CAS 108-86-1 manufacturers and suppliers on PharmaCompass

PharmaCompass

Chemistry

Click the arrow to open the dropdown
read-moreClick the button for full data set
Also known as: 108-86-1, Phenyl bromide, Monobromobenzene, Benzene, bromo-, 1-bromobenzene, Phbr
Molecular Formula
C6H5Br
Molecular Weight
157.01  g/mol
InChI Key
QARVLSVVCXYDNA-UHFFFAOYSA-N
FDA UNII
CO4D5J547L

CAS 108-86-1
Bromobenzene is used for organic synthesis, especially in the production of the synthetic intermediate phenyl magnesium bromide (a Grignard reagent). Bromobenzene is also used as an additive to motor oils and as a crystallizing solvent. Release of bromobenzene to the environment may occur during its production and the production of phenyl magnesium bromide, as well as in its use as a solvent and as an additive in motor oil (HSDB, 2003). It has been detected at low frequencies and at low concentrations in samples of food, ambient air, and finished water.
1 2D Structure

CAS 108-86-1

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
bromobenzene
2.1.2 InChI
InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H
2.1.3 InChI Key
QARVLSVVCXYDNA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)Br
2.2 Other Identifiers
2.2.1 UNII
CO4D5J547L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bromobenzene, 14c-labeled

2.3.2 Depositor-Supplied Synonyms

1. 108-86-1

2. Phenyl Bromide

3. Monobromobenzene

4. Benzene, Bromo-

5. 1-bromobenzene

6. Phbr

7. Nci-c55492

8. C6h5br

9. Bromo-benzene

10. 4-bromobenzene

11. Bromobenzol

12. Hsdb 47

13. Phenylbromide

14. Ccris 5887

15. Nsc 6529

16. Einecs 203-623-8

17. Unii-co4d5j547l

18. Chebi:3179

19. Co4d5j547l

20. Dtxsid5024637

21. Ai3-09059

22. Nsc-6529

23. Dtxcid304637

24. Bromobenzene 100 Microg/ml In Methanol

25. Bromo Benzene

26. Mfcd00000056

27. Smr000112021

28. Un2514

29. Bromanylbenzene

30. Brombenzene

31. Brombenzol

32. Bromobezene

33. 3-bromobenzene

34. 2-bromobenzene

35. 1-bromo-benzene

36. 1-bromobenzene; Bromobenzene; Bromobenzol; Monobromobenzene; Nsc 6529; Phenyl Bromide

37. Bromobenzene--d4

38. Mfcd00000055

39. 64646-03-3

40. Bromobenzene [mi]

41. Bromobenzene [un2514] [flammable Liquid]

42. Wln: Er

43. Bromobenzene [hsdb]

44. Schembl1542

45. Mls000515541

46. Mls002415720

47. Bromobenzene, Lr, >=99%

48. Chembl16068

49. Bromobenzene, Analytical Standard

50. Nsc6529

51. Bromobenzene, >=99.5% (gc)

52. Hms2269p12

53. Bcp26654

54. Bcp30008

55. Str00651

56. Tox21_200849

57. Br1026

58. Bromobenzene, Reagentplus(r), 99%

59. Stl264221

60. Bromobenzene, For Synthesis, 99.5%

61. Akos000120123

62. Un 2514

63. Ncgc00091842-01

64. Ncgc00091842-02

65. Ncgc00091842-03

66. Ncgc00091842-04

67. Ncgc00258403-01

68. Cas-108-86-1

69. Sy061516

70. B0439

71. Ft-0617692

72. Ft-0617909

73. Ft-0623223

74. En300-19359

75. A801934

76. Q410597

77. Bromo(2h5)benzene Pound>>pentadeuterophenyl Bromide

78. J-002199

79. J-519941

80. F1908-0102

81. Inchi=1/c6h5br/c7-6-4-2-1-3-5-6/h1-5

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 157.01 g/mol
Molecular Formula C6H5Br
XLogP33
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area0
Heavy Atom Count7
Formal Charge0
Complexity46.1
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Minimum/Potential Fatal Human Dose

4 (?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OUNCE FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-114


50-500 mg/kg


5 Pharmacology and Biochemistry
5.1 Absorption, Distribution and Excretion

ABSORBED THROUGH LUNGS, GI TRACT & INTACT SKIN. EXCRETED AS CATECHOL DERIVATIVES BOTH FREE & CONJUGATED WITH SULFATE OR MERCAPTURIC ACID.

