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2,4,6-콜리딘

2,4,6-Trimethylpyridine

HCID 7953
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
108-75-8
표준 SMILES
Cc1cc(C)nc(C)c1
InChIKey
BWZVCCNYKMEVEX-UHFFFAOYSA-N
분자식
C8H11N
평균 분자량
121.18 g/mol
단동위원소 질량
121.08914935

개요

Collidine appears as a clear colorless liquid. Less dense than water and insoluble in water. Hence floats on water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.

이름 및 식별자

우선 이름
2,4,6-Trimethylpyridine
IUPAC
2,4,6-trimethylpyridine
현지명
2,4,6-콜리딘
영어명
2,4,6-Collidine
분자식
C8H11N
분자량
121.18

이름 및 동의어

2,4,6-Trimethylpyridine108-75-82,4,6-COLLIDINEs-Collidinegamma-CollidinePyridine, 2,4,6-trimethyl-sym-Collidine2,4,6-Kollidinalpha,gamma,alpha'-Collidine7IE4BK5J5VNSC-460DTXSID1051561
이름 더 보기
2,4,6-콜리딘2,4,6-트리메틸피리딘g-Collidine2,4,6-CoLSYM COLLIDINE246CO246BD
RefChem:82156pyridine, 2,4,6-trimethylDTXCID5030113203-613-3COLLIDINE.gamma.-Collidine2,4,6-trimethyl-pyridineNSC 460

데이터베이스 식별자

CAS
108-75-8、29611-84-5
PubChem CID
7953
DTXSID
DTXSID1051561
ChEMBL
CHEMBL1209580
ChEBI
CHEBI:189131
UNII
7IE4BK5J5V
EC Number
203-613-3
Nikkaji
J5.079B

물성

구조 계산 물성보충 중

XLogP
1.9
극성 표면적
12.9 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
0
무거운 원자 수
9
형식 전하
0
복잡도
80.6

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Pyridines
SpringerMaterials PropertiesBoiling point
LogPlog Kow = 1.88
OdorAromatic odor
Density0.913 @ 20 °C/20 °C
Flavoring AgentsEU Flavoring substances
Color/FormColorless liquid
Solubility · 3건

Sol in methanol, ethanol, chloroform, benzene, toluene, and dil acids; miscible with ether

Sol in acetone

Sol in water (in g/100 ml water): 20.8 g @ 6 °C, 3.5 g @ 20 °C, 1.8 g @ 100 °C

Flash Point · 2건

58 °C

136 °F

Boiling Point170.4 °C
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides/.

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.5% (1 of 187) of reports.

Danger

H226 (99.5%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 187 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

유해성 정보

Regulatory Information · 4건

Chemical: Pyridine, 2,4,6-trimethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 16-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/32320

Pyridine, 2,4,6-trimethyl-: HSNO Approval: HSR001388 Approved with controls

DOT LabelFlammable Liquid
Fire HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Health HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Hazards Summary · 1건

Emergency treatment: Pyridine; Pyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppm; It can cause liver and kidney injury; [HSDB] [HSDB] A skin and strong eye irritant; [Alfa Aesar MSDS] See Pyridine.

Reactive GroupAmines, Phosphines, and Pyridines

화학 및 산업

약리 정보

Metabolism/MetabolitesMETABOLIC FATE OF PYRIDINES IS NOT COMPLETELY KNOWN. HYDROXYLATION, N-METHYLATION, OXIDN & CONJUGATION REACTIONS HAVE BEEN IDENTIFIED. /PYRIDINES/
Absorption, Distribution and ExcretionPYRIDINE & ITS ALKYL DERIV ARE ABSORBED FROM GI TRACT, IP CAVITY, & LUNGS. /PYRIDINE & ITS ALKYL DERIV/

용도 및 제조

Uses · 5건

Used as a chemical intermediate, dehydrohalogenation agent, tissue fixative for electron microscopy, and solvent for the manufacture of anthraquinones; [HSDB]

Chemical intermediate

Used as a chemical intermediate and as a dehydrohalogenation agent

TISSUE FIXATIVE FOR ELECTRON MICROSCOPY

SOLVENT FOR MANUFACTURE OF ANTHRAQUINONES (AS MIXTURE)

U.S. Imports · 2건

(1979) 6.09X10+6 GRAMS (MIXT OF COLLIDINES)

(1981) 1.70X10+6 GRAMS (MIXT OF COLLIDINES)

U.S. Production · 2건

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Methods of Manufacturing · 3건

Produced commercially from coal tar to some extent; also produced by Hantzsch pyridine synthesis: Hantzsch, Ann 215, 1 (1882); Mosher in Heterocyclic Compd vol 1, RC Elderfield, ed, (John Wiley, NY, 1950) pp 462-472...

