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옥살산디에틸

Diethyl Oxalate

HCID 7268
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
95-92-1
표준 SMILES
CCOC(=O)C(=O)OCC
InChIKey
WYACBZDAHNBPPB-UHFFFAOYSA-N
분자식
C6H10O4
평균 분자량
146.14 g/mol
단동위원소 질량
146.0579088

개요

Ethyl oxalate appears as a colorless liquid. Slightly denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes; may be mildly toxic by ingestion; may emit irritating fumes in a fire. Vapors are much heavier than air. Used as a solvent for plastics and in the manufacture of perfumes and pharmaceuticals.

이름 및 식별자

우선 이름
Diethyl Oxalate
IUPAC
diethyl oxalate
현지명
옥살산디에틸
영어명
Diethyl oxalate
분자식
C6H10O4
분자량
146.14

이름 및 동의어

DIETHYL OXALATE95-92-1Ethyl oxalateOxalic etherEthyl oxalate (VAN)NSC 8851Diethylester kyseliny staveloveDTXSID2044472HSDB 2131EINECS 202-464-1UNII-860M3ZWF6JDiethyl ester of oxalic acid
이름 더 보기
다이에틸옥살레이트디에틸옥살산옥살산디에틸디에틸옥살산다이에틸 옥살레이트디에틸옥살레이트OXALIC ACID DIETHYL ESTERDEOiethyl oxalateCeftriaxone Impurity 5GKSWoxalicetherEthyIoxalateDiethyl oxate
UN2525Diethylester kyseliny stavelove [Czech]BRN 0606350860M3ZWF6JETHYL OXOLATENSC-8851C2H5OCOCOOC2H5Ethanedioic acid, 1,2-diethyl ester

데이터베이스 식별자

CAS
95-92-1
PubChem CID
7268
DTXSID
DTXSID2044472
ChEMBL
CHEMBL3183226
UNII
860M3ZWF6J
EC Number
202-464-1
Nikkaji
J43.379I

물성

구조 계산 물성보충 중

XLogP
0.6
극성 표면적
52.6 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
10
형식 전하
0
복잡도
114

실험 및 물리화학적 성질

Chemical Classes · 2건

Other Classes -> Esters, Other

Flammable agents - 2nd degree

CosmeticsChelating; Plasticiser; Hair conditioning
SpringerMaterials PropertiesBoiling point
LogP0.56
OdorAROMATIC ODOR
Food AdditivesFood
Density · 2건

1.0785 @ 20 °C/4 °C

1.079 @ 20°C

Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS, OILY LIQUID
Solubility · 3건

SPARINGLY SOL IN WATER WHICH DECOMP IT GRADUALLY; MISCIBLE WITH USUAL ORG SOLVENTS

SOL IN ALL PROPORTIONS IN ALCOHOL, ETHER, ACETONE

MISCIBLE WITH ETHYL ACETATE

Flash Point · 2건

168 °F (NFPA, 2010)

안전 및 규제

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

GHS 분류

GHS Classification · 6건

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P337+P317, P363, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 6건

Chemical: Ethanedioic acid, diethyl ester

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

Ethanedioic acid, 1,2-diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioic acid, 1,2-diethyl ester 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)

Status: Active Update: 28-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14261

Diethyl oxalate: 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.)

Other Safety InformationIMAP assessments - Oxalate esters (C1-C4): Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2건

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

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

Fire Potential

화학 및 산업

약리 정보

Metabolism/MetabolitesETHYL OXALATE IS HYDROLYZED IN BODY TO FORM OXALIC ACID WHICH ACCOUNTS FOR ITS TOXIC ACTION.

용도 및 제조

Uses · 6건

Used to make pharmaceuticals, plastics, dyes, and dyestuff intermediates; Also used as a solvent for cellulose esters, ethers, resins, perfumes, and lacquers for electronics; [HSDB]

Semiconductor Manufacturing [Category: Industry]

MANUFACTURE OF PHENOBARBITAL, ETHYLBENZYL MALONATE, TRIETHYLAMINE, & SIMILAR CHEMICALS; MANUFACTURE OF PLASTICS, DYESTUFF INTERMEDIATES; SOLVENT FOR CELLULOSE ESTERS

ORGANIC SYNTHESES, ESP IN MFR OF PHARMACEUTICALS; SOLVENT FOR ETHERS & RESINS

RADIO TUBE CATHODE FIXING LACQUERS

SOLVENT FOR PERFUMES & FOR NATURAL & SYNTHETIC RESINS (CELLULOSE ESTERS); AGENT IN RADIO TUBE CATHODE FIXING LACQUERS; CHEM INT FOR PHARMACEUTICALS, PLASTICS & DYES

U.S. Exports · 2건

(1972) No Data

(1975) No Data

U.S. Imports · 2건

(1972) No Data

(1975) No Data

U.S. Production · 3건

2023: 70,547 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

Industry UsesSoil amendments (fertilizers)
Methods of Manufacturing · 3건

ESTERIFICATION OF OXALIC ACID WITH ETHANOL

PREPN: CLARKE, DAVIS, ORG SYN 2, 23 (1922); COLL VOL I, 256; KENYON, COLL VOL I, 258 (P 261 IN 2ND ED).

