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Cas Database

1194-98-5

1194-98-5

Identification

  • Product Name:Benzaldehyde,2,5-dihydroxy-

  • CAS Number: 1194-98-5

  • EINECS:214-789-6

  • Molecular Weight:138.123

  • Molecular Formula: C7H6 O3

  • HS Code:29124990

  • Mol File:1194-98-5.mol

Synonyms:Gentisaldehyde(6CI,7CI,8CI); 2,5-Dihydroxybenzaldehyde; 5-Hydroxysalicylaldehyde;Formylhydroquinone; NSC 72387

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Safety information and MSDS view more

  • Pictogram(s):

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH317 May cause an allergic skin reaction H319 Causes serious eye irritation 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:TRC
  • Product Description:2,5-Dihydroxybenzaldehyde
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Relevant articles and documentsAll total 39 Articles be found

Access to functionalized quinones via the aromatic oxidation of phenols bearing an alcohol or olefinic function catalyzed by supported iron phthalocyanine

Zalomaeva, Olga V.,Sorokin, Alexander B.

, p. 1768 - 1773 (2006)

The controlled oxidation at only one position of compounds with several oxidizable sites, while keeping the other sites intact, has been demonstrated for phenols bearing alcohol or olefinic functional groups. Iron tetrasulfophthalocyanine supported on silica was found to be an efficient catalyst for the preparation of functionalized quinones under mild conditions, with tert-butylhydroperoxide as the oxidant. A novel rapid and mild one-pot procedure for the covalent grafting of iron tetrasulfophthalocyanine onto silica has been developed. The supported catalyst was characterized by chemical analysis, a specific surface study, UV-vis spectroscopy and XPS. A non-radical mechanism for this unusual selective oxidation has been revealed by 18O labelling experiments. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

MgBr2 supported on Fe3O4@SiO2?~?urea nanoparticle: An efficient catalyst for ortho-formylation of phenols and oxidation of benzylic alcohols

Soleimani, Ebrahim,Yaesoobi, Nadieh,Ghasempour, Hamid Reza

, (2018)

Urea was successfully immobilized on the surface of chloropropyl-modified Fe3O4@SiO2 core–shell magnetic nanoparticles, then supported by MgBr2 and acts as a unique catalyst for oxidation of benzylic alcohols to aldehydes and ketones, and ortho-formylation of phenols to salicylaldehydes. The prepared catalyst was characterized by FT-IR, transmission electron microscopy, scanning electron microscopy, X-ray powder diffraction, dispersive X-ray spectroscopy, CHN and TGA. It was found that Fe3O4@SiO2?~?urea/MgBr2 showed higher catalytic activity than homogenous MgBr2, and could be reused several times without significant loss of activity.

Ulrich et al.

, p. 2437,2438 (1974)

Efficient microwave-assisted regioselective one pot direct: Ortho -formylation of phenol derivatives in the presence of nanocrystalline MgO as a solid base catalyst under solvent-free conditions

Naeimi, Hossein,Zakerzadeh, Elham

, p. 4590 - 4595 (2018)

In this research, at first nanocrystalline MgO was prepared and then the solvent-free reactions of phenol derivatives with paraformaldehyde in the presence of the obtained nanocrystalline MgO as a new catalyst under microwave irradiation were investigated. In this reaction, ortho-hydroxyaromatic aldehydes were yielded as products. This method seems to be comparable with other reported methods due to its high yield and regioselectivity. The significant features of this method are short reaction times, high yields, and easy and quick isolation of the products.

-

Rao et al.

, p. 2548 (1975)

-

Platinum(II) complexes with tetradentate schiff bases as ligands: Synthesis, Characterization and detection of DNA interaction by differential pulse voltammetry

Li, Lijun,Tian, Chao,Wang, Cheng,Wang, Guangyuan,Wang, Lianzeng,Du, Jianlong

, p. 1422 - 1430 (2012)

Five sterically hindered platinum(II) complexes with tetradentate schiff bases as ligands, [Pt(L)] (L= N,N'-bisalicylidene-1,2-ethylenediamine (L 1), N,N'-bisalicylidene-1,2-cyclohexanediamine (L2), N,N'-bis(5-hydroxylsalicylidene)-1,2-cyclohexanediamine (L3), N,N'-bisalicylidene-1,2-diphenylethylenediamine (L4) and N,N'-bis(3-tert-butyl-5-methyl-salicylidene)-1,2- diphenylethylenediamine (L5) ) have been synthesized and characterized by IR spectroscopy and elemental analysis. The sterical hindrance of antitumor drug candidates potentially makes them less susceptible to deactivation by sulphur containing proteins and helping to overcome resistance mechanisms. The interaction of these metal complexes with fish sperm single-stranded DNA (ssDNA) was studied electrochemically based on the oxidation signals of guanine and adenine. Differential pulse voltammetry was employed to monitor the DNA interaction in solution by using renewable pencil graphite electrode. The results indicate that ligands with different groups can strongly affect the interaction between [Pt(L)] complexes and ssDNA due to sterical hindrances and complex [Pt(L 1)] has the best interaction with DNA among the five complexes.

