γ-丁内酯-D6 | 77568-65-1

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: γ-丁内酯-D6
• 英文名称: <2H6>γ-Butyrolactone
• 英文别名: hexadeuterio-γ-butyrolactone；dihydro-2(3H)furanone-[3,3,4,4,5,5-D6]；3,3,4,4,5,5-hexadeuteriotetrahydrofuran-2-one；[²H6]-γ-butyrolactone；γ-butyrolactone-d6；gamma-Butyrolactone-d6；3,3,4,4,5,5-hexadeuteriooxolan-2-one
• CAS: 77568-65-1
• 化学式: C₄H₆O₂
• 分子量: 92.0428
• InChiKey: YEJRWHAVMIAJKC-NMFSSPJFSA-N

物化性质

• 熔点：
  -45 °C (lit.)
• 沸点：
  204-205 °C (lit.)
• 密度：
  1.197 g/mL at 25 °C
• 闪点：
  208 °F
• 溶解度：
  乙腈：50 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22
• WGK Germany：
  3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: γ-Butyrolactone-d6
Product name
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 77568-65-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Serious eye damage (Category 1), H318
Specific target organ toxicity - single exposure (Category 3), H336
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22, R41, R67
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
H302 Harmful if swallowed.
H318 Causes serious eye damage.
H336 May cause drowsiness or dizziness.
Precautionary statement(s)
P261 Avoid breathing vapours.
P280 Wear protective gloves/ eye protection/ face protection.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Isotopically labeled
Formula : C4D6O2
Molecular Weight : 92,13 g/mol
CAS-No. : 77568-65-1
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
γ-Butyrolactone-d6
CAS-No. 77568-65-1 Acute Tox. 4; Eye Dam. 1; <= 100 %
STOT SE 3; H302, H318,
H336
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
γ-Butyrolactone-d6
CAS-No. 77568-65-1 Xn, R22 - R41 - R67 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Store under inert gas. hygroscopic
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection
tested and approved under appropriate government standards such as NIOSH (US) or EN
166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid, clear
Colour: colourless
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: -45 °C - lit.
point
f) Initial boiling point and 204 - 205 °C - lit.
boiling range
g) Flash point 98,00 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower Upper explosion limit: 16,00 %(V)
flammability or Lower explosion limit: 1,40 %(V)
explosive limits
k) Vapour pressure 2,0 hPa at 20,00 °C
l) Vapour density no data available
m) Relative density 1,197 g/mL at 25 °C1,197 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: -0,570
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong acids, Strong bases, Strong oxidizing agents, Strong reducing agents, Zinc, Plastics
Hazardous decomposition products
no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
LD50 Oral - rat - 1.540 mg/kg
Remarks: Behavioral:Altered sleep time (including change in righting reflex). Behavioral:Somnolence
(general depressed activity). Respiratory disorder
LC50 Inhalation - rat - 4,00 h - > 5.100 mg/m3
LD50 Dermal - guinea pig - > 5.000 mg/kg
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
This product is or contains a component that is not classifiable as to its carcinogenicity based on its IARC,
ACGIH, NTP, or EPA classification.
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
May cause drowsiness or dizziness.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
an anesthetic effect on the central nervous system characterized by a loss of sensation., Preliminary
excitement is the initial effect followed by relaxation, stupor, or sleep., Nausea, Dizziness, Headache

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SECTION 12: Ecological information
Toxicity
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Dam. Serious eye damage
H302 Harmful if swallowed.
H318 Causes serious eye damage.
H336 May cause drowsiness or dizziness.
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
R41 Risk of serious damage to eyes.
R67 Vapours may cause drowsiness and dizziness.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  γ-丁内酯-D6 在 盐酸 甲醇 、 sodium 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 32.0h， 以94%的产率得到4,4,5,5-d4-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  [EN] HYDROXYETHYLAMINO SULFONAMIDE DERIVATIVES
  [FR] DÉRIVÉS HYDROXYÉTHYLAMINO SULFONAMIDES

  摘要：

  公开号：

  WO2010127272A3
• 作为产物：
  描述：

  丁炔二酸 在 Ru₄H₄(CO)8(PBu₃)4 氘 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到γ-丁内酯-D6
  参考文献：
  名称：

  A Convenient Route to the Synthesis of Isotopomeric Dihydro-2(3H)furanones

  摘要：

  A general synthetic procedure leading to isotopomeric dihydro-2(3H)furanones (gamma-butyrolactones) containing two, four, or six deuterium atoms has been developed. The labeled dihydro-2(3H)furanones were synthesized in quantitative yield from the saturated diacid C-4 (succinic) or unsaturated diacids C-4 (fumaric, maleic, or acetylendicarboxylic) in the presence of Ru4H4(CO)(8)(PBu3)(4) using a deuterium pressure of 180 bar at 180 degrees C. This methodology was applied to the total synthesis of a hexadeuterated matairesinol lignan: The 3,4-bis{[3-methoxy-4-(phenylmethoxy)phenyl]methyl}dihydro-2(3H)furanone-[7,7',8,8',9',9'-D-6] (benzyl-protected matairesinol-D-6) was fully characterized.

  DOI：

  10.1021/jf070305y

文献信息

• Selective aerobic oxidation of cyclic ethers to lactones over Au/CeO₂ without any additives
  作者：Shulin Liu、Shaopeng Li、Xiaojun Shen、Yanyan Wang、Juan Du、Bingfeng Chen、Buxing Han、Huizhen Liu

  DOI：10.1039/c9cc09480f

  日期：——

  Selective oxidation of ethers to lactones with O2 as a benign oxidant using Au/CeO2 as the catalyst has been developed. The oxygen vacancies and Au0 species on the surface of CeO2 contribute to the activation of O2. The excellent selectivity of lactones is due to the adsorption of ethers and activation of the C(sp3)-H bond on Au/CeO2.

