ChemicalBook--->CAS DataBase List--->75726-96-4

75726-96-4

75726-96-4 Structure

75726-96-4 Structure
IdentificationBack Directory
[Name]

2-bromo-N-isopropylacetamide
[CAS]

75726-96-4
[Synonyms]

2-bromo-N-isopropylacetamide
N-(Bromoacetyl)isopropylamine
2-broMo-N-(propan-2-yl)acetaMide
2-Bromo-N-(1-methylethyl)-acetamide
acetamide, 2-bromo-N-(1-methylethyl)-
2-bromo-N-isopropylacetamide(SALTDATA: FREE)
2-bromo-N-isopropylacetamide in stock Factory
[Molecular Formula]

C5H10BrNO
[MDL Number]

MFCD06800256
[MOL File]

75726-96-4.mol
[Molecular Weight]

180.04
Chemical PropertiesBack Directory
[Melting point ]

63-64℃
[Boiling point ]

266℃
[density ]

1.378
[Fp ]

115℃
[storage temp. ]

Inert atmosphere,Room Temperature
[pka]

13.71±0.46(Predicted)
[InChI]

InChI=1S/C5H10BrNO/c1-4(2)7-5(8)3-6/h4H,3H2,1-2H3,(H,7,8)
[InChIKey]

ZLDCRYWMEQJDGW-UHFFFAOYSA-N
[SMILES]

C(NC(C)C)(=O)CBr
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362
[REACH Registrations]

Active
[HazardClass ]

IRRITANT
[HS Code ]

2924297099
Hazard InformationBack Directory
[Uses]

2-Bromo-N-isopropylacetamide is a an intermediate of Belumosudil.
[Synthesis]

Isopropylamine

75-31-0

Bromoacetyl bromide

598-21-0

2-bromo-N-isopropylacetamide

75726-96-4

Dichloromethane (5 mL) and isopropylamine (1.2 mmol) were added to a 25 mL round-bottomed flask, corked tightly and protected under a nitrogen atmosphere. Bromoacetyl bromide (1 mmol) was slowly added dropwise over 2 min under ice bath cooling and stirring conditions. After the dropwise addition, the reaction was continued in an ice bath for 5 min, after which the reaction mixture was transferred to room temperature and stirred for 1 hr. The progress of the reaction was monitored by thin layer chromatography (TLC) until the complete disappearance of bromoacetyl bromide. Upon completion of the reaction, the resulting white solid was collected by filtration and washed with dichloromethane. The filtrate and washings were combined, and the organic layer was sequentially extracted with dilute hydrochloric acid solution, dichloromethane, washed with saturated brine and dried with anhydrous Na2SO4. After concentration under reduced pressure to remove the solvent, the target compound 2-bromo-N-isopropylacetamide was purified by column chromatography to afford the target compound as a white solid in 71% yield.

[References]

[1] Journal of the American Chemical Society, 2006, vol. 128, # 48, p. 15476 - 15489
[2] Patent: CN106916145, 2017, A. Location in patent: Paragraph 0017; 0035-0038; 0058; 0066
[3] Patent: WO2008/54599, 2008, A2. Location in patent: Page/Page column 152
[4] Patent: WO2010/104851, 2010, A1. Location in patent: Page/Page column 147; 148
[5] Patent: WO2014/55999, 2014, A2. Location in patent: Paragraph 0164
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