50675-57-5

Basic information

• Product Name: 2,2-DIMETHYLCYCLOPROPANECARBONYL CHLORIDE
• Synonyms: 2,2-DIMETHYLCYCLOPROPANECARBONYL CHLORIDE
• CAS NO: 50675-57-5
• Molecular Formula: C₆H₉ClO
• Molecular Weight: 132.59
• Mol File: 50675-57-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-DIMETHYLCYCLOPROPANECARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYLCYCLOPROPANECARBONYL CHLORIDE(50675-57-5)
• EPA Substance Registry System: 2,2-DIMETHYLCYCLOPROPANECARBONYL CHLORIDE(50675-57-5)

Safety Data

• Hazardous Substances Data: 50675-57-5(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Strong and pungent

Usage

Reagent in organic synthesis (preparation of pharmaceuticals and fine chemicals)

Building block for

Synthesis of various organic compounds (e.g. lactones and other cyclic compounds)

Reactivity

Highly reactive

Safety precautions

Potential skin and eye irritation, should be handled with caution, used in well-ventilated areas with appropriate personal protective equipment.

Upstream product

• 75885-59-5 2,2-dimethylcyclopropane-1-carboxylic acid 
• 930-50-7 [(1RS)-2,2-dimethylcyclopropyl]methanol 
• 556-82-1 3-methyl-2-buten-1-ol 
• 5722-11-2 rac-2,2-dimethylcyclopropanecarbonitrile 
• 22308-12-9 1,3-bis((p-toluenesulfonyl)oxy)-2,2-dimethylpropane 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 28624-52-4 (R)-2,2-dimethylcyclopropanecarboxylic acid 

Downstream Products

• 870809-25-9 4,5-bis-benzyloxy-2-methyl-benzoic acid 2-(2,2-dimethyl-cyclopropanecarbonyloxy)-3-{1,1-dimethyl-2-[(tetrahydro-furan-3-carbonyl)-amino]-ethylamino}-propyl ester 
• 1276045-05-6 (2,2-dimethyl-cyclopropyl)-[4-(3-methoxy-phenyl)-piperidin-1-yl]-methanone 
• 1428555-91-2 N-(2-aminophenyl)-2,2-dimethylcyclopropanecarboxamide 
• 1428555-92-3 1,2-bis(2,2-dimethylcyclopropyl-1-carbonylamino)benzene 

Relevant articles and documents

Industrial production of chiral intermediate of cilastatin by nitrile hydratase and amidase catalyzed one-pot, two-step biotransformation

An industrial one-pot, two-step bioprocess catalyzed by nitrile hydratase (NHase) and amidase was developed for (S)-2,2-dimethylcyclopropanecarboxamide (1), the key chiral intermediate of cilastatin. The key unit operations of the whole process including fermentative production of enzymes, biotransformation, isolation of product, and recycling of by-product were reported for the first time. The volumetric enzyme activities of NHase and amidase in 1000-L fermentor were enhanced to 351,000 and 5880 U/L, respectively. The two-step, one-pot biotransformation of rac-2,2-dimethylcyclopropanecarbonitrile (2) took full advantage of both enzymes, leading to accumulation of (S)-1 in 47% yield and 99.6% ee. (S)-1 and the by-product (R)-2,2-dimethylcyclopropanecarboxylic acid (3) were obtained with yields of 38% and 45%, respectively, by a novel macroporous resin adsorption chromatography. Moreover, the total yield of (S)-1 was further increased to 53% after one recycling of (R)-3. The new bioprocess dramatically improved process efficiency compared with the chemical route by elimination of six synthetic steps and proved to be a superior and more cost-effective approach towards (S)-1.

PROCESS FOR PREPARING OPTICALLY ACTIVE CYCLOPROPANE CARBOXAMIDE AND DERIVATIVES THEREOF

The present invention relates to a process for preparing optically active cyclopropane carboxamide in a specific structure using an enzyme.

Nitroxyl radical reactions with 4-pentenyl- and cyclopropylketenes: New routes to 5-hexenyl- and cyclopropylmethyl radicals

4-Pentenylketenes 4a and 9 and cyclopropylketenes 3a, 13, 14 (RCH=C=O) are generated by photochemical Wolff rearrangements and observed by IR as relatively long-lived species at room temperature in hydrocarbon solvents. The reactions of these ketenes with the nitroxyl radicals tetramethylpiperidinyloxyl (TEMPO, TO?) and tetramethylisoindoline-2-oxyl (TMIO, IO?) form carboxy substituted 5-hexenyl and cyclopropylmethyl radicals which are either trapped by a second nitroxyl radical or undergo rearrangements followed by trapping. The rate constant of the reaction of 4a with TEMPO was similar to that of n-BuCH=C=O (1b), while 3a was 4.3 times more reactive, indicating cyclopropyl stabilization of the incipient radical.