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N,N-디메틸아닐린

N,N-디메틸아닐린
N,N-디메틸아닐린 구조식 이미지
카스 번호:
121-69-7
한글명:
N,N-디메틸아닐린
동의어(한글):
N,N-다이메틸아닐린;N,N-디메틸아닐린;디메틸아닐린;N,N-다이메틸아닐린및그염류;(다이메틸아미노)벤젠;N,N-다이메틸벤젠아민;N,N-디메틸벤젠아민;N,N-디메틸아미노벤젠;다이메틸아닐린;다이메틸페닐아민;벤젠아민, N,N-다이메틸-;아닐린, N,N-다이메틸-
상품명:
N,N-Dimethylaniline
동의어(영문):
DMA;HLADM;RING6;D6S222E;nl63-10p;Xylidene;NSC 7195;NCI-C56428;N.N-Dimethylan;Dimethylanilin
CBNumber:
CB6852937
분자식:
C8H11N
포뮬러 무게:
121.18
MOL 파일:
121-69-7.mol

N,N-디메틸아닐린 속성

녹는점
1.5-2.5 °C (lit.)
끓는 점
193-194 °C (lit.)
밀도
0.956 g/mL at 25 °C (lit.)
증기 밀도
3 (vs air)
증기압
2 mm Hg ( 25 °C)
굴절률
n20/D 1.557(lit.)
인화점
158 °F
저장 조건
Store below +30°C.
용해도
1.2g/l
물리적 상태
Liquid
산도 계수 (pKa)
5.15(at 25℃)
색상
Clear yellow
상대극성
0.179
수소이온지수(pH)
7.4 (1.2g/l, H2O, 20℃)
폭발한계
1.2-7%(V)
수용성
1 g/L (20 ºC)
Merck
14,3234
BRN
507140
Henry's Law Constant
4.98(x 10-6 atm?m3/mol) at 20 °C (approximate - calculated from water solubility and vapor pressure)
노출 한도
NIOSH REL: TWA 5 ppm (25 mg/m3), STEL 10 ppm (50 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 5 ppm; ACGIH TLV: TWA 5 ppm, STEL 10 ppm (adopted).
안정성
Stable. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides, chloroformates, halogens. Combustible.
InChIKey
JLTDJTHDQAWBAV-UHFFFAOYSA-N
CAS 데이터베이스
121-69-7(CAS DataBase Reference)
NIST
Benzenamine, N,N-dimethyl-(121-69-7)
IARC
3 (Vol. 57) 1993
EPA
N,N-Dimethylaniline (121-69-7)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N
위험 카페고리 넘버 61-20/21-51/53-40-23/24/25
안전지침서 53-45-61-36/37-28A-28
유엔번호(UN No.) UN 2253 6.1/PG 2
WGK 독일 3
RTECS 번호 BX4725000
F 고인화성물질 8
자연 발화 온도 370 °C DIN 51794
TSCA Yes
HS 번호 2921 42 00
위험 등급 6.1
포장분류 II
유해 물질 데이터 121-69-7(Hazardous Substances Data)
독성 LD50 orally in rats: 1.41 ml/kg (Smyth)
기존화학 물질 KE-05-0532
유해화학물질 필터링 97-1-183
함량 및 규제정보 물질구분: 유독물질; 혼합물(제품)함량정보: 알킬 아닐린 및 그 염류를 25% 이상 함유한 혼합물
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H227 가연성 액체 인화성 액체 구분 4 경고 P210, P280, P370+P378, P403+P235,P501
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 P264, P270, P301+P310, P321, P330,P405, P501
H311 피부와 접촉하면 유독함 급성 독성 물질 - 경피 구분 3 위험 P280, P302+P352, P312, P322, P361,P363, P405, P501
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 P264, P280, P305+P351+P338,P337+P313P
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H336 졸음 또는 현기증을 일으킬 수 있음 특정표적장기 독성 물질(1회 노출);마취작용 구분 3 경고 P261, P271, P304+P340, P312,P403+P233, P405, P501
H341 유전적인 결함을 일으킬 것으로 의심됨 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 생식세포 변이원성 물질 구분 2 경고 P201,P202, P281, P308+P313, P405,P501
H351 암을 일으킬 것으로 의심됨 (노출되어도 암을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 발암성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
H370 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴(노출되어도 특정 표적장기 독성을 일으키지 않는다는 결정적인 노출경로가 있다면 노출경로를 기재) 특정 표적장기 독성 - 1회 노출 구분 1 위험 P260, P264, P270, P307+P311, P321,P405, P501
H372 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킴 특정 표적장기 독성 - 반복 노출 구분 1 위험 P260, P264, P270, P314, P501
H411 장기적 영향에 의해 수생생물에 유독함 수생 환경유해성 물질 - 만성 구분 2
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P210 열·스파크·화염·고열로부터 멀리하시오 - 금연 하시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P273 환경으로 배출하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P311 의료기관(의사)의 진찰을 받으시오.
P391 누출물을 모으시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
P307+P311 노출된 경우,독성 물질 센터 또는 의사에게 전화하기
P370+P378 화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
2
3 0

