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Naphthaline-2,6-dicarbonic acid dichloranhydride, also known as 2,6-Naphthalenedicarbonyl dichloride, is a high-production volume chemical that serves as an intermediate in the synthesis of complex organic compounds. It belongs to the naphthalene group, which consists of organic compounds with two fused benzene rings. However, it is distinguished by its dichloranhydride functional groups at the 2 and 6 positions of the naphthalene ring. Due to its potential to cause irritation and damage to the eyes, skin, and respiratory system, as well as its high reactivity, especially with water, handling and use of this chemical should be done with caution to prevent hazardous polymerization.

2351-36-2

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2351-36-2 Usage

Uses

Used in Chemical Synthesis:
Naphthaline-2,6-dicarbonic acid dichloranhydride is used as a key intermediate for the production of various complex organic compounds. Its unique dichloranhydride functional groups at the 2 and 6 positions of the naphthalene ring make it a valuable building block in the synthesis of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Naphthaline-2,6-dicarbonic acid dichloranhydride is used as a synthetic intermediate for the development of new drugs. Its reactivity and functional groups allow for the creation of diverse molecular structures, which can be further modified to produce potential therapeutic agents.
Used in Dye and Pigment Industry:
Naphthaline-2,6-dicarbonic acid dichloranhydride is used as a precursor in the synthesis of dyes and pigments. Its chemical properties enable the production of a variety of colored compounds, which are then utilized in various applications such as textiles, plastics, and printing inks.
Used in Polymer Industry:
In the polymer industry, Naphthaline-2,6-dicarbonic acid dichloranhydride is used as a monomer or a building block in the synthesis of polymers with specific properties. Its dichloranhydride functional groups can be incorporated into polymer chains, leading to materials with tailored characteristics for use in various applications, such as coatings, adhesives, and composites.

Check Digit Verification of cas no

The CAS Registry Mumber 2351-36-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,3,5 and 1 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2351-36:
(6*2)+(5*3)+(4*5)+(3*1)+(2*3)+(1*6)=62
62 % 10 = 2
So 2351-36-2 is a valid CAS Registry Number.

2351-36-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name naphthalene-2,6-dicarbonyl chloride

1.2 Other means of identification

Product number -
Other names 2,6-Naphthoyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2351-36-2 SDS

2351-36-2Synthetic route

2,6-Naphthalenedicarboxylic acid
1141-38-4

2,6-Naphthalenedicarboxylic acid

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

Conditions
ConditionsYield
With thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride In 1,2-dichloro-ethane for 12h; Heating;94%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 4h; Heating;94%
With thionyl chloride; N,N-dimethyl-formamide at 90℃; for 12h;90%
2,6-Naphthalenedicarboxylic acid
1141-38-4

2,6-Naphthalenedicarboxylic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

Conditions
ConditionsYield
In trichlorophosphate65%
2,6-naphthalenedicarboxylic acid dipotassium salt

2,6-naphthalenedicarboxylic acid dipotassium salt

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

Conditions
ConditionsYield
With oxalyl dichloride In toluene for 3h; Heating;56%
oxalyl dichloride
79-37-8

oxalyl dichloride

dimethyl 2,6-naphthalenedicarboxylate
840-65-3

dimethyl 2,6-naphthalenedicarboxylate

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

Conditions
ConditionsYield
In N,N-dimethyl-formamide
sodium dimethyl phosphate
32586-82-6

sodium dimethyl phosphate

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

2,6-naphthalenedicarbonyl bis(dimethyl phosphate)

2,6-naphthalenedicarbonyl bis(dimethyl phosphate)

Conditions
ConditionsYield
In tetrahydrofuran for 3h; Ambient temperature;95%
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

N,N'-[Bis(3-hydroxypropyl)]-2,6-naphthalenedicarboxamide
225663-91-2

N,N'-[Bis(3-hydroxypropyl)]-2,6-naphthalenedicarboxamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; methanol at 20℃; for 6h; Acetylation;88%
3-(3,5,7,9,11,13,15-heptaisobutylpentacyclo[9,5,1,1(3,9),1(7,13),1(5,15)]octasiloxane-1-yl)propylamine
444315-15-5

