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2D Structure
Also known as: 74-95-3, Methylene bromide, Methane, dibromo-, Methylene dibromide, Ch2br2, Dibrommethan
Molecular Formula
CH2Br2
Molecular Weight
173.83  g/mol
InChI Key
FJBFPHVGVWTDIP-UHFFFAOYSA-N
FDA UNII
V69B659W01

dibromomethane is a natural product found in Chondrus crispus and Ascophyllum nodosum with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
dibromomethane
2.1.2 InChI
InChI=1S/CH2Br2/c2-1-3/h1H2
2.1.3 InChI Key
FJBFPHVGVWTDIP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(Br)Br
2.2 Other Identifiers
2.2.1 UNII
V69B659W01
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Methylene Bromide

2. Methylene Bromide Ion (1+)

3. Methylene Bromide, 79br2-labeled

4. Methylene Bromide, 80br-labeled

5. Methylene Bromide, 80br2-labeled

6. Methylene Bromide, 82br-labeled

7. Methylene Bromide, 82br2-labeled

8. Methylene Dibromide

2.3.2 Depositor-Supplied Synonyms

1. 74-95-3

2. Methylene Bromide

3. Methane, Dibromo-

4. Methylene Dibromide

5. Ch2br2

6. Dibrommethan

7. Dibromomethylene

8. Rcra Waste Number U068

9. Methylenbromid

10. Dibromo-methane

11. 1,1-dibromomethane

12. Chebi:47077

13. Nsc-7293

14. Mfcd00000168

15. V69b659w01

16. Ccris 939

17. Hsdb 1334

18. Nsc 7293

19. Einecs 200-824-2

20. Un2664

21. Rcra Waste No. U068

22. Brn 0969143

23. Dibromo Methane

24. Ai3-52311

25. Unii-v69b659w01

26. Dibromomethane, 99%

27. Dibromomethane, >=99%

28. Dsstox_cid_1557

29. Ec 200-824-2

30. Wln: E1e

31. Dsstox_rid_76209

32. Dsstox_gsid_21557

33. Schembl20033

34. 4-01-00-00078 (beilstein Handbook Reference)

35. Methylene Bromide [mi]

36. Chembl1229889

37. Dtxsid4021557

38. Nsc7293

39. Dibromomethane, Analytical Standard

40. Amy11088

41. Tox21_200410

42. Stl282729

43. Akos009031545

44. Dibromomethane [un2664] [poison]

45. Un 2664

46. Cas-74-95-3

47. Ncgc00248598-01

48. Ncgc00257964-01

49. 2bm

50. 4371-77-1

51. Db-029642

52. Dibromomethane, Puriss., >=98.5% (gc)

53. D0192

54. Ft-0624675

55. S0636

56. Q421736

57. J-520238

58. F1908-0088

59. Dibromomethane Solution, 2000 Mug/ml In Methanol, Analytical Standard

60. Dibromomethane Solution, 5000 Mug/ml In Methanol, Analytical Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 173.83 g/mol
Molecular Formula CH2Br2
XLogP31.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass173.85028 g/mol
Monoisotopic Mass171.85233 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count3
Formal Charge0
Complexity2.8
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 MeSH Pharmacological Classification

Mutagens

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)


4.2 Absorption, Distribution and Excretion

IT ... DOES NOT APPEAR TO BE ABSORBED SIGNIFICANTLY EVEN WHEN APPLIED REPEATEDLY /TO EYES AND SKIN OF RABBITS/.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 4052


4.3 Metabolism/Metabolites

IT IS METABOLIZED TO CARBON MONOXIDE AND BROMIDE.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 4052


MASS SPECTRAL STUDIES USING (18)O2 SHOWED THAT (18)O-CO WAS PRODUCED INDICATING THAT OXYGEN WAS INCORPORATED DURING THE REACTION. A PRIMARY DEUTERIUM ISOTOPE EFFECT WAS OBSERVED FOR CONVERSION OF DICHLOROMETHANE TO CARBON MONOXIDE BOTH BY LONG-EVANS RAT HEPATIC MICROSOMAL FRACTIONS & BY STANNOUS PHOSPHATE MODEL SYSTEM. INCUBATION OF DIBROMOMETHANE IN THE MODEL SYSTEM IN THE PRESENCE OF 3,4-DIMETHYLANILINE RESULTED IN FORMATION OF 3,4-FORMOXYLIDIDE, SUPPORTING THE INTERMEDIACY OF A FORMYL HALIDE. A MECHANISM FOR THE METABOLISM OF DIHALOMETHANES TO CARBON MONOXIDE IS PROPOSED.

PMID:728186 KUBIC VL, ANDERS MW; BIOCHEM PHARMACOL 27 (19): 2349-55 (1978)


Halogenated methanes, in particular the brominated homologs, including dibromomethane and tribromomethane were subjected to biochemical decomposition in vitro by the cytochrome p450 rich fraction of the monooxygenase liver system. No significant contribution of GSH addition to the overall rate of metabolism of the halogenated methanes could be observed.

Buether H et al; Chemosphere 15 (8): 1043-62 (1986)


Treatment of Sprague-Dawley rats with sodium phenobarbital (50 mg/kg in 0.9% saline for 4 days) or 3-methylcholanthrene (20 mg/kg in corn oil for 2 days) resulted in increased metabolism of dibromomethane (3 m mol/kg) to carbon monoxide.

PMID:7434361 Stevens JL et al; Toxicol Appl Pharmacol 55 (3): 484-89 (1980)


Biotransformation of dihalomethanes leads to dehalogenation & end product is carbon monoxide. In the case of dichloromethane the carbon monoxide appears to arise from formyl halide. This intermediate, as an alternative to losing carbon monoxide, can covalently bind to cellular protein or lipid. The involvement of nonmicrosomal enzymes in dihalomethane biotransformation leads to prodn of formaldehyde & halide. A necessary step is the reaction of dihalomethane with glutathione, which results in loss of one halide. The resulting halomethylglutathione is postulated to undergo nonenzymatic hydrolytic dehalogenation leaving hydroxymethylglutathione. The next step would result in the release of the hydroxymethyl group as formaldehyde. Alternatively it has been shown that in the presence of formaldehyde dehydrogenase & NAD /nicotinamide-adenine dinucleotide/ formic acid can be formed. /Dichloromethane/

Doull, J., C.D.Klassen, and M.D. Amdur (eds.). Casarett and Doull's Toxicology. 3rd ed., New York: Macmillan Co., Inc., 1986., p. 647


4.4 Biological Half-Life

... REPEATED 6 HR EXPOSURES /OF DOGS/ TO EITHER 25, 75, OR 150 PPM /METHYLENE BROMIDE/ FOR 90 DAYS. PLASMA CLEARANCE WAS AT LEAST BIPHASIC WITH ILL DEFINED ALPHA PHASE & A TERMINAL PHASE (HALF LIFE 103 + OR - 14 MIN) @ ALL 3 CONCN.

Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 4052