N,N-디메틸아닐린 C화학적 특성, 용도, 생산

화학적 성질

Straw to brown-colored oily liquid with a characteristic amine-like odor. Odor threshold concentration is 13 ppb (quoted, Amoore and Hautala, 1983).

물리적 성질

Straw to brown-colored oily liquid with a characteristic amine-like odor. Odor threshold concentration is 13 ppb (quoted, Amoore and Hautala, 1983).

용도

N,N-Dimethylaniline is used in production of dyestuffs, as a solvent, a reagent in methylation reactions, and a hardener in fiberglass reinforced resins.

용도

Intermediate in the manufacture of dyes; solvent; rubber vulcanizing agent and stabilizer

용도

Solvent; manufacture of vanillin, Michler's ketone, methyl violet and other dyes. As reagent for methanol, methyl furfural, H2O2, nitrate, alcohol, formaldehyde.

정의

ChEBI: A tertiary amine that is aniline in which the amino hydrogens are replaced by two methyl groups.

생산 방법

N,N-Dimethylaniline is made by heating aniline, methyl alcohol and sulfuric acid under pressure, followed by hydrolysis of the sulfate formed with sodium hydroxide to the free base (Windholz et al 1983). United States production in 1975 was estimated at 4,600 metric tons (HSDB 1989).

일반 설명

A yellow to brown colored oily liquid with a fishlike odor. Less dense than water and insoluble in water. Flash point 150°F. Toxic by ingestion, inhalation, and skin absorption. Used to make dyes and as a solvent.

공기와 물의 반응

Insoluble in water.

반응 프로필

Explosive decomposition occurred when finely divided benzoyl peroxide was allowed to react with N,N-Dimethylaniline by breaking an ampoule containing 0.5 grams of dimethylaniline in an autoclave, NFPA 491M, 1991. This result may be expected with other peroxides and various oxidants.

건강위험

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

건강위험

Clinical signs of intoxication with N,N-dimethylaniline in man are headaches, cyanosis, dizziness, labored breathing, paralysis and convulsions (HSDB 1989). It is absorbed through the skin to produce a dangerous methemoglobinemia (Gosselin 1984). Treatment is similar to that of aniline with the object of managing methemoglobinemia.

화재위험

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

공업 용도

N,N-Dimethylaniline is used as chemical intermediate in the manufacturing of vanillin, Michler's ketone, and dyes such as Acid Red 2, Basic Green 4 and Basic Violet 1 (Northcott 1978). It is also used as a solvent and an activator for polyesters and as an alkylating agent (Beard and Noe 1981). It is used as an acid scavenger or accepter in the manufacture of beta-lactam antibiotics such as penicillin and cephalosporin (Nachtmann and Gstrein 1981).

Safety Profile

Suspected carcinogen with equivocal tumorigenic data. Human poison by ingestion. Moderately toxic by inhalation and skin contact. A skin irritant. Human systemic effects by ingestion: nausea or vomiting. Physiological action is similar to, but less toxic than, adne. A central nervous system depressant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. Explodes on contact with benzoyl peroxide or disopropyl peroxydicarbonate. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits htghly toxic fumes of adne and NOx. See also ANILINE.

