249766-02-7

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(1-propenyl)-, (1R,3R)- (9CI)
• Synonyms: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(1-propenyl)-, (1R,3R)- (9CI)
• CAS NO: 249766-02-7
• Molecular Formula: C9H14O2
• Molecular Weight: 154.20626
• Product Categories: CARBOXYLICACID
• Mol File: 249766-02-7.mol

Chemical Properties

• Boiling Point: 227.4±29.0 °C(Predicted)
• Appearance: /
• Density: 1.103±0.06 g/cm3(Predicted)
• PKA: 4.94±0.33(Predicted)
• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(1-propenyl)-, (1R,3R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(1-propenyl)-, (1R,3R)- (9CI)(249766-02-7)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(1-propenyl)-, (1R,3R)- (9CI)(249766-02-7)

Safety Data

• Hazardous Substances Data: 249766-02-7(Hazardous Substances Data)

Upstream product

• 55701-03-6 (+)-trans-(1R,3S)-2,2-dimethyl-3-(2',2'-dichlorovinyl)cyclpropanecarboxylic acid 
• 556-82-1 3-methyl-2-buten-1-ol 
• 116347-29-6 [(2S)-3,3-dimethyloxiran-2-yl]methanol 
• 350699-93-3 (1R,3S)-(-)-2,2-Dimethyl-3-formylcyclopropane-1-carboxylic acid 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 93027-37-3 (+/-)-4-Benzoyloxy-3,3-dimethyl-hept-5ξ-ensaeure-nitril 
• 1741-47-5 (+/-)-Toluol-4-sulfonsaeure-<3-aethoxy-2,2-dimethyl-hex-4ξ-enylester> 
• 90608-07-4 (+/-)-4-Hydroxy-3,3-dimethyl-hept-5ξ-ennitril 
• 1741-49-7 (+/-)-4-Ethoxy-3,3-dimethyl-hept-5ξ-ensaeure 
• 1741-48-6 (+/-)-4-Ethoxy-3,3-dimethyl-hept-5ξ-ennitril 
• 92331-73-2 2-Cyan-3,3-dimethyl-4-oxo-6-aethoxy-heptansaeure-aethylester 
• 90642-70-9 3.3-Dimethyl-4-oxo-hept-5ζ-ensaeure-nitril 
• 1802-03-5 (+/-)-trans-2,2-Dimethyl-3-<ξ-propenyl>-cyclopropancarbonsaeure-aethylester; (+/-)-trans-Nor-chrysanthemumsaeure-aethylester' 
• 90642-56-1 (+/-)-2,2-Dimethyl-3t--cyclopropan-carbonitril; '(+/-)-Nor-trans-chrysanthemumsaeure-nitril' 

Downstream Products

• 54407-18-0 C₂₁H₂₃NO₄ 
• 54407-24-8 C₂₆H₂₆O₂ 
• 54407-36-2 C₂₀H₂₆O₂ 
• 240494-65-9 (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 

Relevant articles and documents

A SHORT AND EFFICIENT METHOD FOR PRODUCING (1R,3R)-2,2-DIMETHYL-3-(Z)-PROP-1-EN-1-YL) CYCLOPROPANE CARBOXYLIC ACID AND ESTERS

The present invention relates to a method for producing (1R,3R)-2,2-dimethyl-3-(Z)-prop-1-en-1-yl) cyclopropane carboxylic acid [I] and its salts and esters, shown as figure I from easily available(1R,3S)-3-(2,2-dihaloethenyl)-2,2-dimethyl-cyclopropanecarboxylic acid of structural formula (II) and the salts and esters derived from formula (II).

