2,4′-Dichloroacetanilide

Name: 2,4′-Dichloroacetanilide
Brand: ChemScene
Availability: InStock
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CAS No. 3289-75-6
Cat. No. CS-0072708
Purity≥98%
MDL No.MFCD00018904

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Structure of 3289-75-6

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General Information

CAS No. 3289-75-6
Cat. No. CS-0072708
Purity ≥98%
MDL No. MFCD00018904
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇Cl₂NO
Molecular Weight 204.05
Synonym(s) None
SMILES O=C(CCl)NC(C=C1)=CC=C1Cl

Description

2,4′-Dichloroacetanilide serves as a key intermediate in the synthesis of pharmaceuticals and agrochemicals. This bench-stable compound features two chlorine atoms positioned ortho to the acetamide group, enhancing its reactivity in electrophilic substitution reactions. The electron-withdrawing chlorines stabilize the amide moiety while enabling selective functionalization under mild conditions.

Application

2,4′-Dichloroacetanilide serves as a valuable intermediate in the synthesis of pharmaceuticals and agrochemicals, leveraging its dual chlorinated aryl framework for enhanced electrophilic substitution reactivity. The acetanilide functionality provides a stable, bench-compatible platform for further functionalization via electrophilic or transition-metal-catalyzed coupling reactions. Its defined regiochemistry and moderate solubility facilitate straightforward purification and integration into multi-step synthetic sequences.

Synthesis

Route1
- 106-47-8
- 79-04-9
- ~98%
- In-stock
  
  3289-75-6
References
- Virsis, I. E.; Silaraya, D. A.; Grinberga, B. A.; Prikulis, A. A.; Gerbashevska, I. D.; Orenish, M. E. Pharmaceutical Chemistry Journal, 1981 , vol. 15, # 12 p. 849 - 853 Khimiko-Farmatsevticheskii Zhurnal, 1981 , vol. 15, # 12 p. 23 - 26
Route2
- 19103-78-7
- 106-47-8
- ~%
- In-stock
  
  3289-75-6
References
- Die Pharmazie, , vol. 23, # 10 p. 561 - 566
Route3
- 7664-93-9
- 140854-26-8
- ~%
- In-stock
  
  3289-75-6
References
- Bulletin de la Societe Chimique de France, , vol. <3> 27, p. 542

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS05,GHS07
Signal Word : Danger	UN#: 3261
Class : 8	Packing Group : Ⅲ
Hazard Statements : H317-H318
Precautionary Statements : P261-P272-P280-P302+P352-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 29.1
LogP 2.5173
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Amide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2,4′-Dichloroacetanilide

CAS No. 3289-75-6

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