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N,N-디에틸아닐린

N,N-Diethylaniline

HCID 7061
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
91-66-7
표준 SMILES
CCN(CC)c1ccccc1
InChIKey
GGSUCNLOZRCGPQ-UHFFFAOYSA-N
분자식
C10H15N
평균 분자량
149.23 g/mol
단동위원소 질량
149.12044948

개요

N,n-diethylaniline appears as a colorless to yellow liquid with a fishlike odor, that is strongly corrosive. Irritating to skin, eyes and mucous membranes and moderately toxic by inhalation, absorption and ingestion. Flash point 185 °F. Used in dyes and in the production of organic chemicals.

이름 및 식별자

우선 이름
N,N-Diethylaniline
IUPAC
N,N-diethylaniline
현지명
N,N-디에틸아닐린
영어명
N,N-Diethylaniline
분자식
C10H15N
분자량
149.23

이름 및 동의어

N,N-DIETHYLANILINE91-66-7DiethylanilineDiethylphenylamineN,N-DiethylanilinBenzenamine, N,N-diethyl-PhenyldiethylamineAniline, N,N-diethyl-DiaethylanilinN,N-DiethylbenzenamineN,N-DiethylaminobenzeneN-Phenyldiethylamine
이름 더 보기
N,N-다이에틸아닐린Diethylphenylamine,N-PHENYLDIETHYLAMINE,N,N-디에틸아닐린N,N-디에틸아닐린(다이에틸아미노)벤젠N,N-다이에틸벤젠아민N,N-다이에틸아미노벤젠N,N-다이에틸페닐아민N,N-디에틸벤젠아민N,N-디에틸아미노벤젠N-페닐디에틸아민다이에틸아닐린다이에틸페닐아민디에틸아미노-벤젠DEAN,N-DIETHYLANILINE, 98%N,N-DIETHYLANILINE, 98%N,N-DIETHYLANILINE, 98%N, ≥99%(GC)
(diethylamino)benzeneDTXSID80218001WR1HJ2PGWNSC-7205DTXCID701800RefChem:161183N,N-DEA202-088-8

데이터베이스 식별자

CAS
91-66-7
PubChem CID
7061
DTXSID
DTXSID8021800
ChEMBL
CHEMBL252071
UNII
1WR1HJ2PGW
EC Number
202-088-8
Nikkaji
J3.559I

물성

구조 계산 물성

XLogP
3.3
극성 표면적
3.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
3
무거운 원자 수
11
형식 전하
0
복잡도
91

실험 및 물리화학적 성질

Chemical Classes · 2건

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3건

log Kow= 3.31

3.31

3.11

Density · 4건

0.906 (USCG, 1999) - Less dense than water; will float

0.9307 @ 20 °C/4 °C

Relative density (water = 1): 0.93

0.9307 @ 20°C

Color/Form · 2건

Colorless to yellow liquid

BROWN OILY LIQUID

Solubility · 5건

less than 1 mg/mL at 76.1 °F (NTP, 1992)

1 g dissolves in 70 ml of water at 12 °C; slightly sol in alcohol, chloroform and ether

Sol in acetone

In water, 139 mg/l @ 25 °C

Solubility in water, g/100ml at 25 °C: 0.014

Flash Point · 3건

185 °F (NTP, 1992)

185 °F (85 °C) (CLOSED CUP)

79 °C c.c.

Boiling Point · 3건

419.9 °F at 760 mmHg ; 198 °F at 10 mmHg (NTP, 1992)

안전 및 규제

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

GHS 분류

GHS Classification · 6건

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.2% (1 of 421) of reports.

Danger

H301 (99.8%): Toxic if swallowed [Danger Acute toxicity, oral]

유해성 정보

Regulatory Information · 6건

Chemical: Benzenamine, N,N-diethyl-

Hazard Traits - Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Neurotoxicity

Benzenamine, N,N-diethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N,N-diethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: N,N-diethylaniline (EC: 202-088-8)

Diethylaniline: Does not have an individual approval but may be used under an appropriate group standard

The 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.)

DOT LabelPoison
Fire Hazards · 3건

Special Hazards of Combustion Products: Emits toxic fumes under fire conditions. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79 °C explosive vapour/air mixtures may be formed.

Health Hazards · 2건

May be fatal if inhaled, swallowed or absorbed through the skin. Vapor or mist is irritant to the eyes, mucous membranes, upper respiratory tract; causes skin irritation. Absorption into the body leads to the formation of methemoglobin which, in sufficient concentration, may cause cyanosis. Onset may be delayed 2-4 hours or longer. Exposure can cause nausea, dizziness, headache, damage to the eyes, and blood effects. (USCG, 1999)

화학 및 산업

약리 정보

Metabolism/MetabolitesIN RAT LIVER MICROSOMES N-DEALKYLATION OCCURRED DURING MICROSOMAL METABOLISM OF N,N-DIALKYLANILINES. N-OXIDATION WAS FOUND WITH N,N-DIETHYLANILINE ONLY.
Absorption, Distribution and Excretion · 2건

IT IS READILY ABSORBED THROUGH INTACT SKIN ...

