[ CAS No. 23348-99-4 ] {[proInfo.proName]}

Name: 23348-99-4|1-(4-Nitrophenyl)cyclopropanecarboxylic acid|98%
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SKU: A576300
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DV 2D 3D

3d Animation Molecule Structure of 23348-99-4

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Quality Control of [ 23348-99-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 23348-99-4 ]

SDS Specification

Alternatived Products of [ 23348-99-4 ]

Product Details of [ 23348-99-4 ]

CAS No. :	23348-99-4	MDL No. :	MFCD07374438
Formula :	C₁₀H₉NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GWOWMWDHYGMVSZ-UHFFFAOYSA-N
M.W :	207.18	Pubchem ID :	20026185
Synonyms :

Calculated chemistry of [ 23348-99-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.19
TPSA :	83.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	1.56
Log Po/w (WLOGP) :	1.65
Log Po/w (MLOGP) :	0.8
Log Po/w (SILICOS-IT) :	0.05
Consensus Log Po/w :	1.06

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.21
Solubility :	1.29 mg/ml ; 0.00623 mol/l
Class :	Soluble
Log S (Ali) :	-2.92
Solubility :	0.252 mg/ml ; 0.00121 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.98
Solubility :	2.18 mg/ml ; 0.0105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.67

Safety of [ 23348-99-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 23348-99-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 23348-99-4 ]
Downstream synthetic route of [ 23348-99-4 ]

[ 23348-99-4 ] Synthesis Path-Upstream 1~5

1
[ 408328-42-7 ]
[ 23348-99-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	Heating / reflux	1- (4-Nitrophenyl)-cyclopropanecarbonitrile (12.77g, 67.16 mmol) was placed into a 250 mL three-necked round-bottomed flask then water (79 mL) and conc. sulfuric acid (56 mL) were added. The solution was refluxed overnight and thin-layer chromatography was used to monitor the percentage completion of the reaction (100percent ethyl acetate, Rf 0. 49 for the product). The reaction mixture was cooled and the resultant precipitate was collected. The solid was washed with water (30 mL) and dried overnight under vacuum to give the title compound (8.67 g, 41.45 mmol, 62percent yield).'H-NMR (DMSO-d6) 5 8. 21-8. 11 (d, 2H), 7.58-7. 64 (d, 2H), 1.5- 1.6 (t, 2H), 1.2-1. 3 (t, 2H)
62%	Heating / reflux	1- (4-Nitrophenyl)-cyclopropanecarbonitrile (12.77g, 67.16 mmol) was placed into a 250 mL three-necked round-bottomed flask then water (79 mL) and conc. sulfuric acid (56 mL) were added. The solution was refluxed overnight and thin-layer chromatography was used to monitor the percentage completion of the reaction (100percent ethyl acetate, Rf 0. 49 for the product). The reaction mixture was cooled and the resultant precipitate was collected. The solid was washed with water (30 mL) and dried overnight under vacuum to give the title compound (8.67 g, 41.45 mmol, 62percent yield).'H-NMR (DMSO-d6) 5 8. 21-8. 11 (d, 2H), 7.58-7. 64 (d, 2H), 1.5- 1.6 (t, 2H), 1.2-1. 3 (t, 2H)

Reference： [1] Patent: WO2005/34837, 2005, A2, . Location in patent: Page/Page column 46
[2] Patent: WO2005/34837, 2005, A2, . Location in patent: Page/Page column 46
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311

2
[ 6120-95-2 ]
[ 422280-53-3 ]
[ 23348-99-4 ]

Reference： [1] Patent: US2004/6056, 2004, A1, . Location in patent: Page 39

3
[ 6120-95-2 ]
[ 23348-99-4 ]

Reference： [1] Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 3814 - 3820
[2] Patent: WO2003/99276, 2003, A1, . Location in patent: Page 236-237

4
[ 5445-26-1 ]
[ 23348-99-4 ]

Reference： [1] Patent: EP2832734, 2015, A1,

5
[ 555-21-5 ]
[ 23348-99-4 ]

Reference： [1] Patent: WO2005/34837, 2005, A2,

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Isomers

Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Amide Hydrolysis • Amide Hydrolysis • Anhydride Hydrolysis • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Esters Hydrolyze to Carboxylic Acids and Alcohols • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation • Halogenation of Benzene • Heat of Combustion • Hunsdiecker-Borodin Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction

Historical Records

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P233	Keep container tightly closed.
P234	Keep only in original container.
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Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid
2.5 g	With water; sodium hydroxide In ethanol at 10 - 35℃;	145.B B) 1-(4-nitrophenyl)cyclopropanecarboxylic acid B) 1-(4-nitrophenyl)cyclopropanecarboxylic acid To a solution of ethyl 1-(4-nitrophenyl)cyclopropanecarboxylate (3.0 g) obtained in Step A of Example 145 in ethanol (50 mL) was added 1M aqueous sodium hydroxide solution (25 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 1M hydrochloric acid was added thereto at 0°C. The resulting solid was collected by filtration to give the title compound (2.5 g). 1H NMR (400 MHz, DMSO-d6) δ1.13-1.34 (2H, m), 1.39-1.67 (2H, m), 7.43-7.71 (2H, m), 7.97-8.27 (2H, m), 12.61 (1H, brs).

Yield	Reaction Conditions	Operation in experiment
82%	With sulfuric acid; water Reflux;
62%	With sulfuric acid; water Heating / reflux;	1- (4-Nitrophenyl)-cyclopropanecarbonitrile (12.77g, 67.16 mmol) was placed into a 250 mL three-necked round-bottomed flask then water (79 mL) and conc. sulfuric acid (56 mL) were added. The solution was refluxed overnight and thin-layer chromatography was used to monitor the percentage completion of the reaction (100% ethyl acetate, Rf 0. 49 for the product). The reaction mixture was cooled and the resultant precipitate was collected. The solid was washed with water (30 mL) and dried overnight under vacuum to give the title compound (8.67 g, 41.45 mmol, 62% yield).'H-NMR (DMSO-d6) 5 8. 21-8. 11 (d, 2H), 7.58-7. 64 (d, 2H), 1.5- 1.6 (t, 2H), 1.2-1. 3 (t, 2H)
	With lithium hydroxide In water for 18h; Reflux;

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 23348-99-4 ] {[proInfo.proName]}

Quality Control of [ 23348-99-4 ]

Related Doc. of [ 23348-99-4 ]

Product Details of [ 23348-99-4 ]

Calculated chemistry of [ 23348-99-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 23348-99-4 ]

Application In Synthesis of [ 23348-99-4 ]

[ 23348-99-4 ] Synthesis Path-Upstream 1~5

[ 23348-99-4 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 23348-99-4 ]

Aryls

Carboxylic Acids

Nitroes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 23348-99-4 ]