Ring-Closing Strategy Utilizing Nitrile α-Anions: Chiral Synthesis of (+)-Norchrysanthemic Acid and Expeditious Asymmetric Total Synthesis of (+)-Grandisol

Chiral syntheses of two distinct small cycloalkanes, (1R,3R)-(1Z)-norchrysanthemic acid and (+)-grandisol, were performed by characteristic ring-closing methodologies using carbanions at the α-position of nitriles (nitrile α-anions). (i) (1R,3R)-(1Z)-Norchrysanthemic acid, a highly potent ingredient of synthetic pyrethroid containing a cyclopropane structure, was synthesized from readily available (S)-epoxide derived from 3-methyl-but-2-en-1-ol in 7 steps in 23 % overall yield and with > 98 % ee. This sequence involves a trans-selective cyclopropane formation using the nitrile α-anion of (S)-3-mesyloxynitrile as the key step. The present chiral synthesis was performed with effective stereocontrol of both the chirality in the 1,3-positions on the cyclopropane and the Z-geometry of the propenyl group. (ii) (+)-Grandisol, an insect sex pheromone possessing a characteristic cyclobutane structure, was synthesized from commercially available cyclopropyl methyl ketone (route A) or from commercially available 3-cyanopropylzinc bromide and 1-bromo-1-methylpropene (route B) in 10 or 8 steps in 6 % or 8 % overall yield and with 80 % ee. This sequence involves a Shi asymmetric epoxidation of a trisubstituted olefin and a straightforward Stork-type asymmetric cyclobutane formation with clean SN2 stereoinversion using the nitrile α-anion of the chiral epoxynitrile. The present expedient method is the second asymmetric total synthesis starting from achiral compounds.

Synthesis of All Stereoisomers of the Norchrysanthemic Acid Methyl Ester

Syntheses of eight stereoisomers of methyl norchrysanthemate, (1R)-trans-(Z)-isomer and (1R)-trans-(E)-isomer from (1R)-trans-chrysanthemic acid, and other six isomers from (+)-3-carene, are described.

Process for racemizing optically active vinyl-substituted cyclopropanecarboxylic acid compound

There is disclosed a process for the racemization of a vinyl-substituted cyclopropanecarboxylic acid or a derivative thereof, which is characterized by reacting an optically active vinyl-substituted cyclopropanecarboxylic acid compound of formula (1): 1wherein R1, R2, R3 and R4 each independently represent a hydrogen atom, a halogen atom, alkyl which may be substituted having 1-4 carbon atoms, aryl which may be substituted, or alkoxycarbonyl which may be substituted, or R1 and R2 are bonded to form an alkylene group, which may be substituted; and wherein X represents hydroxyl, a halogen atom, alkoxy which may be substituted having 1-20 carbon atoms, or aryloxy which may be substituted, with a nitric compound or a nitrogen oxide.

Ester Compounds, methods of controlling a pest and uses of the ester compounds

The present invention provides ester compounds, methods of controlling a pest and uses of the ester compounds. The ester compounds are encompassed by formula (1): wherein R represents a C1 to C3 alkyl group. The methods of controlling a pest entail applying the ester compound encompassed by formula (1) to a pest or to a habitat of the pest or both. The uses of the ester compounds encompassed by formula (1) are for controlling pests.

Process for preparing cyclopropane-carboxylic acid esters

A process for preparing an organic acid ester of the formula (I), EQU1 wherein R1 is a hydrogen atom or a methyl group, R2 is a methyl group, a vinyl group, a 2,2-dichlorovinyl group, a 1-propenyl group, a 2-methyl-1-propenyl group, a 2-carbomethoxy-1-propenyl group, a 2-methoxymethyl-1-propenyl group, a 1,3-butadienyl group, a 2-methyl-1,3-butadienyl group or a cyclopentylidenemethyl group when R1 is a hydrogen atom, and R2 is a methyl group when R1 is a methyl group; which comprises reacting an acid of the formula (II), EQU2 wherein R1 and R2 are each as defined above, or its reactive derivative, or mixture of the acid and its reactive derivative with a quaternary ammonium salt of the formula (III), SPC1 wherein X is a halogen atom, A is an alkylamine, pyridine or an N-alkylaniline.