[ CAS No. 148-53-8 ] {[proInfo.proName]}

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Quality Control of [ 148-53-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 148-53-8 ]

SDS Specification

Alternatived Products of [ 148-53-8 ]

Product Citations

Vanillin based phthalonitrile and acetylene bifunctional resins

James D. Sitter ; Tyler Richardson ; Jean M. Wallace , et al. J. Appl. Polym. Sci.,2024,e55879. DOI: 10.1002app.55879

Abstract: The renewable and biosynthetic molecule, vanillin, were used in the preparation of new phthalonitrile (PN) and ethynylbenzene (EB) bifunctional resins without pre-modification of the vanillin structure. This PN resin was characterized by differential scanning calorimetry, thermogravimetric analysis, nuclear magnetic resonance spectroscopy, rheometry, and single crystal x-ray diffraction. The monomers exhibited excellent rheometric viscosities below 250 Cp at processing temperatures and a good pot life. After complete curing, the PN polymers exhibited thermal stability above 500℃, a glass transition temperature (Tg) above the final postcure temperature of 380℃, and exceptional retention of structural integrity over a large temperature range. These results suggest that vanillin derived EBPN based resins are excellent candidates for use in a variety of applications where high temperature and mechanical stability is critical.

Keywords: biopolymers and renewable polymers ; resins ; thermosets

Purchased from AmBeed: 121-33-5 ; 148-53-8 ; 57179-35-8

Product Details of [ 148-53-8 ]

CAS No. :	148-53-8	MDL No. :	MFCD00003322
Formula :	C₈H₈O₃	Boiling Point :	-
Linear Structure Formula :	C₆H₃(CH₃O)(OH)(CHO)	InChI Key :	JJVNINGBHGBWJH-UHFFFAOYSA-N
M.W :	152.15	Pubchem ID :	8991
Synonyms :	3-Methoxysalicylaldehyde	Chemical Name :	2-Hydroxy-3-methoxybenzaldehyde

Calculated chemistry of [ 148-53-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.34
TPSA :	46.53 Å²

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) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	0.51
Log Po/w (SILICOS-IT) :	1.49
Consensus Log Po/w :	1.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.84 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (Ali) :	-1.95
Solubility :	1.71 mg/ml ; 0.0112 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.88
Solubility :	2.0 mg/ml ; 0.0132 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 148-53-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 148-53-8 ]

* 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 [ 148-53-8 ]
Downstream synthetic route of [ 148-53-8 ]

[ 148-53-8 ] Synthesis Path-Upstream 1~1

1
[ 148-53-8 ]
[ 5768-39-8 ]

Reference： [1] Agricultural and Biological Chemistry, 1980, vol. 44, # 2, p. 235 - 243

[ 148-53-8 ] Synthesis Path-Downstream 1~14

1
[ 86-71-5 ]
[ 148-53-8 ]
3,6-bis-(2-hydroxy-3-methoxy-benzylidenamino)-carbazole [ No CAS ]

