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아세트아닐리드

아세트아닐리드
아세트아닐리드 구조식 이미지
카스 번호:
103-84-4
한글명:
아세트아닐리드
동의어(한글):
아세트아닐리드;N-페닐ACETICACIDANILIDE;아세트산아닐리드;아세트아닐;아세트아미도벤젠;아세틸아미노벤젠;안티페브린;페날긴;페날진;아세트아닐라이드;N-아세틸아닐린;N-페닐아세트아마이드;아세토아닐리드;아세트 산 아닐리드;아세틸 아미노벤젠;아세틸아닐린
상품명:
Acetanilide
동의어(영문):
ACETANIL;usafek-3;NSC 7636;Phenalgin;USAF ek-3;ANTIFEBRIN;Phenalgene;Acetanilid;NSC 203231;ACETANILIDE
CBNumber:
CB9444812
분자식:
C8H9NO
포뮬러 무게:
135.16
MOL 파일:
103-84-4.mol

아세트아닐리드 속성

녹는점
113-115 °C(lit.)
끓는 점
304 °C(lit.)
밀도
1,121 g/cm3
증기 밀도
4.65 (vs air)
증기압
1 mm Hg ( 114 °C)
굴절률
1.5700 (estimate)
인화점
173 °C
저장 조건
Store below +30°C.
용해도
5g/l
물리적 상태
Powder
산도 계수 (pKa)
0.5(at 25℃)
색상
Off-white to beige to grayish-blue
수소이온지수(pH)
5-7 (10g/l, H2O, 25℃)
수용성
5 g/L (25 ºC)
Merck
14,50
BRN
606468
안정성
Stable. Combustible. Incompatible with strong oxidizing agents, caustics, alkalies.
CAS 데이터베이스
103-84-4(CAS DataBase Reference)
NIST
Acetamide, N-phenyl-(103-84-4)
EPA
Acetanilide (103-84-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 22-36/37/38
안전지침서 22-26-36
WGK 독일 1
RTECS 번호 AD7350000
자연 발화 온도 540 °C
TSCA Yes
HS 번호 29242995
유해 물질 데이터 103-84-4(Hazardous Substances Data)
독성 LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
기존화학 물질 KE-28264
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P405 밀봉하여 저장하시오.
NFPA 704
1
1 0

아세트아닐리드 MSDS


Acetanilide

아세트아닐리드 C화학적 특성, 용도, 생산

화학적 성질

Acetanilide, also known as Nphenylacetamide, acetanil, or acetanilide is a white to gray solid with molecular formula CH3CONHC6H5. It is an odorless colorless, glossy, crystalline powder or flakes. Acetanilide was the first aniline derivative found to possess analgesic as well as antipyretic properties and was quickly introduced into medical practice (Weast, 1981; Gnanasambandan et al., 2014). Later, it was established that in the human body it is mostly metabolized to paracetamol, this compound being responsible for the analgesic and antipyretic properties of acetanilide (Bertolini et al., 2006; Gnanasambandan et al., 2014). In addition, it was discovered that it has unacceptable toxic effects, so that acetanilide is no longer used as a drug.
Acetanilide flakes
Acetanilide is mainly used as an intermediates in the synthesis of pharmaceuticals and dyes, as an additive for hydrogen peroxide and cellulose ester varnishes, and as a plasticizer in polymer industry as well as accelerator in the rubber industry.

