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2-Bromopropane

April 18, 2024

2-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.[3]

2-Bromopropane
Ball and stick model of 2-bromopropane
Spacefill model of 2-bromopropane
Names
Preferred IUPAC name
2-Bromopropane[2]
Other names
Isopropyl bromide[1]
Identifiers
  • 75-26-3 Y
3D model (JSmol)
  • Interactive image
741852
ChEMBL
  • ChEMBL451810 Y
ChemSpider
  • 6118 Y
ECHA InfoCard 100.000.778
EC Number
  • 200-855-1
MeSH 2-bromopropane
  • 6358
RTECS number
  • TX4111000
UNII
  • R651XOV97Z Y
UN number 2344
  • DTXSID7030197
  • InChI=1S/C3H7Br/c1-3(2)4/h3H,1-2H3 Y
    Key: NAMYKGVDVNBCFQ-UHFFFAOYSA-N Y
  • CC(C)Br
Properties
C3H7Br
Molar mass 122.993 g·mol−1
Appearance Colorless liquid
Density 1.31 g mL−1
Melting point −89.0 °C; −128.1 °F; 184.2 K
Boiling point 59 to 61 °C; 138 to 142 °F; 332 to 334 K
3.2 g L−1 (at 20 °C)
log P 2.136
Vapor pressure 32 kPa (at 20 °C)
1.0 μmol Pa−1 mol−1
1.4251
Viscosity 0.4894 mPa s (at 20 °C)
Thermochemistry
135.6 J K mol−1
−129 kJ mol−1
−2.0537–−2.0501 MJ mol−1
Hazards
GHS labelling:
Danger
H225, H360, H373
P210, P308+P313
NFPA 704 (fire diamond)
Health 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 19 °C (66 °F; 292 K)
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 YN ?)

Preparation edit

2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine,[4] or with phosphorus tribromide.[5]

Safety edit

Short-chain alkyl halides are often carcinogenic.

The bromine atom is at the secondary position, which allows the molecule to undergo dehydrohalogenation easily to give propene, which escapes as a gas and can rupture closed reaction vessels. When this reagent is used in base catalyzed reactions, potassium carbonate should be used in place of sodium or potassium hydroxide.

Further reading edit

  • Max Gergel, “Excuse Me Sir, Would You Like to Buy a Kilo of Isopropyl Bromide?” Pierce Chemical Co. (1979). (story of start-up chemical company).

References edit

  1. ^ Armarego, Wilfred L.F.; Li Lin Chai, Christina (2013). Purification of laboratory chemicals (7th ed.). Butterworth-Heinemann. p. 176. ISBN 9780123821621.
  2. ^ "2-bromopropane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 15 June 2012.
  3. ^ "Monograph 6526". Merck Index of Chemicals and Drugs.
  4. ^ Oliver Kamm and C. S. Marvel (1941). "Alkyl and alkylene bromides". Organic Syntheses; Collected Volumes, vol. 1, p. 25.
  5. ^ C. R. Noller and R. Dinsmore (1943). "Isobutyl bromide". Organic Syntheses; Collected Volumes, vol. 2, p. 358.

April 18, 2024
bromopropane, also, known, isopropyl, bromide, propyl, bromide, halogenated, hydrocarbon, with, formula, ch3chbrch3, colorless, liquid, used, introducing, isopropyl, functional, group, organic, synthesis, prepared, heating, isopropanol, with, hydrobromic, acid. 2 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 3 2 Bromopropane Ball and stick model of 2 bromopropane Spacefill model of 2 bromopropane Names Preferred IUPAC name 2 Bromopropane 2 Other names Isopropyl bromide 1 Identifiers CAS Number 75 26 3 Y 3D model JSmol Interactive image Beilstein Reference 741852 ChEMBL ChEMBL451810 Y ChemSpider 6118 Y ECHA InfoCard 100 000 778 EC Number 200 855 1 MeSH 2 bromopropane PubChem CID 6358 RTECS number TX4111000 UNII R651XOV97Z Y UN number 2344 CompTox Dashboard EPA DTXSID7030197 InChI InChI 1S C3H7Br c1 3 2 4 h3H 1 2H3 YKey NAMYKGVDVNBCFQ UHFFFAOYSA N Y SMILES CC C Br Properties Chemical formula C 3H 7Br Molar mass 122 993 g mol 1 Appearance Colorless liquid Density 1 31 g mL 1 Melting point 89 0 C 128 1 F 184 2 K Boiling point 59 to 61 C 138 to 142 F 332 to 334 K Solubility in water 3 2 g L 1 at 20 C log P 2 136 Vapor pressure 32 kPa at 20 C Henry s lawconstant kH 1 0 mmol Pa 1 mol 1 Refractive index nD 1 4251 Viscosity 0 4894 mPa s at 20 C Thermochemistry Heat capacity C 135 6 J K mol 1 Std enthalpy offormation DfH 298 129 kJ mol 1 Std enthalpy ofcombustion DcH 298 2 0537 2 0501 MJ mol 1 Hazards GHS labelling Pictograms Signal word Danger Hazard statements H225 H360 H373 Precautionary statements P210 P308 P313 NFPA 704 fire diamond 230 Flash point 19 C 66 F 292 K Related compounds Related alkanes Bromoethane1 Bromopropanetert Butyl bromide1 Bromobutane2 Bromobutane Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Safety 3 Further reading 4 ReferencesPreparation edit2 Bromopropane is commercially available It may be prepared in the ordinary manner of alkyl bromides by reacting isopropanol with phosphorus and bromine 4 or with phosphorus tribromide 5 Safety editShort chain alkyl halides are often carcinogenic The bromine atom is at the secondary position which allows the molecule to undergo dehydrohalogenation easily to give propene which escapes as a gas and can rupture closed reaction vessels When this reagent is used in base catalyzed reactions potassium carbonate should be used in place of sodium or potassium hydroxide Further reading editMax Gergel Excuse Me Sir Would You Like to Buy a Kilo of Isopropyl Bromide Pierce Chemical Co 1979 story of start up chemical company References edit Armarego Wilfred L F Li Lin Chai Christina 2013 Purification of laboratory chemicals 7th ed Butterworth Heinemann p 176 ISBN 9780123821621 2 bromopropane Compound Summary PubChem Compound USA National Center for Biotechnology Information 27 March 2005 Identification Retrieved 15 June 2012 Monograph 6526 Merck Index of Chemicals and Drugs Oliver Kamm and C S Marvel 1941 Alkyl and alkylene bromides Organic Syntheses Collected Volumes vol 1 p 25 C R Noller and R Dinsmore 1943 Isobutyl bromide Organic Syntheses Collected Volumes vol 2 p 358 Retrieved from https en wikipedia org w index php title 2 Bromopropane amp oldid 1192797556, wikipedia, wiki, book, books, library,

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