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Cas Database

16064-04-3

16064-04-3

Identification

Synonyms:2-Biphenylcarboxaldehyde,4'-methoxy- (8CI);4'-Methoxy-1,1'-biphenyl-2-carboxaldehyde;4'-Methoxybiphenyl-2-carboxaldehyde;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Matrix Scientific
  • Product Description:4'-Methoxy-1,1'-biphenyl-2-carbaldehyde 97%
  • Packaging:1g
  • Price:$ 617
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  • Manufacture/Brand:Crysdot
  • Product Description:4'-Methoxy-[1,1'-biphenyl]-2-carbaldehyde 95+%
  • Packaging:1g
  • Price:$ 440
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  • Manufacture/Brand:CHESS?
  • Product Description:AD002024:4'-Methoxy-biphenyl-2-carbaldehyde 96
  • Packaging:1 g
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  • Manufacture/Brand:Atlantic Research Chemicals
  • Product Description:4''-Methoxy-1,1''-biphenyl-2-carbaldehyde 95%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:4'-METHOXY-BIPHENYL-2-CARBOXALDEHYDE 95.00%
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  • Manufacture/Brand:AK Scientific
  • Product Description:4'-Methoxy-1,1'-biphenyl-2-carbaldehyde
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  • Manufacture/Brand:Acrotein
  • Product Description:4'-Methoxy-biphenyl-2-carboxaldehyde 97%
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  • Manufacture/Brand:Acrotein
  • Product Description:4'-Methoxy-biphenyl-2-carboxaldehyde 97%
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Relevant articles and documentsAll total 73 Articles be found

First and mild synthesis of fluorene-9-malonic acid and some substituted derivatives via the intramolecular hydroarylation of 2-phenylbenzylidenemalonic acids

Chosson, Elizabeth,Rochais, Christophe,Legay, Remi,Santos, Jana Sopkova De Oliveira,Rault, Sylvain,Dallemagne, Patrick

, p. 2548 - 2554 (2011)

Hitherto unknown fluorene-9-malonic acid and some substituted derivatives were easily synthesized in very mild conditions through the intramolecular hydroarylation of 2-phenylbenzylidenemalonic acids issued from the corresponding biphenylcarboxaldehydes.

A Photochemical Intramolecular C-N Coupling Toward the Synthesis of Benzimidazole-Fused Phenanthridines

Bera, Shyamal Kanti,Boruah, Palash J.,Parida, Shraddha Saraswati,Paul, Amit K.,Mal, Prasenjit

, p. 9587 - 9602 (2021)

Herein, we report a direct photochemical dehydrogenative C-N coupling of unactivated C(sp2)-H and N(sp2)-H bonds. The catalysts or additive-free transformation of 2-([1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazole to benzo[4,5]imidazo[1,2-f]phenanthridine was achieved at ~350 nm of irradiation via ?-hydrogen abstraction. DFT calculations helped to understand that the N-H···πinteraction was essential for the reaction to proceed at a lower energy than expected.

Chromium-Catalyzed Selective Cross-Electrophile Coupling between Unactivated C(aryl)-F and C(aryl)-O Bonds

Fan, Fei,Zhao, Lixing,Luo, Meiming,Zeng, Xiaoming

, p. 561 - 568 (2022/03/15)

Chemically inert C(aryl)-F bonds have rarely been used to couple with other unactivated bonds, and this remains a challenge because of the difficulty of the successive cleavage of two unactivated bonds by metal catalysis. We report here the chromium-catalyzed cleavage of chemically inert C(aryl)-F bonds for coupling with unactivated C(aryl)-O bonds, allowing cross-electrophile coupling between unreactive aryl fluorides and aryl esters to be achieved in high regio- and chemoselectivity. The reactive Cr, which was formed in situ by reducing CrCl2, enables cleavage of the o-C(aryl)-F bonds to afford monovalent and quartet cyclochromate; subsequent bipyridyl-enabled insertion into the ester C(aryl)-O bond followed by reductive elimination allowed the orthogonal coupling of these two different and unactivated bonds. Mechanistic studies indicate that the bipyridyl ligand greatly enhances the reactivity of Cr in the cleavage of C(aryl)-O bonds, and the second oxidative addition may occur sluggishly compared with the reductive elimination in the catalytic cycle.