Produced...from acetone and ammonia: Mosher in Kirk-Othmer Encyclopedia of Chemical Technology vol II (NY, 1953) p 287, Compare Durkopf, Ber 21, 2713 (1888); from paraldehyde, acetone, ammonium acetate, and ammonia water: German patent 349,267; FRDL 14, 539...

Produced...from 3,5-dimethyl-2-cyclohexen-1-one, ammonium acetate, and ammonia water: Frank, Meikle, J Am Chem Soc 72, 4184 (1950).

Formulations/PreparationsGrades: Technical (97.5% purity)

관련 반응

706건
반응 기록 만들기
HRID 992 반응식
HRID 992용매로uspto-grants-1998_03
HRID 2707 반응식
HRID 2707반응물로uspto-grants-1998_03
HRID 4003 반응식
HRID 4003반응물로uspto-grants-1988_02
HRID 4022 반응식
HRID 4022반응물로uspto-grants-1988_02
HRID 4030 반응식
HRID 4030반응물로uspto-grants-1988_02
HRID 4043 반응식
HRID 4043반응물로uspto-grants-1988_02
HRID 4061 반응식
HRID 4061반응물로uspto-grants-1988_02
HRID 4080 반응식
HRID 4080반응물로uspto-grants-1988_02
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
Melting Point
-44.5 °C

물리화학적 성질

녹는점
-44 · -44,5 °C
끓는 점
171 · 171–172 °C
밀도
0.92 · 0.92
증기압
4 hPa · 4 hPa (20 °C)
굴절률
1.5 · 1.50
인화점
58 °C · 58 °C
저장 조건
30 °C · Store below +30°C.
용해도
35 g/L · 35g/L
산도 계수 (pKa)
7.43 · 7.43(at 25℃)
물리적 상태
liquid
색상
colourless
냄새
Peculiar odor
수용성
35 g/L · 35g/L(20℃)
Merck
14 · 14,9718
BRN
107283 · 107283
Henry's Law Constant
1.1 · 1.1×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
1.9 · 1.9(20℃)
안정성
안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
InChI
1S/C8H11N/c1-6-4-7(2)9-8(3)5-6/h4-5H,1-3H3
InChIKey
BWZVCCNYKMEVEX-UHFFFAOYSA-N
SMILES
Cc1cc(C)nc(C)c1
LogP
1.25 at · 1.25 at 20℃
NIST
2 · Pyridine, 2,4,6-trimethyl-(108-75-8)
EPA
2 · 2,4,6-Trimethylpyridine (108-75-8)

화학적 성질

colourless liquid

Reactivity Profile · 1건

COLLIDINE neutralizes acids in exothermic reactions to form salts plus water. These acid-base reactions are exothermic. Incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate flammable gaseous hydrogen in combination with strong reducing agents such as hydrides.

Air and Water ReactionsFlammable. Insoluble in water.
Hazard Classes and Categories · 2건

Flam. Liq. 3 (99.5%)

Flammable liquids - Category 3

안전 및 보호

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
First AidExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Protective Action Criteria (PAC) · 3건

1.3 [ppm]

14 [ppm]

85 [ppm]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.9(2) and a regression-derived equation(3), indicates that 2,4,6-trimethylpyridine is expected to have moderate mobility in soil(SRC). The pKa of 2,4,6-trimethylpyridine is 7.4(4), indicating that this compound will mainly exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts, thus attenuating soil mobility(5). Volatilization of 2,4,6-trimethylpyridine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.8X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0 mm Hg(6), and water solubility, 3.5X10+4 mg/l(7). However, adsorption to soil is expected to attenuate volatilization(SRC). The potential for volatilization of 2,4,6-trimethylpyridine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 2.0 mm Hg(6). Under aerobic and anaerobic conditions, 2,4,6-trimethylpyridine, present at 1 mM, degraded 100% in >97 days at pH 7 using a 0.5% garden soil suspension with glucose-yeast extract (20 ppm) and a screening test(8). Within 2 weeks under aerobic conditions, 100% transformation of 2,4,6-trimethylpyridine occurred in soil previously contaminated with pyridine contaminants(9).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.9(2) and a regression-derived equation(3), indicates that 2,4,6-trimethylpyridine is expected to adsorb slightly to suspended solids and sediment(SRC). However, the pKa of 2,4,6-trimethylpyridine is 7.4(4), indicating that this compound will mainly exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.8X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.0 mm Hg(6), and water solubility, 3.5x10+4 mg/l(7). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.1 and 38 days, respectively(SRC). According to a classification scheme(8), an estimated BCF of 6(SRC), from its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Under aerobic and anaerobic conditions, 2,4,6-trimethylpyridine, present at 1 mM, degraded 100% in >97 days at pH 7 using a 0.5% garden soil suspension with glucose-yeast extract (20 ppm) and a screening test(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,6-trimethylpyridine, which has a vapor pressure of 2.0 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 2,4,6-trimethylpyridine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.3 days(SRC), calculated from its rate constant of 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Effluent Concentrations · 1건

