4-히드록시벤즈알데히드
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4-히드록시벤즈알데히드 속성
- 녹는점
- 112-116 °C (lit.)
- 끓는 점
- 191°C 50mm
- 밀도
- 1,129 g/cm3
- 증기압
- 0.004Pa at 25℃
- 굴절률
- 1.5105 (estimate)
- 인화점
- 174°C
- 저장 조건
- Store below +30°C.
- 용해도
- 13.8g/L
- 물리적 상태
- 결정성 분말
- 산도 계수 (pKa)
- 7.61(at 25℃)
- 색상
- 밝은 노란색에서 밝은 갈색까지
- 냄새
- 100.00%에서. 달콤한 견과류 아몬드 발삼 우디
- ?? ??
- 우디
- 수용성
- 13g/L(30℃)
- 감도
- Air Sensitive
- JECFA Number
- 956
- Merck
- 14,4811
- BRN
- 471352
- 안정성
- 흡습성
- InChIKey
- RGHHSNMVTDWUBI-UHFFFAOYSA-N
- LogP
- 1.3 at 23℃
- CAS 데이터베이스
- 123-08-0(CAS DataBase Reference)
안전
- 위험 및 안전 성명
- 위험 및 사전주의 사항 (GHS)
위험품 표기 | Xi | ||
---|---|---|---|
위험 카페고리 넘버 | 36/37/38-R36/37/38 | ||
안전지침서 | 26-36-24/25-37/39-S24/25 | ||
WGK 독일 | 2 | ||
RTECS 번호 | CU6475000 | ||
자연 발화 온도 | 450 °C | ||
위험 참고 사항 | Irritant/Air Sensitive | ||
TSCA | Yes | ||
HS 번호 | 29124900 | ||
독성 | LD50 orally in Rabbit: 2250 mg/kg | ||
기존화학 물질 | KE-20347 |
4-히드록시벤즈알데히드 C화학적 특성, 용도, 생산
물성
하이드 록시 벤즈알데히드는 페놀 (9.99)과 비교하여 pKs가 현저하게 낮았다. 전자 흡인 알데히드 그룹 (-M 효과)은 산도를 증가시킨다; 페놀 릭 OH 결합은 갈수록 극성을 갖게된다.물성
황색 또는 백색 결정 성 분말.용도
염료, 의약 및 향료 산업에 사용되는 중요한 중간체.화학적 성질
4-Hydroxybenzaldehyde is a yellow to light brown crystalline powder that has a very faint, sweet-woody-balsamic odor and a sweet taste with little or no other flavor impression. The odor is also reported as vanillic/nutty.출처
It is found as a volatile in several food products, including cherries, grapes, papayas, tomatoes, cheese, beer, rum, brandy, wine, tea and peanuts. Occurs in the form of esters in several plants, notably in wintergreen leaves and the bark of sweet birch.용도
4-Hydroxybenzaldehyde maintains bactericidal activity when tested against certain bacteria strains. It also displays antioxidant potential when analyzed through assay. It is widely used starting material for polymers and pharmaceuticals.주요 응용
p-Hydroxybenzaldehyde is the important intermediates of pharmaceutical industry and spices. In foreign , it's also used for synthesis of bromoxynil and chloroxynil which are kind of herbicides, and also used in the manufacture of bactericide, photographic emulsifier, nickel plating luster agent, liquid crystal, etc; In the pharmaceutical field, it can be used for synthesis of amoxicillin, antibacterial synergistic agent named TMP, 3,4,5-Trimethoxybenzaldehyde,Artificial gastrodia elata, farrerol, esmololhydrochloride; In the spicery field, it can be used for synthesis of spicery,for example: vanillin, ethyl vanillin, piperonal, springaldehyde, p-anisaldehyde, raspberry ketone natural,etc.제조 방법
p-Hydroxybenzaldehyde is prepared by heating sodium phenolate with carbon dioxide under pressure.정의
ChEBI: 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor.일반 설명
4-hydroxybenzaldehyde occurs naturally in vanilla beans and is one of the keys contributors to the vanilla flavor.Synthesis
2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ 908 mg, 4 mmol) was added to a solution of 4-hydroxybenzyl alcohol (496 mg, 4 mmol) in dioxane (24 mL). The reaction mixture immediately turned deep green (exothermic reaction), and DDQH2 started precipitating within 1 min. Thin layer chromatography (TLC) analysis indicated consumption of starting material after 15 min. The solvent was removed from the yellow reaction mixture in vacuo. Treatment of the residue with CH2Cl2 left DDQH2 undissolved (quantitatively). Filtration followed by evaporation of CH2Cl2 gave 4-hydroxybenzaldehyde (74% yield) which was recrystallized from water.Reference: Becker, H.-D.; Bjork, A.; Alder, E. J. Org. Chem. 1980, 45, 1596?1600.
