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p-トルエンスルホン酸メチル

Methyl p-toluenesulfonate

HCID 6645
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基本情報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
80-48-8
標準SMILES
COS(=O)(=O)c1ccc(C)cc1
InChIKey
VUQUOGPMUUJORT-UHFFFAOYSA-N
分子式
C8H10O3S
平均分子量
186.23 g/mol
単同位体質量
186.03506535

名称と識別子

優先名称
Methyl p-toluenesulfonate
IUPAC
methyl 4-methylbenzenesulfonate
現地名
p-トルエンスルホン酸メチル
英語名
Methyl p-toluenesulfonate
分子式
C8H10O3S
分子量
186.23

名称と別名

Methyl p-toluenesulfonate80-48-8Methyl 4-methylbenzenesulfonateMethyl tosylateMethyl toluene-4-sulfonateMethyl-p-toluenesulfonateMethyl p-tosylateMethyl toluenesulfonateMethyl toluene-4-sulphonateBenzenesulfonic acid, 4-methyl-, methyl esterp-Toluenesulfonic acid, methyl esterMethyl toluene sulfonate
名称をさらに表示
p-トルエンスルホン酸メチルメチルトシラート4-メチルベンゼンスルホン酸メチルメタノールトシラートメチルp-トルエンスルホナートp-トルエンスルホン酸メチルエステルpトルエンスルホン酸メチルエステルパラ-トルエンスルホン酸メチルP‐トルエンスルホン酸メチルMPTSPTSMEMETHYL 4-TOLUENESULFONATEMETHYL P-TOLUENESULPHONATEMethyl para-toluenesulfonate4-TOLUENESULFONIC ACID METHYL ESTER
p-Methylbenzenesulfonate methyl esterMETHYL P-METHYLBENZENESULFONATEp-Toluolsulfonsaeure methyl esterMethyl 4-toluene sulfonate4-Toluenesulfonic acid, methyl esterMethylester kyseliny p-toluensulfonoveDTXSID40525504SU69KI68L

データベース識別子

CAS
80-48-8
PubChem CID
6645
DTXSID
DTXSID4052550
ChEMBL
CHEMBL5189891
UNII
4SU69KI68L
EC Number
201-283-5
Nikkaji
J54.424H

物性

構造計算による物性補完中

XLogP
2.2
極性表面積
51.8 Ų
水素結合供与体数
0
水素結合受容体数
3
回転可能結合数
2
重原子数
12
形式電荷
0
複雑度
219

実験および物理化学的性質

Density · 2 件

1.230 @ 25 DEG/25 °C

1.230-1.238 @25 °C

Color/Form · 3 件

MONOCLINIC LEAFLETS OR PRISMS FROM ETHER-PETROLEUM ETHER

LIGHT BROWN CRYSTALS

WHITE DAMP CRYSTALS

SolubilityINSOL IN WATER; SLIGHTLY SOL IN PETROLEUM ETHER; SOL IN ETHER; VERY SOL IN ALCOHOL, BENZENE, CHLOROFORM
Flash Point306 °F (152 °C) (open cup)
Boiling Point292 °C @ 760 MM HG
Melting Point28-29 °C
Vapor Density6.45 (AIR= 1)
Physical Description · 2 件

Liquid

White vesicant solid; Solidifies at 24 deg C; [Hawley] White or light brown solid; mp = 28-29 deg C; [HSDB] Off-white low melting solid or clear liquid; mp = 27-28 deg C; [MSDSonline]

Other Experimental Properties · 2 件

LOW-MELTING SOLID OR LIQUID

DECOMP @ 262 °C

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

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (29.9%): Toxic in contact with skin [Danger Acute toxicity, dermal];H314 (22.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H315 (76.9%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (97.2%): May cause an allergic skin reaction [Warning Sensitization, Skin];H319 (35%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (26.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H411 (29.6%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 351 reports by companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzenesulfonic acid, 4-methyl-, methyl ester