ETHYL OXALATE IS PRODUCED BY STANDARD ESTERIFICATION PROCEDURE, USING ETHYL ALCOHOL AND OXALIC ACID.

Use ClassificationCosmetics -> Chelating; Plasticiser; Hair conditioning

관련 반응

1,466건
반응 기록 만들기
HRID 1152 반응식
HRID 1152반응물로uspto-grants-1998_03
HRID 3963 반응식
HRID 3963반응물로uspto-grants-1988_02
HRID 5344 반응식
HRID 5344반응물로uspto-grants-1993_09
HRID 5353 반응식
HRID 5353반응물로uspto-grants-1993_09
HRID 6403 반응식
HRID 6403반응물로uspto-grants-1993_09
HRID 6404 반응식
HRID 6404반응물로uspto-grants-1993_09
HRID 6405 반응식
HRID 6405반응물로uspto-grants-1993_09
HRID 6406 반응식
HRID 6406반응물로uspto-grants-1993_09
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168 °F CC

Boiling Point · 2건

185.7 °C @ 760 MM HG

185.4 °C @760 [mm Hg]

물리화학적 성질

녹는점
-41 °C · -41 °C (lit.)
끓는 점
185 °C · 185 °C (lit.)
밀도
1.076 g/mL · 1.076 g/mL at 25 °C (lit.)
증기 밀도
5.03 · 5.03 (vs air)
증기압
1 mm · 1 mm Hg ( 47 °C)
굴절률
20 · n20/D 1.410(lit.)
인화점
168 °F · 168 °F
저장 조건
30 °C · Store below +30°C.
용해도
알코올, 에테르 및 기타 일반적인 유기 용매와 섞일 수 있습니다.
물리적 상태
액체
색상
투명한
폭발한계
0.42 · 0.42-2.67%(V)
수용성
분해될 수 있음
Merck
14 · 14,3125
BRN
606350 · 606350
Henry's Law Constant
4.5 · 4.5×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
8.2 · 8.2(21℃)
안정성
안정적이지만 습기에 민감합니다. 강한 산화제와 호환되지 않습니다.
화장품 원료 기능
킬레이팅가소제향기헤어 컨디셔닝용제
InChI
1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3
InChIKey
WYACBZDAHNBPPB-UHFFFAOYSA-N
SMILES
CCOC(=O)C(=O)OCC
LogP
0.56 · 0.560
NIST
Ethanedioic acid, diethyl ester(95-92-1)
EPA
Ethyl oxalate (95-92-1)

화학적 성질

A colourless, oily liquid with an aromatic odour. It is miscible with ethanol, ether, acetone, and other common organic solvents, but only slightly soluble in water.

· 3건

MODERATE WHEN EXPOSED TO HEAT OR FLAME

THIS ESTER IS A COMBUSTIBLE LIQ, BUT IT DOES NOT PRODUCE A FLAMMABLE CONCN OF VAPOR @ ROOM TEMP.

SOME ESTERS WITH HIGHER FLASH POINTS, LIKE...ETHYL OXALATE, ARE NOT SO DANGEROUS AT ROOM TEMP. THEY ARE NEVERTHELESS READILY IGNITED AS FLAMMABLE LIQ, & SOURCE OF IGNITION MUST NOT BE ALLOWED TO COME IN CONTACT WITH THEM.

Health Hazards · 2건

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards SummaryA strong skin and mucous membrane irritant; [Hawley] An eye irritant; [eChemPortal: ERMA; ESIS] An irritant; [MSDSonline]
DOT ID and Guide2525 156
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity Profile · 1건

ETHYL OXALATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides

DOT Emergency Guidelines · 5건

/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.

/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

For more DOT Emergency Guidelines (Complete) data for DIETHYL OXALATE (8 total), please visit the HSDB record page.