... Readily absorbed ... by inhalation of vapors.

용도 및 제조

Uses · 3건

Used to make pharmaceuticals and dyes; [HSDB]

USED IN SYNTH OF PHARMACEUTICALS

Chem int for dyes and for other organic syntheses

U.S. Imports · 2건

(1977) 1.50X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 2.11X10+8 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3건

2023: 220,460 lb

(1977) 9.62X10+8 GRAMS

(1979) 1.16X10+9 GRAMS

Industry UsesIntermediate
Methods of Manufacturing · 2건

REACTION OF ANILINE WITH ETHANOL AT HIGH PRESSURE WITH AN ACID CATALYST

...by ethylation of aniline: Whitman, US patent 2,501,556 (1950 to Du Pont); Voltz, J Org Chem 22, 48 (1957). Closson et al, J Org Chem 22, 646 (1957); Horyna, Cerny, Coll Czech Chem Commun 21, 906 (1956); from bromobenzene, sodium azide plus diethylamine: Bunnett, Brotherton, J Org Chem 22, 832 (1957).

Formulations/PreparationsGrade: Technical
General Manufacturing Information · 3건

Miscellaneous Manufacturing

Benzenamine, N,N-diethyl-: ACTIVE

INSECT REPELLING SUBSTANCE, N,N-DIETHYLANILINE WAS WORKED UP WITH POLYETHYLENE GLYCOL, POLYVINYL ALCOHOL, ETHOXYLATED ALCOHOLS, & CELLULOSE DERIVATIVES TO LOTIONS OR OINTMENTS APPLICABLE TO SKIN. THE COMPOSITION IS READILY WASHED OFF AFTER USE.

관련 반응

690건
반응 기록 만들기
HRID 8714 반응식
HRID 8714반응물로uspto-grants-2006_08
HRID 10185 반응식
HRID 10185반응물로uspto-grants-2006_08
HRID 10236 반응식
HRID 10236반응물로uspto-grants-2006_08
HRID 16427 반응식
HRID 16427반응물로uspto-grants-2010_06
HRID 26039 반응식
HRID 26039반응물로uspto-grants-1979_04
HRID 27026 반응식
HRID 27026반응물로uspto-grants-1980_09
HRID 27142 반응식
HRID 27142반응물로uspto-grants-1980_09
HRID 34453 반응식
HRID 34453용매로uspto-grants-1988_08
1 / 87 페이지

화합물 노트

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216.3 °C

216.3 °C @760 [mm Hg]

Decomposition · 2건

When heated to decomposition it emits toxic fumes of nitroxides.

215 °C

Melting Point · 4건

-37.8 °F (NTP, 1992)

-38.8 °C

-38 °C

-38.8 °C

Vapor Density · 2건

1.0 (AIR= 1)

Relative vapor density (air = 1): 5.1

Vapor Pressure · 4건

1 mmHg at 121.5 °F (NTP, 1992)

0.13 [mmHg]

0.14 mm Hg @ 25 °C

Vapor pressure, Pa at 20 °C: 19

물리화학적 성질

녹는점
-38 °C · -38 °C
끓는 점
217 °C · 217 °C(lit.)
밀도
0.938 g/mL · 0.938 g/mL at 25 °C(lit.)
증기 밀도
5.2 · 5.2 (vs air)
증기압
1 mm · 1 mm Hg ( 49.7 °C)
굴절률
20 · n20/D 1.542(lit.)
인화점
208 °F · 208 °F
저장 조건
30 °C · Store below +30°C.
용해도
12 °C에서 · 물: 12°C에서 70ml에 1g이 녹습니다.
산도 계수 (pKa)
6.61 · 6.61(at 22℃)
물리적 상태
액체
색상
맑은 노란색
수소이온지수(pH)
8 · 8 (0.1g/l, H2O, 20℃)
폭발한계
1.1 · 1.1-5.3%(V)
수용성
14 g/L · 14g/L(12℃)
Merck
14 · 14,3114
BRN
742483 · 742483
Henry's Law Constant
6.7 · 6.7×10-2 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
5.5 · 5.5(19℃)
안정성
안정적인. 타기 쉬운. 강한 산화제, 강산과 호환되지 않습니다.
InChI
1S/C10H15N/c1-3-11(4-2)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3
InChIKey
GGSUCNLOZRCGPQ-UHFFFAOYSA-N
SMILES
CCN(CC)c1ccccc1
LogP
3.904 at · 3.904 at 25℃
NIST
Benzenamine, N,N-diethyl-(91-66-7)
EPA
N,N-Diethylaniline (91-66-7)