Reference： [1]Chemisches Zentralblatt,1913,vol. 84,p. 2130

2
[ 148-53-8 ]
[ 2896-67-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;5%-palladium/activated carbon; In acetic acid; ethyl acetate; at 20℃; for 84h;	A 3-liter three-necked flask equipped with a thermometer and a mechanical stirrer was charged with 300 g (1.97 moles) of o-vaniline, 100 g of palladium-carbon supporting 5% by weight of palladium, 2 liters of ethyl acetate and 500 ml of acetic acid. The contents were stirred under a hydrogen atmosphere and at room temperature, for 84 hours. The reaction mixture thus obtained was filtered and the filtrate was condensed. To the condensate, 2 liters of ethyl acetate was added again, and the mixture was washed with 1 liter of water three times. The obtained organic layer was condensed and cooled, to yield 259 g of colorless crystal of 2-hydroxy-3-methoxytoluene having the following properties. The yield was 95% based on the o-vaniline.1H-NMR (270 MHz, deuterated benzene, TMS, ppm) delta : 2.28 (s, 3H. Ar-CH3), 3.19 (s. 3H, Ar-O-CH3), 5.78(s. 1H, Ar-OH), 6.38 (d, 1H), 6.63-6.80 (m. 2H).
	With hydrogen;5%-palladium/activated carbon; In methanol; at 20℃; for 72h;Inert atmosphere;	EXAMPLES[0099] Preparation of 2-methoxy-6-methylphenol from hydrogenation of o-vanillin [00100] This reaction is performed inside a drybox for safety precautions because hydrogen gas is used. During the procedure, the drybox is purged periodically with nitrogen to ensure no build up of hydrogen gas. An adaptor with a balloon on one end is attached to a 250 mL flask with a side arm and a magnetic stir bar. One gram of Pd on carbon (5% Pd) is charged slowly into the flask. Then, 7.6 g of o-vanillin and 100 ml of methanol are added. Through the side-arm, hydrogen gas is introduced into the flask system until the balloon is inflated to a volume of about 250 ml. The reaction is allowed to stir at room temperature for 3 days. Hydrogen gas is added when the balloon deflates due to the reaction and diffusion. GC samples are taken to monitor the reaction. When reaction is complete, as evidenced by the appearance of the intermediate first and then by the appearance of the product, the gas inside the balloon and flask is released slowly. The reaction is stirred openly inside the dry box for another 10 minutes to ensure complete dissipation of hydrogen inside the flask into the dry box. The dry box is also purged several times with nitrogen. The flask is taken out of the drybox. The reaction mixture is filtered to separate off the catalyst. The solvent is removed to yield the crude product. The GC and NMR data are compared with the authentic sample to be 2-methoxy-6-methylphenol. Yield is 7.3 g or 95%

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 12691 - 12699
[2]Organic Letters,2015,vol. 17,p. 2030 - 2033
[3]Zeitschrift fur Naturforschung, B: Chemical Sciences,1993,vol. 48,p. 387 - 393
[4]Journal of Organic Chemistry,1986,vol. 51,p. 4347 - 4353
[5]Journal of Organic Chemistry,2002,vol. 67,p. 6493 - 6502
[6]Patent: EP1489087,2004,A1 .Location in patent: Page 11
[7]Journal of applied chemistry of the USSR,1985,vol. 58,p. 2520 - 2521
[8]Chemical Research in Toxicology,1997,vol. 10,p. 335 - 343
[9]European Journal of Organic Chemistry,2014,vol. 2014,p. 2565 - 2575
[10]Chemische Berichte,1939,vol. 72,p. 367,370
Nippon Kagaku Kaishi,1939,vol. 60,p. 276
[11]Patent: US2366611,1943,
[12]Patent: US2366611,1943,
[13]Helvetica Chimica Acta,1930,vol. 13,p. 482,486
[14]Monatshefte fur Chemie,1954,vol. 85,p. 802,805
[15]Chemische Berichte,1916,vol. 49,p. 1490
[16]Justus Liebigs Annalen der Chemie,1970,vol. 740,p. 18 - 30
[17]Acta Chemica Scandinavica,1989,vol. 43,p. 44 - 50
[18]Gazzetta Chimica Italiana,1982,vol. 112,p. 513 - 518
[19]Journal of Natural Products,2001,vol. 64,p. 2 - 5
[20]Angewandte Chemie - International Edition,2007,vol. 46,p. 4077 - 4080
[21]Patent: WO2012/135189,2012,A2 .Location in patent: Page/Page column 16-17
[22]ACS Catalysis,2015,vol. 5,p. 6964 - 6972
[23]Organic Letters,2019,vol. 21,p. 8761 - 8764
[24]ChemSusChem,2020

3
[ 148-53-8 ]
[ 1569-16-0 ]
[ 123302-67-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 362 - 364

4
[ 148-53-8 ]
[ 1193-24-4 ]
[ 1728-88-7 ]
N-formyl-8-methoxy-3-coumarincarboxamide [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1999,vol. 69,p. 620 - 628

5
[ 148-53-8 ]
[ 1193-24-4 ]
5,5'-(3-methoxysalicyclidene)bis(4,6-dihydroxypyrimidine) [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1999,vol. 69,p. 620 - 628

6
[ 109-99-9 ]
vanadyl(IV) sulphate pentahydrate [ No CAS ]
[ 7732-18-5 ]
[ 148-53-8 ]
[ 4089-07-0 ]
VO(OC₆H₃(OCH₃)CHNCH(CH₂C₆H₄OH)CO₂)(H₂O)*OC₄H₈*H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2003,vol. 356,p. 210 - 214

