2,3-dichloro-N-hydroxybenzenecarboximidoyl chloride

Base Information

• Chemical Name: 2,3-dichloro-N-hydroxybenzenecarboximidoyl chloride
• CAS No.: 265130-17-4
• Molecular Formula: C₇H₄Cl₃NO
• Molecular Weight: 224.474
• Hs Code.: 2928009090
• DSSTox Substance ID: DTXSID40371988
• Mol file: 265130-17-4.mol

Synonyms:2,3-dichloro-N-hydroxybenzenecarboximidoyl chloride;265130-17-4;DTXSID40371988;FT-0609569

Chemical Property of 2,3-dichloro-N-hydroxybenzenecarboximidoyl chloride

Chemical Property:

• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.597
• Boiling Point: 356.5°C at 760 mmHg
• PKA: 9.91±0.70(Predicted)
• Flash Point: 169.4°C
• PSA: 32.59000
• Density: 1.53g/cm³
• LogP: 3.36800
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 222.935847
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98.5% ^*data from raw suppliers

1,2',3'-TRICHLOROBENZALDOXIME 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)Cl)C(=NO)Cl

Technology Process of 2,3-dichloro-N-hydroxybenzenecarboximidoyl chloride

There total 2 articles about 2,3-dichloro-N-hydroxybenzenecarboximidoyl chloride 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: 87.0%

2,3-dichlorobenzaldehyde oxime (4414-54-4) → 2,3-dichlorobenzohydroximoyl chloride (265130-17-4)

Guidance literature:

With N-chloro-succinimide; In N,N-dimethyl-formamide; at 35 ℃; Cooling with ice;

DOI:10.1016/j.bmc.2013.07.049

Reference yield:

2,3-dichlorobenzylaldehyde (6334-18-5) → 2,3-dichlorobenzohydroximoyl chloride (265130-17-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride; pyridine / methanol / 2.5 h / 20 °C

2: N-chloro-succinimide / N,N-dimethyl-formamide / 35 °C / Cooling with ice

With pyridine; N-chloro-succinimide; hydroxylamine hydrochloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2013.07.049

Reference yield: 90.0%

tetraacetyl thioglucose (19879-84-6) + 2,3-dichlorobenzohydroximoyl chloride (265130-17-4) → S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3-dichlorophenylthiohydroxamate (1454839-26-9)

Guidance literature:

With triethylamine; In diethyl ether; dichloromethane; at 20 ℃; for 2h; stereospecific reaction; Inert atmosphere;

DOI:10.1016/j.bmc.2013.07.049

upstream raw materials:

2,3-dichlorobenzaldehyde oxime

2,3-dichlorobenzylaldehyde

Downstream raw materials:

S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3-dichlorophenylthiohydroxamate

potassium 2,3,4,6-tetra-O-acetyl-2,3-dichlorophenylglucosinolate

C₁₃H₁₄Cl₂NO₉S₂^(1-)*K⁽¹⁺⁾

Refernces

• 1、 Vo, Quan V.,Rochfort, Simone,Nam, Pham C.,Nguyen, Tuan L.,Nguyen, Trung T.,Mechler, Adam. "Synthesis of aromatic and indole alpha-glucosinolates". . p. 45 - 53. Retrieved 2017/11/23.
• 2、 Vo, Quan V.,Trenerry, Craige,Rochfort, Simone,White, Jonathan,Hughes, Andrew B.. "Preparation and X-ray analysis of potassium (2,3-dichlorophenyl) glucosinolate". . p. 588 - 594. Retrieved 2014/08/18.