Scott,Beadling

, p. 281,283 (1974)

Sekiguchi,Gaucher

, p. 1785,1786 (1978)

CoTPP-CATALYZED REARRANGEMENT OF 1.4-ENDOPEROXIDES

Balci, Metin,Suetbeyaz, Yasar

, p. 311 - 314 (1983)

Bicyclic endoperoxides with strained and perturbed diene moiety have been submitted to CoTPP-catalyzed rearrangement.Side reaction, like formation of epoxyenone, has been suppressed and yield of the formation of bisepoxides highly increased.

-

Bruce et al.

, p. 594 (1969)

-

Preparation method of 2, 5-dihydroxy benzaldehyde

-

Paragraph 0017; 0020-0022; 0025-0026, (2021/07/17)

The invention discloses a preparation method of 2, 5-dihydroxy benzaldehyde, which is used for preparing an important intermediate of a liquid crystal compound, and relates to the technical field of liquid crystals. The preparation method comprises the steps of by taking p-methoxyphenol as a raw material, alkyl nitrile as a solvent, paraformaldehyde as a formylation reagent and magnesium chloride and triethylamine as catalysts, reacting for 2-4 hours, extracting reaction liquid by using an organic solvent, washing with water, drying, and evaporating to remove the solvent to obtain liquid 2-hydroxy-5-methoxybenzaldehyde, and then by using toluene as a solvent, and enabling the obtained 2-hydroxy-5-methoxybenzaldehyde to be subjected to a demethylation reaction under the action of anhydrous aluminum trichloride to obtain 2, 5-dihydroxy benzaldehyde; and reacting for 2-4 hours, washing the reaction liquid with water, extracting with an organic solvent, drying, evaporating to remove the solvent, and crystallizing the solvent. The method has the advantages of cheap and easily available raw materials, simple operation and convenient industrial production.

Bisketene Equivalents as Diels-Alder Dienes

Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.

supporting information, p. 13328 - 13333 (2020/09/03)

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.

METHOD FOR PRODUCING 2-HYDRAZINOBENZOTHIAZOLE DERIVATIVE

-

Paragraph 0130; 0135, (2020/06/15)

The present invention provides a novel method for producing a 2-hydrazinobenzothiazole derivative. The present invention also provides a method for producing a compound by using the 2-hydrazinobenzothiazole derivative obtained by the production method, and a composition that contains the compound. The present invention also provides a polymerizable composition that is useful in producing film-shaped polymers and contains the compound obtained by the production method. The invention of the present application provides a method for producing a compound represented by general formula (I-C), the method including a step of reacting a compound represented by general formula (I-B) with a compound represented by general formula (I-A) in the presence of at least one compound selected from the group consisting of metal amides, metal hydrides, metal alkoxides, and organic alkali metals. A compound derived from the compound produced by the production method, and a composition that contains the compound are also provided.

Substrate-Induced Dimerization Assembly of Chiral Macrocycle Catalysts toward Cooperative Asymmetric Catalysis

Ao, Yu-Fei,Guo, Hao,Meng, Wei,Wang, De-Xian,Wang, Qi-Qiang,Zhang, Lie-Wei,Zhou, Hao

supporting information, p. 2623 - 2627 (2020/02/04)

An artificial system of substrate-induced dimerization assembly of chiral macrocycle catalysts enables a highly cooperative hydrogen-bonding activation network for efficient enantioselective transformation. These macrocycles contain two thiourea and two chiral diamine moieties and dimerize with sulfate to form a sandwich-like assembly. The macrocycles then adopt an extended conformation and reciprocally complement the hydrogen-bonding interaction sites. Inspired by the guest-induced dynamic assembly, these macrocycles catalyze the decarboxylative Mannich reaction of cyclic aldimines containing a sulfamate heading group. The imine substrate can be activated toward nucleophilic attack of β-ketoacid by a cooperative hydrogen-bonding network enabled by sulfamate-induced dimerization assembly of the macrocycle catalysts. Highly efficient (>95 % yield in most cases) and enantioselective (up to 97.5:2.5 er) transformation of a variety of substrates using only 5 mol % macrocycle was achieved.

