[ CAS No. 93-09-4 ] {[proInfo.proName]}

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2D 3D

Structure of 93-09-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 93-09-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 93-09-4 ]

SDS Specification

Alternatived Products of [ 93-09-4 ]

Product Details of [ 93-09-4 ]

CAS No. :	93-09-4	MDL No. :	MFCD00004101
Formula :	C₁₁H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	172.18	Pubchem ID :	-
Synonyms :	Naphthalene-2-carboxylic acid

Calculated chemistry of [ 93-09-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.91
TPSA :	37.3 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.64
Log Po/w (XLOGP3) :	3.28
Log Po/w (WLOGP) :	2.54
Log Po/w (MLOGP) :	2.64
Log Po/w (SILICOS-IT) :	2.35
Consensus Log Po/w :	2.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0574 mg/ml ; 0.000333 mol/l
Class :	Soluble
Log S (Ali) :	-3.74
Solubility :	0.0315 mg/ml ; 0.000183 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0622 mg/ml ; 0.000361 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 93-09-4 ]

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 [ 93-09-4 ]

* 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 [ 93-09-4 ]
Downstream synthetic route of [ 93-09-4 ]

[ 93-09-4 ] Synthesis Path-Upstream 1~1

1
[ 93-09-4 ]
[ 835-58-5 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 1715 - 1720[2] Zhurnal Organicheskoi Khimii, 1974, vol. 10, p. 1698 - 1704

[ 93-09-4 ] Synthesis Path-Downstream 1~14

1
[ 93-09-4 ]
[ 1013-83-8 ]

Yield	Reaction Conditions	Operation in experiment
53.4%	With bromine; iodine; In acetic acid; for 0.5h;Heating / reflux;	To a boiling solution of 2-naphthoic acid (10.00 g, 58.14 mmol) in acetic acid (50 mL) is added dropwise bromine (3 mL) containing iodine (0.25 g). After the addition is complete, the solution is refluxed for 0.5 hr. A white precipitate forms during cooling and is isolated by filtration, washed with acetic acid and then water. The solid is triturated in methanol (100 mL) and 7.01 g (53.4percent yield) of the desired product is obtained as a white solid. m.p. 248-250° C. 1H NMR (300 MHz, CD3OD): delta 8.94 (d, J=1.8 Hz, 1H), 8.52-8.42 (m, 3H), 8.27 (dd, J=1.8, 7.5 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H).
46%	With bromine;iodine; In acetic acid; for 0.583333h;Heating / reflux;	Preparation 3 [0106] Preparation of 6-Iodo-1-methoxy-naphthalene. [CHEMMOL-00022] [0107] Preparation of 5-Bromo-2-naphthalenecarboxylic acid. [0108] 2-Naphthoic acid (50;0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with 100 mL of the filtrate. The solid was dried in vacuo at 55° C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50° C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield).
76 g (75%)	With I2; bromine; acetic acid;	A. 5-Bromo-2-Naphthoic Acid A 75 g (0.44 mole) portion of 2-naphthoic acid, 375 ml of acetic acid, 22.5 ml of Br2 (70 g, 0.44 mole) and 1.9 g (0.015 mole) of I2 were placed in a 1 l. 3-necked flask and refluxed with stirring for 0.6 hours. The reaction mixture was cooled to 25° and filtered. The cream solid was washed with small portions of the filtrate, air dried and dried to a constant weight at 60° to give 76 g (75percent) of a light tan-cream solid, m.p. 224°-233° dec. The crude product was slurried with 375 ml of 1 N NaOH for 0.5 hours and filtered.

With bromine;iodine; In acetic acid; at 20 - 116℃; for 1.58333h;Heating / reflux;

2-Naphthoic acid (50.0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with ?100 mL of the filtrate. The solid was dried in vacuo at 55 C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50 C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield).

Reference： [1]Patent: US2008/58423,2008,A1 .Location in patent: Page/Page column 9
[2]Patent: US2004/6229,2004,A1 .Location in patent: Page/Page column 15
[3]Synthetic Communications,2011,vol. 41,p. 2017 - 2024
[4]Journal of Medicinal Chemistry,2004,vol. 47,p. 1893 - 1899
[5]Helvetica Chimica Acta,1938,vol. 21,p. 62,65
[6]Chemische Berichte,1876,vol. 9,p. 1519
[7]Chemische Berichte,1876,vol. 9,p. 1519
[8]Australian Journal of Chemistry,1965,vol. 18,p. 1351 - 1364
[9]ChemMedChem,2010,vol. 5,p. 65 - 78
[10]Patent: US3932452,1976,A
[11]Patent: US2003/225281,2003,A1 .Location in patent: Page 13

2
[ 93-09-4 ]
[ 2243-82-5 ]

Yield	Reaction Conditions	Operation in experiment
97%		Unless otherwise specified, carboxylic acid (0.542 mmol), TCT (0.0400 g, 0.216 mmol) and K2CO3 (0.2247 g, 1.626 mmol) were mixed together and hand ground for one minute using porcelain mortar and pestle. After addition of ammonium thiocyanate (0.0495 g, 0.650 mmol), the mixture was ground manually for further five minute. During the grinding, THF (calculated to be less than 1 L/mg of solids) was added to aid homogeneous mixing. The crude material was then purified by short column chromatography (column diameter 1.5 cm, packed with 3-4 g silica gel ) using 40-50percent ethyl acetate/hexane as an eluent.
	With ammonium hydroxide;N,N-dimethyl-formamide; In oxalyl dichloride; hexane; water;	(1) PREPARATION OF NAPHTHALENE-2-CARBOXYLIC ACID AMIDE To a solution of 2-naphthoic acid (25 g, 0.145 mol) in MC (200 ml), oxalyl chloride (38 ml, 0.4356 mol) and a catalytic amount of DMF were added and stirred at room temperature for 2 hrs. After the solvent was evaporated, the crude acyl chloride was diluted with MC (200 ml), to which a solution of ammonium hydroxide in water (160 ml) was dropwise added at an ice bath temperature. After stirring for 1 hr, the precipitated product was collected by suction filtration, triturated in hexane and dried to obtain the title compound, which was used next step without further purification.
	With ammonia; at 195℃; for 0.5h;	General procedure: Into a 1L open reactor was added 500g of carboxylic acid raw material (chemically pure) and stirring was turned on (600 r/min) from the reactorThe bottom is continuously fed with ammonia gas (chemical purity, water content of 5.1percent by weight, flow rate of 100 g/min) to the carboxylic acid feed. After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and subjected to nuclear magnetic proton and elemental analysis to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the amide intermediates obtained have an extremely high purity (above 99percent).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wtpercent of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min).

