenated solvents Category:Industrial hygiene Category:Alkylating agents Category:IARC Group 2B carcinogens Category:Ozone-depleting chemical substances Category:Propyl compounds