7
vanadyl(IV) sulphate pentahydrate [ No CAS ]
[ 64-17-5 ]
[ 7732-18-5 ]
[ 148-53-8 ]
[ 4089-07-0 ]
VO(OC₆H₃(OCH₃)CHNCH(CH₂C₆H₄OH)CO₂)(H₂O)*0.5C₂H₅OH*H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2003,vol. 356,p. 210 - 214

8
[ 148-53-8 ]
[ 2345-56-4 ]
[ 13229-91-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In acetic acid butyl ester; ethyl acetate; at 120℃;	General procedure: T3P mediated synthesis of coumarins: To a mixture of 2-hydroxyaryl aldehyde/ketone (1, 0.01 mol) and appropriate acetic acid (2, 0.01 mol) in n-BuOAc (10 mL) was added T3P (0.02 mol, 50% soln in EtOAc) followed by triethylamine (0.02 mol). The resulting reaction mixture was stirred at 120 C for 6-10 h under conventional heating. When the reaction was completed (monitored by TLC), the mixture was cooled and washed with saturated NaHCO3 solution (1 × 10 mL), water and brine. The organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was passed through a small plug of silica to afford the coumarins (3) in good purity and yield.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4422 - 4425

9
[ 52851-41-9 ]
[ 52147-97-4 ]
[ 148-53-8 ]
rac-(6bR,14S,14aR)-3-methoxy-14-phenyl-14,14a-dihydro-6bH-benzo[5',6'][1,2]oxathiino [4',3':4,5]pyrano[3,2-c]quinolin-7(8H)-one 1,1-dioxide [ No CAS ]
rac-(6aR,7S,14bR)-4-methoxy-7-phenyl-9,14b-dihydro-6aH-benzo[5',6'][1,2]oxathiino[4',3':4,5]pyrano[2,3-b]quinolin-14(7H)-one 6,6-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%; 19%		General procedure: To a stirring solution of 2-hydroxybenzaldehyde derivative 1 (1.0 mmol), styrenesulfonyl chloride (0.20 g, 1.0 mmol), and K2CO3 (0.14 g, 1.0 mmol) in H2O (15 mL) for 2 h was added 4-hydroxycoumarin derivative 2 (1.2 mmol) or 4-hydroxyquinolinone (0.19 g, 1.2 mmol) and EDDA (20 mmol%) and the mixture was heated at reflux for 12 h. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature and the organics were extracted using CH2Cl2 (30 mL). Evaporation of the solvent under reduced pressure followed by column chromatography on silica gel using hexane-ethyl acetate (3:1), afforded products 3 and 4.

Reference： [1]Tetrahedron,2013,vol. 69,p. 4979 - 4989

10
[ 57497-39-9 ]
[ 148-53-8 ]
C₁₂H₁₇NO₃ [ No CAS ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 84 - 91

11
[ 148-53-8 ]
[ 4922-98-9 ]
[ 67-64-1 ]
7-methoxy-5-methyl-2-phenyl-11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With hydrogenchloride; In 1,4-dioxane; ethanol; at 150℃; for 0.5h;Microwave irradiation; Sealed tube;	General procedure: 3-Amino-1,2,4-triazole 8a?f (1.0 mmol), o-hydroxybenzaldehyde9a?e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150°C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3×1 ml), and dried. Compounds 1a?w were obtainedin a form of white solids.

Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 1261 - 1267
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 1261 - 1267,7

12
[ 5627-11-2 ]
[ 148-53-8 ]
[ 103860-60-2 ]

Reference： [1]Molecules,2018,vol. 23

13
[ 66640-86-6 ]
[ 148-53-8 ]
C₁₈H₂₄N₄O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; for 5h;Reflux;	Weigh 2.58 g of <strong>[66640-86-6]biotin hydrazide</strong> and 1.52 g of o-vanillin in a container.Add 150 mL of ethanol and reflux for 5 h to obtain a yellow solid product.The yield was 78percent.

Reference： [1]Patent: CN108558914,2018,A .Location in patent: Paragraph 0032; 0033; 0034

14
[ 148-53-8 ]
[ 85614-43-3 ]

Reference： [1]Patent: CN109836351,2019,A

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Isomers

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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[ 148-53-8 ]

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P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 148-53-8 ] {[proInfo.proName]}

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[ 148-53-8 ] Synthesis Path-Upstream 1~1

[ 148-53-8 ] Synthesis Path-Downstream 1~14

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Aryls

Aldehydes

Ethers

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[ 148-53-8 ]