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3,5-DICHLOROSALICYLALDEHYDE structure

3,5-DICHLOROSALICYLALDEHYDE
  • CAS：90-60-8
  • MW:191.007
  • MF：C7H4Cl2O2
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1. Names and Identifiers
1.1 Name
3,5-DICHLOROSALICYLALDEHYDE
1.2 Synonyms
2-Hydroxy-3,5-dichlorobenzaldehyde; 3,5-DICHLORO SALICYLAL; 3,5-DICHLORO-2-HYDROXYBENZALDEHYDE; AKOS B029257; Benzaldehyde, 3,5-dichloro-2-hydroxy-; Benzaldehyde,3,5-dichloro-2-hydroxy-; EINECS 202-005-5; LABOTEST-BB LT00089371; MFCD00003320; Salicylaldehyde, 3,5-dichloro-; Salicylaldehyde,3,5-dichloro-; VHR BQ CG EG;
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1.3 CAS No.
90-60-8
1.4 CID
66660
1.5 EINECS
202-005-5
1.6 Molecular Formula
C7H4Cl2O2
1.7 Inchi
InChI=1S/C7H4Cl2O2/c8-5-1-4(3-10)7(11)6(9)2-5/h1-3,11H
1.8 InChkey
FABVMBDCVAJXMB-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=C(C=C(C(=C1C=O)O)Cl)Cl
1.10 Isomers Smiles
C1=C(C=C(C(=C1C=O)O)Cl)Cl
2. Properties
2.1 Solubility
几乎不溶 (0.097 g/L) (25 oC),
2.2 Appearance
pale yellow crystalline powder
2.3 Storage
Air Sensitive. Store under Nitrogen. Ambient temperatures.
2.4 Chemical Properties
pale yellow crystalline powder 3,5-DICHLOROSALICYLALDEHYDESupplier
2.5 Color/Form
Pale yellow
2.6 pKa
6.27±0.23(Predicted)
2.7 Water Solubility
Insoluble in water. Solubility in methanol is almost transparent.
2.8 StorageTemp
Inert atmosphere,Room Temperature
3. Use and Manufacturing
3.1 Description
3,5-DICHLOROSALICYLALDEHYDE (CAS 90-60-8) is a chemical compound that appears as a yellow crystalline solid. Its basic structure consists of a salicylaldehyde ring with two chlorine atoms attached at positions 3 and 5. This compound is sparingly soluble in water, but it can dissolve in organic solvents such as ethanol and acetone.

3,5-DICHLOROSALICYLALDEHYDE has several physical properties, including a melting point of approximately 120-122°C and a boiling point of around 300°C. It has a characteristic odor and may have a yellowish color. Chemically, it is reactive and can undergo various reactions, such as condensation, oxidation, and reduction.

Applicable Fields
3,5-DICHLOROSALICYLALDEHYDE finds applications in different fields due to its chemical properties. Here are some examples:

Pharmaceutical Industry: This chemical is used as an intermediate in the synthesis of various pharmaceutical compounds. It can be utilized to introduce the salicylaldehyde moiety into drug molecules, which can contribute to their biological activity. The mechanism of action in this context involves its role as a building block in the synthesis of specific pharmaceuticals.

Chemical Research: 3,5-DICHLOROSALICYLALDEHYDE is also employed in chemical research as a reagent or starting material for the synthesis of other compounds. Its reactive nature allows it to participate in various chemical reactions, enabling the creation of new molecules with desired properties.

