Basic information
- CAS
1759-53-1- Standard SMILES
O=C(O)C1CC1- InChIKey
YMGUBTXCNDTFJI-UHFFFAOYSA-N- Molecular formula
- C4H6O2
- Average molar mass
- 86.09 g/mol
- Monoisotopic mass
- 86.03677943
Overview
Cyclopropanecarboxylic acid is a monocarboxylic acid and a member of cyclopropanes. It is a conjugate acid of a cyclopropanecarboxylate.
Names & identifiers
- Preferred name
- Cyclopropanecarboxylic acid
- IUPAC
- cyclopropanecarboxylic acid
- English name
- Cyclopropanecarboxylic acid
- Molecular formula
- C4H6O2
- Molecular weight
- 86.09
Names & synonyms
CYCLOPROPANECARBOXYLIC ACID1759-53-1CarboxycyclopropaneCyclopropylcarboxylic acidCyclopropionic acidCyclopropane carboxylic acidNSC-1112DTXSID1040665CHEBI:23500008803351SCPCA cpdRefChem:581141
Show more names
cyclopropanecarboxylicCyclopropane cCyclopropanic acidRARECHEM AL BO 0005Ring propyl forMateOlapali impurity 20
DTXCID9020665217-162-5CyclopropanecarboxylicacidCPC-acidMFCD00001287Cyclopropane-carboxylic acidNSC1112cyclopropyl carboxylic acid
Database identifiers
- CAS
1759-53-1- PubChem CID
- 15655
- DTXSID
DTXSID1040665- ChEMBL
CHEMBL4649900- ChEBI
CHEBI:23500- UNII
- 008803351S
- EC Number
- 217-162-5
- Nikkaji
- J23.483D
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 73.6
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
SpringerMaterials PropertiesSchoenflies notation
Vapor Pressure1.53 [mmHg]
Physical DescriptionClear light yellow liquid; mp = 14-17 deg C; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 14 · 14-17 °C (lit.)
- Boiling point
- 182 · 182-184 °C (lit.)
- Density
- 1.081 g/mL · 1.081 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.438(lit.)
- Flash point
- 161 °F · 161 °F
- storage temp.
- 2 · 2-8°C
- solubility
- soluble in Chloroform, Ethyl Acetate
- form
- Liquid
- pka
- 4.83 · 4.83(at 25℃)
- color
- Clear colorless to light yellow
- PH
- 3 · 3 (10g/l, H2O, 22℃)
- BRN
- 969839 · 969839
- InChI
- 1S/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6)
- InChIKey
- YMGUBTXCNDTFJI-UHFFFAOYSA-N
- SMILES
- OC(=O)C1CC1
- LogP
- 0.63 · 0.630
- CAS DataBase Reference
- 1759 · 1759-53-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 8803351 S · 008803351S
- NIST Chemistry Reference
- Cyclopropanecarboxylic acid(1759-53-1)
- EPA Substance Registry System
- Cyclopropanecarboxylic acid (1759-53-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 280 · P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C,Xi
- Risk Statements
- 34 · 34-22
- Safety Statements
- 26 · 26-36/37/39-45-27
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 1100000 · GZ1100000
- Hazard Note
- Irritant/Corrosive
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29162000 · 29162000
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 B · Skin Corr. 1B
- Toxicity
- 50 · mouse,LD50,intraperitoneal,172mg/kg (172mg/kg),Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 25.5% (37 of 145) of reports.
Danger
H302 (46.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 145 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Cyclopropanecarboxylic acid
Status: Active Update: 29-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/21214
Cyclopropanecarboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryIntraperitoneal LD50 (mouse) = 172 mg/kg; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (46.2%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GZ1100000
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29162000
- Toxicity
- mouse,LD50,intraperitoneal,172mg/kg (172mg/kg),Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
- risk_code
- 34-22
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C,Xi
- hazard_note
- Irritant/Corrosive
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Skin Corr. 1B
- Precautionary statements
- P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
Chemistry & industry
Uses & manufacturing
UsesUsed as an intermediate for agrochemicals, pharmaceuticals, and other organic chemicals; [REPROTOX]
General Manufacturing InformationCyclopropanecarboxylic acid: ACTIVE
Applications
DescriptionCyclopropanecarboxylic acid (1759-53-1) is a kind of organic acid. It is a clear liquid used as an intermediate for agrochemicals, pharmaceuticals, and other organic synthesis for the applications of electronics, chemicals, polymer additives, coatings, adhesives, surfactants, and other applications1. Moreover, its derivatives of are used against parasites in plants and animals. For example, the alkynyl esters of cyclopropane-carboxylic acid are used as pesticides. Similarly, cyclopropane carboxylic acid esters containing a polyhalogenated substituent are used as fungicides. The ethyl derivative is reagent used in the addition of cyclopropane and can act as annulation reagent for the conversion of aromatics to 2-methylindanones under Friedel-Crafts conditions2.
UsesCyclopropanecarboxylic acid (1759-53-1) is a monocarboxylic acid and a member of cyclopropanes. It is a conjugate acid of a cyclopropanecarboxylate.
UsesCyclopropanecarboxylic Acid is used as a reagent in the synthesis of substituted 4-(thiophen-2-ylmethyl)-2H-phthalazin-1-ones as potent PARP-1 inhibitors. Also used as a reagent in the synthesis of 2-alkyloxazoles as potent and selective PI4KIIIb inhibitors demonstrating inhibition of HCV replication.
Preparation methods
PreparationCyclopropanecarboxylic acid has been prepared by the hydrolysis of cyclopropyl cyanide, although it is unnecessary to isolate the nitrile; by heating cyclopropanedicarboxylic acid; and by the action of alkali on ethyl γ-chlorobutyrate.7 The last two methods do not appear to be of practical importance. The oxidation of cyclopropyl methyl ketone with sodium hypobromite is reported to be an excellent preparative method for this acid.Org. Synth. 1944, 24, 36DOI: 10.15227/orgsyn.024.0036
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Upstream raw materials
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Additional notes
DefinitionChEBI: Cyclopropanecarboxylic acid is a monocarboxylic acid and a member of cyclopropanes. It is a conjugate acid of a cyclopropanecarboxylate.
Related reactions
368 records
Compound notes
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