화학적 성질

Acetanilide orthorhombic plates or scales; or white, shining, crystalline solid or powder. Odorless

역사

The department of internal medicine at the University of Strassburg in the 1880s was noted for its investigations into intestinal worms. Adolf Kussmaul, the director, asked two young assistants, Arnold Cahn and Paul Hepp, to treat patients with naphthalene as it had been used elsewhere as an internal antiseptic. The young doctors were disappointed with the initial results, but Hepp persevered with the naphthalene treatment in a patient suffering from a variety of complaints besides worms. Surprisingly, the fever chart revealed a pronounced antipyretic effect from this treatment. This had not been observed before, but further investigation revealed that Hepp had wrongly been supplied by Kopp’s Pharmacy in Strassburg with acetanilide instead of naphthalene! Cahn and Hepp lost no time in publishing a report on their discovery of a new antipyretic.
For many years after its discovery in 1886, Acetanilide was used as an alternative to aspirin (i.e. acetyl salicylate) - an analgesic (painkiller) and antipyretic (fever reducing) drug to relieve e.g. headache, menstrual pain, and rheumatic pain. Under the name “Acetanilide” it formerly appeared in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that Acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately causing damage to the liver and kidneys. Thus, Acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen (i.e. paracetamol), which is a metabolite of Acetanilide and whose use Axelrod and Brodie suggested in the same study.

용도

Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and to stabilize cellulose ester varnishes. It is also used in the intermediation of rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs. It is also a precursor in the synthesis of penicillin and other pharmaceuticals. In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.
Acetanilide is used as a EOF (electroosmotic flow) marker in the studies of affinity capillary electrophoresis for drug–protein binding.
Acetanilide undergoes palladium-catalyzed cross-coupling reaction to form ortho-acylacetanilide.

용도

manufacture of medicinals and dyes; stabilizer for H2O2 solution; as addition to cellulose ester varnishes.

정의

ChEBI: A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.

제조 방법

Acetanilide is medicinally important as it is used as febrifuge (antifibrin).
Synthesis of Acetanilide from aniline
In a 100 ml round bottom flask fitted with a reflux condensor place 5ml of aniline and 10 ml of 1:1 acetic acid and acetic anhydride mixture (5ml acetic acid and 5 ml acetic anhydride). Heat the mixture gently under reflux for 15-20 minutes on oil bath and then pour the contents while still hot with stirring into a 200ml beaker containing 100ml ice cold water. Stir the mixture vigorously to hydrolyse the excess acetic anhydride. After all the acetanilide has precipitated, collct it on buchner funnel and wash with cold water. Recrystallise the crude product from boiling water. If the product is excessively coloured add a pinch of animal charcoal to hot water and filter hot through glass wool/ cotton plug. Pure colourless crystals of acetanilide melts at 114°C (5-5.5g).

World Health Organization (WHO)

Acetanilide, a para-aminophenol derivative with analgesic, antipyretic and weak antiinflammatory activity, was introduced into medicine in 1886. It subsequently proved to be excessively myelosuppressive and has been superseded by safer alternatives.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 4533, 1983 DOI: 10.1016/S0040-4039(00)85947-X

일반 설명

White to gray solid.

공기와 물의 반응

Acetanilide is sensitive to prolonged exposure to air . Water insoluble.

반응 프로필

Acetanilide is an amide. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

화재위험

Acetanilide is combustible.

Safety Profile

A human poison by an unspecified route. Poison by ingestion and intravenous routes. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: hallucinations and dstorted perceptions, sleepiness, constipation, cyanosis, respiratory stimulation, hdney damage, me themoglobinemiacarboxyhemoglobinemia, and decreased body temperature. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,. Combustible when exposed to heat or flame. See also ANILINE.

잠재적 노출

This amide compound is used in rubber industry as accelerator, in plastics industry as cellulose ester stabilizer, in pharmaceutical manufacture, stabilizer for hydrogen peroxide, azo dye manufacture

운송 방법

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Recrystallise acetanilide from water, aqueous EtOH, *benzene or toluene. [Beilstein 12 IV 373.]

비 호환성

Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, alkyl nitrates, alkalis (liberate aniline), chloral hydrate, phenols, ferric salts

폐기물 처리

Add to flammable solvents (alcohol or benzene) and incinerate. Oxides of nitrogenmay be scrubbed from combustion gases with alkaline solution

아세트아닐리드 준비 용품 및 원자재

원자재

준비 용품


아세트아닐리드 공급 업체

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