DOT Hazard Classification · 4건

Ethyl oxalate

UN2525

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG III: the degree of danger presented by the material is minor

안전 및 보호

Fire FightingExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
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

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresFOAM, CARBON DIOXIDE, DRY CHEMICAL
Storage Conditions · 2건

STORAGE TANKS CONTAINING FLAMMABLE ESTERS SHOULD BE SITUATED IN MOUNDED COMPOUND CONSTRUCTED TO RETAIN MAX QUANTITY OF LIQ THAT COULD ESCAPE FROM TANKS. /ESTERS/

...DRUMS & OTHER SMALLER RECEPTACLES CONTAINING ESTERS SHOULD BE KEPT IN /FIRE RESISTANT/ STOREROOM...WITH MOUNDED OR RAMPED DOORWAY TO PREVENT ESCAPE OF SPILLED LIQ. /ESTERS/

Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Preventive Measures · 3건

...PROVISION SHOULD BE MADE FOR REMOVAL OF VAPORS AS THEY ARE EVOLVED &...HEATING SHOULD NOT BE SUCH AS TO EXPOSE VAPOR TO OPEN FLAME. /ESTERS/

BEFORE HEAT (EG IN FORM OF WELDING OR CUTTING FLAME) IS USED TO CUT OR REPAIR A VESSEL THAT HAS CONTAINED ORGANIC ESTER, ANY SLUDGE...MUST BE REMOVED & VESSEL PURGED WITH STEAM TO INSURE THAT EXPLOSIVE CONCN OF VAPOR WILL NOT FORM IN COURSE OF WORK. /ESTERS/

ATMOSPHERE SHOULD BE TESTED FOR PRESENCE OF FLAMMABLE VAPOR & ONLY WHEN TESTING ESTABLISHES THAT VESSEL IS SAFE SHOULD HEAT BE APPLIED. /ESTERS/

Isolation and Evacuation · 2건

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Immediate precautionary measure

Protective Action Criteria (PAC) · 3건

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

Personal Protective Equipment (PPE) · 2건

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

EYE & FACE PROTECTION & RESPIRATORY PROTECTIVE EQUIPMENT SHOULD BE AVAILABLE...IN CASE OF EXPOSURE TO THESE ESTERS IN EMERGENCIES ASSOC, FOR EXAMPLE, WITH SERIOUS ESCAPE OF LIQUID. /ESTERS/

Emergency Response Planning Guidelines· Note: Most foams will react with the material and release corrosive/toxic gases.

독성 정보

Adverse EffectsNeurotoxin - Acute solvent syndrome
Human Toxicity Excerpts · 5건

...COMPLAINTS OF WEAKNESS, HEADACHE, AND NAUSEA, TOGETHER WITH EVIDENCE OF SOME SLIGHT ANEMIA AND LEUKOPENIA, NEUTROPENIA, AND EOSINOPHILIA WERE ENCOUNTERED IN WORKMEN WHO HAD BEEN EXPOSED FOR SEVERAL MONTHS TO CONCN OF 0.76 MG/L. ...SYMPTOMS REGRESSED WHEN EXPOSURE CEASED.

SYMPTOMATOLOGY: 1. BURNING PAIN IN THROAT, ESOPHAGUS, & STOMACH. ... 2. VOMITING...BURNING PAIN, SEVERE PURGING. 3. PULSE...WEAK, IRREGULAR... SOMETIMES IMPERCEPTIBLE. HYPOTENSION &...SIGNS OF CARDIOVASCULAR COLLAPSE APPEAR. 5. ...OLIGURIA, ALBUMINURIA, & HEMATURIA MAY PERSIST FOR WK. /OXALATE/

SYMPTOMATOLOGY: 4. IF DEATH IS DELAYED FOR FEW HR, NERVOUS OR NEUROMUSCULAR SYMPTOMS DEVELOP: HEADACHE, MUSCLE CRAMP (PARTICULARLY OF JAWS & EXTREMITIES), TETANY, SOMETIMES CONVULSIONS, STUPOR, COMA, & DEATH. /OXALATE/

WHILE EVIDENCE FOR TOXICITY...REMAINS OBSCURE, IT WOULD SEEM REASONABLE TO USE STRICT PRECAUTIONS TO AVOID PROLONGED INHALATION OR SKIN CONTACT...

STRONG IRRITANT TO SKIN AND MUCOUS MEMBRANES, ESP BY INGESTION.

Non-Human Toxicity Excerpts · 2건

DOSES OF 10 ML/KG ON GUINEA PIG SKIN CAUSED NO FATALITIES AND LITTLE IRRITATION.