The concn of 2,4,6-trimethylpyridine in Australian oil shale retort water (basic fraction) was 2 mg/l(1). The concn of 2,4,6-trimethylpyridine in condensate and process retort water produced in modified in situ oil-shale retort were 70.1 and 4.0 mg/l, respectively(2). In a closed system, 2,4,6-trimethylpyridine was detected in air above 1 of 3 samples of shale oil wastewaters (detection limit of 0.4 ng per 1 ml air)(3); a concn of 8.3 ng of 2,4,6-trimethylpyridine per 1 ml of air was measured above a 1 ml sample of wastewater with a concn of <0.8 ng/ml of 2,4,6-trimethylpyridine(3).

Soil Adsorption/Mobility · 1건

The Koc of 2,4,6-trimethylpyridine is estimated as 250(SRC), using a log Kow of 1.9(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4,6-collidine is expected to have moderate mobility in soil(SRC). The pKa of 2,4,6-trimethylpyridine is 7.4(4), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5).

Natural Pollution Sources2,4,6-Trimethylpyridine is found in small amounts in coal tar and shale oil(1).
Human Toxicity Excerpts · 5건

MAJOR ACTIONS OF PYRIDINE & ITS SIMPLE ALKYL DERIV ARE...NERVOUS SYSTEM DEPRESSION... /PYRIDINE & ITS ALKYL DERIV/

...PYRIDINE AND ITS DERIV CAUSE LOCAL IRRITATION ON CONTACT WITH SKIN, MUCOUS MEMBRANES AND CORNEA. /PYRIDINE & DERIVATIVES/

TRANSIENT SYMPTOMS OF NAUSEA, HEADACHE, INSOMNIA, NERVOUSNESS, & LOW BACK OR ABDOMINAL DISCOMFORT WITH URINARY FREQUENCY HAVE BEEN OBSERVED IN PERSONS WITH REPEATED EXPOSURES TO PYRIDINE IN CONCN VARYING FROM 15-330 PPM. /PYRIDINE/

...EXPOSURE TO...MIXT OF PYRIDINE, PICOLINE, LUTIDINE, & COLLIDINE...IN 2 MEN. BOTH HAD GI DISTURBANCES, & 1 HAD...LOSSES OF CONSCIOUSNESS...FACIAL PARALYSIS, ANISOCORIA, & ATAXIA. OTHER HAD HEADACHE... RIGHT-SIDE FACIAL PARALYSIS, & 2 DAYS LATER...PTOSIS...ANISOCORIA, & LEFT-SIDED ABDUCENS PARESIS.

...COLLIDINES, CAUSE SYMPTOMS RESEMBLING THOSE OBSERVED WITH PYRIDINE. THESE ARE LARGELY, NONSPECIFIC & INCL WEAKNESS, ATAXIA, DIARRHEA, & UNCONSCIOUSNESS. DELAYED DEATHS FOLLOWING SINGLE DOSE ARE UNCOMMON & SURVIVORS GENERALLY GAIN WT NORMALLY. /COLLIDINES/

Artificial Pollution Sources2,4,6-Trimethylpyridine's production and use as a chemical intermediate and as a dehydrohalogenation agent(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 2건

AEROBIC: 2,4,6-Trimethylpyridine, present at 1 mM, degraded 100% in >97 days at pH 7 using a 0.5% garden soil suspension with glucose-yeast extract (20 ppm) and a screening test(1). Within 2 weeks, 100% transformation of 2,4,6-trimethylpyridine occurred in soil previously contaminated with pyridine contaminants(2).

ANAEROBIC: 2,4,6-Trimethylpyridine, present at 1 mM, degraded 100% in >97 days at pH 7 using a 0.5% garden soil suspension with glucose-yeast extract (20 ppm) and a screening test(1).