Benzenesulfonic acid, 4-methyl-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 4-methyl-, 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: 22-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21794;Status: Active Update: 11-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18934

化学と産業

用途と製造

Uses · 4 件

Used as methylating agent in organic synthesis and as a catalyst for alkyd resins; [HSDB]

METHYLATING AGENT IN ORGANIC SYNTHESIS

ACCELERATOR; CATALYST FOR ALKYD RESINS

CHEM INT FOR BASIC DYE C.I. 46000

U.S. Imports · 2 件

(1977) 1.35X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 7.99X10+6 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3 件

2022: 119,181 lb;2021: 54,718 lb;2020: 31,482 lb

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Industry UsesCorrosion inhibitor
Methods of ManufacturingPROBABLY BY REACTION OF P-TOLUENESULFONYL CHLORIDE WITH METHYL ALCOHOL
Formulations/PreparationsGRADE: 97% MIN
General Manufacturing Information · 2 件

Fabricated Metal Product Manufacturing

Benzenesulfonic acid, 4-methyl-, methyl ester: ACTIVE

応用分野 · 4 件

用途メチル化剤

使用Methyl p-Toluenesulfonate can be used in the manufacture of dyes and organic synthesis, and also is the raw materials of methylation.

一般的な説明Methyl p-toluenesulfonate is a solid or liquid with a low melting point. Its melting point is 25–28°C, and it undergoes a phase transition between liquid and solid at room temperature depending on the season. Caking occurs when temperatures are low, which is a normal physical phenomenon. It is hygroscopic, so care must be taken to protect it from moisture during storage.

Methyl p-toluenesulfonate is sulfonate ester present as potentially genotoxic impurity in drug substances. Kinetics of reactions of methyl p-toluenesulfonate with N,N-dimethylaniline has been investigated. It participates in selective 1-substitution reaction of tetrazole.

関連反応

446 件
反応記録を作成
HRID 6971 の反応式
HRID 6971反応物としてuspto-grants-2006_08
HRID 6989 の反応式
HRID 6989反応物としてuspto-grants-2006_08
HRID 7199 の反応式
HRID 7199反応物としてuspto-grants-2006_08
HRID 7280 の反応式
HRID 7280反応物としてuspto-grants-2006_08
HRID 13923 の反応式
HRID 13923反応物としてuspto-grants-2010_06
HRID 13930 の反応式
HRID 13930反応物としてuspto-grants-2010_06
HRID 13941 の反応式
HRID 13941反応物としてuspto-grants-2010_06
HRID 13942 の反応式
HRID 13942反応物としてuspto-grants-2010_06
1 / 56 ページ

化合物ノート

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このページの内容基本情報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
その他の操作
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物理化学的性質

融点
25 · 25-28 °C(lit.)
沸点
144 · 144-145 °C5 mm Hg(lit.)
比重(密度)
1.234 g/mL · 1.234 g/mL at 25 °C(lit.)
蒸気密度
6.45 · 6.45 (vs air)
蒸気圧
1 mm · 1 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.5172(lit.)
闪点
230 °F · >230 °F
貯蔵温度
2 · 2-8°C
溶解性
クロロホルム(微量)、メタノール(微量)
外見
液体または低融点固体
色
白から黄色
水溶解度
不溶性
BRN
609209 · 609209
InChI
1S/C8H10O3S/c1-7-3-5-8(6-4-7)12(9,10)11-2/h3-6H,1-2H3
InChIKey
VUQUOGPMUUJORT-UHFFFAOYSA-N
SMILES
COS(=O)(=O)c1ccc(C)cc1
LogP
1.88 at · 1.88 at 25℃
CAS データベース
80 · 80-48-8(CAS DataBase Reference)
NISTの化学物質情報
4 · Benzenesulfonic acid, 4-methyl-, methyl ester(80-48-8)
EPAの化学物質情報
4 · Benzenesulfonic acid, 4-methyl-, methyl ester (80-48-8)

化学的性質

化学的特性white to slightly yellow low melting solid. Soluble in alcohol, ether, benzene, insoluble in water. Hygroscopic.

