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Chemistry

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Also known as: Fluorotrichloromethane, 75-69-4, Trichloro(fluoro)methane, Trichloromonofluoromethane, Fluorochloroform, Cfc-11
Molecular Formula
CCl3F
Molecular Weight
137.36  g/mol
InChI Key
CYRMSUTZVYGINF-UHFFFAOYSA-N
FDA UNII
990TYB331R

Trichlorofluoromethane
trichlorofluoromethane is a natural product found in Basella alba with data available.
1 2D Structure

Trichlorofluoromethane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
trichloro(fluoro)methane
2.1.2 InChI
InChI=1S/CCl3F/c2-1(3,4)5
2.1.3 InChI Key
CYRMSUTZVYGINF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(F)(Cl)(Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
990TYB331R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Fc-11

2. Fluorotrichloromethane

3. Freon 11

4. Genetron 11

5. Trichlorofluoromethane Hydrate

6. Trichlorofluoromethane, (18)f-labeled

7. Trichloromonofluoromethane

2.3.2 Depositor-Supplied Synonyms

1. Fluorotrichloromethane

2. 75-69-4

3. Trichloro(fluoro)methane

4. Trichloromonofluoromethane

5. Fluorochloroform

6. Cfc-11

7. Eskimon 11

8. Trichlorofluorocarbon

9. Refrigerant 11

10. Algofrene Type 1

11. Freon Mf

12. Freon 11

13. Arcton 9

14. Monofluorotrichloromethane

15. Arcton 11

16. Methane, Trichlorofluoro-

17. Electro-cf 11

18. Fluorocarbon 11

19. Propellant 11

20. Chladone 11

21. Genetron 11

22. Genetron 11sba

23. Daiflon 11

24. Isotron 11

25. Kaltron 11

26. Khladon 11

27. Daiflon S 1

28. Frigen 11

29. Frigen 11a

30. Dymel 11

31. Fluon 11

32. Freon 11a

33. Halon 11

34. Ledon 11

35. Ccl3f

36. Frigen S 11

37. Isceon 131

38. F 11 (halocarbon)

39. Trichloromethyl Fluoride

40. Methane, Fluorotrichloro-

41. Cfcl3

42. Fkw 11

43. F 11b

44. Fc 11

45. F 11

46. R 11

47. Trichloromonofluoromethane [nf]

48. Chebi:48236

49. 990tyb331r

50. Freon He

51. Halocarbon 11

52. Refrigerant R 11

53. Trichloromonofluoromethane (nf)

54. Ucon Flurocarbon 11

55. Ucon Refrigerant 11

56. Freon 11b

57. Freon-11

58. Caswell No. 878

59. Fluorocarbon No. 11

60. R 11 (refrigerant)

61. Fc 11 (halocarbon)

62. Ccris 604

63. Fluorotrojchlorometan

64. Fluorotrojchlorometan [polish]

65. Cfc 11

66. Hsdb 138

67. Nci-c04637

68. Einecs 200-892-3

69. Rcra Waste No. U121

70. Epa Pesticide Chemical Code 000013

71. Brn 1732469

72. F-11

73. Unii-990tyb331r

74. Distillex Ds6

75. Refrigerant R11

76. Triclorofluormethane

77. R 11, Halocarbon

78. Fc 11, Halocarbon

79. Trichlorfluomethane

80. Freon 11 (tn)

81. Dsstox_cid_1384

82. Fluorotrichloromethane 99%

83. Schembl1320

84. Dsstox_rid_76126

85. Chlorofluoromethane (ccl3f)

86. Dsstox_gsid_21384

87. Chlorofluorocarbon 11

88. 4-01-00-00054 (beilstein Handbook Reference)

