2,6-디클로로벤조니트릴

2,6-디클로로벤조니트릴 · 디클로베닐 · 다이클로베닐 · DICHLOBENIL · DICLOBENIL · SILBENIL · Benzonitrile, 2,6-dichloro- · H-133

식별자 및 물리적 특성

CAS No.	104809-79-2
분자식	C7H3Cl2N
평균 분자량	172.01 g/mol
단동위원소 질량	170.96425446 g/mol
SMILES	N#Cc1c(Cl)cccc1Cl
InChIKey	YOYAIZYFCNQIRF-UHFFFAOYSA-N
PubChem CID	3031
ChEMBL	CHEMBL3039332
ChEBI	CHEBI:943
EC No.	214-787-5
DTXSID	DTXSID5032365
현지명	2,6-디클로로벤조니트릴

화학 및 물리적 성질

XLogP	2.7
극성 표면적	23.8
수소 결합 공여자 수	0
수소 결합 수용자 수	1
회전 가능 결합 수	0
무거운 원자 수	10
형식 전하	0
복잡도	150
SpringerMaterials Properties	Fusion temperature
농약	HerbicidesActive substance -> EU Pesticides database: Not approvedPesticides -> Herbicides, NitrileEnvironmental transformation -> Pesticides (parent, predecessor)Pesticides -> Herbicides
LogP(분배 계수)	log Kow = 2.742.642.65
냄새	Aromatic odor
밀도	1.3 g/cm³1.4980 (rough estimate)
Color/Form	White crystalline solid
용해도	In water, 14.6 mg/L at 20 °CSolubility in solvents (w/v) (approx): acetone 5% at 8 °Cbenzene 5% at 8 °Ccyclohexanone 7% at 15-20 °Cethanol 5% at 8 °Cfurfural 7% at 8 °Cmethylene chloride 10% at 20 °Cmethylethylketone 7% at 15-20 °Ctetrahydrofuran 9% at 8 °Ctoluene 4% at 20 °Cxylene 5% at 8 °C.Solubility in water: none
Corrosivity	NON-CORROSIVE
인화점	Not Applicable. Not flammable. (USCG, 1999)270°C
끓는 점	518 °F at 760 mmHg (USCG, 1999)270 °C270-275 °C
Decomposition	When heated to decomposition it emits toxic fumes of /hydrogen chloride, hydrogen cyanide, and nitrogen oxides/.
녹는점	293 to 294.8 °F (USCG, 1999)144-145 °C145-146 °C143-146 °C(lit.)
증기압	0.14Pa at 25℃
굴절률	1.6000 (estimate)
저장 조건	Sealed in dry,Room Temperature
물리적 상태	powder
색상	흰색에서 거의 흰색
용해도	25mg/L(25℃)
Merck	14,3042
BRN	1909167
헨리 상수	4.8×10-1 mol/(m3Pa) at 25℃, Schoene and Steinhanses (1985)
주요 응용	농업환경
InChI	1S/C7H3Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H
InChIKey	YOYAIZYFCNQIRF-UHFFFAOYSA-N
SMILES	Clc1cccc(Cl)c1C#N
LogP(분배 계수)	2.7 at 20℃
NIST	2,6-Dichlorobenzoic acid nitrile(1194-65-6)
EPA	Dichlobenil (1194-65-6)

화학적 성질

2,6-Dichlorobenzonitrile [1194-65-6], 1- cyano-2,6-dichlorobenzene, Mr 172.02, mp 144.5 –146.5 ℃, is a colorless, crystalline substance. Its solubility in water is 10 ppm at 25℃. 2,6-Dichlorobenzonitrile is produced industrially by the ammoxidation of 2,6-dichlorotoluene. In addition the nitrile is obtained by oxidation or side-chain-chlorination of 2,6-dichlorotoluene via 2,6-dichlorobenzoic acid and 2,6-dichlorobenzaldehyde, respectively. 2,6-Dichlorobenzonitrile shows herbicidal activity (Casoron, Duphar) and is used in fruit and vine cultivation. It is also used as an intermediate in the production of 2,6-difluorobenzonitrile and of 2,6-dichlorothiobenzamide (Prefix, Shell) which shows herbicidal activity.

안전 및 규제

GHS 분류	WarningH312: Harmful in contact with skin [Warning Acute toxicity, dermal]P273, P280, P302+P352, P317, P321, P362+P364, P391, and P501 (click each P-code to see the statement)H312 (99%): Harmful in contact with skin [Warning Acute toxicity, dermal]
규제 정보	Commission Regulation (EC) No 1490/2002Dichlobenil is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)Status: Active Update: 26-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12680Dichlobenil: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
기타 안전 정보	IMAP assessments - Benzonitrile, 2,6-dichloro-: Environment tier I assessment
운송 라벨(DOT)	Class 9
화재 위험	Not flammable. (USCG, 1999)Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.
화재 가능성	The formulated product is nonflammable.
건강 유해성	SOLID: Harmful if swallowed. (USCG, 1999)Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
유해성 요약	A nitrile herbicide[Hayes, p. 771] Listed as potential inducer of chloracne[Rosenstock, p. 714] According to Recognition and Management of Pesticide Poisonings, it has an acute LD50 of greater than 4,460 mg/kg and has minimal toxic, irritant effects. [EPA Pesticides, p. 119] A major metabolite of the herbicide chlorthiamidCan be absorbed through skinMay cause chloracne[ICSC] Reports of chloracne in a manufacturing facility[HSDB] Causes hepatitis in animal experiments[Reference #1]The major hazards encountered in the use and handling of dichlobenil stem from its toxicologic properties as a pesticide. Dermal effects appear to be the most common: ranging from possible contact burns to the skin and eyes, to dermatitis, including chloracne. However, dichlobenil also may be fatal if sufficiently high doses are inhaled, swallowed, or absorbed through the skin. Breathing of dichlobenil's aromatic, off-white, crystaline dust, and its contact with skin or eyes should be avoided. Where avoidance is not possible, wear boots and protective clothing, gloves, and goggles (also, a positive pressure breathing apparatus in emergency situations). Remove and isolate contaminated clothing at the exposure site and wash exposed skin well with soap and water, particularly before smoking, eating or using toilet facilities. Formulated dichlobenil is nonflammable. However, when heated to decomposition, it may evolve highly toxic fumes including phosgene or cyanide. If dichlobenil is involved in a fire, extinguish the fire using an agent suitable for the type of surrounding material. Fire-control water should be diked, as necessary to prevent dichlobenil from entering water sources and sewers. While dichlobenil is non-corrosive and thermally stable, it nevertheless should be stored in a cool, dry place, in tightly closed containers, and away from alkalis, feed and feedstuffs. Containers of dichlobenil may be shipped via air, water, road, or rail. Small spills of dichlobenil should be carefully shovelled into a clean dry container (liquid dichlobenil is first absorbed by a non-combustible material, like sand) for later disposal. Large land spills should be deposited in excavated pits, ponds, or holding areas that have been sealed with an impermeable flexible membrane liner (solids also should be covered with plastic sheeting). Spills of dichlobenil in bodies of water, first may need to be treated with activated carbon ... Before permanent land disposal of dichlobenil, consult with environmental regulatory agencies.

용도

2,6-dichlorobenzonitrile in which Q-amino-G- chlorobenzonitrile is used as starting material. And it is used for the synthesis of diclofenac sodium oxacillin and guanabenz acetate.

일반 설명

2,6-Dichlorobenzonitrile is a white solid dissolved or suspended in a water-emulsifiable liquid carrier. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Can cause illness by inhalation, skin absorption and/or ingestion. Used as a herbicide.