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-114


BROMOBENZENE MAY BE METAB TO AN EPOXIDE...EXCRETED IN BILE, REABSORBED THROUGH ENTEROHEPATIC CIRCULATION, & METAB IN SEVERAL STEPS TO S-(P-BROMOPHENYL)MERCAPTURIC ACID, WHICH IS THEN EXCRETED IN URINE.

National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 693


This investigation was designed to determine whether biliary excretion of bromobenzene-glutathione conjugate can be used as an index of in vivo activation of bromobenzene. To test this hypothesis, the effect of chemicals known to alter the toxicity and biotransformation of bromobenzene (ie, cytochrome p450 inducers and inhibitors) on the biliary excretion of bromobenzene-glutathione was studied in rats. Bromobenzene-glutathione was the major bromobenzene metabolite in bile. A linear relationship was observed between the dosage of bromobenzene administered and bromobenzene-glutathione excreted into bile, up to a dosage of 250 umol/kg of bromobenzene. Of the inducers tested, Phenobarbital, which is known to increase the toxicity of bromobenzene, dramatically increased 1700 m1 the rate of biliary excretion of bromobenzene-glutathione over that in control animals. In contrast, 3-methylcholanthrene, which is known to decrease the hepatotoxicity of bromobenzene, decreased the biliary excretion of bromobenzene-glutathione (56%). Inhibitors of p450, such as SKF 525-A and piperonyl butoxide which are known to decrease the activation and hepatotoxicity of bromobenzene, also decreased the biliary excretion of bromobenzene-glutathione. These findings are in agreement with the hypothesis that the biliary excretion of bromobenzene-glutathione reflects the formation of the reactive bromobenzene metabolite in liver and the rate of biliary excretion can be used to determine factors that are important in determining the toxicity of bromobenzene.

Madhu C, Klaassen CD; Toxicol Lett (AMST) 60 (2): 227-36 (1992)


5.2 Metabolism/Metabolites

IT APPEARS THAT IN BROMOBENZENE NECROSIS /OF LIVER/, THE TOXIC /SRP: BROMOBENZENE EPOXIDE METABOLITES, MAINLY THE 3,4-EPOXIDE, ARE/...DEGRADED THROUGH THE ACTION OF GLUTATHIONE TRANSFERASE & EPOXIDE HYDRATASE.

Amdur, M.O., J. Doull, C.D. Klaasen (eds). Casarett and Doull's Toxicology. 4th ed. New York, NY: Pergamon Press, 1991., p. 346


BROMOBENZENE IS METABOLIZED VIA THE HEPATIC MIXED-FUNCTION OXIDASE SYSTEM TO REACTIVE INTERMEDIATES 2,3- AND 3,4-BROMOBENZENE EPOXIDES. THESE METABOLITES PRESUMABLY BIND TO TISSUE MACROMOLECULES. THE SPECIFIC SITES OF MACROMOLECULAR PROTEINS WERE INVESTIGATED. THE 3,4-EPOXIDE IS MORE REACTIVE, BINDING COVALENTLY TO MICROSOMAL PROTEIN AT THE SITE OF ITS SYNTHESIS, WHEREAS BROMOBENZENE 2,3-EPOXIDE IS MORE STABLE, LEAVING THE MICROSOMAL PROTEIN COMPARTMENT AND BINDING COVALENTLY TO SOL PROTEIN, IE THE HEMOGLOBIN BETA CHAIN.

