2,2-Dichloroacetamide

Name: 2,2-Dichloroacetamide
Brand: ChemScene
Availability: InStock
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CAS No. 683-72-7
Cat. No. CS-0149993
Purity≥98%
MDL No.MFCD00008015

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 683-72-7

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General Information

CAS No. 683-72-7
Cat. No. CS-0149993
Purity ≥98%
MDL No. MFCD00008015
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂H₃Cl₂NO
Molecular Weight 127.96
Synonym(s) Dichloroacetamide; 2,2-Dichloroacetamide
SMILES NC(C(Cl)Cl)=O

Description

2,2-Dichloroacetamide is a stable, moisture-tolerant acylating agent featuring two chlorine atoms at the alpha position, enhancing electrophilicity for selective amide bond formation. This electron-deficient scaffold facilitates efficient coupling in synthetic pathways requiring high reactivity under mild conditions.

Application

2,2-Dichloroacetamide serves as a versatile building block in synthetic organic chemistry, enabling the introduction of a difluoromethyl-like electronic profile through its stable dichloroacetyl group. It functions as a key intermediate in the construction of heterocyclic scaffolds and bioactive molecules, particularly in medicinal chemistry campaigns requiring electron-withdrawing substituents. The compound exhibits bench stability, moderate reactivity under standard conditions, and facilitates clean transformations in amide coupling and nucleophilic substitution reactions.

Synthesis

Route1
- 594-65-0
- ~52%
- In-stock
  
  683-72-7
References
- Gertsyuk, M. N.; Dorokhov, V. I.; Samarai, L. I. Journal of Organic Chemistry USSR (English Translation), 1985 , vol. 21, # 4 p. 822 - 823 Zhurnal Organicheskoi Khimii, 1985 , vol. 21, # 4 p. 903 - 904
Route2
- In-stock
  
  37764-25-3
- ~10%
- In-stock
  
  683-72-7
References
- Cadierno, Victorio; Gimeno, Jose; Nebra, Noel Chemistry - A European Journal, 2007 , vol. 13, # 23 p. 6590 - 6594
Route3
- 3018-12-0
- ~84%
- In-stock
  
  683-72-7
References
- Garcia-Alvarez, Rocio; Zablocka, Maria; Crochet, Pascale; Duhayon, Carine; Majoral, Jean-Pierre; Cadierno, Victorio Green Chemistry, 2013 , vol. 15, # 9 p. 2447 - 2456

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 43.09
LogP 0.2754
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Amide

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2,2-Dichloroacetamide

CAS No. 683-72-7

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