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말로노니트릴

말로노니트릴
말로노니트릴 구조식 이미지
카스 번호:
109-77-3
한글명:
말로노니트릴
동의어(한글):
말로노나이트릴;말론니트릴;디시아노메탄;말로노니트릴;시아노아세토니트릴;프로판디니트릴
상품명:
Malononitrile
동의어(영문):
MDN;malonic;CH2(CN)2;usafkf-19;USAF KF-19;usafa-4600;MALONITRILE;USAF a-4600;MALONONITRILE;dicyanmethane
CBNumber:
CB2259712
분자식:
C3H2N2
포뮬러 무게:
66.06
MOL 파일:
109-77-3.mol

말로노니트릴 속성

녹는점
30-32 °C (lit.)
끓는 점
220 °C (lit.)
밀도
1.049 g/mL at 25 °C (lit.)
증기압
1 hPa (50 °C)
굴절률
1.4150
인화점
234 °F
저장 조건
2-8°C
용해도
133g/l
산도 계수 (pKa)
11(at 25℃)
물리적 상태
Crystalline Low Melting Mass
Specific Gravity
1.049
색상
White to yellow-brown
수소이온지수(pH)
pH : 4.5
수용성
13.3 g/100 mL (20 ºC)
Merck
14,5711
BRN
773697
노출 한도
TLV-TWA 8 mg/m3 (3 ppm) (NIOSH).
InChIKey
CUONGYYJJVDODC-UHFFFAOYSA-N
CAS 데이터베이스
109-77-3(CAS DataBase Reference)
NIST
Malononitrile(109-77-3)
EPA
Malononitrile (109-77-3)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N
위험 카페고리 넘버 23/24/25-50/53
안전지침서 23-27-45-60-61
유엔번호(UN No.) UN 2647 6.1/PG 2
WGK 독일 3
RTECS 번호 OO3150000
F 고인화성물질 8
자연 발화 온도 365 °C
TSCA Yes
위험 등급 6.1
포장분류 II
HS 번호 29269090
유해 물질 데이터 109-77-3(Hazardous Substances Data)
독성 LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)
기존화학 물질 KE-10262
유해화학물질 필터링 97-1-65
함량 및 규제정보 물질구분: 유독물질; 혼합물(제품)함량정보: 말로노니트릴 및 이를 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
H300 삼키면 치명적임 급성 독성 물질 - 경구 구분 1,2 위험 P264, P270, P301+P310, P321, P330,P405, 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
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 P264, P280, P302+P352, P321,P332+P313, P362
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H318 눈에 심한 손상을 일으킴 심한 눈 손상 또는 자극성 물질 구분 1 위험 P280, P305+P351+P338, P310
H331 흡입하면 유독함 급성 독성 물질 흡입 구분 3 위험 P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H400 수생생물에 매우 유독함 수생 환경유해성 물질 - 급성 구분 1 경고 P273, P391, P501
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 P273, P391, P501
예방조치문구:
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.
P272 작업장 밖으로 오염된 의복을 반출하지 마시오.
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.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P405 밀봉하여 저장하시오.
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.
NFPA 704
1
3 2

말로노니트릴 C화학적 특성, 용도, 생산

개요

Malonitrile is an aliphatic nitrile. It can release cyanide through either chemical or biological transformation. Malonitrile was used decades ago for treating certain forms of mental illness.

화학적 성질

Malononitrile may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.

화학적 성질

Solidified melt

화학적 성질

Malononitrile is a white powder or colorless, odorless crystalline substance.

용도

In organic synthesis.

용도

Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet

용도

The chemical properties of malononitrile are determined by the nucleophilicity of the malononitrile anion, formed by deprotonation with relatively weak bases and by the two electrophilic cyano groups.

용도

Malononitrile is used in organic synthesis.

정의

ChEBI: A dinitrile that is methane subtituted by two cyano groups.

생산 방법

Malononitrile is prepared by continuous introduction of preheated acetonitrile and cyanogen chloride into a tube reactor until the reaction mixture reaches a temperature of approximately 780°C.

일반 설명

A white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.

공기와 물의 반응

Soluble in water.

반응 프로필

Malononitrile is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].

위험도

Toxic by ingestion and inhalation.

건강위험

Metabolized by body to cyanide and thiocyanate; effects of inhalation of toxic fumes will be related to cyanide. Causes brain and heart damage related to lack of cellular oxygen. It is classified as extremely toxic. Probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful, for a 70 kg (150 lb.) person.

건강위험

In the late 1940's, malononitrile was used experimentally in the treatment of schizophrenia and depression. Patients were given an iv infusion of 5% malononi-trile for 10-69 min. The total dose during such treatments was 1-6 mg/kg and treatments were given 2-3 times/wk. Ten to twenty min after beginning infusion, all patients experienced tachycardia. In addition, redness, nausea, vomiting, headache, shivering, muscle spasms, and numbness were reported with varying frequency.