PMID:7288634 LAU SS, ZANNONI VG; J PHARMACOL EXP THER 219 (2): 563 (1981)


BROMOBENZENE YIELDS N-ACETYL-S-(4-BROMO-1,2-DIHYDRO-2-HYDROXYPHENYL)-L-CYSTEINE IN RABBIT & RAT; N-ACETYL-S-(P-BROMOPHENYL)-L-CYSTEINE IN DOG & IN MOUSE. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. B-23


BROMOBENZENE MAY BE METABOLIZED TO AN EPOXIDE...EXCRETED IN BILE, REABSORBED THROUGH ENTEROHEPATIC CIRCULATION, & METABOLIZED IN SEVERAL STEPS TO S-P-BROMOPHENYL MERCAPTURIC ACID, WHICH IS THEN EXCRETED IN URINE.

National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 693


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


Bromobenzene is converted to either the 3,4-oxide derivative catalyzed primarily by phenobarbital-induced cytochrome isozymes (e.g., CYP 450 1A2, 2A6, 2B6, and 3A4), or the 2,3-oxide derivative catalyzed primarily by 3-methylcholanthrene and -naphthoflavone-induced CYP isozymes (e.g., CYP 450 1A1, 1A2, and 1B1). This is followed by urinary excretion as premercapturic and mercapturic acids.


5.3 Mechanism of Action

FOLLOWING BROMOBENZENE (1.0 MMOL) ADMIN TO RAT HEPATOCYTES, LIPID PEROXIDATION OCCURRED ONLY AT A LATER STAGE, COMPARED TO TREATMENT WITH CCL4, AND ONLY AFTER CELL DEATH. APPARENTLY LIPID PEROXIDATION DURING BROMOBENZENE TOXICITY WAS MERELY A CONSEQUENCE OF GSH DEPLETION AND CELL DEATH. APPARENTLY, ARYLATION OF CRITICAL CELLULAR NUCLEOPHILES IS MORE IMPORTANT THAN LIPID PEROXIDATION IN BROMOBENZENE HEPATOTOXICITY.

PMID:6838624 SMITH MT ET AL; BIOCHEM PHARMACOL 32 (5): 763 (1983)


FRESHLY ISOLATED HEPATOCYTES FROM PHENOBARBITAL-TREATED RATS WERE INCUBATED IN THE PRESENCE OR ABSENCE OF EXTRACELLULAR CALCIUM WITH BROMOBENZENE. IN THE ABSENCE OF CALCIUM IT WAS FAR MORE TOXIC TO THE CELLS THAN IN ITS PRESENCE. THIS RESULT IS INCONSISTENT WITH THE HYPOTHESIS THAT AN INFLUX OF EXTRACELLULAR CALCIUM IS REQUIRED AS THE FINAL STEP IN TOXIC LIVER CELL INJURY.

SMITH MT ET AL; SCIENCE (WASH DC) 213 (4513): 1257 (1981)


A NOVEL METHOD IS DESCRIBED FOR MEASURING THE COVALENT BINDING OF BROMOBENZENE TO MACROMOLECULES IN RAT HEPATIC MICROSOMES OF HEPATOCYTES. COVALENT BINDING IN HEPATOCYTES SUGGESTS THAT THE BINDING OCCURS FIRST WITH MACROMOLECULES IN 20000-40000 DALTON RANGE.

DENT JG, SUN JD; ADV EXP MED BIOL 136A(BIOL REACT INTERMED-2, CHEM MECH BIOL EFF, PT A) 275 (1982)


BUILDING BLOCK

Upload your portfolio for free, ask us

END USE APIs

read-more
read-more
Ask Us for Pharmaceutical Supplier and Partner
Ask Us, Find A Supplier / Partner
No Commissions, No Strings Attached, Get Connected for FREE

What are you looking for?

How can we help you?

The request can't be empty

Please read our Privacy Policy carefully

You must agree to the privacy policy

The name can't be empty
The company can't be empty.
The email can't be empty Please enter a valid email.
The mobile can't be empty