2-[(Chloroacetyl)oxy]benzoic acid

Base Information

• Chemical Name: 2-[(Chloroacetyl)oxy]benzoic acid
• CAS No.: 6090-79-5
• Molecular Formula: C9H7ClO4
• Molecular Weight: 214.605
• Hs Code.: 2918990090
• Mol file: 6090-79-5.mol

Synonyms:Acetic acid,chloro-,ester with salicylic acid;Salicylic acid,chloroacetate;2-chloroacetoxy-benzoic acid;acido 2-cloroacetilsalicilico;O-Chloroacetylsalicylic acid;(chloroacetyl)salicylic acid;2-(2-chloroacetoxy)benzoic acid;2-Chloracetoxy-benzoesaeure;WLN: QVR BOV1G;O-(Chloracetyl)-salicylsaeure;

Chemical Property of 2-[(Chloroacetyl)oxy]benzoic acid

Chemical Property:

• Vapor Pressure: 9.46E-06mmHg at 25°C
• Boiling Point: 358.1°Cat760mmHg
• Flash Point: 170.4°C
• PSA: 63.60000
• Density: 1.421g/cm³
• LogP: 1.52900

Purity/Quality:

99% ^*data from raw suppliers

2-[(CHLOROACETYL)OXY]BENZOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[(Chloroacetyl)oxy]benzoic acid

There total 2 articles about 2-[(Chloroacetyl)oxy]benzoic acid 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: 53.6%

chloroacetyl chloride (79-04-9) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → acido 2-cloroacetilsalicilico (6090-79-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield:

sodium salicylate (54-21-7) + chloroacetyl chloride (79-04-9) → acido 2-cloroacetilsalicilico (6090-79-5)

Guidance literature:

With diethyl ether;

DOI:10.1002/ardp.19242620206

Reference yield:

acido 2-cloroacetilsalicilico (6090-79-5) → 2-{Bis-[(2S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-benzoic acid (3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester

Guidance literature:

Multi-step reaction with 6 steps

1: thionyl chloride / 4 h / Heating

2: Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

3: thiourea / methanol; CH₂Cl₂ / 48 h / 50 °C

4: POCl₃, Et₃N / CH₂Cl₂ / 0 °C

5: pyridine / CH₂Cl₂ / 3.5 h / 4 - 20 °C

6: 20 percent / H₂ / 10percent Pd/C / acetone; methanol / 2585.7 Torr

With pyridine; thionyl chloride; hydrogen; triethylamine; thiourea; trichlorophosphate; palladium on activated charcoal; In methanol; dichloromethane; acetone;

DOI:10.1021/jm9600757

upstream raw materials:

sodium salicylate

chloroacetyl chloride

salicylic acid

Downstream raw materials:

2-Hydroxy-benzoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

2-{Bis-[(2S,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-benzoic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

(2-cloroacetilsaliciloil)-4-nitrofenolo

O-(2-cloroacetilsaliciloil)-N-(2-acetilsaliciloil)-4-amminofenolo

Refernces

• 1、 Khamnei, Shahrzad,Torrence, Paul F.. "Neighboring group catalysis in the design of nucleotide prodrugs". . p. 4109 - 4115. Retrieved 2007/10/03.