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1-オクタンチオール

1-Octanethiol

HCID 8144
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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
111-88-6
標準SMILES
CCCCCCCCS
InChIKey
KZCOBXFFBQJQHH-UHFFFAOYSA-N
分子式
C8H18S
平均分子量
146.3 g/mol
単同位体質量
146.11292175

概要

1-octanethiol appears as a clear colorless liquid. Flash point 115 °F. Insoluble in water and less dense than water. Used to make other chemicals.

名称と識別子

優先名称
1-Octanethiol
IUPAC
octane-1-thiol
現地名
1-オクタンチオール
英語名
1-Mercaptooctane
分子式
C8H18S
分子量
146.29

名称と別名

1-OCTANETHIOLOctane-1-thiol111-88-61-Mercaptooctanen-Octyl mercaptanOctyl mercaptanOctylthiol1-Octylthioln-OctanethiolOctylmercaptann-Octylthioln-Octylmercaptan
名称をさらに表示
1-オクタンチオールオクチルメルカプタンN-オクチルメルカプタンn-オクチルメルカプタン(1-オクタンチオール)オクタン‐1‐チオール1‐オクタンチオール1-オクタンチオール, 98%NOMOctanethiolNOM(TM)n-Octyl m
1-Octyl mercaptann-OctanethiolateDTXSID402689442GO2PA46LNSC-41903DTXCID506894CHEBI:188351NSC-151955

データベース識別子

CAS
111-88-6、94805-33-1
PubChem CID
8144
DTXSID
DTXSID4026894
ChEMBL
CHEMBL3182056
ChEBI
CHEBI:188351
UNII
42GO2PA46L
EC Number
203-918-1
Nikkaji
J5.116K

物性

構造計算による物性

XLogP
4.4
極性表面積
1 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
6
重原子数
9
形式電荷
0
複雑度
43.8

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Thiols

Flammable agents - 2nd degree

SpringerMaterials PropertiesBoiling point
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP4.21 (estimated)
OdorMild odor
Density · 5 件

0.84 (NIOSH, 2024) - Less dense than water; will float

0.8433 at 20 °C/4 °C

Relative density (water = 1): 0.84

0.8433 @ 20°C

0.84

Color/FormWater-white liquid
Solubility · 5 件

Insoluble (NIOSH, 2024)

Soluble in ethanol; slightly soluble in carbon tetrachloride

Insoluble in water

Solubility in water: none

Insoluble

Flash Point · 5 件

115 °F (NIOSH, 2024)

69 °C

156 °F (69 °C) (Open cup)

69 °C o.c.

(oc) 115 °F

Boiling Point

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

This chemical does not meet GHS hazard criteria for 5.9% (17 of 286) of reports.

Warning

H315 (14%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 286 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 5 件

Chemical: 1-Octanethiol

1-Octanethiol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Octanethiol 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: Octane-1-thiol (EC: 203-918-1)

1-Octanethiol: 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 LabelFlammable Liquid Poison
Fire Hazards · 2 件

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

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 69 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible
Health HazardsExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Hazards Summary

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Simple aliphatic and aromatic thiols undergo S-methylation in mammals to produce the corresponding methyl thioether or sulfide. Methylation is catalysed by thiopurine methyltransferase in the cytoplasm and thiol methyltransferase in microsomes, and both reactions require S-adenosyl-l-methionine as a methyl group donor. Thiopurine methyltransferase is present in human liver, kidney, and erythrocytes; preferential substrates for this enzyme include aromatic and heterocyclic thiols. S-Methylation of aliphatic thiols is catalysed by microsomal thiol methyltransferase, and the resulting methyl thioether (sulfide) metabolite would undergo S-oxidation to give the methyl sulfoxide and methyl sulfone analogues as urinary products. Thiols may react with glutathione and other endogenous thiol substances to form mixed disulfides. Both microsomal and cytoplasmic thioltransferasess have been reported to catalyse the formation of mixed disulfides. The resulting mixed disulfides can undergo reduction back to thiols, oxidative desulfuration, or oxidation to a sulfonic acid via the intermediate thiosulfinate and sulfinic acids. The principal form in the circulation would probably be a mixed disulfide formed with albumin. /Simple thiols/

用途と製造

Uses · 2 件

Used in organic synthesis and polymerization; [Hawley]]

Polymerization conditioner; in synthesis

U.S. Production · 2 件

2023: 1,000,000 - <8,500,000 lb

1-Octanethiol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Consumer UsesAntioxidant
Industry UsesChain transfer agent
Methods of Manufacturing1-Octanethiol is produced using 1-octene and hydrogen sulfide (anti-Markownikoff addition)

