5-Chloro-2-(methylthio)aniline

Base Information

• Chemical Name: 5-Chloro-2-(methylthio)aniline
• CAS No.: 16423-54-4
• Molecular Formula: C7H8 Cl N S
• Molecular Weight: 173.666
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID40383228
• Nikkaji Number: J364.563K
• Wikidata: Q82174875
• Mol file: 16423-54-4.mol

Synonyms:5-chloro-2-(methylthio)aniline;16423-54-4;5-chloro-2-methylsulfanylaniline;5-chloro-2-(methylsulfanyl)aniline;Benzenamine, 5-chloro-2-(methylthio)-;SCHEMBL110557;DTXSID40383228;RWUQNIPYCAHKMO-UHFFFAOYSA-N;5-chloro-2-(methylthio)benzenamine;MFCD00052816;5-chloro-2-methylsulfanyl-phenylamine;AKOS000204466;MS-22101;CS-0252053;FT-0620222;EN300-58693

Chemical Property of 5-Chloro-2-(methylthio)aniline

Chemical Property:

• Vapor Pressure: 0.00493mmHg at 25°C
• Melting Point: 29 °C
• Refractive Index: 1.627
• Boiling Point: 276°Cat760mmHg
• PKA: 2.52±0.10(Predicted)
• Flash Point: 120.7°C
• PSA: 51.32000
• Density: 1.28g/cm³
• LogP: 3.22530
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 173.0065981
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

98%min ^*data from raw suppliers

5-Chloro-2-(methylthio)aniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC1=C(C=C(C=C1)Cl)N

Technology Process of 5-Chloro-2-(methylthio)aniline

There total 9 articles about 5-Chloro-2-(methylthio)aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

trimethyl phosphite (512-56-1) + 4-chloro-2-aminobenzenethiol (1004-00-8) → 2-amino-4-chlorophenyl methyl sulphide (16423-54-4)

Guidance literature:

With calcium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 0.133333h; Sealed tube;

DOI:10.1055/a-1731-3852

Reference yield: 61.0%

4-chloro-2-aminobenzenethiol (1004-00-8) + methyl iodide (74-88-4) → 2-amino-4-chlorophenyl methyl sulphide (16423-54-4)

Guidance literature:

4-chloro-2-aminobenzenethiol; With potassium tert-butylate; In ethanol; at 0 ℃; for 1.25h;

methyl iodide; In ethanol; at 0 - 20 ℃; for 2.5h; Further stages.;

DOI:10.1021/jm000542r

Reference yield:

dimethylsulfide (75-18-3) + 1-azido-3-chlorobenzene (3296-06-8) → 2-amino-4-chlorophenyl methyl sulphide (16423-54-4) + 3-Chloro-4-methylsulfanyl-phenylamine (5211-01-8) + 2-amino-6-chlorophenyl methyl sulphide (19284-91-4) + 3-chloro-aniline (108-42-9)

Guidance literature:

With trifluorormethanesulfonic acid; trifluoroacetic acid; at 25 ℃; for 4h; Title compound not separated from byproducts;

upstream raw materials:

(4-chloro-2-nitrophenyl)(methyl)sulfane

dimethylsulfide

1-azido-3-chlorobenzene

4-chloro-2-aminobenzenethiol

Downstream raw materials:

1-Benzoyl-3-(5-chloro-2-methylsulfanyl-phenyl)-thiourea

5-chloro-2-phenylbenzo[b]thiophene

2,5-Dichloro-benzothiazole

(5-chloro-2-(methylthio)phenyl)hydrazine hydrochloride

Refernces

• 1、 Tang, Yu,Yu, Biao. "A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination". . . Retrieved 2022/03/27.
• 2、 Hari, Durga Prasad,Hering, Thea,Koenig, Burkhard. "Visible light photocatalytic synthesis of benzothiophenes". supporting information. p. 5334 - 5337,4. Retrieved 2012/12/12.