METHOD FOR PRODUCING ESTER GROUP-CONTAINING COMPOUND

-

Paragraph 0131, (2019/03/08)

The present invention provides a novel method for producing an ester group-containing compound and a derivative produced using the compound as a synthetic intermediate. The invention also provides a polymerizable composition containing the compound obtained by the production method and a film-shaped polymer obtained by polymerizing the polymerizable composition. The present invention is a method for producing an ester group-containing compound, the method including a mixing step of mixing a condensing agent, a Bronsted acid, a carboxylic acid, and a phenol or an alcohol to prepare a reaction mixture. The Bronsted acid selected is other than the condensing agent, the carboxylic acid, and the phenol.

Process route upstream and downstream products

Process route

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-benzaldehyde
123-08-0,65581-83-1

4-hydroxy-benzaldehyde

salicylaldehyde
90-02-8

salicylaldehyde

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

Conditions
Conditions Yield
With oxygen; titanium(IV) oxide; In water; Irradiation;
anthracene
120-12-7

anthracene

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

benzoic acid
65-85-0,8013-63-6

benzoic acid

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

Conditions
Conditions Yield
In water; Further byproducts given; Formation of xenobiotics; simulated solar irradiation;
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

2,3-dihydroxybenzaldehyde
24677-78-9

2,3-dihydroxybenzaldehyde

Conditions
Conditions Yield
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

methylene chloride
74-87-3

methylene chloride

Conditions
Conditions Yield
at 140 - 150 ℃;
benzaldehyde
100-52-7

benzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

Conditions
Conditions Yield
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride; at -20 ℃; for 0.5h; Mechanism; Product distribution;
10%
8%
With dihydrogen peroxide; hydrogen fluoride; antimony pentafluoride; at -20 ℃; for 0.5h;
8%
10%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

hydroquinone
123-31-9,8027-02-9

hydroquinone

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
Conditions Yield
With 9,10-dihydroanthracene; at 526.84 ℃; under 5E-05 Torr; Further Variations:; Temperatures; Activation energy;
2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

Conditions
Conditions Yield
With boron tribromide; In dichloromethane; at -78 - 0 ℃; for 1h;
97%
With boron triiodide;
With boron tribromide; In chloroform;
With hydrogen bromide; acetic acid; for 12h; Reagent/catalyst; Inert atmosphere; Reflux;
12 g
With hydrogen bromide; acetic acid; for 6h; Inert atmosphere; Reflux;
14.6 g
With boron tribromide; In dichloromethane; for 2h; Inert atmosphere; Cooling with ice;
18.7 g
With boron tribromide; In dichloromethane; for 2h; Inert atmosphere; Cooling with ice;
18.7 g
With hydrogen bromide; acetic acid; for 6h; Inert atmosphere; Reflux;
14.6 g
2,5-dimethoxybenzaldehyde; With aluminum (III) chloride; In 1,2-dichloro-ethane; at 65 ℃; for 3h; Inert atmosphere;
With hydrogenchloride; In 1,2-dichloro-ethane; at 65 ℃; for 2h;
23.5 g
With hydrogen bromide; acetic acid; for 6h; Inert atmosphere; Reflux;
14.6 g
5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

Conditions
Conditions Yield
5-bromosalicyclaldehyde; With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine; In water; dimethyl sulfoxide; tert-butyl alcohol; at 120 ℃; for 36h; Inert atmosphere;
With hydrogenchloride; In water; dimethyl sulfoxide; tert-butyl alcohol; pH=1 - 2; Inert atmosphere;
65%
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide; In water; at 110 ℃; for 48h; Inert atmosphere;
62%
2-hydroxy-5-acetyloxybenzaldehyde
64418-88-8

2-hydroxy-5-acetyloxybenzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

Conditions
Conditions Yield
With water; potassium carbonate; In methanol; at 20 ℃; for 3h;
90%
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

2,5-Dihydroxybenzaldehyde
1194-98-5

2,5-Dihydroxybenzaldehyde

Conditions
Conditions Yield
With 1-butylpyridinium bromide; at 100 ℃; Microwave irradiation; Neat (no solvent);
70%
Multi-step reaction with 2 steps
1: sodium acetate; acetic acid; bromine / 1 h / 20 °C
2: boron tribromide / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere
With bromine; sodium acetate; boron tribromide; acetic acid; In dichloromethane;
With aluminum (III) chloride; In toluene; for 4h; Reflux;
440 g

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