화학적 성질

N,N-Diethylaniline is a pale yellow liquid. It is slightly soluble in water (1.40 g/L at 12°C), and soluble in alcohol and ether.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1건

A skin and eye irritant; May be absorbed through skin; Can induce methemoglobinemia; May cause anemia; [ICSC] A skin, eye, mucous membrane, and upper respiratory tract irritant; Can induce methemoglobinemia; [CAMEO] An irritant; [MSDSonline] See Aniline.

DOT ID and Guide2432 153
Reactive GroupAmines, Aromatic
EC ClassificationSymbol: T, N; R: 23/24/25-33-51/53; S: (1/2)-28-37-45-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Reactivity Profile · 1건

N,N-DIETHYLANILINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Chemical DangersDecomposes on heating. This produces toxic fumes including nitrogen oxides.
Packaging and LabellingDo not transport with food and feedstuffs.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4건

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

Accidental Release Measures · 2건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Safe StorageStore in an area without drain or sewer access. Well closed. Separated from food and feedstuffs.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresIf material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Keep run-off water out of sewers and water sources.
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
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.

Spillage Disposal · 1건

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 2건

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.

Personnel protection: Keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material.

Isolation and Evacuation · 2건

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,500(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that N,N-diethylaniline is expected to have low mobility in soil(SRC). A pKa value of 6.57(4) suggests that N,N-diethylaniline will exist partially in the protonated form in moist soils and the protonated form of N,N-diethylaniline is expected to bind strongly to soil surfaces(SRC). Volatilization of N,N-diethylaniline from moist soil surfaces is expected to be an important fate process for the neutral species(SRC) given an estimated Henry's Law constant of 1.9X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 0.14 mm Hg(5) and water solubility of 139 mg/l(6) at 25 °C. N,N-Diethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). N,N-Diethylaniline achieved 0% of the theoretical BOD in a sewage sludge test during a 5 day incubation period and was considered persistent(7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,500(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that N,N-diethylaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.9X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 0.14 mm Hg(4) and water solubility of 139 mg/l(5) at 25 °C. Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 6.5 days, respectively(SRC). A pKa of 6.57(6) suggests that N,N-diethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of N,N-diethylaniline is not expected to volatilize from water. According to a classification scheme(7), BCF values of 17-161 measured in carp(8) suggest bioconcentration in aquatic organisms is low to high. N,N-Diethylaniline achieved 0% of the theoretical BOD in a sewage sludge during a 5 day incubation period and was considered persistent(9). Using the Japanese MITI test, N,N-diethylaniline achieved 0% of theoretical BOD in an acclimated study during a 4 week incubation(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-diethylaniline, which has a vapor pressure of 0.14 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N,N-diethylaniline 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 hours(SRC), calculated from its estimated rate constant of 1.6X10-10 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, by ingestion and through the skin.
Signs and Symptoms · 4건

Blue lips, fingernails and skin. Convulsions. Dizziness. Laboured breathing. Vomiting. Symptoms may be delayed.

Redness. MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

See Inhalation.

Effluent ConcentrationsN,N-Diethylaniline was detected in the effluent of a publicly owned treatment works in NJ at a concn of 3 ppb(1) and at 2 mg/l in the retort water fraction from a shale oil facility(2).
ICSC Environmental Data · 1건

The substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur along the food chain. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment.

Soil Adsorption/Mobility · 1건

A pKa value of 6.57(1) suggests that N,N-diethylaniline will exist partially in the protonated form in moist soils and the protonated form of N,N-diethylaniline is expected to bind strongly to soil surfaces(SRC). The Koc of N,N-diethylaniline is estimated as 1,500(SRC), using a log Kow of 3.31(2) and a regression-derived equation(3). According to a classification scheme(4), this estimated Koc value suggests that N,N-diethylaniline is expected to have low mobility in soil.

TSCA Test Submissions · 2건

Developmental toxicity of diethylaniline was evaluated in groups of 24 pregnant CD rats fed dose levels of 0, 50, 250, or 500 mg/kg bw/day, by gavage, on gestation days 6-15, followed by fetal examination on gestation day 20. The treatment killed 0, 0, and 5 rats in the low-, mid-, and high-dose groups, respectively. Symptoms of maternal toxicity that were observed in all dose groups included decreased body weight gain and food consumption, and excessive salivation; rats in the mid- and high- dose groups also had excessive lacrimation and staining of the skin/fur in the ano-genital region. The treatment was fetotoxic (reduced fetal weight gain and retarded sternebral ossification), but not embryotoxic or teratogenic, at the high-dose level. The treatment was not embryotoxic, fetotoxic, or teratogenic at the low- and mid-dose levels.