Electrochemical Decarboxylative Cyclization of α-Amino-Oxy Acids to Access Phenanthridine Derivatives

Zhan, Yanling,Dai, Changhui,Zhu, Zitong,Liu, Ping,Sun, Peipei

supporting information, (2022/02/07)

Phenanthridines are a class of useful heterocycles in the field of drug development. In this work, a method via electrochemical decarboxylative cyclization of α-amino-oxy acids to access phenanthridine derivatives was developed. This reaction proceeded th

Design and development of FGF-23 antagonists: Definition of the pharmacophore and initial structure-activity relationships probed by synthetic analogues

Downs, Ryan P.,Xiao, Zhousheng,Ikedionwu, Munachi O.,Cleveland, Jacob W.,Lin Chin, Ai,Cafferty, Abigail E.,Darryl Quarles,Carrick, Jesse D.

supporting information, (2020/11/30)

Hereditary hypophosphatemic disorders, TIO, and CKD conditions are believed to be influenced by an excess of Fibroblast Growth Factor-23 (FGF-23) which activates a binary renal FGFRs / α-Klotho complex to regulate homeostatic metabolism of phosphate and vitamin D. Adaptive FGF-23 responses from CKD patients with excess FGF-23 frequently lead to increased mortality from cardiovascular disease. A reversibly binding small molecule therapeutic has yet to emerge from research and development in this area. Current outcomes described in this work highlight efforts related to lead identification and modification using organic synthesis of strategic analogues to probe structure-activity relationships and preliminarily define the pharmacophore of a computationally derived hit obtained from virtual high-throughput screening. Synthetic strategies for the initial hit and analogue preparation, as well as preliminary cellular in vitro assay results highlighting sub micromolar inhibition of the FGF-23 signaling sequence at a concentration well below cytotoxicity are reported herein.

Process route upstream and downstream products

Process route

6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol
1018955-96-8

6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

4-methoxylbiphenyl
613-37-6

4-methoxylbiphenyl

4-(4'-methoxyphenyl)benzaldehyde
52988-34-8

4-(4'-methoxyphenyl)benzaldehyde

4'-methoxy-[1,1'-biphenyl]-3-carbaldehyde
118350-17-7

4'-methoxy-[1,1'-biphenyl]-3-carbaldehyde

Conditions
Conditions Yield
6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol; With toluene-4-sulfonic acid; In benzene; for 3h; Reflux;
With chromium(VI) oxide; acetic acid; In water; at 10 - 20 ℃; for 23h;
33%
21%
7%
13%
(Z)-1-(4-methoxyphenyl)-7-(phenylsulfonyl)-3-heptene-1,5-diyne
702706-51-2

(Z)-1-(4-methoxyphenyl)-7-(phenylsulfonyl)-3-heptene-1,5-diyne

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

{2-[(phenylsulfonyl)methyl]phenyl}-4-methoxybenzene

{2-[(phenylsulfonyl)methyl]phenyl}-4-methoxybenzene

Conditions
Conditions Yield
With cyclohexa-1,4-diene; triethylamine; In benzene; at 80 ℃; for 24h;
51%
38%
6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol
1018955-96-8

