p-Hydroxybenzaldehyde

对羟基苯甲醛

Molecular Formula	C7H6O2	Molecular Weight	122.121
Density	1.2±0.1 g/cm3	Boiling Point	246.6±13.0 °C at 760 mmHg
Flash Point	101.3±12.4 °C	Melting Point	112-116 °C(lit.)

Like many stuff, it has many synonyms as follows

EINECS 204-599-1

MFCD00006939

4-Hydroxy benzaldehyde

4-Hydroxybenzaldehyde

p-Hydroxybenzaldehyde

Bisoprolol Impurity 15

First, the chemical is very special, some technical indexes as below

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CAS number: 123-08-0

MDL Number: MFCD00006939

EINECS number: 204-599-1

RTECS number: CU6475000

BRN number: 471352

PubChem number: 24848630

Physical property data

1. Appearance: Colorless crystalline powder with a weak and pleasant aromatic odor.

2. Melting point (º C): 117~119

3. Relative density (g/mL, 130/4 º C): 1.129

4. Solubility: Easy to dissolve in ethanol, ether, acetone, ethyl acetate, slightly soluble in water (solubility in 30.5 ℃ water is 1.38g/100ml), soluble in benzene (solubility in 65 ℃ benzene is 3.68g/ml)

5. Relative density (20 ℃, 4 ℃): 1.143117

6. Relative density (25 ℃, 4 ℃): 1.136

7. Refractive index (n130D): 1.5705

toxicology data

1. Acute toxicity: Rat oral LD50: 3980mg/kg; Mouse peritoneal LD50: 500mg/kg

2. Mutability: Human lymphocyte dual chromosome exchange testing system: 1mmol/L

3. Irritating to eyes, respiratory system, and skin.

Molecular structure data

1. Molar refractive index: 34.88

2. Molar volume (cm3/mol): 99.5

3. Waiting for Zhang Biarong (90.2K): 367.3

4. Surface tension (dyne/cm): 52.0

5. Polarization rate (10-24cm3): 13.83

Calculate chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): None

2. Number of hydrogen bond donors: 1

3. Number of hydrogen bond acceptors: 2

4. Number of rotatable chemical bonds: 1

5. Number of tautomers: 4

6. Topological molecule polarity surface area 37.3

7. Number of heavy atoms: 9

8. Surface charge: 0

9. Complexity: 93.1

10. Number of isotopic atoms: 0

11. Determine the number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13. Determine the number of chemical bond stereocenters: 0

14. Number of uncertain chemical bond stereocenters: 0

15. Number of covalent bond units: 1

Nature and stability

1. Colorless crystalline powder. Easy to sublime in the air. There is a fragrant smell.

2. This product has strong irritant and corrosive properties, with a lethal dose of 3000mg/kg for intraperitoneal injection in guinea pigs and 3000mg/kg in rats

The oral LD50 is 2700mg/kg.

3. Exists in tobacco leaves and smoke.

Second, the Synthetic Route we will recommend is the most important for your reference?

First, synthesis line of P-Hydroxybenzaldehyde CAS NO.123-08-0 as follows

Manufacturing method:

There are multiple production routes for hydroxybenzaldehyde, and currently industrial production mainly includes raw material routes such as phenol, p-cresol, and p-nitrotoluene. 1. Phenol method can be divided into various synthetic process routes, such as Reimer Tiemann reaction, Gattermann reaction, phenol trichloroacetaldehyde route, phenol glyoxylate route, phenol formaldehyde route, etc. The process characteristics of phenol method are easy availability of raw materials, simple manufacturing process, but low yield and high cost. (1) The Reimer Tiemann reaction involves heating phenol and trichloromethane in an alkaline aqueous solution at 60-100 ℃ for 2-4 hours, producing both p-hydroxybenzaldehyde and o-hydroxybenzaldehyde (commonly known as salicylaldehyde) with a total yield of about 50%. The highest yield for p-hydroxybenzaldehyde is only 17%. This process is mainly used to synthesize salicylaldehyde and p-hydroxybenzaldehyde as by-products, but it is one of the main production methods currently available. The conversion rate of raw materials and product yield in this process are both very low, and a large amount of tar is produced. Chloroform must be in excess, and unreacted phenol is difficult to recover, making it difficult to separate and purify the product. Therefore, it is necessary to vigorously develop new efficient catalysts, improve reaction selectivity, and develop simple and efficient methods for product separation and purification in order to reduce costs and improve product yield. (2) Gattermann reacted phenol and HCN, and in the presence of AlCl3, dry HCl was introduced for catalytic reaction, which was then decomposed in ice water to obtain p-hydroxybenzaldehyde with high product yield. If zinc cyanide is used instead of HCN, the yield is almost the theoretical amount. This process has high product selectivity, but its disadvantages include high cyanide toxicity, high operational requirements, and difficulty; Secondly, due to the use of anhydrous operation, the requirements for reaction equipment are strict and the cost is high; Thirdly, a small amount of salicylaldehyde is produced, which makes it difficult to separate and purify the product, thus limiting large-scale production.

