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Also known as: 109-65-9, Butyl bromide, N-butyl bromide, Butane, 1-bromo-, 1-butyl bromide, N-butylbromide
Molecular Formula
C4H9Br
Molecular Weight
137.02  g/mol
InChI Key
MPPPKRYCTPRNTB-UHFFFAOYSA-N
FDA UNII
SAV6Y78U3D

CAS 109-65-9
1-Bromobutane is a colorless liquid that is insoluble in water, but soluble in ethanol and diethyl ether. As a primary haloalkane, it is especially prone to SN2 type reactions. It is commonly used as an alkylating agent, or in combination with magnesium metal in dry ether (Grignard reagent) to form carbon-carbon bonds. It can be used as a cleaning agent, an agent for chemical synthesis or as a solvent for extractions. It is highly flammable.
1 2D Structure

CAS 109-65-9

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-bromobutane
2.1.2 InChI
InChI=1S/C4H9Br/c1-2-3-4-5/h2-4H2,1H3
2.1.3 InChI Key
MPPPKRYCTPRNTB-UHFFFAOYSA-N
2.2 Other Identifiers
2.2.1 UNII
SAV6Y78U3D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Butyl Bromide

2. Butylbromide

2.3.2 Depositor-Supplied Synonyms

1. 109-65-9

2. Butyl Bromide

3. N-butyl Bromide

4. Butane, 1-bromo-

5. 1-butyl Bromide

6. N-butylbromide

7. Butylbromide

8. 1-bromo-butane

9. Ccris 831

10. Bromo Butane

11. Hsdb 2195

12. Einecs 203-691-9

13. Sav6y78u3d

14. Un1126

15. Ai3-15308

16. N-c4h9br

17. N-butyl Bromide [mi]

18. N-butyl Bromide [hsdb]

19. Dtxsid6021903

20. Ec 203-691-9

21. Butyl Bromide, (normal)

22. Butyl Bromide, [normal]

23. Nbutyl Bromide

24. 1butyl Bromide

25. Butane, 1bromo

26. N-bromobutane

27. Dtxcid101903

28. 203-691-9

29. Inchi=1/c4h9br/c1-2-3-4-5/h2-4h2,1h

30. Bromobutane

31. Mfcd00000260

32. 1-bromobutane-1d4

33. Butane, Bromo-

34. 1-bromobutane--d5

35. Unii-sav6y78u3d

36. L-bromobutane

37. N-butylbromid

38. N-butyl Bromine

39. N-butyl-bromide

40. 1-butylbromide

41. 4-bromobutane

42. 1-bromanylbutane

43. Bubr

44. 1 -bromobutane

45. 1- Bromobutane

46. 1-bromo Butane

47. 4-bromo-butane

48. 1-bromo-n-butane

49. N-bu-br

50. Propyl Methyl Bromide

51. 1219805-37-4

52. Schembl8141

53. Chembl160949

54. 1-bromobutane, Analytical Standard

55. Fca72442

56. Hy-y0554

57. Yda19536

58. Stl282740

59. Akos000118760

60. 1-bromobutane, Reagentplus(r), 99%

61. Fb53760

62. Un 1126

63. 1-bromobutane, Reagentplus(r), >=99%

64. Bbu

65. Ls-13004

66. Db-050412

67. B0560

68. Cs-0015331

69. Ns00006184

70. En300-19285

71. 1-bromobutane [un1126] [flammable Liquid]

72. G77188

73. Q59081

74. A802070

75. F0001-0198

76. 1-bromobutane; 1-butyl Bromide; Butyl Bromide; N-butyl Bromide;

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 137.02 g/mol
Molecular Formula C4H9Br
XLogP32.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count2
Exact Mass Da
Monoisotopic Mass Da
Topological Polar Surface Area0
Heavy Atom Count5
Formal Charge0
Complexity13.1
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

/n-Butyl bromide administered orally (at the LD50) was deposited mainly in the brain, liver, and perirenal cellular system, and excreted primarily by the lungs./

Kosenko AM, Salyaev VN; Farmakol Toksikol Nov Prod Dhim Sint, Mater, Resp Konf 3: 174-5 (1975)


4.2 Metabolism/Metabolites

The hydrolysis of inorganic bromine in the liver following treatment with brominated hydrocarbons was studied. White-mice were administered ...n-butyl-bromide by inhalation in concentrations of 0.75-25 mmol/mL for up to 60 minutes. ...Concentrations of inorganic bromide in the liver were higher in animals that inhaled saturated, brominated hydrocarbons /(including n-butyl bromide)/ than in those that inhaled the unsaturated compounds. The degree of hydrolysis was also higher with the saturated compounds than with the unsaturated compounds. /It was concluded/ that liver tissue damage is probably caused directly by the brominated hydrocarbons rather than by hydrobromic-acid since this acid is released very slowly during hydrolysis.

Abreu BE, Emerson GA; Univ of California, Berkeley, Pubs in Pharmacol 1: 313-9 (1940)


Rabbits and rats dosed with 1-bromobutane excrete in urine, in addition to butylmercapturic acid, (2-hydroxybutyl)mercapturic acid, (3-hydroxybutyl)mercapturic acid and 3-(butylthio)lactic acid. Although both species excrete both the hydroxybutylmercapturic acids, only traces of the 2-isomer are excreted by the rabbit. The 3-isomer has been isolated from rabbit urine as the dicyclohexylammonium salt. 3-(Butylthio)lactic acid is formed more readily in the rabbit; only traces are excreted by the rat. Traces of the sulphoxide of butylmercapturic acid have been found in rat urine but not in rabbit urine. In the rabbit about 14% and in the rat about 22% of the dose of 1-bromobutane is excreted in the form of the hydroxymercapturic acids. Slices of rat liver incubated with S-butylcysteine or butylmercapturic acid form both (2-hydroxybutyl)mercapturic acid and (3-hydroxybutyl)mercapturic acid, but only the 3-hydroxy acid is formed by slices of rabbit liver. S-Butylglutathione, S-butylcysteinylglycine and S-butylcysteine are excreted in bile by rats dosed with 1-bromobutane. Rabbits and rats dosed with 1,2-epoxybutane excrete (2-hydroxybutyl)mercapturic acid to the extent of about 4% and 11% of the dose respectively. The following have been synthesized: N-acetyl-S-(2-hydroxybutyl)-l-cysteine [(2-hydroxybutyl)mercapturic acid] and N-acetyl-S-(3-hydroxybutyl)-l-cysteine [(3-hydroxybutyl)mercapturic acid] isolated as dicyclohexylammonium salts, N-toluene-p-sulphonyl-S-(2-hydroxybutyl)-l-cysteine, S-butylglutathione and N-acetyl-S-butylcysteinyl-glycine ethyl ester.

PMID:5696863 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1187022 James SP et al; Biochem J 109 (5): 727-736 (1968)


Rabbits and rats dosed with 1-bromobutane excrete in urine, in addition to butylmercapturic acid, (2-hydroxybutyl)mercapturic acid, (3-hydroxybutyl)mercapturic acid and 3-(butylthio)lactic acid. In the rabbit about 14% and in the rat about 22% of the dose of 1-bromobutane is excreted in the form of the hydroxymercapturic acids. 1-bromobutane also forms glutathione conjugates. Three kinds of GSH conjugates, including S-butyl GSH, S-butyl cysteine, and (hydroxybutyl)mercapturic acid, have been identified in mice livers after oral dosing with 375-1500 mg/kg of the compound.


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