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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 79-04-9, 2-chloroacetyl chloride, Acetyl chloride, chloro-, Chloracetyl chloride, Chloroacetic chloride, Monochloroacetyl chloride

Molecular Formula

C₂H₂Cl₂O

Molecular Weight

112.94 g/mol

InChI Key

VGCXGMAHQTYDJK-UHFFFAOYSA-N

FDA UNII

K5UML06YUO

1 2D Structure

Chloroacetyl Chloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-chloroacetyl chloride

2.1.2 InChI

InChI=1S/C2H2Cl2O/c3-1-2(4)5/h1H2

2.1.3 InChI Key

VGCXGMAHQTYDJK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(C(=O)Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

K5UML06YUO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Monochloroacetyl Chloride

2.3.2 Depositor-Supplied Synonyms

1. 79-04-9

2. 2-chloroacetyl Chloride

3. Acetyl Chloride, Chloro-

4. Chloracetyl Chloride

5. Chloroacetic Chloride

6. Monochloroacetyl Chloride

7. Chloroacetylchloride

8. Chloroacetic Acid Chloride

9. Chlorure De Chloracetyle

10. Chloracetylchloride

11. Chlorid Kyseliny Chloroctove

12. Chloro Acetyl Chloride

13. Chloro-acetyl Chloride

14. Chloroethanoyl Chloride

15. K5uml06yuo

16. Acetyl Chloride, 2-chloro-

17. Monochloroacetic Acid Chloride

18. .alpha.-chloroacetyl Chloride

19. Chebi:34624

20. Mfcd00000725

21. Ccris 9145

22. Hsdb 973

23. Chlorure De Chloracetyle [french]

24. Chlorid Kyseliny Chloroctove [czech]

25. Einecs 201-171-6

26. Unii-k5uml06yuo

27. Un1752

28. Brn 0605439

29. Chloroacetylchlonde

30. Chloroacetylchoride

31. Chloroactylchloride

32. Chloroacetylchlorid

33. Chloro Acetylchlorid

34. Chloroacetyl Choride

35. Chloroactyl Chloride

36. Choroacetyl Chloride

37. Chioroacetyl Chloride

38. Chloro-acetylchloride

39. Chloroacetyl-chloride

40. Chloro Acetylchloride

41. Ch2clcocl

42. Clch2cocl

43. Chloro-actyl Chloride

44. Chloroacethyl Chloride

45. 2-chloroacetylchloride

46. Chloroacetyl Chloride-

47. A-chloroacetyl Chloride

48. 2-chloro Acetylchloride

49. 2-chloro-acetylchloride

50. 2-chloroacetic Chloride

51. Alpha-chloroacetylchloride

52. 2-chloro-acetyl Chloride

53. Alpha-chloro-acetylchloride

54. Dsstox_cid_6472

55. Alpha-chloroacetyl Chloride

56. Ec 201-171-6

57. 2-chloranylethanoyl Chloride

58. Schembl9584

59. 2-chloroacetic Acid Chloride

60. Chloroacetyl Chloride, 98%

61. Dsstox_rid_78120

62. Dsstox_gsid_26472

63. Chembl3187685

64. Dtxsid4026472

65. Chloracetyl Chloride [mi]

66. Amy40193

67. Bcp25293

68. Zinc3860850

69. Chloroacetyl Chloride [hsdb]

70. Tox21_200644

71. Bbl013127

72. Stk399762

73. Akos000121312

74. Un 1752

75. Cas-79-04-9

76. Ncgc00248777-01

77. Ncgc00258198-01

78. Vs-03683

79. Chloroacetyl Chloride [un1752] [poison]

80. Chloroacetyl Chloride, Purum, >=99.0% (gc)

81. A839561

82. Q411258

83. J-520024

84. F2190-0033

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₂H₂Cl₂O
Molecular Weight	112.94 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	111.9482701 g/mol
Monoisotopic Mass	111.9482701 g/mol
Topological Polar Surface Area	17.1 Å²
Heavy Atom Count	5
Formal Charge	0
Complexity	42.9
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Metabolism/Metabolites

Oxidation of the vinyl halide carcinogen and hepatotoxin vinylidene chloride (VDC) by microsomal cytochrome p450 yields 2,2-dichloroacetaldehyde, 2-chloroacetyl chloride, 2-chloroacetic acid, and l,l-dichloroethylene oxide. The roles of these metabolites in covalent modification of proteins and reduced glutathione (GSH) were examined. 2-Chloroacetyl chloride reacted with model thiols at least 10(3)-fold faster than did l,l-dichloroethylene oxide and at least 10(5)-fold faster than did 2,2-dichloroacetaldehyde or 2-chloroacetic acid.

PMID:3965130 Liebler DC et al; Cancer Res 45 (1): 186-93 (1985)

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