1-Propene, 3-bromo-

Formula: C₃H₅Br
Molecular weight: 120.976
IUPAC Standard InChI: InChI=1S/C3H5Br/c1-2-3-4/h2H,1,3H2
IUPAC Standard InChIKey: BHELZAPQIKSEDF-UHFFFAOYSA-N
CAS Registry Number: 106-95-6
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: Propene, 3-bromo-; Allyl bromide; 1-Bromo-2-propene; 2-Propenyl bromide; 3-Bromo-1-propene; 3-Bromopropene; 3-Bromopropylene; CH2=CHCH2Br; Bromallylene; UN 1099; NSC 7596
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- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	47.7	kJ/mol	Ion	Traeger, 1984
Δ_fH°_gas	45.6 ± 6.7	kJ/mol	Cm	Gellner and Skinner, 1949	Heat of formation derived by Cox and Pilcher, 1970

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C₃H₄Br^- + = 1-Propene, 3-bromo-

By formula: C₃H₄Br^- + H⁺ = C₃H₅Br

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1570. ± 8.8	kJ/mol	G+TS	Poutsma, Nash, et al., 1997	gas phase; Between iPrOH, HF; near tBuOH; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1540. ± 8.4	kJ/mol	IMRB	Poutsma, Nash, et al., 1997	gas phase; Between iPrOH, HF; near tBuOH; B

1-Propene, 3-bromo- + = +

By formula: C₃H₅Br + H₂O = HBr + C₃H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-15.	kJ/mol	Cm	Gellner and Skinner, 1949	liquid phase; Heat of hydrolysis; ALS

1-Propene, 3-bromo- =

By formula: C₃H₅Br = C₃H₅Br

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-3.0 ± 0.4	kJ/mol	Ciso	Abell and Adolf, 1969	gas phase; HBr catalyst; ALS

= 1-Propene, 3-bromo-

By formula: C₃H₅Br = C₃H₅Br

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1.3 ± 0.50	kJ/mol	Eqk	Alfassi, Golden, et al., 1973	gas phase; ALS

= 1-Propene, 3-bromo-

By formula: C₃H₅Br = C₃H₅Br

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	4.5 ± 0.4	kJ/mol	Eqk	Alfassi, Golden, et al., 1973	gas phase; ALS

Gas phase ion energetics data

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Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₃H₅Br⁺ (ion structure unspecified)

Ionization energy determinations

IE (eV)	Method	Reference	Comment
9.96	PI	Traeger, 1984, 2	LBLHLM
10.0	PE	Bieri, Asbrink, et al., 1982	Vertical value; LBLHLM
10.01	PE	Worrell, 1974	Vertical value; LLK
10.18	PE	Schmidt and Schweig, 1973	Vertical value; LLK
10.06	PE	Mines and Thompson, 1973	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₃H₅⁺	10.39	Br	PI	Traeger, 1984, 2	LBLHLM

De-protonation reactions

C₃H₄Br^- + = 1-Propene, 3-bromo-

By formula: C₃H₄Br^- + H⁺ = C₃H₅Br

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1570. ± 8.8	kJ/mol	G+TS	Poutsma, Nash, et al., 1997	gas phase; Between iPrOH, HF; near tBuOH; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1540. ± 8.4	kJ/mol	IMRB	Poutsma, Nash, et al., 1997	gas phase; Between iPrOH, HF; near tBuOH; B

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

Traeger, 1984
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259-271. [all data]

Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A., Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X, J. Chem. Soc., 1949, 1145-1148. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Abell and Adolf, 1969
Abell, P.I.; Adolf, P.K., HBr catalyzed photoisomerization of allyl halides, J. Chem. Thermodyn., 1969, 1, 333-338. [all data]

Alfassi, Golden, et al., 1973
Alfassi, Z.B.; Golden, D.M.; Benson, S.W., The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the C_d-(H)(X) group, J. Chem. Thermodyn., 1973, 5, 411-420. [all data]

Traeger, 1984, 2
Traeger, J.C., A study of the allyl cation thermochemistry by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Worrell, 1974
Worrell, C.W., The photoelectron and absorption spectra of allyl halides, J. Electron Spectrosc. Relat. Phenom., 1974, 3, 359. [all data]

Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A., Semiquantitative proof of hyperconjugation, Angew. Chem. Int. Ed. Engl., 1973, 12, 307. [all data]

Mines and Thompson, 1973
Mines, G.W.; Thompson, H.W., Photoelectron spectra of vinyl and allyl halides, Spectrochim. Acta Part A, 1973, 29, 1377. [all data]

Notes

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Symbols used in this document:

AE Appearance energy

Δ_fH°_gas Enthalpy of formation of gas at standard conditions

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions