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Also known as: 106-94-5, N-propyl bromide, Propyl bromide, Propane, 1-bromo-, Propane, bromo-, 1-bromo-propane
Molecular Formula
C3H7Br
Molecular Weight
122.99  g/mol
InChI Key
CYNYIHKIEHGYOZ-UHFFFAOYSA-N
FDA UNII
Y9746DNE68

CAS 106-94-5
1-bromopropane is an organobromide compound. It is a widely used organic solvent used for the cleaning of metal surfaces, removal of soldering residues from electronic circuit boards, and in the hole transport layer (HTL) of multi-layered OLEDs. It is also a solvent for adhesives and has been deployed as a replacement for perchloroethylene as a dry cleaning solvent. Its use as a solvent in aerosol glues used to glue foam cushions has been especially problematic. 1-bromopropanes increasing use in the 21st century resulted from need for a substitute for chlorofluorocarbons and perchloroethylene (tetrachloroethylene). In 2013, a peer-review panel convened by the National Toxicology Program unanimously recommended that 1-bromopropane should be classified as a reasonably anticipated human carcinogen.
1 2D Structure

CAS 106-94-5

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-bromopropane
2.1.2 InChI
InChI=1S/C3H7Br/c1-2-3-4/h2-3H2,1H3
2.1.3 InChI Key
CYNYIHKIEHGYOZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCBr
2.2 Other Identifiers
2.2.1 UNII
Y9746DNE68
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-bp, Propane

2. N-propylbromide

3. Propyl Bromide

2.3.2 Depositor-Supplied Synonyms

1. 106-94-5

2. N-propyl Bromide

3. Propyl Bromide

4. Propane, 1-bromo-

5. Propane, Bromo-

6. 1-bromo-propane

7. 1-propyl Bromide

8. Propylbromide

9. Mfcd00000254

10. Dtxsid6021874

11. Chebi:47105

12. Y9746dne68

13. 1-bromopropane-d7

14. Bromopropane

15. N-propylbromide

16. Ccris 30

17. Bromopropane, 1-

18. 40422-05-7

19. Hsdb 1068

20. Einecs 203-445-0

21. Bromo-propane

22. Unii-y9746dne68

23. 1-propylbromide

24. 1-bp

25. 3-bromopropane

26. Ai3-18129

27. 1-brompropane

28. 26446-77-5

29. 1-bromo Propane

30. 3-bromo Propane

31. Prbr

32. 1-bromanylpropane

33. N-prbr

34. 1-bromopropane, 99%

35. N-c3h7br

36. Ec 203-445-0

37. Schembl2478

38. Propyl Bromide [mi]

39. 1-bromopropane [hsdb]

40. 1-bromopropane [iarc]

41. Dtxcid401874

42. Schembl6999850

43. Chembl1230095

44. 1-bromopropane, Analytical Standard

45. Tox21_200619

46. Br1117

47. Stl264215

48. Akos000118833

49. Ncgc00091561-01

50. Ncgc00091561-02

51. Ncgc00258173-01

52. 3br

53. Cas-106-94-5

54. Ls-12961

55. B0638

56. Ft-0607548

57. Ft-0656570

58. En300-19391

59. Inchi=1/c3h7br/c1-2-3-4/h2-3h2,1h

60. A801541

61. Q161589

62. J-504471

63. F0001-0130

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 122.99 g/mol
Molecular Formula C3H7Br
XLogP32.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count1
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area0
Heavy Atom Count4
Formal Charge0
Complexity7.2
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

... In this study, the factors influencing the disposition and biotransformation of 1-bromopropane (1-BrP) were examined in male F344 rats and B6C3F1 mice following inhalation exposure (800 ppm) or intravenous administration (5, 20, and 100 mg/kg). (1,2,3-(13)C)1-BrP and (1-(14)C)1-BrP were administered to enable characterization of urinary metabolites using NMR spectroscopy, LC-MS/MS, and HPLC coupled radiochromatography. Exhaled breath volatile organic chemicals (VOC), exhaled CO(2), urine, feces, and tissues were collected for up to 48 h post-administration for determination of radioactivity distribution. Rats and mice exhaled a majority of the administered dose as either VOC (40-72%) or (14)CO(2) (10-30%). For rats, but not mice, the percentage of the dose exhaled as VOC increased between the mid ( approximately 50%) and high ( approximately 71%) dose groups; while the percentage of the dose exhaled as (14)CO(2) decreased (19 to 10%). The molar ratio of exhaled (14)CO(2) to total released bromide, which decreased as dose increased, demonstrated that the proportion of 1-BrP metabolized via oxidation relative to pathways dependent on glutathione conjugation is inversely proportional to dose in the rat. ((14)C)1-BrP equivalents were recovered in urine (13-17%, rats; 14-23% mice), feces (<2%), or retained in the tissues and carcass (<6%) of rats and mice administered i.v. 5 to 100 mg/kg ((14)C)1-BrP. ... Rats pretreated with 1-aminobenzotriazole (ABT), a potent inhibitor of P450 excreted less in urine (down 30%), exhaled as (14)CO2 (down 80%), or retained in liver (down 90%), with a concomitant increase in radioactivity expired as VOC (up 52%). Following ABT pretreatment, rat urinary metabolites were reduced in number from 10 to 1, N-acetyl-S-propylcysteine, which accounted for >90% of the total urinary radioactivity in ABT pretreated rats. Together, these data demonstrate a role for cytochrome P450 and glutathione in the dose-dependent metabolism and disposition of 1-BrP in the rat.

PMID:16513153 Garner CE et al; Toxicol Appl Pharmacol 215 (1): 23-36 (2006)


.../It is/ reported that orally administered 1-bromopropane is excreted in expired air.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V5 190


Parent compound and metabolites are excreted in urine as mercapturic acids.

Jones AR et al; Xenobiotica 9 (12): 763 (1980)


/Investigators/ injected Sprague-Dawley rats intraperitoneally with 200 mg/kg 1-BP and observed a rapid excretion of greater than half of the administered dose in expired air. By hour 100, 25% of the 1-BP dose was excreted in the urine.

American Conference of Governmental Industrial Hygienists. Documentation of the TLVs and BEIs with Other World Wide Occupational Exposure Values. 7th Ed. CD-ROM Cincinnati, OH 45240-1634 2013.


For more Absorption, Distribution and Excretion (Complete) data for 1-Bromopropane (7 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

... Six workers, 1 male and 5 female, were exposed to high ambient 1-Bromopropane (1-BP) concentrations while employed in a golf club cleaning factory. 1-BP was identified in the bulk solvent sample used by the workers and confirmed the workers' daily occupational exposure to 1-BP for 3-10 months. The major presenting symptoms were tingling pain, soreness in lower extremities, and paresthesia. N-acetyl-S-(n-propyl)-L-cysteine (AcPrCys), a 1-BP metabolite, was identified by LC/MS/MS in the urine (0.171-1.74 mg/g-Cr) of these workers 5-26 days following 1-BP exposure. ...

PMID:26161839 Wang TH et al; Clin Toxicol (Phila) 53 (8): 823-6 (2015)


... In this study, the factors influencing the disposition and biotransformation of 1-bromopropane (1-BrP) were examined in male F344 rats and B6C3F1 mice following inhalation exposure (800 ppm) or intravenous administration (5, 20, and 100 mg/kg). (1,2,3-(13)C)1-BrP and (1-(14)C)1-BrP were administered to enable characterization of urinary metabolites using NMR spectroscopy, LC-MS/MS, and HPLC coupled radiochromatography. ... Metabolites characterized in urine of rats and mice include N-acetyl-S-propylcysteine, N-acetyl-3-(propylsulfinyl)alanine, N-acetyl-S-(2-hydroxypropyl)cysteine, 1-bromo-2-hydroxypropane-O-glucuronide, N-acetyl-S-(2-oxopropyl)cysteine, and N-acetyl-3-[(2-oxopropyl)sulfinyl]alanine. These metabolites may be formed following oxidation of 1-bromopropane to 1-bromo-2-propanol and bromoacetone and following subsequent glutathione conjugation with either of these compounds. ...

PMID:16513153 Garner CE et al; Toxicol Appl Pharmacol 215 (1): 23-36 (2006)


Three metabolites of 1-bromopropane (1-BP) were measured in urine samples collected from 30 workers exposed to 1-BP at two facilities making furniture seat cushions and evaluated for use as biomarkers of exposure. The mercapturic acid metabolite, N-acetyl-S-(n-propyl)-l-cysteine (AcPrCys), 3-bromopropionic acid (3-BPA), and bromide ion levels (Br(-)) were quantitated for this evaluation. ...

PMID:22519856 Mathias PI et al; Toxicol Mech Methods 22 (7): 526-32 (2012)


Glutathione S-alkyl transferase catalyzes the conjugation of alkyl halides and nitroalkanes in which halogen or nitro group is replaced. Further metabolism of conjugates of this group to alkylmercapturic acid sulfoxides has been reported for...1-bromopropane.

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 326


For more Metabolism/Metabolites (Complete) data for 1-Bromopropane (13 total), please visit the HSDB record page.


1-bromopropane is metabolized rapidly in the liver. Three mercapturic acids are produced: N-acetyl-S-propyl cysteine, N-acetyl-S-propyl cysteine-S-oxide and N-acetyl-S-(2-hydroxypropyl)cysteine. 1-bromopropoane also reacts rapidly with glutathione and can form glutathione conjugates.


4.3 Biological Half-Life

Wistar male rats were exposed to 1-bromopromane (1-BP) vapor for 6 hr a day, 5 days a week, for 3 and 4 weeks (1500 ppm) and 1 day, and 4 and 12 weeks (700 ppm). ... 1-BP in blood decreased rapidly to the detection limit within 0.7 hr. On the other hand, bromide ion persisted longer in both blood and urine; the biological half-life of bromide ion was 4.7-15.0 days in blood and 5.0-7.5 days in urine. ...

PMID:12191883 Ishidao T et al; Toxicol Lett 134 (1-3): 237-43 (2002)


4.4 Mechanism of Action

1-Bromopropane, either directly or via reactive metabolites, causes molecular alterations that typically are associated with carcinogenesis, including genotoxicity, oxidative stress, and glutathione depletion. These alterations, observed mainly in vitro and in toxicity studies in rodents, are relevant to possible mechanisms of human carcinogenicity and support the relevance of the cancer studies in experimental animals to human carcinogenicity.

NTP; Report on Carcinogens, Fourteenth Edition: 1-Bromopropane CAS No. 106-94-5 (2016); Available from, as of April 2, 2018: https://ntp.niehs.nih.gov/pubhealth/roc/index-1.html


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