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クロロ酢酸メチル

Methyl chloroacetate

HCID 7295
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
96-34-4
標準SMILES
COC(=O)CCl
InChIKey
QABLOFMHHSOFRJ-UHFFFAOYSA-N
分子式
C3H5ClO2
平均分子量
108.52 g/mol
単同位体質量
107.99780708

概要

Methyl chloroacetate appears as a crystalline solid or a solid dissolved in a liquid. Insoluble in water and denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

名称と識別子

優先名称
Methyl chloroacetate
IUPAC
methyl 2-chloroacetate
現地名
クロロ酢酸メチル
英語名
Methyl chloroacetate
分子式
C3H5ClO2
分子量
108.52

名称と別名

METHYL CHLOROACETATEmethyl 2-chloroacetateChloroacetic acid methyl esterMethyl monochloroacetateMethyl chloroethanoateAcetic acid, chloro-, methyl esterMethyl monochloracetateMethyl alpha-chloroacetateMonochloroacetic acid methyl esterNSC 2635UN2295ClH2CCOOCH3
名称をさらに表示
クロロ酢酸メチルメチルクロロアセタート2-クロロ-1-メトキシエタノン2-クロロ酢酸メチルメチルクロロアセテートメチル=クロロアセタートメチル=クロロアセタート, 1000 µg/mL in MtBEメチル=クロロアセタート, 60 µg/mL in MtBEMONO METHYL CHLORO ACETATEIHT-FC MCAChloroacetic acid methylAKOS BBS-00004061MethylechloroacetateMathyl Chloroacetate
CCRIS 7749Methylester kyseliny chloroctoveHSDB 5303EINECS 202-501-1Acetic acid, 2-chloro-, methyl esterUNII-450VSB182IMethylester kyseliny chloroctove [Czech]2-Chloroacetic acid methyl ester

データベース識別子

CAS
96-34-4
PubChem CID
7295
DTXSID
DTXSID9041576
UNII
450VSB182I
EC Number
202-501-1
Nikkaji
J3.968C

物性

構造計算による物性補完中

XLogP
0.7
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
2
重原子数
6
形式電荷
0
複雑度
52.8

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Chloroacetic Acid Derivatives

Corrosives

SpringerMaterials PropertiesBoiling point
LogP0.76 (calculated)
OdorSweet pungent odor
Density · 4 件

1.2337 at 68 °F (USCG, 1999) - Denser than water; will sink

1.236 g/cu cm at 20 °C

1.2 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.02

Viscosity2.95X10-3 Pa.s at 241.03 K
Color/Form · 2 件

Liquid

Colorless liquid

Solubility · 6 件

In water, 4.6X10+4 mg/L at 20 °C

In water, 5.2 g/100 mL at 19.8 °C (5.2X10+4 mg/L)

Miscible with alcohol, ether

Very soluble in acetone, benzene, ethyl ether, ethanol

Miscible with oxygenated solvents

Solubility in water, g/100ml at 19.8 °C: 5.2

CorrosivityCorrosive

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.6% (1 of 159) of reports.

Danger

H226 (99.4%): Flammable liquid and vapor [Warning Flammable liquids]

危険有害性情報

Regulatory Information · 5 件

Chemical: Acetic acid, chloro-, methyl ester

Acetic acid, 2-chloro-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, 2-chloro-, methyl 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: 10-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13502

Methyl chloroacetate: HSNO Approval: HSR003022 Approved with controls

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 Flammable Liquid
Fire Hazards · 3 件

Special Hazards of Combustion Products: Toxic fumes of hydrogen chloride (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 57 °C explosive vapour/air mixtures may be formed.

Fire PotentialFlammable when exposed to heat or flame ...
Health Hazards

化学と産業

用途と製造

Uses · 6 件

Used as a solvent and chemical intermediate; [Hawley]

Solvent; intermediate

Methyl chloroacetate acts as extraction solvent during the separation of neutral compounds with concentration enhancement using coupling liquid-liquid semimicroextraction with micellar electrokinetic chromatography through on-capillary decomposition. It regenerates the PdCl2-CuCl2/activated carbon catalyst used for synthesis of dimethyl carbonate.