6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol

1-(4-methoxyphenyl)cyclohepta-1,3,5-triene
29304-89-0

1-(4-methoxyphenyl)cyclohepta-1,3,5-triene

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

4-(4'-methoxyphenyl)benzaldehyde
52988-34-8

4-(4'-methoxyphenyl)benzaldehyde

4'-methoxy-[1,1'-biphenyl]-3-carbaldehyde
118350-17-7

4'-methoxy-[1,1'-biphenyl]-3-carbaldehyde

Conditions
Conditions Yield
6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol; With toluene-4-sulfonic acid; In benzene; for 3h; Reflux;
With oxygen; In benzene; for 168h; Mechanism;
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
With palladium diacetate; anhydrous sodium carbonate; In ethanol; water monomer; at 20 ℃; for 12h;
100%
With palladium diacetate; anhydrous sodium carbonate; triphenylphosphine; In ethanol; water monomer; toluene; at 100 ℃; for 24h; Inert atmosphere;
99%
With anhydrous sodium carbonate; In ethanol; water monomer; at 120 ℃; for 0.0833333h; Sealed tube; Microwave irradiation; Green chemistry;
96%
With [Pd] catalyst; In 1,4-dioxane;
95%
With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate; In N,N-dimethyl-formamide; for 6h; Inert atmosphere; Reflux;
93%
With anhydrous sodium carbonate; In ethanol; water monomer; at 20 ℃; for 8h; Inert atmosphere;
92%
4-methoxyphenylboronic acid; ortho-bromobenzaldehyde; With anhydrous sodium carbonate; In water monomer; N,N-dimethyl-formamide; for 0.0833333h;
With palladium diacetate; In water monomer; N,N-dimethyl-formamide; at 20 ℃;
91%
With Supported Pd(OAc)2(PPh3)2 Over Mixed Magnesium Hydroxide and Cerium Carbonate Hydroxide Composite; In water monomer; at 79.84 ℃; for 2h;
87.6%
With anhydrous sodium carbonate; In N,N-dimethyl-formamide; at 156 ℃; for 20h; Inert atmosphere;
86%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; anhydrous sodium carbonate; tris-(o-tolyl)phosphine; In water monomer; N,N-dimethyl-formamide; at 80 ℃; for 15h; Inert atmosphere;
83%
With C10H9Cl2N3O3Pd; potassium hydroxide; In ethanol; water monomer; at 120 ℃; for 0.0333333h; Microwave irradiation;
83.5%
With tetrakis-(triphenylphosphine)-palladium; tripotassium phosphate monohydrate; In 1,2-dimethoxyethane; at 137 ℃; for 2h; under 3000.3 Torr; Microwave irradiation;
81%
With tetraamminepalladium(II) chloride; tetra(n-butyl)ammonium hydroxide; In water monomer; at 45 ℃; for 2h; Green chemistry;
80%
With anhydrous sodium carbonate; tetrakis-(triphenylphosphine)-palladium; In ethanol; toluene; Heating;
63%
With anhydrous sodium carbonate; palladium diacetate; In water monomer; N,N-dimethyl-formamide; at 25 ℃; for 12h;
With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate; In ethanol; toluene; Reflux;
With palladium diacetate; anhydrous sodium carbonate; In water monomer; N,N-dimethyl-formamide; at 20 ℃;
With potassium fluoride; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine; In 1,4-dioxane; at 60 ℃; for 1.5h;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In water monomer; N,N-dimethyl-formamide; at 110 ℃;
With anhydrous sodium carbonate; triphenylphosphine; palladium (II) chloride; In N,N-dimethyl-formamide; at 110 ℃; Inert atmosphere;
4-methoxyphenylboronic acid; With palladium diacetate; anhydrous sodium carbonate; In water monomer; N,N-dimethyl-formamide; for 0.25h;
ortho-bromobenzaldehyde; In water monomer; N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); tripotassium phosphate tribasic; In dimethyl sulfoxide; at 80 ℃; for 10h; Inert atmosphere;
With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate; In ethanol; tert-butyl methyl ether; water monomer; at 90 ℃; for 6h; Inert atmosphere;
With palladium diacetate; anhydrous sodium carbonate; In water monomer; N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;
With anhydrous sodium carbonate; In water monomer; acetonitrile; at 50 ℃; for 12h;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate; In ethanol; water monomer; toluene; Inert atmosphere; Heating;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous sodium carbonate; In water monomer; acetonitrile; at 50 ℃; for 12h;
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); anhydrous sodium carbonate; In water monomer; acetonitrile; at 50 ℃; for 12h;
With palladium diacetate; In ethanol; for 8h; Reflux;
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate; In 1,4-dioxane; water monomer; Inert atmosphere; Reflux;
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

2-formylbenzene boronic acid
40138-16-7

2-formylbenzene boronic acid

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
With potassium phosphate monohydrate; C64H118O20; In water; at 45 ℃; for 24h; Reagent/catalyst; Inert atmosphere;
95%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; methylmagnesium chloride; at 45 ℃; for 12h;
86%
With potassium carbonate; In ethanol; water; at 20 ℃; for 3h;
86%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium acetate; In tetrahydrofuran; Reflux; Inert atmosphere;
66%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; In tetrahydrofuran; at 22 ℃; for 2h;
87%
1-bromo-4-methoxy-benzene; With Zn(OPiv)2*2LiCl; magnesium; In tetrahydrofuran; at 22 ℃; for 2h; Inert atmosphere;
ortho-bromobenzaldehyde; With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In tetrahydrofuran; at 25 ℃; for 1h; Inert atmosphere;
349 mg
4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In 1,4-dioxane; at 100 - 110 ℃; Inert atmosphere;
89%
With potassium phosphate tribasic trihydrate; (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; palladium diacetate; Aliquat 336; In water; at 20 - 100 ℃; for 8h; Inert atmosphere;
86%
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); at 100 ℃; for 10h; Schlenk technique; Inert atmosphere;
85%
With C18H17Cl2N3Pd; caesium carbonate; In water; N,N-dimethyl-formamide; at 100 ℃; for 24h;
74%
para-iodoanisole
696-62-8

para-iodoanisole

2-formylphenylboronic acid N-methyliminodiacetic acid ester

2-formylphenylboronic acid N-methyliminodiacetic acid ester

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
With potassium carbonate; In ethanol; water; at 120 ℃; for 0.166667h; Microwave irradiation; Sealed tube;
83%
With potassium carbonate; In ethanol; water; for 9h; Reflux; Green chemistry;
78%
2-bromopyridine-3-carboxaldehyde
128071-75-0

2-bromopyridine-3-carboxaldehyde

potassium 4-(methoxy)phenyltrifluoroborate

potassium 4-(methoxy)phenyltrifluoroborate

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
With palladium diacetate; caesium carbonate; ruphos; In water; toluene; at 100 ℃; for 16h;
87%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

N-tert-butyl-1-(2-methoxyphenyl)methanimine
82632-38-0

N-tert-butyl-1-(2-methoxyphenyl)methanimine

2-(4-methoxyphenyl)benzaldehyde
16064-04-3

2-(4-methoxyphenyl)benzaldehyde

Conditions
Conditions Yield
1-bromo-4-methoxy-benzene; N-tert-butyl-1-(2-methoxyphenyl)methanimine; With chromium dichloride; magnesium; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere; Schlenk technique;
With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 0.5h; regioselective reaction; Inert atmosphere; Schlenk technique;
37%

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