  已经开发了使用Au / CeO2作为催化剂，使用O2作为良性氧化剂将醚选择性氧化为内酯的方法。CeO2表面的氧空位和Au0物种有助于O2的活化。内酯的优异选择性是由于醚的吸附和Au / CeO2上C（sp3）-H键的活化所致。
• Ring-chain tautomerism in 2,2-bis(2-thienyl)tetrahydrofurans: preparation of [butene-2H5]-tiagabine
  作者：John M. Herbert、Trevor W. Mathers

  DOI：10.1002/jlcr.1787

  日期：2010.7

  A concise preparation of [butene-2H5]-tiagabine hydrochloride starting from [2H6]-γ-butyrolactone is described. It was necessary to ring-open the labeled γ-butyrolactone precursor before the addition of 2-thienyllithium to avoid cyclisation of the intermediate to a 2,2-bis(2-thienyl)tetrahydrofuran. Copyright © 2010 John Wiley & Sons, Ltd.

  描述了从 [2H6]-γ-丁内酯开始的 [丁烯-2H5]-tiagabine 盐酸盐的简明制备。有必要在添加 2-噻吩基锂之前将标记的 γ-丁内酯前体开环，以避免中间体环化为 2,2-双（2-噻吩基）四氢呋喃。版权所有 © 2010 John Wiley & Sons, Ltd.
• Stereoselective Preparation of Six Diastereomeric Quatercyclopropanes from Bicyclopropylidene and Some Derivatives
  作者：Malte von Seebach、Sergei I. Kozhushkov、Heiko Schill、Daniel Frank、Roland Boese、Jordi Benet-Buchholz、Dmitry S. Yufit、Armin de Meijere

  DOI：10.1002/chem.200600799

  日期：2007.1

  Diastereomeric meso- and d,l-bis(bicyclopropylidenyl) (5) were obtained upon oxidation with oxygen of a higher-order cuprate generated from lithiobicyclopropylidene (4) in 50 and 31 % yield, respectively. Their perdeuterated analogues meso-[D(14)]- and d,l-[D(14)]-5 were obtained along the same route from perdeuterated bicyclopropylidene [D(8)]-3 (synthesized in six steps in 7.4 % overall yield from

  通过用由硫代二环亚丙基（4）生成的高阶铜酸盐的氧气氧化，分别以50％和31％的收率得到非对映异构的内消旋和d，l-双（双环丙烯基）（5）。他们的全氘化类似物meso- [D（14）]-和d，l- [D（14）]-5是通过相同的路线从全氘化的双环亚丙基[D（8）]-3（按6个步骤以7.4％的合成率）获得的[D（8）]-THF）的总收率各为20.5％。1,1-二溴-2-环丙基环丙烷（6）的脱卤偶合反应以1,69％的产率得到了1,5-二环丙基双环亚丙基16的所有可能的立体异构体的混合物，通过制备型气相色谱从中分离出（Z）-cis-16（ 26％的收率）。meso-5的晶体结构看起来像是两个外部双环亚丙基单元（3）和一个内部s-反式-双环丙基单元的晶体结构的叠加，而两个外部环丙基部分相对于（Z）-顺式16的内部双环亚丙基单元上的环丙烷环采用gauche取向。在Meso-5和d，l-5的液氨中用锂桦
• The Intriguing Molecular Dynamics of Cer[EOS] in Rigid Skin Barrier Lipid Layers Requires Improvement of the Model
  作者：Ferdinand Fandrei、Tomáš Havrišák、Lukáš Opálka、Oskar Engberg、AlbertA. Smith、Petra Pullmannová、Norbert Kučerka、Veronika Ondrejčeková、Bruno Demé、Lucie Nováková、Miloš Steinhart、Kateřina Vávrová、Daniel Huster

  DOI：10.1016/j.jlr.2023.100356

  日期：2023.3

  results along with neutron diffraction data suggest an LPP structure with alternating fluid (sphingosine chain-rich), rigid (acyl chain-rich), isotropic (linoleate-rich), rigid (acyl-chain rich), and fluid layers (sphingosine chain-rich). Such an arrangement of the skin barrier lipids with rigid layers separated with two different dynamic "fillings" i) agrees well with ultrastructural data, ii) satisfies

  Omega-O-酰基神经酰胺，如 32-亚油酰氧基三十二酰鞘氨醇 (Cer[EOS]) 是脂质皮肤屏障的重要组成部分，可保护我们的身体免受过度水分流失和有害物质的渗透。这些神经酰胺将脂质组装驱动至表皮特异性长周期相 (LPP)，其结构与传统脂质双层有很大不同。在这里，我们用超长 N-酰基链的选择性氘化片段或氘化或13 C 标记的亚油酸合成了 Cer[EOS]，并研究了它们在皮肤脂质模型中的分子行为。固态2H NMR 数据揭示了 Cer[EOS] 超长 N-酰基链令人惊讶的分子动力学，其向各向同性酯结合的亚油酸酯的各向同性运动增加。Cer[EOS] 的鞘氨醇部分在皮肤温度下也具有高度流动性，这与其他 LPP 成分（N-木蜡酰鞘氨醇酰基、木蜡酸和胆固醇）形成鲜明对比，这些成分主要是刚性的。通过相关时间的分布并使用动态检测器分析来定量描述亚油酸链的动态。这些 NMR 结果与中子衍射数据表明 LPP
• [EN] HYDROXYETHYLAMINO SULFONAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS HYDROXYÉTHYLAMINO SULFONAMIDES
  申请人：CONCERT PHARMACEUTICALS INC

  公开号：WO2010127272A3

  公开（公告）日：2011-04-21