CHEM INT FOR VITAMIN A SYNTHESIS

CHEM INT FOR SODIUM FLUOROACETATE (RODENTICIDE)

CHEM INT FOR RO-7-1051, AN EXPTL ANTIPROTOZOAL AGENT

U.S. Production · 3 件

2023: <75,000 lb

(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Methyl chloroacetate:

Methods of Manufacturing · 2 件

Methanol and chloroacetic acid (esterification)

Chloroacetate esters are usually made by removing water from a mixture of chloroacetic acid and the corresponding alcohol. Reaction of alcohol with chloroacetyl chloride is an anhydrous process that liberates HCl. Chloroacetic acid will react with olefins in the presence of a catalyst to yield chloroacetate esters. /Chloroacetate esters/

General Manufacturing InformationAcetic acid, 2-chloro-, methyl ester: ACTIVE
応用分野 · 2 件

使用Methyl chloroacetate is used as a solvent and chemical intermediate. It acts as a precursor in the preparation of (carboxymethyl) trimethylammonium chloride esters. Further, it is used in the preparation of octakis-(carbethoxymethoxy)calix[8]arene. It is employed as an extraction solvent during the separation of neutral compounds. In addition to this, it is used in the synthesis of dimethyl carbonate.

一般的な説明A crystalline solid or a solid dissolved in a liquid. Insoluble in water and denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

関連反応

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HRID 25051 の反応式
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1 / 51 ページ

化合物ノート

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Flash Point · 4 件

125 °F (USCG, 1999)

57 °C

135 °F (57 °C) (open cup)

57 °C o.c.

Boiling Point · 4 件

266 °F at 760 mmHg (USCG, 1999)

130 °C

BP: 130-132 °C

129.5 °C

Decomposition · 2 件

Hazardous decomposition products formed under fire conditions: Carbon oxides, hydrogen chloride gas

When heated to decomposition it emits toxic fumes of /hydrogen chloride/.

物理化学的性質

融点
-33 °C · -33 °C
沸点
130 °C740 · 130 °C740 mm Hg(lit.)
比重(密度)
1.238 g/mL · 1.238 g/mL at 25 °C(lit.)
蒸気密度
3.8 · 3.8 (vs air)
蒸気圧
10 mm · 10 mm Hg ( 25 °C)
屈折率
20 · n20/D 1.422(lit.)
闪点
125 °F · 125 °F
貯蔵温度
20 °C · Store at <= 20°C.
溶解性
51.6 g/l · 51.6g/l(遅分解)
外見
液体
色
無色透明
PH
4.6 · 4.6 (28g/l, H2O, 20℃)
爆発限界(explosive limit)
4.6 · 4.6-18.5%(V)
水溶解度
28 g/L · 28g/L(20℃)
Merck
14 · 14,6042
BRN
506255 · 506255
Henry's Law Constant
4.9 · 4.9×10-1 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
12.9 · 12.9(20℃)
InChI
1S/C3H5ClO2/c1-6-3(5)2-4/h2H2,1H3
InChIKey
QABLOFMHHSOFRJ-UHFFFAOYSA-N
SMILES
ClCC(=O)OC
LogP
0.63 at · 0.63 at 20℃
CAS データベース
96 · 96-34-4(CAS DataBase Reference)
NISTの化学物質情報
Acetic acid, chloro-, methyl ester(96-34-4)
EPAの化学物質情報
2 · Acetic acid, 2-chloro-, methyl ester (96-34-4)

化学的性質

化学的特性clear colorless liquid with a slight irritating odor. It is miscible with organic solvents such as ethanol, ether, acetone and benzene. Slightly soluble in water.

· 2 件

Extremely corrosive to the eyes, skin, nose, throat, and upper respiratory tract. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

Hazards Summary · 1 件

Corrosive to skin; Severe eye irritant; Respiratory tract irritant; May be absorbed through skin; [ICSC] Toxic by inhalation and ingestion; [eChemPortal: ESIS] Danger of skin sensitization; [MAK] Inhalation may induce upper and lower airway inflammation and edema; [CHRIS] Oral LD50 (mouse) = 240 mg/kg; [RTECS] An irritant; [MSDSonline]

DOT ID and Guide2295 131
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EC ClassificationSymbol: T; R: 10-23/25-37/38-41; S: (1/2)-26-37/39-45
UN ClassificationUN Hazard Class: 6.1; UN Subsidiary Risks: 3; UN Pack Group: I
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 件

METHYL CHLOROACETATE is a halogenated 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.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Use water spray, dry powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

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. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 件

· 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 · 2 件

Call a physician.

General First Aid:

Safe StorageFireproof. Separated from food and feedstuffs and incompatible materials. See Chemical Dangers.
Exposure Control and Personal Protection · 2 件

· Wear positive pressure self-contained breathing apparatus (SCBA).

