2'-Chloroacetanilide

Base Information

• Chemical Name: 2'-Chloroacetanilide
• CAS No.: 533-17-5
• Molecular Formula: C8H8ClNO
• Molecular Weight: 169.611
• Hs Code.: 29242998
• European Community (EC) Number: 208-555-2
• NSC Number: 40562,8455
• UNII: 20C42PA69Y
• DSSTox Substance ID: DTXSID2060200
• Nikkaji Number: J6.999J
• Wikidata: Q27116406
• Mol file: 533-17-5.mol

Synonyms:Acetanilide, o-chloro- (3CI);N-(2-Chlorophenyl)acetamide;NSC 8455;o-Chloroacetanilide;

Chemical Property of 2'-Chloroacetanilide

Chemical Property:

• Appearance/Colour: beige to light brown crystalline powder
• Melting Point: 88-90 °C(lit.)
• Refractive Index: 1.5430 (estimate)
• Boiling Point: 325.2 °C at 760 mmHg
• PKA: 14.19±0.70(Predicted)
• Flash Point: 150.5 °C
• PSA: 29.10000
• Density: 1.261 g/cm³
• LogP: 2.37140
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: practically insoluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 169.0294416
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

2''-Chloroacetanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CC(=O)NC1=CC=CC=C1Cl
• Uses: 2''-Chloroacetanilide

Technology Process of 2'-Chloroacetanilide

There total 84 articles about 2'-Chloroacetanilide 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: 84.5%

Acetanilid (103-84-4) → N-(2-chlorophenyl)acetamide (533-17-5) + N-(4-chlorophenyl)acetamide (539-03-7)

Guidance literature:

With tert-butylhypochlorite; In tetrahydrofuran; at 0 ℃; for 12h;

DOI:10.1080/00397919808007021

Reference yield: 75.6%

N-Phenylacetohydroxamic acid (1795-83-1) → N-(2-chlorophenyl)acetamide (533-17-5) + 4-acetaminophenol (103-90-2,8055-08-1) + N-(4-chlorophenyl)acetamide (539-03-7) + 2-(acetylamino)phenol (614-80-2)

Guidance literature:

With tetrachloromethane; tributylphosphine; In acetonitrile; for 41h; Ambient temperature;

DOI:10.1246/cl.1993.1369

Reference yield:

N-sulfonoxyacetanilide pyridinium salt (91631-52-6) → N-(2-chlorophenyl)acetamide (533-17-5) + 4-acetaminophenol (103-90-2,8055-08-1) + N-(4-chlorophenyl)acetamide (539-03-7) + 2-(acetylamino)phenol (614-80-2)

Guidance literature:

With potassium chloride; In water; acetonitrile; at 40 ℃; Further byproducts given;

DOI:10.1021/ja00331a036

upstream raw materials:

N-chloroacetanilide

(2-chlorophenyl)urea

acetic anhydride

o-chloroaniline

Downstream raw materials:

N-phenyl-2-chloroaniline

N-(2-(phenylthio)phenyl)acetamide

thioacetic acid-(2-chloro-anilide)

1-(2-chloro-phenyl)-5-methyl-1H-tetrazole

Refernces

• 1、 Newell et al.. "". . p. 6122. Retrieved 1956.
• 2、 Jerzy, Gaca,Slawomir, Zak. "Oxidative chlorination of acetanilides by metal chlorides-hydrogen peroxide in acid-aqueous medium systems". . p. 3291 - 3299. Retrieved 1997.
• 3、 Bell,Danckwerts. "-". . p. 1774. Retrieved 1939.
• 4、 Kianmehr, Ebrahim,Afaridoun, Hadi. "Nickel(II)- And Silver(I)-Catalyzed C-H Bond Halogenation of Anilides and Carbamates". . p. 1513 - 1523. Retrieved 2020/12/14.
• 5、 Zhao, Chenxi,Tang, Chu,Li, Changhao,Ning, Wentao,Hu, Zhiye,Xin, Lilan,Zhou, Hai-Bing,Huang, Jian. "Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy". . . Retrieved 2021/05/10.