Developmental toxicity of diethylaniline was evaluated in groups of 5 pregnant Sprague-Dawley CD rats fed dose levels of 0, 100, 250, 500, 750, 1000, 1500, or 2000 mg/kg bw/day, by gavage, on gestation days 6-15, followed by fetal examination on gestation day 20. The treatment killed 0, 0, 0, and 4 rats in the 100, 250, 500, and 750 mg/kg dose groups, respectively. All rats in the 1000, 1500, and 2000 mg/kg dose groups died by gestation day 7, after receiving 1-2 treatments; embryotoxic, fetotoxic, and teratogenic effects could not be evaluated in those groups. Symptoms of maternal toxicity in surviving dams included decreased body weight gain and food consumption (100, 250, 500, and 750 mg/kg), and staining of the fur in the ano-genital region (250, 500, and 750 mg/kg). Gross necropsy revealed discolored lungs in some dams at all dose levels. The treatment was not embryotoxic (rate of uterine implantation was normal) or teratogenic at any dose level, but was fetotoxic (reduced fetal weight gain) at 500 and 750 mg/kg.

Human Toxicity ExcerptsPOISONING MAY ... OCCUR THROUGH INHALATION OF VAPORS. ... HAZARDS MAY BE CONSIDERED AS SIMILAR TO THOSE OF ANILINE.
Artificial Pollution SourcesN,N-Diethylaniline's production and use in the synthesis of dyes(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1건

N,N-Diethylaniline, present at 100 mg/l, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). N,N-Diethylaniline achieved 0% of the theoretical BOD in a sewage sludge during a 5 day incubation period and was considered persistent(2).

Environmental Bioconcentration · 1건

BCF values of 44-161 were measured for carp exposed to 0.2 mg/l of N,N-diethylaniline for 8 weeks and BCF values of 17-125 were measured for carp exposed to 0.02 mg/l(1). According to a classification scheme(2), this BCF data suggests the potential for bioconcentration in aquatic organisms is low to high.

규제 정보

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
BX3400000
ridadr
UN 2432
독성
LD50 orally in Rabbit: 610 mg/kg LD50 dermal Rat > 5000 mg/kg
HS 번호
2921 42 00
risk_code
23/24/25-33-51/53
hazard_code
T,N
safety_code
28-37-45-61-28A
포장분류
III
위험 등급
6.1
기존화학 물질
KE-10434
F 고인화성물질
8
위험 참고 사항
Toxic
자연 발화 온도
500 °C
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Skin Irrit. 2STOT RE 2 Oral
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
91-66-7(Hazardous Substances Data)
함량 및 규제정보
물질구분: 유독물질; 혼합물(제품)함량정보: 알킬 아닐린과 그 염류 및 이를 25% 이상 함유한 혼합물
유해화학물질 필터링
97-1-183
응용 분야 · 2건

용도N,N-Diethylaniline is used in dyestuffs and in the synthesis of other intermediates and pharmaceuticals.

일반 설명A colorless to yellow liquid with a fishlike odor, that is strongly corrosive. Irritating to skin, eyes and mucous membranes and moderately toxic by inhalation, absorption and ingestion. Flash point 185°F. Used in dyes and in the production of organic chemicals.

상·하류 제품 정보

상류 원료

에틸알코올아닐린

하류 제품

4-Amino-2-chloro-6-methyl-5-nitropyrimidine2-Chloro-4,5-diaminopyrimidineN,N-디에틸-P-페닐렌디아민모노히드로클로라이드락톤4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine2,4-dichloropyrimidine-5-carbonitrile2-Methoxy-5-nitropyrimidin-4-amine2,4,6-Trichloropyrimidin-5-amine2,4-Dichloro-5-nitropyrimidineN,N-Diethyl-p-phenylenediamine sulfate4,6-Diamino-5-nitropyrimidine8-Hydroxy-7-methoxycoumarin스코폴레틴2-Chloro-5-nitropyrimidin-4-amineN-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide2,4-Dichloro-6-methyl-5-nitropyrimidine4,5-Diamino-6-methylpyrimidine2,4-Dichloro-5-cyanopyrimidine5-Bromo-2-chloro-4-(dimethylamino)pyrimidine2-브로모푸란6-Amino-5-nitropyrimidin-4-ol4,4'-벤질리덴비스[N,N-디에틸아닐린]XANTHOTOXOL2,4,6-Trichloro-5-nitropyrimidine2-Chloro(bromo)pyrimidine