1.0 [ppm]

Fire Fighting Procedures · 1 件

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Further information: Use water spray to cool unopened containers.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Cleanup Methods · 1 件

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

Nonfire Spill ResponseExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Disposal Methods · 2 件

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Spillage Disposal · 1 件

Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in covered plastic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

毒性情報

Ecotoxicity ValuesEC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static; Concentration: 84 mg/L for 24 hr; Effect: behavior, equilibrium /formulation/
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl chloroacetate is expected to have very high mobility in soil(SRC). Volatilization of methyl chloroacetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 7.63 mm Hg at 25 °C(3), and water solubility, 4600 mg/L(4). Methyl chloroacetate is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 45-95% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6(SRC), determined from a structure estimation method(2), indicates that methyl chloroacetate is not 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 2.4X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 7.63 mm Hg(4), and water solubility, 4.6X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 16 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.63(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 45-95% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is an important environmental fate process in water(SRC). A measured base-catalyzed hydrolysis rate constant of 140 L/mole-sec at 25 °C was reported with corresponding hydrolysis half-lives of 140 to 0.14 hrs at pH values of 6-9(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl chloroacetate, which has a vapor pressure of 7.63 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl chloroacetate 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 65 days(SRC), calculated from its rate constant of 2.5X10-13 cu cm/molecule-sec at 25 °C(3). Methyl chloroacetate does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
Toxicity Summary · 1 件

IDENTIFICATION AND USE: Methyl chloroacetate (MCA) is a colorless liquid. It is used as a solvent and intermediate. HUMAN STUDIES: In man, delayed occurrence of irritation of the conjunctiva is observed after exposure to the vapor. It was suggested that cross reactivity to MCA may occur in an industrial situation. ANIMAL STUDIES: In guinea-pigs MCA induced sensitization. Cross-sensitization with chloroacetic acid ethyl ester has been observed in this species. MCA is corrosive to rabbit skin and is absorbed through the skin (0.5 mL undiluted substance/rabbit leads to death). The substance is severely irritating to the rabbit eye. In rats MCA produced pronounced eye and respiratory tract irritation at concentrations as low as 250 ppm; some animals exposed to this concentration died within a few days. After repeated inhalation exposure to MCA for 28 days at concentrations of 10, 33 or 100 ppm, adverse effects on the breathing (irregular breathing) and on movement (uncoordinated gait) as well as irritant effects (closing together of the eyelids, sneezing, increased frequency of cleaning) and an increase in relative lung weight occurred in rats at the highest concentration. No increase in the incidence of lung tumors has been established after intraperitoneal administration to strain A mice. MCA was not mutagenic in the Salmonella/microsome test in five strains of Salmonella typhimurium or in Escherichia coli either with or without metabolic activation. No induction of micronuclei has been observed in the micronucleus test in the mouse. ECOTOXICITY STUDIES: Testing the acute toxicity to the Daphnia resulted in a 24 hr EC0 of 3.2 mg/L and a 24 hr EC50 of 5.5 mg/L for inhibition of the swimming capability. The 48 hr and 96 hr LC0 in the zebra fish was 1.13 mg/L. For the rainbow trout, 48 hr LC0 < 2.5 mg/L and 48 hr LC100 of 6 mg/L are reported.

Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ Testing the acute toxicity to the Daphnia resulted in a 24 hr EC0 of 3.2 mg/L and a 24 hr EC50 of 5.5 mg/L for inhibition of the swimming capability. The 48 hr and 96 hr LC0 in the zebra fish was 1.13 mg/L. For the rainbow trout, 48 hr LC0 < 2.5 mg/L and 48 hr LC100 of 6 mg/L are reported.

Signs and Symptoms · 4 件

Cough. Shortness of breath. Sore throat.

MAY BE ABSORBED! Redness. Pain. Skin burns.

Redness. Pain. Blurred vision.

Abdominal pain. Nausea. Vomiting. Diarrhoea.

ICSC Environmental DataThe substance is toxic to aquatic organisms.
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of methyl chloroacetate can be estimated to be 6(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl chloroacetate is expected to have very high mobility in soil(SRC).

TSCA Test Submissions · 1 件

Methyl chloroacetate (CAS# 96-34-4) was evaluated for acute inhalation toxicity in male and female rats at dose levels of 1.75, 4.26, and 4.44 mg/L for one-hour. Mortality ratios were 0/5 M, 0/5 F; 2/5 M, 3/5 F; and 4/5 M, 4/5 F, respectively. The estimated LC50 value was 3.69 mg/L (831 ppm).