Purification Methods
Crystallise it from water (containing some H2SO4). Dry it over P2O5 under vacuum. [Beilstein 8 H 64, 8 IV 251.]참고 문헌
[1] HANS DIETER BECKER Erich A Anders Bjoerk. Quinone dehydrogenation. Oxidation of benzylic alcohols with 2,3-dichloro-5,6-dicyanobenzoquinone[J]. The Journal of Organic Chemistry, 1980, 45 9: 1596-1600. DOI:10.1021/jo01297a010.[2] CHAN WOO KANG. 4-Hydroxybenzaldehyde accelerates acute wound healing through activation of focal adhesion signalling in keratinocytes.[J]. Scientific Reports, 2017: 14192. DOI:10.1038/s41598-017-14368-y.
[3] M. EDDOUKS. Insulin Resistance as a Target of Some Plant-Derived Phytocompounds[J]. Studies in natural products chemistry, 1900, 26 1: 351-373. DOI:10.1016/B978-0-444-63430-6.00011-4.
[4] DOUGLASS F. TABER. Vanillin Synthesis from 4-Hydroxybenzaldehyde[J]. Journal of Chemical Education, 2007, 84 7: 1158. DOI:10.1021/ed084p1158.
[5] MAKOTO KOMIYAMA Hidefumi H. Selective synthesis of 4-hydroxybenzaldehyde with cyclodextrin as catalyst[J]. Macromolecular Rapid Communications, 1981, 2 12: 715-717. DOI:10.1002/marc.1981.030021202.
[6] HIROAKI MATSUDA . Mutagenicity of ozonation and chlorination products from p-hydroxybenzaldehyde[J]. Science of the Total Environment, 1991, 103 2: Pages 141-149. DOI:10.1016/0048-9697(91)90140-A.
4-히드록시벤즈알데히드 준비 용품 및 원자재
원자재
클로랄
아연 시아니드
산소, 냉각된 액체
클로로포름
P-크레졸
살리실 알데히드
Cyanide, Quant Test Strips
4-니트로톨루엔
Efficient catalysts
염산
수산화나트륨
글리옥실산
Methanediol,1-[4-(acetyloxy)phenyl]-, 1,1-diacetate
4-(TETRAHYDRO-PYRAN-2-YLOXY)-벤잘데하이드
준비 용품
4-히드록시-3-니트로벤즈알데히드
트로글리타존
4-[(3,4-DICHLOROBENZYL)OXY]벤잘데하이드
4-N-데실록시벤잘데하이드
N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline
2-(4-플루오로벤조일)-1-벤조푸란-5-카르발데하이드
2,6-다이브로모-4-시아노페닐옥타노에이트
4-Vinylphenol
4-(2-클로로-6-플루오로벤질록시)벤잘데하이드
3,4,5-트리메톡시벤즈알데히드
4-[2-(다이메틸아미노)에톡시]벤잘데히드
2-(4-PENTYLBENZOYL)-1-BENZOFURAN-5-CARBALDEHYDE
2-(4-클로로벤조일)-1-벤조푸란-5-카르발데하이드
베타-(4-아세톡시페닐)프로피온산
2-(4-브로모벤졸)-1-벤조푸란-5-카발데하이드
2-Bromobenzonitrile
Ciprofibrate
4-사이아노페놀
4-(2-히드록시에톡시)벤즈알데히드
아니스알데히드
4-(4-플루오로벤질록시)벤잘데하이드
2-(4-METHOXYBENZOYL)-1-BENZOFURAN-5-CARBALDEHYDE
패스트그린FCF
4-(4-히드록시페닐)-2-부타논
4-히드록시벤즈알데히드 공급 업체
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