3-(3,5,7,9,11,13,15-heptaisobutylpentacyclo[9,5,1,1(3,9),1(7,13),1(5,15)]octasiloxane-1-yl)propylamine

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

C43H77NO15Si8

C43H77NO15Si8

Conditions
ConditionsYield
Stage #1: 3-(3,5,7,9,11,13,15-heptaisobutylpentacyclo[9,5,1,1(3,9),1(7,13),1(5,15)]octasiloxane-1-yl)propylamine; 2,6-dichloroformyl naphthalene With triethylamine In dichloromethane at 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride; water pH=2; Inert atmosphere;
87%
cyclohexylamine
108-91-8

cyclohexylamine

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

N,N'-Dicyclohexyl-2,6-naphthalenedicarboxamide

N,N'-Dicyclohexyl-2,6-naphthalenedicarboxamide

Conditions
ConditionsYield
With pyridine; triethylamine In N,N-dimethyl-formamide; toluene at 50℃; for 5h;86.8%
With triethylamine In toluene at 20 - 50℃; for 6.5h; Reagent/catalyst;75.3%
[CpFe(CO)2]2

[CpFe(CO)2]2

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

C10H6(CO(C5H5)Fe(CO)2)2

C10H6(CO(C5H5)Fe(CO)2)2

Conditions
ConditionsYield
With sodium amalgam; mercury In tetrahydrofuran byproducts: NaCl; anaerobic, anhyd. conditions, ambient temp., liquefaction of Na/Hg by addn. of Hg, addn. of THF and CpFe(CO)2, stirring 1 h to get NaCpFe(CO)2, draining excess Na/Hg, filtration, cooling (-78°C, dry ice-acetone bath), addn. of the acid chloride; slowly warming the stirred soln. to room temp. (about 1 h), drying in vac., recrystn., drying in vac., elem. anal., not isolated in analytically pure form;85%
1,2,4-Triazole
288-88-0

1,2,4-Triazole

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

naphthalene-2,6-dicarbonyl ditriazole

naphthalene-2,6-dicarbonyl ditriazole

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide at 50℃; for 1h;85%
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N2,N6-bis(4-aminophenyl)naphthalene-2,6-dicarboxamide

N2,N6-bis(4-aminophenyl)naphthalene-2,6-dicarboxamide

Conditions
ConditionsYield
With pyridine; triphenyl phosphite In 1-methyl-pyrrolidin-2-one at 20 - 100℃; for 14h; Inert atmosphere;85%
6-(2H-tetrazol-5-yl)-2,2'-bipyridine

6-(2H-tetrazol-5-yl)-2,2'-bipyridine

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

2,6-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]naphthalene

2,6-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]naphthalene

Conditions
ConditionsYield
Stage #1: 6-(2H-tetrazol-5-yl)-2,2'-bipyridine; 2,6-dichloroformyl naphthalene With pyridine at 110℃; for 1h; Heating / reflux;
Stage #2: With sodium hydroxide In water at 20℃;
84%
3,6,9,12-tetraoxapentadec-14-yn-1-amine
1013921-36-2

3,6,9,12-tetraoxapentadec-14-yn-1-amine

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

N2,N6-di(3,6,9,12-tetraoxapentadec-14-yn-1-yl)naphthalene-2,6-dicarboxamide

N2,N6-di(3,6,9,12-tetraoxapentadec-14-yn-1-yl)naphthalene-2,6-dicarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;84%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

bis(4-nitrobenzyl) naphthalene-2,6-dicarboxylate

bis(4-nitrobenzyl) naphthalene-2,6-dicarboxylate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl acetamide at 100℃; for 24h; Cooling with ice; Inert atmosphere;81.6%
N-p-toluenesulfonyl-1-trioxa-4,10,16-triaza-1,7,13-cyclooctadecane
78600-10-9