건강위험

Malononitrile is a highly toxic compound by all toxic routes. Its acute toxicity is somewhat greater than that of the aliphatic mononitriles, propionitrile, and butyronitrile. The increased toxicity may be attributed to the greater degree of reactivity in the molecule arising from two- CN functional groups. The acute toxic symptoms in test animals have not been well documented. An intraperitoneal dose of 10 mg/kg was lethal to rats.
LD50 value, intravenous (rabbits): 28 mg/kg
LD50 value, oral (mice): 19 mg/kg
Malononitrile is an eye irritant. The irritation from 5 mg in 24 hours was severe in rabbits’ eyes. There is no report of teratogenic and carcinogenic action in animals or humans.

화재위험

When heated to decomposition, Malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures.

공업 용도

Malononitrile is used primarily as an intermediate in the synthesis of drugs and vitamins (thiamine). It has also been employed in the manufacture of photosensitizes, acrylic fibers and dyestuffs and as an oil-soluble polar additive in lubricating oil.
Malononitrile was used formerly in treatment of various forms of mental illness such as alteration of psychic functions and schizophrenic disorders.

Safety Profile

Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. A severe eye irritant. Combustible when exposed to heat or flame. Polymerizes violently when heated to 130°C or on contact with strong base. May spontaneously explode when stored at 70-80°C. To fight fire, use water, fog, spray, foam. When heated to decomposition it emits toxic fumes of NOx and CN-. See also NITRILES.

잠재적 노출

Malononitrile is used in organic synthesis; as a lubricating oil additive; for thiamine synthesis; for pteridine-type anticancer agent synthesis; and in the synthesis of photosensitizers, acrylic fibers, and dyestuffs. It has also been used in the treatment of various forms of mental illness. It has been used as a leaching agent for gold

환경귀착

When heated to decomposition, nitriles may release cyanide. Malonitrile appears to decompose rapidly in contact with soil and sediment.

신진 대사

The in vitro metabolsim of malononitrile has been described by Stern et al. In the presence of thiosulphate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulphate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. Stern et al indicated that thiosulphate increased cyanide and thiocyanate formed from malononitrile in tissue slices.

운송 방법

UN2647 Malononitrile, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Purification Methods

Crystallise the nitrile from water, EtOH, *benzene or chloroform. Distil it in a vacuum from, and store over, P2O5. [Bernasconi et al. J Am Chem Soc 107 7692 1985, Gratenhuis J Am Chem Soc 109 8044 1987, Beilstein 2 IV 1892.]

Toxicity evaluation

The acute toxicity of malonitrile and related alkyl nitriles is thought to be due to release of cyanide through metabolism of the parent compound. Signs of acute malonitrile intoxication including dyspnea, ataxia, and convulsions are similar to those noted with acute cyanide intoxication. The onset and duration indicate that these nitriles require metabolism to elicit toxicity. Cyanide and thiocyanate have both been found in urine and blood after malonitrile exposure.

비 호환성

Incompatible with strong bases. May polymerize violently on prolonged heating @ 129C, or in contact with strong bases at lower temperatures. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

폐기물 처리

Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal

말로노니트릴 준비 용품 및 원자재

원자재

준비 용품

1,4,5,8-나프탈렌테트라카르복실산 2-Aminonicotinic acid 2-Amino-3-cyanopyridine 2-AMINO-6-CHLORO-3,5-DICYANOPYRIDINE 4-AMINO-1,2,5-OXADIAZOLE-3-CARBONITRILE 2-Chloro-4,6-dimethoxypyrimidine 5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER 2-AMINO-3-CYANO-4-METHYL-5-CARBMETHOXY THIOPHENE 2,4-DIAMINOPYRIMIDINE-5-CARBOXYLIC ACID 2-AMINO-3,5-DICYANOPYRIDINE 3-CYANO-7-ETHOXYCOUMARIN 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBONITRILE 2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE 2-AMINO-3-CYANO-4-CHLORO-5-FORMYLTHIOPHENE 2-AMINO-4-METHYL-QUINOLINE-3-CARBONITRILE 2,4,6-TRIAMINO-5-NITROPYRIMIDINE 2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE 2,4-DIAMINOPYRIMIDINE-5-CARBONITRILE 2,4,6-트리아미노피리미딘 3,5-Difluorophenylacetic acid 5-(AMINOMETHYL)PYRIMIDIN-4-AMINE [2-[4-(dihexylamino)-2-methylbenzylidene]benzo[b]thien-3(2H)-ylidene]malononitrile S,S-dioxide 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE 2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE Levosimendan 4,6-DIAMINO-2-MERCAPTOPYRIMIDINE 3-CYANO-7-METHOXYCOUMARIN 5-AMINO-4-ISOXAZOLECARBONITRILE 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBONITRILE 4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE 4-AMINOPYRIMIDINE-5-CARBONITRILE 4,6-Dimethyl-2-hydroxypyridine 5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE 4-Amino-6-methylpyrimidine-5-carbonitrile ,97% 4-AMINOPYRIMIDINE-5-CARBOXAMIDE 아짐설푸론 5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE Solvent Red 197

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