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T32808

Sigma-Aldrich

Thiophenol

97%

Sinonimo/i:

Benzenethiol, Phenyl mercaptan

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About This Item

Formula condensata:
C6H5SH
Numero CAS:
108-98-5
Peso molecolare:
110.18
Beilstein:
506523
Numero CE:
203-635-3
Numero MDL:
MFCD00004826
Codice UNSPSC:
12352100
ID PubChem:
24900127
NACRES:
NA.22

Densità del vapore

3.8 (vs air)

Livello qualitativo

100

Tensione di vapore

1.4 mmHg ( 20 °C)

Saggio

97%

Indice di rifrazione

n20/D 1.588 (lit.)

P. eboll.

169 °C (lit.)

Punto di fusione

−15 °C (lit.)

Densità

1.073 g/mL at 25 °C (lit.)

Stringa SMILE

Sc1ccccc1

InChI

1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
RMVRSNDYEFQCLF-UHFFFAOYSA-N

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Descrizione generale

Thiophenol is an organosulfur compound used as an intermediate to produce polymers.

Applicazioni

Thiophenol can undergo:
  • Asymmetric Michael addition to diisopropyl maleate in the presence of a catalytic amount of cinchonine to form (s)-(−)-diisopropyl phenylthiosuccinate, which can be further converted to (R)-(+)-3,4-epoxy-1-butanol.
  • Regioselective and stereoselective 1,4-addition to alkenylidenecyclopropanes leading to endo- or cis-vinyl sulfide adducts, a key step in the synthesis of karahanaenone.
  • Diastereoselective addition to (S)-N-(α,β-unsaturated carbonyl)-γ-[(trityloxy)methyl]-γ-butyrolactams to form the corresponding β-(phenylthio)carboxylates.

Avvertenze

Danger

Classi di pericolo

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

122.0 °F - closed cup

Punto d’infiammabilità (°C)

50 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificati d'analisi (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Thiophenol additions to alkenylidenecyclopropanes. A novel synthesis of karahanaenone.
Cairns P M, et al.
Tetrahedron Letters, 23(13), 1405-1408 (1982)
Palladium-Catalyzed Regioselective Addition of Thiophenol to Conjugated Enynes. Efficient Syntheses of 2-(Phenylsulfinyl) and 2-(Phenylsulfonyl) 1, 3-Dienes.
Baeckvall J-E and Anna E
The Journal of Organic Chemistry, 59(20), 5850-5851 (1994)
A ratiometric fluorescent probe for selective detection of thiophenol derivatives
Li F, et al.
Spectrochimica Acta Part A: Molecular Spectroscopy, 271, 120870-120870 (2022)
Diastereoselective Thiophenol Addition to (S)-N-. alpha.,. beta.-Unsaturated carbonyl-. gamma.-[(trityloxy) methyl]-. gamma.-butyrolactams.
Tomioka K, et al.
The Journal of Organic Chemistry, 60(19), 6188-6190 (1995)
Ki-Jeong Kim et al.
Scientific reports, 10(1), 2119-2119 (2020-02-09)
The surface morphology and electronic structure of hexagonal graphene onion rings (HGORs), a modified graphene structure, were investigated to confirm the possibility as an efficient catalyst when compared to graphene. After confirming the formation of HGORs with a smaller width
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