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Also known as: Tert-butyl alcohol, 2-methyl-2-propanol, 2-methylpropan-2-ol, 75-65-0, T-butanol, T-butyl alcohol

Molecular Formula

C₄H₁₀O

Molecular Weight

74.12 g/mol

InChI Key

DKGAVHZHDRPRBM-UHFFFAOYSA-N

FDA UNII

MD83SFE959

An isomer of butanol that contains a tertiary butyl group that consists of three methyl groups, each separately attached to a central (tertiary) carbon.

1 2D Structure

Tert-Butanol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methylpropan-2-ol

2.1.2 InChI

InChI=1S/C4H10O/c1-4(2,3)5/h5H,1-3H3

2.1.3 InChI Key

DKGAVHZHDRPRBM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)O

2.2 Other Identifiers

2.2.1 UNII

MD83SFE959

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alcohol, Tert-butyl

2. Alcohol, Tertiary-butyl

3. T Butanol

4. T-butanol

5. Tert Butanol

6. Tert Butyl Alcohol

7. Tert-butyl Alcohol

8. Tertiary Butyl Alcohol

9. Tertiary-butyl Alcohol

2.3.2 Depositor-Supplied Synonyms

1. Tert-butyl Alcohol

2. 2-methyl-2-propanol

3. 2-methylpropan-2-ol

4. 75-65-0

5. T-butanol

6. T-butyl Alcohol

7. 1,1-dimethylethanol

8. Trimethylcarbinol

9. T-butyl Hydroxide

10. Trimethyl Carbinol

11. Trimethyl Methanol

12. Tertiary-butyl Alcohol

13. Trimethylmethanol

14. Tert-butylalcohol

15. 2-propanol, 2-methyl-

16. Butanol Tertiaire

17. Dimethylethanol

18. Tertiary Butanol

19. Tertiary-butanol

20. Alcool Butylique Tertiaire

21. Tert- Butyl Alcohol

22. Methanol, Trimethyl-

23. Tertiary Butyl Alcohol

24. Tert.-butanol

25. T-buoh

26. Nci-c55367

27. T-butyl Alchohol

28. Tert-buoh

29. Tert-butyl Hydroxide

30. 2-methyl N-propan-2-ol

31. Md83sfe959

32. Chebi:45895

33. Mfcd00004464

34. Arconol

35. 25-65-0

36. Tert-butyl Alcohol, Anhydrous

37. Caswell No. 124a

38. T-butylalcohol

39. Tert Butanol

40. Tbuoh

41. Butanol Tertiaire [french]

42. Tert Butyl Alcohol

43. Hsdb 50

44. Tbu

45. 2-methylpropanol-2

46. Alcohol, Tert-butyl

47. Ccris 4755

48. Alcool Butylique Tertiaire [french]

49. Einecs 200-889-7

50. Brn 0906698

51. Terbutanol

52. Tertbutanol

53. Tertiarybutanol

54. Unii-md83sfe959

55. Ter-butanol

56. Tert.butanol

57. T-butylalkohol

58. T-butyl-alcohol

59. Terbutyl Alcohol

60. Ai3-01288

61. Tert -butanol

62. Tertbutyl Alcohol

63. Tert. Butanol

64. T- Butanol

65. Hotbu

66. Ter-butyl Alcohol

67. Tert-buyl Alcohol

68. Tert-butyl-alcohol

69. Tert.-butylalcohol

70. Tert.butyl Alcohol

71. Trimethyl-methanol

72. Tert-butanol, Ar

73. 2methyl-2-propanol

74. Tert. Butyl Alcohol

75. Hot-bu

76. Tert.-butyl Alcohol

77. Tert-c4h9oh

78. 2-methyl,2-propanol

79. Methyl-2 Propanol-2

80. T-bu-oh

81. 1,1-dimethyl Ethanol

82. 2-methyl Propan-2-ol

83. 2-methyl-propan-2-ol

84. Tert-butanol Hplc Grade

85. Tert-butanol Acs Reagent

86. Ethanol, 1,1-dimethyl-

87. 2-methyl-2-propyl Alcohol

88. Ec 200-889-7

89. Butyl Alcohol, Tert-

90. (ch3)3coh

91. 4-01-00-01609 (beilstein Handbook Reference)