2. The process of producing p-hydroxybenzaldehyde by p-nitrotoluene method involves three steps: oxidation-reduction, diazotization, and hydrolysis. (1) Simultaneous oxidation-reduction of para nitrotoluene using sodium polysulfide yields para aminobenzaldehyde. The specific process is as follows: Mix p-nitrotoluene, ethanol solvent, and surfactant (such as OP Tween) in a mass ratio of 1:5:0.02-0.04, and add sodium sulfide aqueous solution dropwise at 80-85 ℃ for 2-3 hours. The product is distilled with steam to remove p-nitrotoluene and p-aminotoluene. Extracting para aminobenzaldehyde with ether. The conversion rate and yield of the reaction are both above 90%. Sodium polysulfide can be prepared from sodium hydrosulfide, caustic soda, and sulfur as raw materials. (2) The diazotization and hydrolysis of para aminobenzaldehyde will be treated with 40% sulfuric acid, and a 30% sodium nitrite solution will be added at 0-3 ℃ for about 30 minutes. Excess sodium nitrite will be decomposed with a small amount of urea to obtain a solution of para aminobenzaldehyde diazonium salt. This solution is hydrolyzed in the presence of sulfuric acid at a temperature of 80-85 ℃ for about 30 minutes. The product was extracted, purified, and dried to obtain p-hydroxybenzaldehyde product with a yield of over 90%. The advantage of this process is that the raw material price is cheap, but the disadvantage is that the process route is long, the equipment is large, and the intermediate product is toxic to aminobenzaldehyde. The diazotization reaction temperature is low and the freezing conditions are high. At present, the fine chemical plant in Qixian County, Shanxi Province, China adopts this process to produce p-hydroxybenzaldehyde.

3. The catalytic oxidation method for p-cresol involves the direct oxidation of p-cresol to p-hydroxybenzaldehyde using air or oxygen under the action of a catalyst. In the 1980s, Japan, the United States, Germany, and others conducted in-depth research and reporting on this process route. In the late 1980s and early 1990s, several research and production units in Jiangsu, Shanghai, Dalian and other places in China also conducted research and development on this process and applied it to industrial production. The specific process flow is as follows: add p-cresol, sodium hydroxide, and methanol to a stainless steel pressure vessel, stir until completely dissolved, add cobalt acetate to seal the reaction vessel, raise the temperature to 55 ℃ and start introducing oxygen to maintain the pressure inside the vessel at 1.5 MPa for 8-10 hours. During the reaction process, the oxygen flow rate is strictly controlled, and a coil cooling system is equipped inside the vessel. When the temperature rises during the reaction, cooling water can be passed through the jacket of the vessel. At this time, cooling water begins to flow through the coil, and the total amount of oxygen flow is strictly controlled while maintaining the temperature inside the vessel at around 60 ℃. At the end of the reaction, place the material into the initial distillation kettle, evaporate the solvent methanol for recycling, dissolve it in water, and add hydrochloric acid for salt precipitation. Filter the solid-liquid material using a centrifuge, and place the obtained solid in a vacuum oven to dry at around 60 ℃ for 3-5 hours to obtain p-hydroxybenzaldehyde with a content greater than 98%.

4. Obtain needle crystals from water.

5. Manufacturing method:

Add 496mg (4mmol) of p-hydroxybenzyl alcohol (2) and 24mL of dioxane to the reaction flask, followed by 908mg (4mmol) of 2,3-dichloro-4,5-dicyano-1,4-dibenzoquinone (DDQ). The reaction immediately occurs, producing a dark green color (exothermic reaction), and about 1 minute produces a DDQH2 precipitate. Thin layer analysis proves that the reaction ends after 15 minutes. Evaporate the solvent under reduced pressure from the yellow reaction mixture, add dichloromethane to the residue, and filter off insoluble substances (DDQH2, almost quantitatively). The filtrate was concentrated to obtain compound (1) with a yield of 74%. It can be recrystallized with water.

Third, what is the usage of P-Hydroxybenzaldehyde CAS NO.123-08-0 ? pleas see below

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Main Usage: This product is an intermediate in pharmaceuticals, fragrances, and liquid crystals, and is also used as a solvent. Hydroxybenzaldehyde is used for the production of antibacterial enhancers TMP (trimethoprim), amoxicillin, amoxicillin cephalosporin, artificial gastrodia elata, rhododendron, benzimidazole, and esolol; Used for producing spices such as anise aldehyde, vanillin, ethyl vanillin, and raspberry ketone.

Used for the synthesis of 4-but-3-enoxybenzaldehyde,Cas no. 105534-98-3

Used for the synthesis of 2-[4-[(Z)-(3-methyl-5-oxo-1H-pyrazol-4-ylidene)methyl]phenoxy]-N-[(3-n

itrophenyl)methylideneamino]acetamide,Cas no. 107044-94-0

Used for the synthesis of 5-hydroxy-3-[(4-hydroxyphenyl)methylidene]-1-benzofuran-2-one Cas no. 107680-50-2

Besides Safety Information of P-Hydroxybenzaldehyde CAS NO.123-08-0 is also important when handling it

Hazard Codes	Xi
WGK Germany	3
H．S．Code：	2912499000
TSCA	Yes
HazardClass	IRRITANT

What is the appearance of P-Hydroxybenzaldehyde CAS NO.123-08-0? Please see the picture ofP-Hydroxybenzaldehyde CAS NO.123-08-0, below