N-p-toluenesulfonyl-1-trioxa-4,10,16-triaza-1,7,13-cyclooctadecane

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

C62H74N6O14S2
78600-11-0

C62H74N6O14S2

Conditions
ConditionsYield
80%
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE
36768-62-4

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

C30H44N4O2

C30H44N4O2

Conditions
ConditionsYield
With triethylamine; lithium chloride In DMF (N,N-dimethyl-formamide) at 0 - 65℃; for 5h;76%
benzamidin
618-39-3

benzamidin

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

naphthalene-2,6-dicarboxylic acid bis(1-amino-1-phenylmethylideneamide)
1313436-61-1

naphthalene-2,6-dicarboxylic acid bis(1-amino-1-phenylmethylideneamide)

Conditions
ConditionsYield
Stage #1: benzamidin With triethylamine In dichloromethane at 20℃; for 0.5h;
Stage #2: 2,6-dichloroformyl naphthalene In dichloromethane at -10 - 20℃;
76%
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

4-fluoroaniline
371-40-4

4-fluoroaniline

N2,N6-di-p-fluorophenylnaphthalenedicarboxamide

N2,N6-di-p-fluorophenylnaphthalenedicarboxamide

Conditions
ConditionsYield
In toluene at 30℃; for 0.583333h; Sonication;76%
C20H40N2

C20H40N2

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

3,14-diaza-1(2,6)-naphthalenacyclopentadecaphane-2,15-dione

3,14-diaza-1(2,6)-naphthalenacyclopentadecaphane-2,15-dione

Conditions
ConditionsYield
Stage #1: C20H40N2; 2,6-dichloroformyl naphthalene In dichloromethane at 75℃; for 6h;
Stage #2: With water; sodium hydroxide In dichloromethane for 0.5h;
75%
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

2,6-dithionaphthalenedicarboxylic acid

2,6-dithionaphthalenedicarboxylic acid

Conditions
ConditionsYield
With thioacetamide In tetrahydrofuran at 20℃; for 3h;72%
1,4,10,13-tetraoxa-7,16-diazacyclooctadecane
23978-55-4

1,4,10,13-tetraoxa-7,16-diazacyclooctadecane

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

C48H60N4O12
75359-90-9

C48H60N4O12

Conditions
ConditionsYield
70%
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

N2,N6-di(pyridin-3-yl)naphthalene-2,6-dicarboxamide

N2,N6-di(pyridin-3-yl)naphthalene-2,6-dicarboxamide

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane for 12h; Reflux;70%
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

phenol
108-95-2

phenol

Naphthalin dicarbonsaeure-(2.6)-diphenylester
2412-00-2

Naphthalin dicarbonsaeure-(2.6)-diphenylester

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water for 0.5h; Ambient temperature;62.7%
With pyridine; dmap30%
isonicotinoyl hydrazide

isonicotinoyl hydrazide

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

2,6-naphthalene dicarbonyldiisonicotinic acidhydrazide

2,6-naphthalene dicarbonyldiisonicotinic acidhydrazide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux;60%
octane-1,8-bis(2,2-dimethylpropan-1-imine)

octane-1,8-bis(2,2-dimethylpropan-1-imine)

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

3,12-diaza-1(2,6)-naphthalenacyclotridecaphane-2,13-dione

3,12-diaza-1(2,6)-naphthalenacyclotridecaphane-2,13-dione

Conditions
ConditionsYield
Stage #1: octane-1,8-bis(2,2-dimethylpropan-1-imine); 2,6-dichloroformyl naphthalene In dichloromethane at 20℃; for 6h; Inert atmosphere; Glovebox;
Stage #2: With water; sodium hydroxide In dichloromethane for 0.5h;
58%
2-methyl-propan-1-ol
78-83-1

2-methyl-propan-1-ol

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

bis(2-methylpropyl) naphthalene-2,6-dicarboxylate
259145-00-1

bis(2-methylpropyl) naphthalene-2,6-dicarboxylate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 5.08333h; Inert atmosphere;56%
C48H70N6O6
349545-18-2