92. Hoc(ch3)3

93. Chembl16502

94. Tertiary Butyl Alcohol Reagent

95. T-butyl Alcohol [hsdb]

96. T-butyl Alcohol [inci]

97. Dtxsid8020204

98. Tert-butyl Alcohol [ii]

99. Tert-butyl Alcohol [mi]

100. Tert-butanol, >=99% (gc)

101. Tert-butanol, Analytical Standard

102. Tert-butanol, P.a., 99.0%

103. Amy11058

104. Zinc1680021

105. Stl282741

106. Tert-butanol, Anhydrous, >=99.5%

107. Akos009029221

108. Db03900

109. Tert-butanol, For Hplc, >=99.5%

110. Tert-butanol, Technical Grade, 95.0%

111. Tert-butanol 100 Microg/ml In Methanol

112. Tert-butanol, Acs Reagent, >=99.0%

113. Bp-20656

114. Butyl Alcohol (tert)- Reagent Grade Acs

115. Tert-butanol 100 Microg/ml In Acetonitrile

116. Tert-butanol, Saj First Grade, >=98.0%

117. B0706

118. Ft-0688093

119. Tert-butanol, Tebol(r) 99, >=99.3%

120. Tert-butanol, Saj Special Grade, >=99.0%

121. C21389

122. A838477

123. Q285790

124. J-510082

125. F0001-1901

126. Tert-butanol, Puriss. P.a., Acs Reagent, >=99.7% (gc)

127. Tert-butanol, Certified Reference Material, 5000 Mug/ml In Methanol

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₄H₁₀O
Molecular Weight	74.12 g/mol
XLogP3	0.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	74.073164938 g/mol
Monoisotopic Mass	74.073164938 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	5
Formal Charge	0
Complexity	25.1
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 Absorption, Distribution and Excretion

/Researchers/ found that t-butyl alcohol is eliminated slowly from the blood of rats. t-Butyl alcohol was dissolved in water and a dose of 25 mmol/kg was administered by gastric intubation to female Wistar rats (number unspecified). The t-butyl alcohol blood concentration at 2 hr was 13.24 mM, at 5 hr it was 12.57 mM, and at 20 hr it was 11.35 mM.

Cosmetic Ingredient Review; Amended Final Report of the Safety Assessment of t-Butyl Alcohol as Used in Cosmetics; International Journal of Toxicology 24 (Suppl 1): 1-20 (2005)

The purpose of this study was to fully characterize the pharmacokinetics of tertiary butyl alcohol in male and female F-344 rats following intravenous administration of 37.5, 75, 150 and 300 mg/kg TBA. TBA was observed to undergo a rapid distribution phase followed by a slower elimination phase. The steady-state volume of distribution for TBA was roughly 4.5 times greater than total body water, and the clearance was lower than the estimated glomerular filtration rate. The elimination of TBA appears to saturate at higher doses, as evidenced by a disproportional increase in area under the concentration-time curve and decreased rate of clearance.

PMID:9334828 Poet TS et al; Toxicol Lett 92 (3): 179-86 (1997)

In animals, tert-butanol is absorbed through the lungs and gastrointestinal tract ... .

WHO/FAO; Environmental Health Criteria Document No. 65: Butanols: Four Isomers (1-Butanol, 2-Butanol, tert-Butanol (1987). Available from, as of November 8, 2013: https://www.inchem.org/pages/ehc.html

t-Butyl alcohol moves rapidly from the blood into the tissues. Eleven male Sprague-Dawley rats were cannulated and intravenously given 350 mg/kg (14)C-t-butyl alcohol. At numerous times following injection, blood samples were withdrawn and the samples measured for radioactivity. There were two phases in the elimination of (14)C-t-butyl alcohol from the blood. The first was a rapid phase, which probably represented the distribution of (14)C-t-butyl alcohol from the blood to other body tissues. The second represented a first-order elimination of radioactivity from the blood with a half-life of approximately 8 hr, indicating that (14)C-t-butyl alcohol was being eliminated primarily as metabolic product(s).

