sec-Butyl Alcohol
Title: sec-Butyl Alcohol
CAS Registry Number: 78-92-2
CAS Name: 2-Butanol
Additional Names: butylene hydrate; 2-hydroxybutane; methyl ethyl carbinol
Molecular Formula: C4H10O
Molecular Weight: 74.12
Percent Composition: C 64.82%, H 13.60%, O 21.59%
Line Formula: CH3CH2CH(OH)CH3
Literature References: Prepn by reduction of 2-butanone: Chaikin, Brown, J. Am. Chem. Soc. 71, 122 (1949); Nystrom et al., ibid. 3245. Manuf by hydration of 2-butene or hydrocarbons contg butene: Dale et al., Ind. Eng. Chem. 48, 913 (1956); Archibald, Mottern, US 2543820 (1951 to Standard Oil); Limerick, Wylie, US 2776324 (1957 to Shell). Purification and vapor pressure: Biddiscombe et al., J. Chem. Soc. 1963, 1954. Prepn of l-form or d-form by hydroboration of cis-2-butene: Brown, US 3078313 (1963); Brown et al., J. Am. Chem. Soc. 86, 397 (1964). Resolution of dl-form: Kantor, Hauser, ibid. 75, 1744 (1953). Absolute configuration of l-form: Brown et al., ibid. 86, 1071 (1964). Toxicity: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 10, 61 (1954).
 
Derivative Type: dl-Form
Properties: Liquid, bp 99.5°. mp -114.7°. d420 0.808. nD25 1.3949. Flash pt, open cup: 88°F (31°C). Sol in 12 parts water; misc with alcohol, ether. LD50 orally in rats: 6.48 g/kg (Smyth).
Melting point: mp -114.7°
Boiling point: bp 99.5°
Flash point: Flash pt, open cup: 88°F (31°C)
Index of refraction: nD25 1.3949
Density: d420 0.808
Toxicity data: LD50 orally in rats: 6.48 g/kg (Smyth)
 
Derivative Type: d-Form
Literature References: Ref: Leroux, Lucas, J. Am. Chem. Soc. 73, 41 (1951).
Properties: Liquid, d427 0.8025. nD20 1.3954. [a]D27 +13.52°.
Optical Rotation: [a]D27 +13.52°
Index of refraction: nD20 1.3954
Density: d427 0.8025
 
Derivative Type: l-Form
Literature References: Ref: Leroux, Lucas, loc. cit.
Properties: Liquid, bp744 98°. d425 0.8042. nD20 1.3970, nD25 1.3949. [a]D25 -13.51°.
Boiling point: bp744 98°
Optical Rotation: [a]D25 -13.51°
Index of refraction: nD20 1.3970; nD25 1.3949
Density: d425 0.8042
 
CAUTION: Potential symptoms of overexposure are eye, skin, nose, throat irritation; narcosis. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 40.
Use: In the synthesis of flotation agents, flavors, perfumes, dyestuffs, wetting agents. In industrial cleaners, paint removers. Solvent for many natural resins, linseed and castor oils.

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