Carcinogenicity

A 2-year corn oil gavage bioassay conducted by NTP in F344/N rats (0.3 or 30 mg/kg) and B6C3F1 mice (0, 15, or 30 mg/kg) for 103 weeks concluded that there was some evidence of carcinogenic activity for male F344/N rats as indicated by the increased incidences of sarcomas or osteosarcomas in the spleen; there was no evidence of carcinogenic activity in the female rats or male mice; there was equivocal evidence of carcinogenic activity for female mice as indicated by an increased incidence of squamous cell papillomas of the forestomach. Both rats and mice could have tolerated doses higher than those used in these studies.

환경귀착

Photolytic. A rate constant of 1.48 x 10-10 cm3/molecule?sec was reported for the reaction of N,N-dimethylaniline and OH radicals in air at room temperature (Atkinson et al., 1987).
Chemical/Physical. Products identified from the gas-phase reaction of ozone with N,Ndimethylaniline in synthetic air at 23 °C were: N-methylformanilide, formaldehyde, formic acid, hydrogen peroxide, and a nitrated salt having the formula: [C6H6NH(CH3)2]+NO3 - (Atkinson et al., 1987). Reacts with acids forming water-soluble salts.

신진 대사

Ν,Ν-Dimethylaniline undergoes N-demethylation, N-oxidation, and ring hydroxylation in animals. Urinary metabolites produced by dogs and rabbits injected with this compound included 4-aminophenol, 4-dimethylaminophenol, 2-aminophenol and N-methylaniline (Williams 1959; Kiese and Renner 1974). N-oxidation, N-demethylation and ring hydroxylation of Ν,Ν-dimethylaniline was demonstrated in vitro using liver microsomal preparations from pigs, rats, rabbits, chickens, and guinea pigs (Fish et al 1955; Zeigler and Pettit 1964, 1966; Abou-Donia and Menzel 1968). N-oxidation was also demonstrated using whole homogenate of human liver (Zeigler and Gold 1971; Rane 1974). Evidence has been obtained with rabbit liver microsomes for two pathways for Ν,Ν-dimethylaniline N-oxidation (Hlavica and Kehl 1977). One pathway involves cytochrome P-450 while the second makes use of flavin-containing monooxygenase. N,N-Dimethylaniline was also metabolized to formaldehyde in the nasal and respiratory mucosa of Fischer 344 rats (McNulty et al 1983). Alveolar type II cells from rabbit and rat lungs catalyzed the N-oxidation of this compound (Devereux and Fouts 1974; Ohmiya and Mehendale 1981). The microsomal preparation from rat seminal vesicles when fortified with arachidonic acid catalyzed the dealkylation of N,Ndimethylaniline (Sivarajah et al 1982).

Purification Methods

Primary and secondary amines (including aniline and monomethylaniline) can be removed by refluxing for 4-5hours with excess acetic anhydride, and then fractionally distilling. Crocker and Jones (J Chem Soc 1808 1959) used four volumes of acetic anhydride, then distilled off the greater part of it, and dissolved the residue in ice-cold dilute HCl. Non-basic materials were removed by ether extraction, then the dimethylaniline was liberated with ammonia, extracted with ether, dried, and distilled under reduced pressure. Metzler and Tobolsky (J Am Chem Soc 76 5178 1954) refluxed with only 10% (w/w) of acetic anhydride, then cooled and poured it into excess 20% HCl, which, after cooling, was extracted with diethyl ether. (The amine hydrochloride remains in the aqueous phase.) The HCl solution was cautiously made alkaline to phenolphthalein, and the amine layer was drawn off, dried over KOH and fractionally distilled under reduced pressure, under nitrogen. Suitable drying agents for dimethylaniline include NaOH, BaO, CaSO4, and CaH2. Other purification procedures include the formation of the picrate (m 163o from Me2CO or EtOH/H2O), prepared in *benzene solution and crystallised to constant melting point, then decomposed with warm 10% NaOH and extracted into ether: the extract was washed with water and distilled under reduced pressure. The oxalate salt has also been used for purification. The base has been fractionally crystallised by partial freezing and also from aqueous 80% EtOH then from absolute EtOH. It has been distilled from zinc dust, under nitrogen. [Beilstein 12 H 141, 12 I 151, 12 II 2, 12 III 245, 12 IV 243.]

N,N-디메틸아닐린 준비 용품 및 원자재

원자재

준비 용품


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