C48H70N6O6

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

C60H74N6O8
78600-13-2

C60H74N6O8

Conditions
ConditionsYield
55%
isopropyl alcohol
67-63-0

isopropyl alcohol

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

diisopropyl naphthalene-2,6-dicarboxylate
141262-30-8

diisopropyl naphthalene-2,6-dicarboxylate

Conditions
ConditionsYield
54%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4.25h; Inert atmosphere;615 mg
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

benzyl alcohol
100-51-6

benzyl alcohol

dibenzyl naphthalene-2,6-dicarboxylate

dibenzyl naphthalene-2,6-dicarboxylate

Conditions
ConditionsYield
51%
Phenyl 4-hydroxybenzoate
17696-62-7

Phenyl 4-hydroxybenzoate

2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

2,6-bis<(4-phenyloxycarbonyl)phenyloxycarbonyl>naphthalene

2,6-bis<(4-phenyloxycarbonyl)phenyloxycarbonyl>naphthalene

Conditions
ConditionsYield
With triethylamine In dichloromethane for 2h; Heating;48.8%
2,6-dichloroformyl naphthalene
2351-36-2

2,6-dichloroformyl naphthalene

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Naphthalene-2,6-dicarboxylic acid di-tert-butyl ester

Naphthalene-2,6-dicarboxylic acid di-tert-butyl ester

Conditions
ConditionsYield
With pyridine; dmap48%

2351-36-2Relevant academic research and scientific papers

Metallogels and Silver Nanoparticles Generated from a Series of Transition Metal-Based Coordination Polymers Derived from a New Bis-pyridyl-bis-amide Ligand and Various Carboxylates

Nath, Karabi,Husain, Ahmad,Dastidar, Parthasarathi

, p. 4635 - 4645 (2015)

A new series of coordination polymers, namely, CP2 [{(H2O)Co1.5(μ-3-bpna)1.5(μ-btc)}·3DMF·3H2O]α, CP3 [{Cd(μ-3-bpna)(μ-hbtc)}·CH3OH·2H2O]α, CP4 [{Co(μ-3-bpna)(μ-ipa)}·DMF·2H2O]α, CP5 [{Co(μ-3-bpna)(μ-1,3-pda)}·DMF]α, CP6 [Cd(μ-3-bpna)0.5(μ-1,3-pda)]α, CP7 [(H2O)Co0.5(μ-3-bpna)0.5(μ-1,4-pda)0.5]α, and CP8 [{Zn(μ-3-bpna)(μ-oba)}·DMF·2H2O]α, has been synthesized by reacting a hydrogen-bond-functionalized bis-pyridyl ligand, namely, N′,N″-di(pyridin-3-yl)naphthalene-2,6-dicarboxamide, with various transition metal salts and different di- or tricarboxylates (as co-ligand) displaying 2D and 3D network topology and having lattice-occluded solvents in the majority of cases. A 1D coordination polymer, namely, CP1 [{Ag0.5(μ-3-bpna)}0.5·0.5BF4·CH3CN]α, has also been isolated by reacting 3-bpna with AgBF4 in the absence of any carboxylate co-ligand. All of the CPs were characterized by single crystal X-ray diffraction. Interestingly, two such CPs, namely, CP1 and CP2, produced metallogels, which were characterized by rheology, transmission electron microscopy, and X-ray powder diffraction. The metallogel of CP1 produced Ag nanoparticles within the gel bed upon exposure to light. (Chemical Equation Presented).

Electronic Coupling between Two Covalently Bonded Dimolybdenum Units Bridged by a Naphthalene Group

Zhu, Guang Yuan,Meng, Miao,Tan, Ying Ning,Xiao, Xuan,Liu, Chun Y.