Methyl 4-toluenesulphonate: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

A strong skin and eye irritant; [Hawley] Urticaria and skin sensitization have been reported; [HSDB] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; May cause skin sensitization; [MSDSonline]

NFPA Hazard Classification · 4 件

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and Categories · 3 件

Acute Tox. 4 (100%);Acute Tox. 3 (29.9%);Skin Corr. 1B (22.8%);Skin Irrit. 2 (76.9%);Skin Sens. 1B (97.2%);Eye Irrit. 2 (35%);STOT SE 3 (26.2%);Aquatic Chronic 2 (29.6%)

Skin corrosion/irritation - Category 2;Serious eye damage/eye irritation - Category 2

Skin corrosion/irritation - Category 1C;Serious eye damage/eye irritation - Category 1

Skin, Eye, and Respiratory IrritationsHIGHLY TOXIC BY INHALATION; STRONG IRRITANT TO SKIN & EYES.

安全と保護具

Fire Fighting ProceduresWATER OR FOAM MAY CAUSE FROTHING.
Cleanup Methods...DECONTAMINATION OF FLOORS & EQUIPMENT MAY BE EFFECTED BY FLUSHING WITH DILUTE ALKALI OR AMMONIA.
Disposal Methods · 1 件

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.

Preventive Measures · 1 件

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Protective Action Criteria (PAC) · 3 件

1.0 [mg/m3]

11 [mg/m3]

68 [mg/m3]

Personal Protective Equipment (PPE)CONTAMINATED AREAS SHOULD BE ENTERED ONLY BY TRAINED PERSONNEL WITH IMPERVIOUS CLOTHING & AIR-SUPPLIED RESPIRATORS.

毒性情報

Adverse EffectsDermatotoxin - Skin burns.;Skin Sensitizer - An agent that can induce an allergic reaction in the skin.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Human Toxicity Excerpts · 4 件

...CONTACT WITH SOLN OR SOLID MAY GIVE RISE TO NO SYMPTOMS FOR SEVERAL HR. ... /THEN/ THERE MAY BE...VESICATION AT SITE OF CONTACT, FREQUENTLY WITH LITTLE... PAIN. VERY LARGE BULLAE MAY BE FORMED... GENERALIZED TOXIC SYMPTOMS DO NOT SEEM TO OCCUR AND...BURNS HEAL USUALLY WITH SOME PIGMENTATION...

...THERE HAVE BEEN FEW INSTANCES OF PULMONARY IRRITATION. ...ONE INSTANCE WAS NOTED OF URTICARIAL REACTION FROM HEATED VAPOR; SKIN SENSITIZATION ALSO OCCURS.

...STRONG IRRITANT TO...EYES.

HIGHLY TOXIC BY INHALATION; STRONG IRRITANT TO SKIN & EYES.

Non-Human Toxicity Excerpts · 3 件

BD RATS RECEIVING SC 15 WEEKLY X 53 MG/KG FOR 470 DAYS: 7/10 HAD LOCAL SARCOMA, 1 BRONCHIAL, 1 MAMMARY & 1 OVARIAN CARCINOMA. /FROM TABLE/

Several direct acting mutagens were tested for mutagenic activity in adult Drosophila melanogaster when administered in feeding or as an injected dose. An inhibitor or cytochrome p450, 1-phenylimidazole, administered at concentrations of 2.5, 4 and 10 mmol, was not mutagenic in Drosophila. Methyl-p-toluenesulfonate applied orally was a weak mutagen. When administered simultaneously with 1-phenylimidazole, a concentration dependent increase was noted in mutagenic activity of methyl-p-toluenesulfonate. Following injection, mutagenesis by methyl-p-toluenesulfonate was considerable. Ethyl-p-toluenesulfonate demonstrated marginal mutagenesis in Drosophila when orally applied but was decidedly mutagenic on injection. Simultaneous treatment with 4 mmol 1-phenylimidazole and 1 mmole of ethyl-p-toluenesulfonate did not alter mutagenesis nor did treatment with diethylmaleate (glutathione depletion). Combined treatment with 2 mmol ethyl-p-toluenesulfonate and 2 mmol 1-phenylimidazole produced a statistically significant increase in mutagenesis. /It was concluded/ that weak mutagenesis by p-toluenesulfonates after feeding experiments compared to considerable effects after injection suggests metabolic deactivation in the gut.