関連反応

96 件
反応記録を作成
HRID 8422 の反応式
HRID 8422反応物としてuspto-grants-2006_08
HRID 8423 の反応式
HRID 8423反応物としてuspto-grants-2006_08
HRID 21694 の反応式
HRID 21694反応物としてuspto-grants-1995_06
HRID 34422 の反応式
HRID 34422反応物としてuspto-grants-1988_08
HRID 54735 の反応式
HRID 54735反応物としてuspto-grants-1997_04
HRID 95406 の反応式
HRID 95406反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 113108 の反応式
HRID 113108反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 138514 の反応式
HRID 138514反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
1 / 12 ページ

化合物ノート

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その他の操作
ノートを作成反応を作成見積依頼を出す
· 5 件

390 °F at 760 mmHg (NIOSH, 2024)

199.1 °C at 760 mm Hg

199 °C

198.1 °C @760 [mm Hg]

390 °F

DecompositionThe substance decomposes on burning producing toxic gases including hydrogen sulfide and sulfur oxides.
Melting Point · 5 件

-57 °F (NIOSH, 2024)

-49.2 °C

Liquid molar volume = 0.174195 cu m/kmol; IG Heat of Formation = -1.7010X10+8 J/kmol; Heat Fusion at Melting Point = 2.4000X10+7 J/kmol

-49 °C

-57 °F

物理化学的性質

融点
-49 °C · -49 °C
沸点
197 · 197-200 °C (lit.)
比重(密度)
0.843 g/mL · 0.843 g/mL at 25 °C (lit.)
蒸気圧
0.3 hPa · 0.3 hPa (20 °C)
屈折率
20 · n20/D 1.452(lit.)
闪点
55 °F · 55 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
0.004 g/リットル · 0.004g/リットル
外見
液体
酸解離定数(Pka)
10.55 · 10.55±0.10(Predicted)
色
無色透明
比重
0.843 · 0.843 (20/4℃)
臭い (Odor)
0.1 · ジプロピレングリコール中0.10%。硫黄の
臭気閾値(Odor Threshold)
0.0016 ppm · 0.0016ppm
水溶解度
水には混和しません。
BRN
1733101 · 1733101
Henry's Law Constant
7.1 · 7.1×10-4 mol/(m3Pa) at 25℃, Yaws et al. (2003)
安定性
安定。強酸、強酸化剤、アルカリ金属とは相容れない。
InChI
1S/C8H18S/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3
InChIKey
KZCOBXFFBQJQHH-UHFFFAOYSA-N
SMILES
CCCCCCCCS
LogP
4.21 at · 4.21 at 20℃
CAS データベース
111 · 111-88-6(CAS DataBase Reference)
NISTの化学物質情報
1 · 1-Octanethiol(111-88-6)
EPAの化学物質情報
1 · 1-Octanethiol (111-88-6)

化学的性質

化学的特性colourless liquid

· 1 件

May irritate or burn skin and eyes; Vapors may cause dizziness or suffocation. [CAMEO] An eye irritant; Absorption of large amounts by ingestion or inhalation could produce CNS depression and convulsions. Workers avoid because of obnoxious smell. [CHEMINFO] See THIOLS;

DOT ID and Guide1228 131
Reactive GroupSulfides, Organic
Reactivity Profile1-OCTANETHIOL is incompatible with the following: Oxidizers, reducing agents, strong acids & bases, alkali metals (NIOSH, 2024).
Chemical Dangers · 1 件

Decomposes on burning. This produces toxic gases including hydrogen sulfide and sulfur oxides. Reacts violently with oxidants. This generates fire hazard. Reacts with strong acids, strong bases and strong reducing agents. Attacks metals and rubber.

Flammable LimitsClass II Combustible Liquid: Fl.P. at or above 100 °F and below 140 °F.
Air and Water ReactionsFlammable. Insoluble in water.

安全と保護具

Fire Fighting · 2 件

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

Use powder, carbon dioxide, foam.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap.

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

Rinse mouth. Refer for medical attention .

First Aid · 2 件

Excerpt from NIOSH Pocket Guide for 1-Octanethiol:

(General first aid procedures)

Safe StorageFireproof. Separated from strong bases, strong acids and oxidants.
Fire Fighting ProceduresAlcohol foam.
Storage ConditionsFireproof. Separated from strong bases, strong acids and oxidants.
Cleanup Methods · 1 件

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. (Extra personal protection: filter respirator for organic gases and vapours.) Do NOT let this chemical enter the environment.

Nonfire Spill ResponseExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. 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. Do NOT let this chemical enter the environment.

Preventive Measures · 4 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.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

/Upon contact with eyes/, first rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor.

Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

毒性情報

InteractionsLipophilic thiol compounds interact spectrally with liver microsomes from phenobarbital-treated rats. N-octanethiol competitively displaced metyrapone and n-octane from the active site of cytochrome P450.
Target OrgansEyes, skin, respiratory system, blood, central nervous system
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 930(SRC), determined from a structure estimation method(2), indicates that 1-octanethiol is expected to have low mobility in soil(SRC). Volatilization of 1-octanethiol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1-Octanethiol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.42 mm Hg(SRC), determined from a fragment constant method(4). Insufficient data are available to determine biodegradability of 1-octanethiol(SRC) but its linear alkyl chemical structure would suggest that biodegradation may be an important environmental fate process in soil(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 930(SRC), determined from a structure estimation method(2), indicates that 1-octanethiol 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 2.3X10-2 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.6 hours and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 35(SRC), from an estimated log Kow of 4.2(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Insufficient data are available to determine biodegradability of 1-octanethiol(SRC) but its linear alkyl chemical structure would suggest that biodegradation may be an important environmental fate process in water(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-octanethiol, which has an extrapolated vapor pressure of 0.42 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-octanethiol 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 8 hours(SRC), calculated from its rate constant of 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Octanethiol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values1-Octanethiol was identified as a volatile component of cooked beef flavor(1).
Adverse EffectsOther Poison - Chemical Asphyxiant
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 件

Cough. Sore throat. Headache. Nausea. Vomiting. Dizziness.

Redness.

Redness.

Headache. Nausea. Vomiting. Dizziness.

irritation eyes, skin, nose, throat; lassitude (weakness, exhaustion), cyanosis, increased respiration, nausea, drowsiness, headache, vomiting

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

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-octanethiol can be estimated to be 930(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-octanethiol is expected to have low mobility in soil.

Human Toxicity Excerpts · 3 件

/SIGNS AND SYMPTOMS/ Inhalation /may cause/, cough, sore throat, headache, nausea, vomiting, and dizziness.

/SIGNS AND SYMPTOMS/ /1-Octanethiol/ is mildly irritating to the eyes, the skin and the respiratory tract. The substance may cause effects on the central nervous system. Exposure at high levels may result in lowering of consciousness.

/SPECIAL STUDIES/ The oral and inhalation toxicity of n-octylmercaptan ... is similar to that of butane- and hexanethiol.

Artificial Pollution Sources1-Octanethiol's production and use as a polymerization conditioner and in synthesis(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

Insufficient data are available to determine biodegradability of 1-octanethiol(SRC) but its linear alkyl chemical structure would suggest that biodegradation is important in water(1). 1-Octanethiol, present at 500 mg/L, was not aerobically biodegraded by a pure culture of Alcaligenes faecalis over a period of 115-195 hours(2).

安全データ

OEL
Ceiling: 0.5 ppm (3.0 mg/m3) [15-minute]
wgk
3
tsca
TSCA listed
ridadr
UN 1170 3/PG 2
毒性
LD50 orally in Rabbit: 2000 - 2450 mg/kg
hs_code
29309070
risk_code
11-67-65-50/53-43-36/37-20-36/37/38
化審法
(2)-464
消防法
危-4-3-III
hazard_code
F,N,Xn,Xi
safety_code
7-16-57-45-36/37/39-29-26
hazard_class
9
packing_group
III
自然発火温度
240 °C
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Skin Sens. 1STOT SE 3
ストレージクラス
10 - Combustible liquids
有毒物質データの
111-88-6(Hazardous Substances Data)
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information · 3 件

Rubber Product Manufacturing

1-Octanethiol: ACTIVE

Thiols can be prepared by a variety of methods. The most-utilized of these synthetic methods for tertiary and secondary thiols is acid-catalyzed synthesis; for normal and secondary thiols, the most-utilized methods are free-radical-initiated, alcohol substitution, or halide substitution; for mercaptoalcohols, the most-utilized method is oxirane addition; and for mercaptoacids and mercaptonitriles, the most-utilized methods are Michael-type additions. /Thiols/

応用分野 · 4 件

用途有機合成原料。

用途医薬品、農薬の合成原料

使用1-Octanethiol can be used to improve charge injection by creating a monolayer of this material on gold source-drain electrode surfaces for bottom-contact thin-film transistors (TFTs).

一般的な説明A clear colorless liquid. Flash point 115°F. Insoluble in water and less dense than water. Used to make other chemicals.

調製方法 · 1 件

純化方法Pass the thiol through a column of alumina and work under N2, or Ar. Distil it under N2 and a vacuum. Store it under N2, or Ar in the dark. [Battacharyya et al. J Chem Soc, Faraday Trans 1 82 135 1986, Fletcher J Am Chem Soc 68 2727 1946]. [Beilstein 1 III 1710, 1 IV 1767.]

上流・下流製品情報

上流原料

1-ブロモオクタンナトリウムヒドロスルフィドチオ尿素

下流製品

4,4'-(3,3,5-トリメチル-1,1-シクロヘキサンジイル)ビス(フェノール)3-ヨードベンゼンメタノールビスオクチルペルスルフィド2,4-ビス(オクチルチオメチル)-6-メチルフェノール1-ヨードオクタンn-Octyl-beta-D-thiogalactopyranoside1-(エテニルチオ)オクタンOctyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside1-オクタンスルホニルクロリド