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either of two phenols derived from naphthalene

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/03/09 09:57:13」(JST)

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1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C₁₀H₇OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.^[1]

Production

1-Naphthol is prepared by two main routes.^[2] In one method, naphthalene is nitrated to give 1-nitronaphthalene, which is hydrogenated to the amine followed by hydrolysis:

C₁₀H₈ + HNO₃ → C₁₀H₇NO₂ + H₂O

C₁₀H₇NO₂ + 3 H₂ → C₁₀H₇NH₂ + 2 H₂O

C₁₀H₇NH₂ + H₂O → C₁₀H₇OH + NH₃

Alternatively, naphthalene is hydrogenated to tetralin, which is oxidized to 1-tetralone, which undergoes dehydrogenation.

Occurrence

1-Naphthol is a metabolite of the insecticide carbaryl and naphthalene. Along with TCPy, it has been shown to decrease testosterone levels in adult men.^[3]

Applications

1-Naphthol is a precursor to a variety of insecticides including carbaryl and pharmaceuticals including nadolol. It undergoes azo coupling to give various azo dyes, but these are generally less useful than those derived from 2-naphthol.^[2]

Other uses

In Molisch's test, 1-naphthol dissolved in ethanol, known as Molisch's reagent, is used as reagent for detecting the presence of carbohydrates. The test known as Molisch's test would give a red- or purple-colored compound to indicate the presence of carbohydrate. The rapid furfural test, similar to Molisch's test, also uses 1-naphthol.

The Sakaguchi test uses 1-naphthol with sodium hypobromite to detect the presence of arginine in proteins.

The Voges–Proskauer test uses 1-naphthol in potassium hydroxide (KOH) solution to detect the breakdown of glucose into acetoin which is used by bacteria for external energy storage. A positive test will be indicated by the appearance of a red color of the original yellow solution.

References

^ Sreekanth, R; Prasanthkumar, KP; Sunil Paul, MM; Aravind, UK; Aravindakumar, CT (7 November 2013). "Oxidation reactions of 1- and 2-naphthols: an experimental and theoretical study.". The Journal of Physical Chemistry A. 117 (44): 11261–70. doi:10.1021/jp4081355. PMID 24093754. Retrieved 2 December 2013.
^ ^a ^b Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.
^ Meeker, John D.; Ryan, Louise; Barr, Dana B.; Hauser, Russ (January 2006). "Exposure to Nonpersistent Insecticides and Male Reproductive Hormones". Epidemiology. 17 (1): 61–68. doi:10.1097/01.ede.0000190602.14691.70. PMID 16357596.

External links

NIST Chemistry WebBook 1-Naphthalenol

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1-Naphthol
Names
	IUPAC name Naphthalen-1-ol
	Other names 1-Hydroxynaphthalene; 1-Naphthalenol; alpha-Naphthol
Identifiers
CAS Number	90-15-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:10319
ChEMBL	ChEMBL122617
ChemSpider	6739
ECHA InfoCard	100.001.791
KEGG	C11714
PubChem	7005
UNII	2A71EAQ389
	InChI InChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H Key: KJCVRFUGPWSIIH-UHFFFAOYSA-N ; InChI=1/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H Key: KJCVRFUGPWSIIH-UHFFFAOYAZ ;
	SMILES Oc2cccc1ccccc12 ;
Properties
Chemical formula	C10H8O
Molar mass	144.17 g/mol
Appearance	Colorless or white solid; commercial material is often strongly colored
Density	1.10 g/cm3
Melting point	95 to 96 °C (203 to 205 °F; 368 to 369 K)
Boiling point	278 to 280 °C (532 to 536 °F; 551 to 553 K)
Magnetic susceptibility (χ)	-98.2·10−6 cm3/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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英: α-naphthol
同: 1-naphthol, naphthalen-1-ol

[1] Sreekanth, R; Prasanthkumar, KP; Sunil Paul, MM; Aravind, UK; Aravindakumar, CT (7 November 2013). "Oxidation reactions of 1- and 2-naphthols: an experimental and theoretical study.". The Journal of Physical Chemistry A. 117 (44): 11261–70. doi:10.1021/jp4081355. PMID 24093754. Retrieved 2 December 2013.

[Ullmann-2] Gerald Booth "Naphthalene Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_009.

[3] Meeker, John D.; Ryan, Louise; Barr, Dana B.; Hauser, Russ (January 2006). "Exposure to Nonpersistent Insecticides and Male Reproductive Hormones". Epidemiology. 17 (1): 61–68. doi:10.1097/01.ede.0000190602.14691.70. PMID 16357596.

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1-naphthol