The carcinogenic activity of 12 direct alkylating substances was tested in 535 BD rats. Local sarcomas were produced by the subcutaneous injections once a week of p-toluene sulfonic acid methylester. Only a jew tumors were observed following treatment with p-toluene sulfonic acid ethylester and p-toluenesulfonic acid butylester were not carcinogenic.

Antidote and Emergency TreatmentFIRST AID TREATMENT: CONTACT...WITH SKIN OR EYES IS INDICATION FOR RAPID AND PROLONGED IRRIGATION OF AREA WITH LARGE VOL OF WATER.

法規制情報

Regulatory Information · 4 件

Chemical: Benzenesulfonic acid, 4-methyl-, methyl ester

Benzenesulfonic acid, 4-methyl-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 4-methyl-, 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: 22-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21794;Status: Active Update: 11-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/18934

Methyl 4-toluenesulphonate: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F
21
wgk
3
tsca
TSCA listed
rtecs
XT7000000
ridadr
UN 3261 8/PG 2
毒性
LD50 orally in Rabbit: 341 mg/kg
hs_code
29051900
risk_code
22-34-43-40-36/37/38
化審法
(3)-1896
安衛法
変異原性物質
消防法
危-4-3-III
hazard_code
C,Xn
safety_code
26-36/37/39-45-24
hazard_class
8
packing_group
III
自然発火温度
896 °F
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Skin Corr. 1BSkin Sens. 1B
ストレージクラス
8A - Combustible corrosive hazardous materials
有毒物質データの
80-48-8(Hazardous Substances Data)
一般的な説明
調製方法 · 2 件

製造方法Methyl p-toluenesulfonate was synthesized by the reaction of p-toluenesulfonyl chloride with methanol. Mix p-toluenesulfonyl chloride and methanol, slowly add 25% sodium hydroxide solution, control the temperature below 25 °C, stop adding alkali when the pH is 9, continue stirring for 2 hours, and leave overnight. The lower layer of reactant was taken, the upper layer was extracted with benzene, the extract was recovered with benzene and then combined with the lower layer, washed with water and 5% potassium carbonate solution in turn, dried and distilled under reduced pressure to obtain the finished product of methyl p-toluenesulfonate.

純化方法The ester is purified by distillation in vacuo and could be crystallised from pet ether or Et2O/pet ether at low temperature. It is a powerful methylating agent, is TOXIC andis a skin irritant, so it is better to purify it by repeated distillation. [IR: Schreiber Anal Chem 21 1168 1949, Buehler et al. J Org Chem 2 167 1937, Roos et al. Org Synth Coll Vol I 145 1948, Beilstein 11 IV 247.]

上流・下流製品情報

上流原料

p-トルエンスルホニルクロリド4-メチルベンゼンジアゾニウム·テトラフルオロボラートp-トルエンスルホナート·テトラブチルアミニウム[ヒドロキシ(トシルオキシ)ヨード]ベンゼン4-Toluenesulfonyl bromide2,2,2-トリフルオロエチルメチルエーテルジメチル亜鉛オルト酢酸トリメチル

下流製品

1,3,3-トリメチル-2-メチレンインドリン5-ブロモ-1,2-ジメチル-1H-イミダゾール2,5-diphenylthiazole3,5-ビス(1-シアノ-1-メチルエチル)トルエンビス(トルエン-4-スルホン酸)メチレン2-ノニンフッ化メチル3,5-ジメチル安息香酸メチル2-クロロ-1-メチルピリジニウムp-トルエンスルホナートエチルメチルエーテルベーシックイエロー5Basic Orange 5