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2-Aminobenzenethiol

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Identification
Molecular formula
C6H7NS
CAS number
137-07-5
IUPAC name
2-aminobenzenethiol
State
State

At room temperature, 2-aminobenzenethiol is in a solid state. It can exist as crystals and should be handled with caution due to its sensitivity to light and air.

Melting point (Celsius)
32.00
Melting point (Kelvin)
305.15
Boiling point (Celsius)
223.00
Boiling point (Kelvin)
496.15
General information
Molecular weight
125.19g/mol
Molar mass
125.1900g/mol
Density
1.1480g/cm3
Appearence

2-Aminobenzenethiol, also known as ortho-aminobenzenethiol or mercaptoaniline, typically appears as a pale yellow to light brown crystalline solid. It is sensitive to light and air, which may cause it to darken over time. The compound may be presented in powdered form as well.

Comment on solubility

Solubility of 2-aminobenzenethiol

2-aminobenzenethiol, commonly known as o-aminothiophenol, exhibits interesting solubility characteristics that are worth noting. This compound is categorized as a thiol, which typically influences its solubility in various solvents.

The solubility of 2-aminobenzenethiol can be summarized as follows:

  • Water: It shows limited solubility in water due to its hydrophobic aromatic ring structure.
  • Organic solvents: It demonstrates good solubility in a variety of organic solvents, including ethanol, acetone, and dichloromethane, due to its ability to participate in hydrogen bonding and favorable interactions with non-polar environments.
  • Acidic conditions: In acidic solutions, the solubility can increase significantly, as protonation of the amino group can enhance its interaction with water.

When discussing solubility, it is important to highlight that the structure of the compound plays a significant role. The presence of the –NH2 (amino) and –SH (thiol) groups contributes to its behavior in aqueous and organic solvents:

  1. The amino group enhances solubility in polar solvents due to its capacity to engage in hydrogen bonding.
  2. The thiol group contributes to solubility in non-polar conditions, allowing for flexibility in solvation.

Overall, the solubility of 2-aminobenzenethiol reveals a complex interplay between its functional groups and solvent properties, making it a compound of interest for studies in organic chemistry and material science.

Interesting facts

Interesting Facts about 2-Aminobenzenethiol

2-Aminobenzenethiol, also known as ortho-aminothiophenol, is a fascinating compound with numerous intriguing characteristics:

  • Structural Characteristics: The compound features both an amino (-NH2) and a thiol (-SH) functional group, strategically positioned on the benzene ring. This unique arrangement significantly influences its reactivity and the properties of related compounds.
  • Applications: 2-Aminobenzenethiol plays a vital role in the synthesis of various organic compounds. It is often used in:
    • Dyes and pigments - where it acts as a key building block.
    • Pharmaceuticals - as an intermediate in the creation of medicinal compounds.
    • Agrochemicals - contributing to the development of effective pesticides and herbicides.
  • Biological Relevance: This compound has drawn attention in medicinal chemistry due to its potential as a ligand in coordination chemistry and its ability to stabilize metal ions, which is crucial in biological systems.
  • Toxicity and Safety: Like many thiol compounds, 2-aminobenzenethiol can be hazardous. It is essential to handle it with care, as it may cause irritation upon contact with skin or eyes. Proper personal protective equipment (PPE) should always be worn in a laboratory environment.

The versatility and significance of 2-aminobenzenethiol extend far beyond its basic chemical structure, making it a noteworthy subject of study in the realms of organic chemistry and material science. As a chemist, understanding such compounds not only enriches our knowledge of chemical behavior but also opens up new avenues for innovation in various fields.

Synonyms
2-Aminothiophenol
137-07-5
2-AMINOBENZENETHIOL
o-Aminothiophenol
2-Mercaptoaniline
o-Mercaptoaniline
o-Aminobenzenethiol
Benzenethiol, 2-amino-
2-Mercaptaniline
1-Amino-2-mercaptobenzene
Benzenethiol, o-amino-
2-aminobenzene-1-thiol
o-Aminophenyl mercaptan
2-Aminophenyl mercaptan
USAF EK-4376
2-Amino-1-mercaptobenzene
ortho-aminothiophenol
2-Amino-benzenethiol
aminothiophenol
CCRIS 9096
2-thioaniline
KIT82KOK2Z
NSC 4738
EINECS 205-277-3
MFCD00007702
BRN 0606076
AI3-52263
2-AMINITHIOPHENOL
NSC-4738
AMINOBENZENETHIOL, 2-
.ALPHA.-AMINOTHIOPHENOL
2-Amino thiophenol
DTXSID6051693
CHEBI:91019
4-13-00-00910 (Beilstein Handbook Reference)
NSC-106635
aniline, 2-mercapto-
2-Aminothiophenol 90%
40451-21-6
oAminothiophenol
oMercaptoaniline
2mercaptoaniline
aminobenzenethiol
oAminobenzenethiol
0-mercaptoaniline
2Aminobenzenethiol
2-aminobenzenthiol
orthoaminothiophenol
o-amino benzenthiol
2-Amino-thiophenol
o-amino thio-phenol
Benzenethiol, oamino
2-amino benzenethiol
2-(amino)thiophenol
Benzenethiol, 2amino
1Amino2mercaptobenzene
UNII-KIT82KOK2Z
WLN: ZR BSH
2-Aminothiophenol, 99%
UNII-D4F3JSV4X6
ALPHA-AMINOTHIOPHENOL
SCHEMBL7807
D4F3JSV4X6
2-Aminothiophenol 90per cent
CHEMBL116835
DTXCID5030248
NSC4738
Indole-3-butanoyl ?-D-Glucopyranose
STL281873
AKOS000119325
AT19637
FA07685
GS-6722
2-Aminothiophenol, technical grade, 90%
AC-10751
BP-20299
DB-042373
A0267
NS00021632
EN300-17914
Q471781
2-Aminothiophenol 2-Mercaptoaniline 2-Aminobenzenethiol
F2190-0442
2-Aminobenzenethiol ; 2-Mercaptoaniline; 2-Mercaptoaniline; 2-Aminobenzenethiol
205-277-3
QuadraPure(R) MPA, 100-400 mum particle size, extent of labeling: 1.5 mmol/g loading, 1 % cross-linked with divinylbenzene