RAT ORAL LD50 IS 0.4-1.6 G/KG WITH DISTURBANCE OF RESPIRATION AND MUSCLE TWITCHING NOTED AS PROMINENT SYMPTOMS. MASSIVE RENAL OXALATE DEPOSITS AND DILATATION OF TUBULES WERE SEEN AFTER ORAL DOSE OF 400 MG/KG IN RAT.

Probable Routes of Human ExposureNO CASES OF LETHAL POISONING FROM ETHYL OXALATE IN INDUSTRY ARE KNOWN, BUT ITS POTENTIAL TOXIC ACTION MUST BE TAKEN INTO CONSIDERATION.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
RO2800000
ridadr
UN 2525
독성
LD50 orally in Rabbit: 400 mg/kg
HS 번호
29171900
risk_code
22-36-68/21-48/25-35-61-60
hazard_code
Xn,T
safety_code
23-45-36/37/39-28-26-25-24-53
포장분류
III
위험 등급
6.1
기존화학 물질
KE-13158
자연 발화 온도
410 °C
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Skin Corr. 1BSTOT RE 2 Oral
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
95-92-1(Hazardous Substances Data)
General Manufacturing Information · 2건

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Ethanedioic acid, 1,2-diethyl ester: ACTIVE

응용 분야 · 2건

용도Diethyl oxalate is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates. It is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics. It is involved in the transesterification reaction with phenol to get dipheny oxalate. It is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives. Further, it is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine. In addition to this, it is utilized in the microemulsion synthesis of zinc oxide nanoparticles.

일반 설명Ethyl oxalate appears as a colorless liquid. Slightly denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes; may be mildly toxic by ingestion; may emit irritating fumes in a fire. Vapors are much heavier than air. Used as a solvent for plastics and in the manufacture of perfumes and pharmaceuticals.

제조 방법

생산 방법Diethyl oxalate is produced via esterification of ethanol and oxalic acid. It is a preferred solvent for cellulose acetate and nitrate.

상·하류 제품 정보

상류 원료

옥살산에틸알코올톨루엔Ethanol 95%메틸알콜

하류 제품

Ethyl 1-methyl-5-propyl-1H-pyrazole-3-carboxylate5-tert-Butyl-1H-pyrazole-3-carboxylic acid3-Phenyl-1H-pyrazole-5-carboxamide ,97%Ethyl 3-(3-chlorophenyl)-1H-pyrazole-5-carboxylate ,97%5-(3-클로로페닐)-1H-피라졸-3-카복실산Ethyl 5-(3-nitrophenyl)-1H-pyrazole-3-carboxylateEthyl 2,4-dioxoheptanoate5-플루오로인돌-2-카르복실 산3-(4-Methoxyphenyl)-1H-pyrazole-5-carboxamide ,97%1-Methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide ,97%에틸5-(2-FURYL)-1H-PYRAZOLE-3-CARBOXYLATE에틸5-메틸리속사졸-3-카르복실레이트에틸5-(tert-부틸)-2H-피라졸-3-카르복실레이트3-(4-클로로페닐)-1H-피라졸-5-탄수화물에틸A-에톡시옥살릴페닐아세테이트5-Chloroindole5-메틸-1H-피라졸-3-카르복실산수화물Ethyl 2,4-dioxovalerate2,2-dichloro-1-(4-ethyoxy phenyl)cy-clopropane carboxylic acid다이소듐크로몰린dimethyl 4-chloropyridine-2,6-dicarboxylate4-Fluoroindole5-(4-메톡시-페닐)-2H-피라졸-3-카르복실산에틸에스테르글리클라지드에틸5-티엔-2-일-1H-피라졸-3-카르복실레이트이마자목스 암모늄염1-메틸-3-프로피롤라졸-5-카복실산에틸3-(4-클로로페닐)-1H-피라졸-5-카르복실레이트Ethyl propionyl pyruvateEthyl 3-(5-methylfuran-2-yl)-1H-pyrazole-5-carboxylate ,97%Orotic acid monohydrate1-Methyl-5-propyl-1H-pyrazole-3-carboxylic acid5-페닐-2H-피라졸-3-카르복실산에틸에스테르에틸1,3-벤조티아졸-2-카르복실레이트메틸옥사아세트산디에틸에스테르5-메틸-1H-피라졸-3-카르복실산4-브로모-5-메틸-1H-피라졸-3-카르복실산첼리돈산Ethyl 2-(1-methyl-1H-imidazol-2-yl)-2-oxoacetate3-(tert-부틸)-1H-피라졸-5-카르보히드라지드