, p. 6315 - 6322 (2016)

Using 2,6-naphthalenedicarboxylate and its thiolated derivatives as bridging ligands, three Mo2 dimers of the type [Mo2(DAniF)3](E2CC10H6CE2)[Mo2(DAniF)3] (DAniF = N,N′-di-p-anisylformamidinate; E = O, S) have been synthesized and characterized by X-ray diffraction. These compounds can be generally formulated as [Mo2]-naph-[Mo2], where the complex unit [Mo2] ([Mo2(DAniF)3(μ-E2C)]) functions as an electron donor (acceptor) and the naphthalene (naph) group is the bridge. The mixed-valence (MV) complexes, generated by one-electron oxidation of the neutral precursors, display weak, very broad intervalence charge-transfer absorption bands in the near-to-mid-IR regions. The electronic coupling matrix elements for the MV complexes, Hab = 390-570 cm-1, are calculated from the Mulliken-Hush equation, which fall between those for the phenyl (ph) and biphenyl (biph) analogues reported previously. The three series consisting of three complexes with the same [Mo2] units exhibit exponential decay of Hab as the bridge changes from ph to biph via naph, with decay factors of 0.21-0.17 ?-1. Therefore, it is evidenced that while the extent of the bridge conjugacy varies, the electronic coupling between the two [Mo2] units is dominated by the Mo2···Mo2 separation. The absorption band energies for metal-to-ligand charge transfer are in the middle of those for the ph and biph analogues, which is consistent with variation of the HOMO-LUMO energy gaps for the complex series. These results indicate that the interplay of the bridge length and conjugacy is to affect the enegy for charge transfer crossing the intervening moiety, in accordance with a superechange mechanism.

With high planarity of the naphthalene structure function diamine monomer and its synthetic method and application

-

Paragraph 0040; 0041; 0042, (2017/08/25)

The invention discloses functional diamine monomers having high planarity and containing a naphthaline structure and a synthesis method and application thereof. The novel functional diamine monomers are prepared from raw materials monomers such as dihalogenated naphthaline, naphthalic acid, naphthalenediol or naphthylenediamine through a series of chemical reactions such as substitution reaction, Suzuki reaction, amidation reaction, esterification reaction, Grignard reaction, Kumada coupling reaction. The diamine monomers containing a naphthaline structure, which have a lowest energy state 3D molecular structure and have high planarity, can be obtained. Due to planar space structure, the diamine monomers disclosed by the invention can serve as monomers used for preparing polymers with strong molecular chain interaction force, tight molecular chain packing and small free volume and the polymers can be endowed with an excellent barrier property. The synthesis method of the diamine monomers is simple in process and purification operation is easy; therefore, the synthesis method is suitable for industrial production. The diamine monomers disclosed by the invention can be used for synthesizing functional polymers such as polyamide, polyimide, polyamide-imide and polyester-imide.

Self-assembled Pd6L4 cage and Pd4L4 square using hydrazide based ligands: Synthesis, characterization and catalytic activity in Suzuki-Miyaura coupling reactions

Pradhan, Subhashis,John, Rohith P.

, p. 12453 - 12460 (2016/02/12)

A discrete Pd6L4Td-symmetric molecular cage and a discrete Pd4L4 square assembly were obtained using a coordination-driven self-assembly technique. The assembly, Pd6L4, was prepared via a face-directed method, utilising a 'cis-clipped' palladium(ii) species and a new C3 symmetric tripodal hydrazinic ligand. The Pd4L4 square assembly was prepared via an edge directed method, using the 'cis-clipped'-palladium(ii) species and a new C2 symmetric dipodal hydrazinic ligand. Both assemblies were characterised using multinuclear NMR and ESI-MS spectroscopic techniques and elemental analysis. The size of the assemblies were assigned from HR-TEM measurements, while DOSY NMR analysis established the presence of single component species in solution. Optimised structures obtained using Hartree-Fock calculations are in conformity with the experimental results. Both the assemblies show significant catalytic activity as heterogeneous catalysts for Suzuki-Miyaura coupling reactions under mild, aerobic and phosphine free conditions in aqueous ethanolic medium.

Method of manufacturing imidoyl diazidosulfochloride compd. various compd. and manufacturing method of using the same

-

Paragraph 0059, (2016/12/16)

PROBLEM TO BE SOLVED: To provide a new production method for synthesizing an imidoyl chloride compound dispensing with chlorination agents having poor handleability, to provide a method for producing various compounds in high yield and purity by using the imidoyl chloride compound, and to provide a method for isolating the imidoyl chloride compound in high efficiency and purity from a mixture of the imidoyl chloride compound and a phthalic anhydride compound.SOLUTION: The method for producing the imidoyl chloride compound comprises reaction of a specific amide compound with a specific phthaloyl chloride compound to produce a specific imidoyl chloride compound.

