75885-59-5

Basic information

• Product Name: 2,2-DIMETHYL CYCLOPROPYL CARBOXYLIC ACID
• Synonyms: Dimethyl cyclopropyl carboxylic acid;2,2-DIMETHYL CYCLOPR;2,2-dimethylcyclopropanecarboxylic acid(SALTDATA: FREE);2-DiMethyl cyclopropyl carboxylic acid;2,2-DiMethylcyclopropaneforMic acid;Cyclopropanecarboxylic acid, 2,2-diMethyl-;2,2-diMethylcyclopropane-1-carboxylic acid;RARECHEM AL BO 0965
• CAS NO: 75885-59-5
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Product Categories: CARBOXYLICACID
• Mol File: 75885-59-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 103-103.5 °C
• Boiling Point: 184.2 °C at 760 mmHg
• Flash Point: 83.4 °C
• Appearance: /
• Density: 1.098 g/cm³
• Vapor Pressure: 0.339mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 4.99±0.22(Predicted)
• Stability: Stench
• CAS DataBase Reference: 2,2-DIMETHYL CYCLOPROPYL CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYL CYCLOPROPYL CARBOXYLIC ACID(75885-59-5)
• EPA Substance Registry System: 2,2-DIMETHYL CYCLOPROPYL CARBOXYLIC ACID(75885-59-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41-43
• Safety Statements: 26-36/37-39
• Hazardous Substances Data: 75885-59-5(Hazardous Substances Data)

Usage

Uses

2,2-Dimethylcyclopropylcarboxylic acid

InChI:InChI=1/C6H10O2/c1-6(2)3-4(6)5(7)8/h4H,3H2,1-2H3,(H,7,8)

Upstream product

• 33422-32-1 1,1-dimethyl-2-(2-methyl-1-propenyl)cyclopropane 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 3123-97-5 dihydro-5,5-dimethyl-2(3H)-furanone 
• 22308-12-9 1,3-bis((p-toluenesulfonyl)oxy)-2,2-dimethylpropane 
• 556-82-1 3-methyl-2-buten-1-ol 
• 930-50-7 [(1RS)-2,2-dimethylcyclopropyl]methanol 
• 932-58-1 l-methyl dl-2,2-dimethylcyclopropane-1-carboxylate 
• 1192-44-5 (+/-)-2-Brom-3.3-dimethyl-cyclobutanon 
• 31044-87-8 neopentyl glycol bis(benzenesulfonate) 
• 143-33-9 sodium cyanide 
• 16783-11-2 ethyl (±)-2,2-dimethylcyclopropanecarboxylate 
• 5722-11-2 rac-2,2-dimethylcyclopropanecarbonitrile 
• 854432-02-3 4-bromo-3,3-dimethyl-butyric acid ethyl ester 
• 71441-79-7 4-chloro-4-methyl-valeric acid ethyl ester 

Downstream Products

• 1428555-91-2 N-(2-aminophenyl)-2,2-dimethylcyclopropanecarboxamide 
• 1428555-92-3 1,2-bis(2,2-dimethylcyclopropyl-1-carbonylamino)benzene 
• 1374883-86-9 [(S)-1-((S)-2-{4-[5'-Chloro-4'-({6-[(R)-4-((S)-2,2-dimethyl-cyclopropanecarbonyl)-2-methyl-piperazin-1-yl]-pyridine-3-carbonyl}-amino)-2'-trifluoromethyl-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester 
• 1374882-92-4 [(S)-1-((S)-2-{4-[4'-({6-[(R)-4-((S)-2,2-Dimethyl-cyclopropane-carbonyl)-2-methyl-piperazin-1-yl]-pyridine-3-carbonyl}-amino)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester 
• 61971-69-5 1-(3,5-Bis-trifluoromethyl-phenyl)-1-(2,2-dimethyl-cyclopropyl)-ethanol 
• 61971-68-4 1-(2,2-Dimethyl-cyclopropyl)-1-(4-trifluoromethyl-phenyl)-ethanol 
• 59671-39-5 1-(2,2-Dimethyl-cyclopropyl)-1-phenyl-ethanol 
• 82009-34-5 cilastatine 
• 85394-14-5 (+)-(Z)-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid 
• 75885-58-4 (S)-2,2-dimethylcyclopropanecarboxamide 
• 191476-68-3 2,2-Dimethyl-cyclopropanecarbothioic acid S-(2,4,6-trimethyl-phenyl) ester 
• 14590-53-5 (+)-1S-2,2-dimethylcyclopropane-carboxylic acid 
• 50675-57-5 dl-2,2-dimethylcyclopropane-1-carboxylic acid chloride 

Relevant articles and documents

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.

Process for resolution of racemates of 2,2-dimethylcyclopropanecarboxylic acid

The enantiomers of 2,2-dimethylcyclopropanecarboxylic acid are separated by esterification with the hydroxy group of optically active mandelic acid methyl ester, crystallization of the diastereomeric esters and subsequent hydrolysis of the diastereomeric esters.

Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same

An ester obtained from 2,2-dimethylcyclopropanecarboxylic acid and optically active menthol, represented by the formula, STR1 is effectively resolved into diastereomers, which upon hydrolysis give optically active 2,2-dimethylcyclopropanecarboxylic acid.