Storage Conditions
The recommended storage conditions for 3,5-DICHLOROSALICYLALDEHYDE are to store it in a cool and dry place, away from direct sunlight.
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3.2 Methods of Manufacturing
Chromene acids are made starting from phenols via salicylic aldehydes. 2, 4- Dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mL methanesulfonic acid and heated at 100 C for 1.5 h. The reaction was diluted with ethyl acetate and the organic layer was washed with water, followed by saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated. The product 3, 5-dichloro-2- hydroxybenzaldehyde (INT-01) was purified by chromatography using ethyl acetate/hexane gradient to give a yellow oil (7.5 g, 64percent yield). 1H NMR (400 MHz, CDC10205] Chromene acids are made starting from phenols via salicylic aldehydes. 2, 4- Dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mL methanesulfonic acid and heated at 100 C for 1.5 h. The reaction was diluted with ethyl acetate and the organic layer was washed with water, followed by saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated. The product 3, 5-dichloro-2- hydroxybenzaldehyde (INT-01) was purified by chromatography using ethyl acetate/hexane gradient to give a yellow oil (7.5 g, 64percent yield). 1H NMR (400 MHz, CDC1Step 1: 3, 5-Dichloro-2-hydroxybenzaldehyde (INT-01)Chromene acids are made starting from phenols via salicylic aldehydes. 2, 4-Dichlorophenol (10.0 g, 61.3 mmol) and hexamethylenetetramine (17.2 g, 122.6 mmol) were dissolved in 80 mE methanesulfonic acid and heated at 1000 C. for 1.5 h. The reaction was diluted with ethyl acetate and the organic layer was washed with water, followed by saturated sodium bicarbonate, dried over magnesium sulfate, and evaporated. The product 3, 5-dichioro-2-hydroxy- benzaldehyde (INT-Ol) was purified by chromatography using ethyl acetate/hexane gradient to give a yellow oil (7.564percent yield). ‘H NMR (400 MHz, CDC13) ? 11.39 (s, 1H), 7.64 (s, 1H), 7.52 (s, 1H). EC tr=3.95 mm (C-18 column, 5 to 95percent acetonitrile/water over 6 mm at 1.7 mE/mm with detection 254 nm, at 23° C.).To a three-neckflask, equipped with a reflux condenser, thermometer, anitrogen source, and magnetic stirrer, was added 2, 4-dichlorophenol (12 mmol), urotropine (24 mmol), andTFA (12.4 mL). The mixture was heated to 115 °C andto refluxed for 20 h. The reaction mixture was cooled to60 °C and added 33percent sulfuric acid (6.2 mL), then thereaction mixture was heated to 130 °C and refluxed for1 h. After cooling, the reaction mixture was acidified topH 6–7 with sodium bicarbonate, and extracted withethyl acetate. The reaction was monitored by TLC. Theethyl acetate extract was treated with vacuum distillation, to give crude 3, 5-dichlorosalicylaldehyde. Thecrude product was purified by column chromatographygave pale yellow product (1.218 g, 51.9percent).
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4. Safety and Handling
4.1 Sensitive
Air Sensitive
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in CDCl3  
IR : CCl4 solution  
IR : KBr disc  
Raman : 4880 A,200 M,powder  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
90-60-8Total: 12 Synthesis Route
 
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635-93-8
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90-60-8
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8. Precursor and Product
precursor:
120-83-2
120-83-2
855156-83-1
855156-83-1
6333-33-1
6333-33-1
6641-02-7
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90-02-8
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127-68-4
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product:
3004-26-0
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2199-86-2
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76008-04-3
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72570-87-7
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83823-07-8
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50477-27-5
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13673-92-2
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52828-99-6
52828-99-6
6641-02-7
6641-02-7
83823-28-3
83823-28-3
9. Computed Properties
10.Other Information
Usage
3,5-Dichlorosalicylaldehyde has been used in the preparation of Schiff base ligands and (RS)-3,5-dichloro-2-[[(1-phenylethyl)imino]methyl]phenol.
BRN
973391
Chemical Properties
pale yellow crystalline powder
Manufacturing Info
Benzaldehyde, 3,5-dichloro-2-hydroxy-: ACTIVE
11. Toltal 65 Suppliers View more
3,5-Dichlorosalicylaldehyde
Dayang Chem (Hangzhou) Co., Ltd.
 1YR   China
Tel: Update Time:2024/06/17
inquire
3,5-DICHLOROSALICYLALDEHYDE
Jiaxing Isen Chemical Co.,Ltd
  China
Tel: Update Time:2022/05/26
inquire
3,5-Dichloro-2-hydroxybenzaldehyde
Shanghai FWD Chemicals ltd
  China
Tel: Update Time:2019/10/26
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3,5-DICHLOROSALICYLALDEHYDE
Shanghai Forever Synthesis Co.,Ltd.
  China
Tel: Update Time:2019/06/12
inquire
3,5-Dichlorosalicylaldehyde
Shanghai Hope Chem Co., Ltd.
  China
Tel: Update Time:2018/11/21
inquire
12. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
10. Other Information
11. Toltal 65 Suppliers
12. Realated Product Infomation
 
 
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