New preparation method for Vilsmeier reagent and related imidoyl chlorides

Kimura, Yoshikazu,Matsuura, Daisuke,Hanawa, Takeshi,Kobayashi, Yukimoto

experimental part, p. 1116 - 1118 (2012/03/26)

An environmentally benign and inexpensive preparation method is described of some imidoyl chlorides, including the Vilsmeier reagent (VR), by using phthaloyl dichloride. Synthetic applications were demonstrated using the isolated VR or VR prepared in situ for the transformation of acids to acid chlorides, alcohols to chlorides, and the formylation of dimethylaminobenzene.

Enantioselective annulation reactions of bisenolates prepared through dearomatization reactions of aromatic and heteroaromatic diesters

Perez-Vazquez, Jaime,Veiga, Alberte X.,Prado, Gustavo,Sardina, F. Javier,Paleo, M. Rita

supporting information; experimental part, p. 975 - 987 (2012/04/04)

A one-pot, enantioselective strategy for the dearomatization-annulation of aromatic diesters to give a range of highly functionalized polycyclic molecules with excellent enantioselectivity is presented. This methodology is based on the reaction of bisenolates, prepared by treating aromatic diesters with trialkyltin lithium reagents, which involves a stanna-Brook rearrangement, with 1,ω-dihaloalkanes and other biselectrophiles. We have also developed experimental conditions for performing these reactions with substoichiometric amounts of the required tin reagent by in situ recycling of Me 6Sn2 into Me3SnLi with excess lithium metal, and provide a study of the scope and limitations of this synthetic methodology. The alkylation of chiral bisenolates opens a straightforward one-pot access to highly functionalized bicyclic compounds from aromatic diesters. A stanna-Brook rearrangement originates the key bisenolate intermediate. Copyright

A palladium-catalyzed multicomponent coupling approach to π-conjugated oligomers: Assembling imidazole-based materials from imines and acyl chlorides

Siamaki, Ali R.,Sakalauskas, Marc,Arndtsen, Bruce A.

supporting information; experimental part, p. 6552 - 6556 (2011/09/13)

Just like tinkertoys: An alternative approach to access imidazole-containing π-conjugated materials is presented. The imidazole core was assembled at the same time as the oligomer by the palladium-catalyzed multicomponent coupling of imines, diimines, and di(acyl chloride)s, thus providing access to families of new conjugated materials, each formed in a one-step, catalytic reaction (see scheme; Ts=4-toluenesulfonyl). Copyright

NOVEL INHIBITORS OF HEPATITIS C VIRUS REPLICATION

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Page/Page column 259-260, (2011/07/06)

The embodiments provide compounds of the general Formulae I, II, III, IV, or V as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

Self-assembly of porphyrin-azulene-porphyrin and porphyrin-azulene conjugates

Xiao, Ze-Yun,Zhao, Xin,Jiang, Xi-Kui,Li, Zhan-Ting

experimental part, p. 2540 - 2547 (2009/10/31)

In this paper we report the synthesis and self-assembling behavior of new porphyrin-azulene-porphyrin and porphyrin-azulene conjugates. The porphyrin-azulene-porphyrin conjugate gelates a number of organic solvents, while the porphyrin-azulene conjugates form vesicles in a chloroform-methanol binary mixture. The structures of the organogels and vesicles have been characterized by SEM and AFM. Two porphyrin-naphthalene-porphyrin and porphyrin-naphthalene conjugates were also prepared. A comparison of their properties with those of the azulene analogues reveals that the intermolecular dipole-dipole interaction of the azulene units plays an important role in promoting the self-assembly of the porphyrin-azulene-porphyrin and porphyrin-azulene conjugates. The Royal Society of Chemistry 2009.

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