89. Chembl348290

90. Dtxsid5021384

91. Trichlorofluoromethane [mi]

92. Trichlorofluoromethane, >=99.5%

93. Amy33469

94. Zinc8214698

95. Tox21_201190

96. Mfcd00000784

97. Trichlorofluoromethane [mart.]

98. Akos007930402

99. Trichloromonofluoromethane [ii]

100. Trichlorofluoromethane [who-dd]

101. Cas-75-69-4

102. Trichloromonofluoromethane [hsdb]

103. Ncgc00091043-01

104. Ncgc00091043-02

105. Ncgc00258742-01

106. Trichloromonofluoromethane [vandf]

107. Trichlorofluoromethane, Analytical Standard

108. Db-055980

109. Ft-0631315

110. D06220

111. Fluorotrichloromethane 100 Microg/ml In Methanol

112. Trichlorofluoromethane 100 Microg/ml In Methanol

113. Fluorotrichloromethane 5000 Microg/ml In Methanol

114. Q423000

115. Trichlorofluoromethane Solution, 200 Mug/ml In Methanol, Analytical Standard

116. Trichlorofluoromethane Solution, Certified Reference Material, 5000 Mug/ml In Methanol

117. Trichlorofluoromethane Solution, Nmr Reference Standard, 10% In Acetone-d6 (99.9 Atom % D), 1,2-dichloro-1,1-difluoroethane 1 %, Tms 6 %

118. Trichlorofluoromethane Solution, Nmr Reference Standard, 50% In Chloroform-d (99.8 Atom % D), Nmr Tube Size 5 Mm X 8 In.

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 137.36 g/mol
Molecular Formula CCl3F
XLogP32.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass135.904961 g/mol
Monoisotopic Mass135.904961 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count5
Formal Charge0
Complexity28.4
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

Pulmonary uptake of inhaled CFC-11 by rabbits and dogs is prompt. Peak circulating concentrations after exposure at 4500 to 5000 ppm were achieved in 15 seconds with steady-state reached at 20 minutes. Elimination is relatively rapid. Dogs exhaled within 1 hr essentially all the CFC-11 inhaled during a 6 to 20 min exposure at 5,000 ppm. Inhaled CFC-11 was promptly detected in blood, cerebrospinal fluid, bile, and urine of anesthetized rabbits and dogs ... . Unanesthetized dogs exposed to 1,000-10,000 ppm for 10 minutes showed a rapid rise in blood conc of CFC-11 during the first 5 min, which was followed by a rapid and then more gradual decline after exposure.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. Trichlorofluoromethane p. 2 CD-ROM Cincinnati, OH 45240-4148 2012.


In male and female adult humans, 79% to 100% of inhaled (14)C-CFC-11 was exhaled within the first hour after a 7- or 17- minute inhalation at 1000 ppm. Only 0.12% of the inhaled compound was recovered as the carbon dioxide metabolite and only 0.08% appeared in the urine. At 30 minutes, retention of the labeled dose (approximately 7 mg Cl-CFC-11) inhaled in a single breath was 23% versus 10%, 20%, and 12% for comparable doses of CFC-12 1,1,2-trichloro-1,1,2-trifluoroethane (CFC-113), and dichlorotetrafluoroethane (CFC-114), respectively.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. Trichlorofluoromethane p. 2 CD-ROM Cincinnati, OH 45240-4148 2012.


Radiocarbon-labeled trichlorofluoromethane (FC-11; (14)CC13F) and dichlorodifluormethane (FC-12; (14)CC12F2) were separately inhaled by a female subject and a male subject. A predetermined volume of fluorocarbon (1000 ppm; 100 muCi) in air was delivered through a non-rebreathing system and a tight-fitting face mask for 7-17 minutes. Total expired gases were collected during fluorocarbon exposure and afterward until no radioactivity was detectable. Expired (14)CO2 and (14)C-fluorocarbon were assayed. Urine was collected for 72 hours and assayed for nonvolatile radioactivity. Total recoveries of FC-11 were 99.5 and 79.4 per cent in the woman and the man, respectively. Total recoveries of FC-12 were 95.4 and 103.2 per cent. Traces of radioactivity were found in urine (FC-11, 0.07 and 0.09 per cent; FC-12, 0.02 and 0.03 per cent) and in exhaled carbon dioxide (FC-11, 0.13 and 0.10 per cent; FC-12, 0.08 per cent in both subjects). Total metabolites were equal to or less than 0.2 per cent of the administered dose. The amount of radioactivity in urine was insufficient to permit identification of possible fluorocarbon metabolites. The trace of metabolites could be products of radiolabeled impurities.