Environmental Bioconcentration · 1건

An estimated BCF of 6 was calculated for 2,4,6-trimethylpyridine(SRC), using a log Kow of 1.9(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for 2,4,6-trimethylpyridine is estimated as 8.8X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2 mm Hg(1), and water solubility, 3.5X10+4 mg/l(2). This Henry's Law constant indicates that 2,4,6-trimethylpyridine is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 3.1 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 38 days(SRC). 2,4,6-Trimethylpyridine's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, the pKa of 2,4,6-trimethylpyridine is 7.4(4) which suggests that volatilization from water surfaces is expected to be attenuated slightly since ions are not expected to volatilize(SRC). 2,4,6-Trimethylpyridine is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Non-Human Toxicity Excerpts · 3건

THE AMINO DERIVATIVES, THE 2- & 4-VINYL DERIVATIVES, & COLLIDINE APPEAR TO BE THE MOST POTENT PRIMARY IRRITANTS OF THE /PYRIDINE/ SERIES.

...RANGE-FINDING STUDIES... /TABLE:/ APPROX LD50 (G/KG) RATS ORAL 0.4; IP 0.05-0.1. MICE ORAL 0.2-0.4; IP 0.1-0.2. APPROX LD50 (ML/KG) GUINEA PIGS PERCUTANEOUS 1.0-2.0. WHERE RANGE IS GIVEN, ALL ANIMALS DIED AT HIGH DOSE & ALL SURVIVED AT LOWER DOSE. WHERE SINGLE FIGURE IS GIVEN, APPROX 1/2 THE ANIMALS DIED AT THAT DOSE.

THREE OF THREE RATS DIED FOLLOWING EXPOSURE TO 2500 PPM FOR 2 HR. CONCENTRATED VAPOR PRODUCED BY BUBBLING AIR THROUGH COMPD AT ROOM TEMP. /FROM TABLE/

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of 2,4,6-trimethylpyridine with photochemically-produced hydroxyl radicals has been estimated as 7.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.3 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4,6-Trimethylpyridine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 3,5-Lutidine, a structurally similar alkylated pyridine, has a weak absorption band that extends into the environmental UV spectrum(3), which suggests that direct photolysis is not likely to be an important fate process for alkylated pyridines(SRC).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
UU0970000
ridadr
UN 1992 3/PG 3
독성
LD50 orally in Rabbit: 400 mg/kg
HS 번호
2933399090
risk_code
10-20/21/22-36/37/38
hazard_code
Xn
safety_code
26-36/37-36
포장분류
III
위험 등급
3
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
스토리지 클래스
3 - Flammable liquids
유해 물질 데이터
108-75-8(Hazardous Substances Data)
General Manufacturing InformationPyridine, 2,4,6-trimethyl-: ACTIVE
응용 분야 · 2건

용도2,4,6-Collidine is an reagent used for various synthetic preparations such as the synthesis of methylated pyridines by three-componet catalytic condensation of acetylene, acetone and ammonia.

일반 설명2,4,6-Trimethylpyridine is a pyridine derivative. It has a pK of 7.4. The product can react with trifluoroiodomethane in cyclopentane solution to afford 1:1 complex. This complex was investigated by NMR (Nuclear Magnetic Resonance) spectroscopy. Collidine-buffered osmium tetroxide solutions have been prepared by adding osmium tetroxide solution to it. These solutions have been used as fixative for electron microscopic studies.2,4,6-Trimethylpyridine can undergo oxidation with potassium permanganate to form 2,4,6-pyridinetricarboxylic acid.

제조 방법

한쯔쉬 파이리딘 중합체에 의해 생산될 경우 콜타르에서부터 어느정도까지는 상업적으로 생산됨 아세톤과 암모니아로부터 생산 3,5-다이메틸-2-사이클로헥센-1-일, 암모늄 아세트산, 암모니아수로부터 생산

상·하류 제품 정보

상류 원료

아세톤염화 아연요소벤젠오산화 인황산암모니아(가스)2,3,6-Trimethylpyridine1,2,4-트리메틸벤젠1,3,5-트라이메틸벤젠아세토나이트릴메틸 아세틸렌

하류 제품

4,6-Dimethyl-pyridine-2-carboxylic acid시클로펜텐온에스트론2.4.6-Trimethyl-3-nitropyridine

추가 설명

정의Methyl, ethyl, propyl, and trimethyl homologs of pyridine.