Reference： [1]Heterocycles,2006,vol. 68,p. 1149 - 1162
[2]Tetrahedron Letters,2018,vol. 59,p. 3571 - 3573
[3]Bioscience, Biotechnology and Biochemistry,2001,vol. 65,p. 1761 - 1765
[4]Synthesis,1983,p. 142 - 143
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692
[6]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
Chemische Berichte,1875,vol. 8,p. 1278
[7]Patent: US2004/53331,2004,A1
[8]Patent: WO2012/159666,2012,A1
[9]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1324 - 1332
[10]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1424 - 1427
[11]Patent: CN104557357,2018,B .Location in patent: Paragraph 0135; 0136; 0137; 0139

3
[ 613-46-7 ]
[ 64-17-5 ]
sodium [ No CAS ]
[ 2243-82-5 ]
[ 74-90-8 ]
[ 7664-41-7 ]
[ 93-09-4 ]

Reference： [1]Chemische Berichte,1887,vol. 20,p. 1711

4
[ 861546-41-0 ]
sodium amide [ No CAS ]
[ 108-88-3 ]
[ 2243-82-5 ]
[ 91-20-3 ]
[ 926-04-5 ]
[ 93-09-4 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1910,vol. 150,p. 1176

5
[ 861546-41-0 ]
sodium amide [ No CAS ]
[ 71-43-2 ]
[ 2243-82-5 ]
[ 91-20-3 ]
[ 926-04-5 ]
[ 93-09-4 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1910,vol. 150,p. 1176

6
[ 65473-13-4 ]
[ 93-09-4 ]
naphthalene-2-carboxylic acid methyl-naphthalen-1-ylmethyl-amide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1997,vol. 7,p. 98 - 108

7
[ 93-09-4 ]
N^a-Fmoc-His-D-Phe-Arg-Trp-resin conjugate [ No CAS ]
[ 2243-82-5 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3822 - 3839

8
[ 93-09-4 ]
permanganate [ No CAS ]
[ 1013-83-8 ]

Reference： [1]Journal of Fluorine Chemistry,1988,vol. 38,p. 139 - 152

9
[ 532-02-5 ]
[ 93-09-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1888,vol. <2> 38,p. 161
    Journal fuer Praktische Chemie (Leipzig),1891,vol. 43,p. 432
[2]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
    Chemische Berichte,1875,vol. 8,p. 1278
[3]Journal of the American Chemical Society,1921,vol. 43,p. 901
[4]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
    Chemische Berichte,1875,vol. 8,p. 1278
[5]Journal of the American Chemical Society,1916,vol. 38,p. 416

10
[ 56503-39-0 ]
[ 93-09-4 ]
C₁₆H₁₂N₂O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5420 - 5431

11
[ 2243-82-5 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	With cell-free extract of amidase gene cloned from Klebsiella oxytoca KCTC 1686 and functionally expressed in Escherichia coli BL21(DE3); In methanol;Enzymatic reaction;	General procedure: The substrate specificity of recombinant KamH was tested using various aliphatic and aromatic amides. Cell-free extract of E. coli BL21(DE3)/pET-Ami2 was mixed with various concentrations of substrate under standard reaction conditions; 10percent (v/v) methanol was added as cosolvent to solubilize the substrate. The enzyme activity toward the various amides was determined by monitoring the formation of either carboxylic acid or ammonia [36]. Several racemic amides were used to study the stereoselectivity of the recombinant enzyme, including 2-phenylacetamide, mandelamide, 2,2-dimethylcyclopropanecarboxamide, and 2-(4-chlorophenyl)-3-methylbutyramide. Enantiomeric excess values were obtained by HPLC analysis using an AY-RH column. The enantiomeric excess and enantiomeric ratio of the product were determined according to Chen et al. [37].

Reference： [1]Process Biochemistry,2015,vol. 50,p. 1264 - 1271

12
[ 124-38-9 ]
[ 532-02-5 ]
[ 93-09-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2022 - 2026

13
[ 93-09-4 ]
[ 256652-04-7 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 7440 - 7443
[2]Organic Letters,2017,vol. 19,p. 4291 - 4294
[3]Synlett,2017,vol. 28,p. 2594 - 2598

14
[ 67-56-1 ]
[ 2243-82-5 ]
[ 2459-25-8 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogensulfate; water; at 65℃; for 48h;	General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products

Reference： [1]Arkivoc,2018,vol. 2018,p. 174 - 183

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Technical Information

? Arndt-Eistert Homologation ? Hunsdiecker-Borodin Reaction ? Passerini Reaction ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction

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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

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[ CAS No. 93-09-4 ] {[proInfo.proName]}

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[ 93-09-4 ] Synthesis Path-Upstream 1~1

[ 93-09-4 ] Synthesis Path-Downstream 1~14

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Aryls

Carboxylic Acids

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