Cosmetic Ingredient Review; Amended Final Report of the Safety Assessment of t-Butyl Alcohol as Used in Cosmetics; International Journal of Toxicology 24 (Suppl 1): 1-20 (2005)

For more Absorption, Distribution and Excretion (Complete) data for T-BUTYL ALCOHOL (9 total), please visit the HSDB record page.

4.2 Metabolism/Metabolites

/Researchers/ administered 12 mmol of t-butyl alcohol by stomach tube to three chinchilla rabbits. t-Butyl alcohol was conjugated to a large extent with glucuronic acid, and glucuronides were readily isolated from the rabbit urine; as a percentage of dose, the average extra glucuronic acid excreted over 24 hr was 24.4%. The researchers suggested that volatile alcohols might also be eliminated to some extent in an unchanged state by the lungs. No aldehydes or ketones were detected in the expired air of a rabbit given 6 mL t-butyl alcohol (route unspecified).

Cosmetic Ingredient Review; Amended Final Report of the Safety Assessment of t-Butyl Alcohol as Used in Cosmetics; International Journal of Toxicology 24 (Suppl 1): 1-20 (2005)

t-Butyl alcohol is not a substrate for alcohol dehydrogenase or for the peroxidative activity of catalase, therefore, it is used frequently as an example of a non-metabolizable alcohol. tert-Butyl alcohol is a scavenger of the hydroxyl radical and can be oxidized to formaldehyde and acetone from four different systems; (a) iron catalyzed oxidation of ascorbic acid (b) hydrogen peroxide and iron (c) coupled oxidation of xanthine oxidase, an enzymatic bound system (d) NADPH-dependent microsomal electron transfer, a membrane bound system. Because of its special biochemical properties, t-butyl alcohol may be a valuable probe for the detection of hydroxyl radicals in intact cells and in vivo.

Cederbaum AI et al; Biochem Pharmacol 32 (1983)

In vitro reactions with liver microsomes of mice produced tert-butanol from isobutane.

PMID:3913777 Tsukamoto S et al; J Toxicol Sci 10 (4): 323-32 (1985)

Male Wistar rats exposed to 50, 100, or 300 ppm methyl tertiary-butyl ether vapor ... showed ... blood concns of tert-butanol which were dose dependent indicating metabolic breakdown of the ether in vivo.

PMID:4091653 Salvolainen H et al; Arch Toxicol 57 (4): 285-8 (1985)

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

Tert-butanol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-Trihydroxy-6-[(2-methylpropan-2-yl)oxy]oxane-2-carboxylic acid and Tert-butyl hydrogen sulfate.

Tert-butanol is a known human metabolite of tert-butyl ethyl ether (ETBE) and tert-butyl methyl ether.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

4.3 Biological Half-Life

In Long-Evans rats treated with tert-butanol (1 g/kg body weight, route not specified), the rate of disappearance of tert- butanol from the blood was apparently of first order with a half life of 9.1 hr.

Two Sprague-Dawley rats were given 1500 mg/kg (14)C-t-butyl alchol by oral gavage. Their blood was sampled at various times following the dosage. ... There was a half-life of 9 hr similar to that seen following intravenous dosing with 350 mg/kg (14)C-t-butyl alchol.

Cosmetic Ingredient Review; Amended Final Report of the Safety Assessment of t-Butyl Alcohol as Used in Cosmetics; International Journal of Toxicology 24 (Suppl 1): 1-20 (2005)

In mice, after a single ip injection of 8.1 mmol tert-butanol/kg body weight, initial blood levels of 8 mmol took 8-9 hr for elimination (blood- tert-butanol half-life was approximately 5 hr). However, after 3 days, inhalation at a vapor concentration to give levels of 8 mmol/L blood, tert-butanol disappeared within 3 hr of removal of mice from the inhalation chamber (half-life of tert- butanol in blood was approximately 1.5 hr).

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