PMID:1115387 Mergner GW et al; Anesthesiology 42 (3): 345-51 (1975)


A free compartment open model was proposed for disposition of iv trichlorofluoromethane in dogs with average half-lives of 3.2, 16 and 93 min for 3 disposition phases. Tissue compartment distribution following a single dose showed that about 2 hr were required to achieve pseudo distribution equilibrium, following which more than 90% of the drug remaining in the body was retained in tissue compartments.The volume of distribution was approximately 6 times the body weight in terms of blood concn and about 30% of the propellant was cleared from blood passing through the lungs in each cycle. Disposition of propellant followed dose independent kinetics after multiple dosing, and accumulation in tissues continued for a much longer period, resulting in high tissue compartment levels.

Niazi S, Chiou WL; J Pharm Sci 64 763-9 May (1975)


For more Absorption, Distribution and Excretion (Complete) data for TRICHLOROFLUOROMETHANE (15 total), please visit the HSDB record page.


4.2 Metabolism/Metabolites

Dogs /were/ exposed for 6-20 minutes to levels of

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: 513


When trichlorofluoromethane was inhaled by humans, recovery of intact cmpd in exhaled air was 79-99% & in urine, 0.07-0.09%, & metabolites amt to 0.2% or less ... .

National Research Council. Drinking Water & Health Volume 1. Washington, DC: National Academy Press, 1977., p. 781


Rat-liver microsomes dechlorinate trichlorofluoromethane to dichlorofluoromethane. This reaction ... is mediated via the hepatic microsomal P450 enzyme system. Trichlorofluoromethane & dichlorofluoromethane admin as high acute inhalation dosages were expired unchanged by both dogs & rabbits.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 241


Theoretical metabolites of trichlorofluoromethane are dichlorofluoromethane & tetrachlorodifluoroethane. No evidence of free-radical formation in rats or mice has been shown; nor is there evidence of significant metabolism of trichlorofluoromethane ...

National Research Council. Drinking Water and Health. Volume 3. Washington, DC: National Academy Press, 1980., p. 166


For more Metabolism/Metabolites (Complete) data for TRICHLOROFLUOROMETHANE (6 total), please visit the HSDB record page.


4.3 Biological Half-Life

The distribution half-life of the common fluorocarbons (Freon 11, Freon 12) averages 13 to 14 seconds; the elimination half-life is longer (1.5 hours) because of slower release from fat stores.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 884


... Fluorotrichloromethane (R-11) concentrations in urine--in contrast to blood or alveolar air--depend on the dose taken up. After termination of exposure, R-11 concentrations in alveolar air and in blood are excreted with biological half-lives of seven and eleven minutes respectively during the first phase of elimination and with 1.8 and 1.0 hr respectively during the second phase of elimination. ...

PMID:4030118 Angerer Jet al; Int Arch Occup Environ Health 56 (1): 67-72 (1985)


Volunteers exposed to CFC-11 at 3751 mg/cu m (657 ppm) for 150-210 min showed half-lives for the initial and second phases of elimination from venous blood of 11 min and 1 hr respectively. Half-lives for the initial and second phases of CFC-11 elimination in alveolar air were 7 min and 1.8 hr, respectively.

WHO; Environmental Health Criteria 113: Fully Halogenated Chlorofluorocarbons p.60 (1990)


...Analysis of the human data also utilized a two-compartment pharmacokinetic model and found initial elimination half-times from blood and alveolar air of 7 and 11 minutes, respectively and half-times for the slow elimination phase from blood and alveolar air of 1.8 to 1.0 hour.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. Trichlorofluoromethane p. 3 CD-ROM Cincinnati, OH 45240-4148 2012.


Analyses of a two-compartment pharmacokinetic model in dogs found an initial elimination half-time of 0.6 +/- 0.25 minute.

American Conference of Governmental Industrial Hygienists. Documentation of the TLV's and BEI's 7th Edition. Trichlorofluoromethane p. 3 CD-ROM Cincinnati, OH 45240-4148 2012.


4.4 Mechanism of Action

... The mechanism of FC-11 cardiotoxicity ... /originates/ from irritation of the respiratory tract which in turn reflexly influences the heart rate even prior to absorption of the fluorocarbon, followed by direct depression of the heart after absorption. FC-11 causes only depression of respiratory minute volume that is not preceded by stimulation of breathing. There is ultimate cessation of respiration, which is a manifestation of generalized depression of the CNS by FC-11.

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. 1183


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