Human Toxicity Excerpts · 2 件

/HUMAN EXPOSURE STUDIES/ A 23 year old chemical laboratory technician presented with erythema and small blisters on the dorsum of his right hand and forearm. The reaction resulted from a spill of monochloroacetic-acid (MCA). The solution contained 1.5 molar MCA in 94 percent ethanol. He attempted to wash the spill from his arm using water for 10 minutes. After 10 days, the lesions healed, leaving small scars. These scars, after 14 days, became the sites of itchy vesicles. A patch test was performed on day 28, at which time, the patient gave a positive result to the MCA solution at 1 percent in 70 percent methanol. Since it was not considered likely that MCA was the active agent, possible sensitivity to monochloroacetic-acid-ethyl-ester (EMCA) was examined. Strong positive reactions were observed to patch tests with EMCA, whereas the MCA tests were negative. Because plans were underway to use EMCA in a large production process, a guinea-pig maximization test was initiated. Five of the 20 animals tested reacted to EMCA, indicating that this compound is at least a moderate sensitizer. All animals reacted to monochloroacetic-acid-methyl-ester (MMCA). The authors suggest that cross reactivity to MMCA may occur in an industrial situation.

/SIGNS AND SYMPTOMS/ In man, delayed occurrence of irritation of the conjunctiva is observed after exposure to the vapor.

Artificial Pollution SourcesMethyl chloroacetate's production and use as an intermediate and solvent(1) may result in its release to the environment through various waste streams(SRC).

安全データ

F
19
wgk
2
tsca
TSCA listed
rtecs
AF9500000
ridadr
UN 2295
毒性
LD50 orally in Rabbit: 107 mg/kg
hs_code
2915 40 00
risk_code
10-23/25-37/38-41-40-36/37/38-38
化審法
(2)-1149
消防法
危-4-2-III
hazard_code
T,Xi,F
safety_code
26-37/39-45-36-16
hazard_class
6.1
packing_group
I
毒劇物取締法
毒物
自然発火温度
869 °F
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Flam. Liq. 3Skin Irrit. 2STOT SE 3
ストレージクラス
3 - Flammable liquids
有毒物質データの
96-34-4(Hazardous Substances Data)
調製方法 · 2 件

製造方法Methyl chloroacetate is prepared by esterification of chloroacetic acid with methanol. Reaction: Methanol and chloroacetic acid are uniformly mixed in a weight ratio of 0.366:1, heated with stirring, and the esterification reaction is carried out at 105-110 °C. In the reaction process, the ternary azeotrope of methyl chloroacetate, water and methanol is continuously steamed, layered through the ester separator, the separated methanol and water are returned to the reaction pot, and the separated crude ester is made of sodium carbonate. neutralize. The neutralized crude ester is firstly cut out the 130°C fraction by atmospheric distillation, and then subjected to vacuum distillation to collect the 65°C (8kPa) fraction, which is the finished product of methyl chloroacetate. The yield is about 96%.

純化方法Shake the ester with saturated aqueous Na2CO3 (three times), aqueous 50% CaCl2 (three times), saturated aqueous NaCl (twice), dry (Na2SO4) and fractionally distil it. Very toxic. [Beilstein 2 IV 480.]

上流・下流製品情報

上流原料

クロロ酢酸ふっ化カリウム塩素塩化カルボニル酢酸メタノール

下流製品

チオフェン-3-アセトニトリルジチオりん酸O,O-ジメチルS-(N-メチルカルバモイルメチル)3-チオフェンエタノール3-メチル-2-フランカルボン酸メチルチオフェン-3-酢酸1,2-Dihydro-4-(methoxymethyl)-6-methyl-5-nitro-2-oxonicotinonitrile2-オキソピロリジン-1-アセトアミド(4,6-Dimethyl-pyrimidin-2-ylsulfanyl)-acetic acid hydrazideノコダゾールフェニルチオホスホン酸O-エチルO-(8-キノリル)[(ジメトキシホスフィニル)チオ]酢酸メチルChloromethylacetamideグリシンアミド 塩酸塩Thiophen-3-yl-acetyl chloride2-メトキシフェノキシ酢酸チオりん酸O,O-ジメチルS-(N-メチルカルバモイルメチル)Methyl 3-(6-methoxy-2-naphthyl)-3-methyl glycidate1,2-ジヒドロピラジン-2-オン2-Piperazin-1-yl-acetamidehydrochloride3-メチル-2-フランカルボン酸2-ブロモ-5-チアゾールカルボキシアルデヒド 臭化物メトキシ酢酸 メチル(ジメトキシチオホスフィノイルチオ)酢酸メチルフルオロ酢酸メチルシアノ酢酸メチル